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31 Chestnut Hill Drive, Upper Brookville

Introducing 31 Chestnut Hill Drive, an extraordinary contemporary estate situated on five private acres at the end of a prestigious cul-de-sac in Upper Brookville. Originally designed by renowned architect Gary Gallagher and comprehensively reimagined from 2023 to 2026 by award-winning architect Stuart Narofsky, this exceptional residence seamlessly blends striking modern architecture with sophisticated design, cutting-edge technology, and resort-style amenities. Spanning over 10,000 square feet, the home features six bedrooms, six full and four half bathrooms, including a luxurious first-floor primary suite. Dramatic architectural details, including two custom floating staircases with glass railings, expansive walls of glass, porcelain flooring, and polished white oak floors, create a remarkable sense of openness and light. Thoughtfully designed living and entertaining spaces are complemented by a state-of-the-art chef's kitchen featuring custom cabinetry, integrated Thermador appliances, specialty quartz countertops, and an expansive center island. The home's extensive accommodations include multiple home offices, a library, and beautifully appointed guest suites. The fully finished lower level offers an exceptional collection of recreational and wellness amenities, including a Dolby Atmos home theater, custom wine room and tasting area, wet bar, fitness room, Finnish sauna, and dedicated yoga and massage space. Outdoors, the estate unfolds into a private resort-like setting, complete with a newly rebuilt heated saline pool and spa, expansive porcelain patios, and a fully renovated guest/pool house with its own kitchen. An outdoor kitchen and beautifully landscaped grounds provide an ideal setting for both intimate gatherings and large-scale entertaining. Additional highlights include a heated four-car garage, five-zone energy-efficient climate control, whole-house generator, and comprehensive smart-home technology managing lighting, security, motorized shades, and numerous additional systems. Offering exceptional privacy, architectural distinction, and an extraordinary level of modern luxury, 31 Chestnut Hill Drive represents a rare opportunity to experience contemporary estate living on Long Island's Gold Coast.

6 Beds ⋅ 10 Baths ⋅ 1061123 MLS

Introducing 31 Chestnut Hill Drive, an extraordinary contemporary estate situated on five private acres at the end of a prestigious cul-de-sac in Upper Brookville. Originally designed by renowned architect Gary Gallagher and comprehensively reimagined from 2023 to 2026 by award-winning architect Stuart Narofsky, this exceptional residence seamlessly blends striking modern architecture with sophisticated design, cutting-edge technology, and resort-style amenities. Spanning over 10,000 square feet, the home features six bedrooms, six full and four half bathrooms, including a luxurious first-floor primary suite. Dramatic architectural details, including two custom floating staircases with glass railings, expansive walls of glass, porcelain flooring, and polished white oak floors, create a remarkable sense of openness and light. Thoughtfully designed living and entertaining spaces are complemented by a state-of-the-art chef's kitchen featuring custom cabinetry, integrated Thermador appliances, specialty quartz countertops, and an expansive center island. The home's extensive accommodations include multiple home offices, a library, and beautifully appointed guest suites. The fully finished lower level offers an exceptional collection of recreational and wellness amenities, including a Dolby Atmos home theater, custom wine room and tasting area, wet bar, fitness room, Finnish sauna, and dedicated yoga and massage space. Outdoors, the estate unfolds into a private resort-like setting, complete with a newly rebuilt heated saline pool and spa, expansive porcelain patios, and a fully renovated guest/pool house with its own kitchen. An outdoor kitchen and beautifully landscaped grounds provide an ideal setting for both intimate gatherings and large-scale entertaining. Additional highlights include a heated four-car garage, five-zone energy-efficient climate control, whole-house generator, and comprehensive smart-home technology managing lighting, security, motorized shades, and numerous additional systems. Offering exceptional privacy, architectural distinction, and an extraordinary level of modern luxury, 31 Chestnut Hill Drive represents a rare opportunity to experience contemporary estate living on Long Island's Gold Coast.

31 Chestnut Hill Drive, Upper Brookville

18 Chestnut Hill Drive, Upper Brookville

$4,980,000

Set on five magnificent acres of sprawling, level grounds along one of Long Island’s most coveted residential streets, this extraordinary contemporary estate, designed by acclaimed architectural firm Mojo Stumer, represents a sophisticated expression of modern luxury, architectural innovation, and resort-inspired living. Distinguished by dramatic proportions, soaring ceilings, expansive walls of glass, and a seamless connection between indoor and outdoor spaces, the residence offers an exceptional combination of architectural significance, privacy, and grand-scale entertaining. A grand entrance foyer introduces interiors defined by remarkable volume and natural light, leading to a breathtaking double-height great room anchored by a striking marble fireplace. Expansive windows frame picturesque views of the surrounding landscape, enhancing the home's connection to its private, park-like setting. The thoughtfully designed main level features an elegant formal dining room, spacious eat-in kitchen, inviting family room, and sophisticated lounge with a wet bar. A powder room and first-floor laundry provide additional convenience. Occupying a private wing of the main level, the luxurious first-floor primary suite offers an exceptional retreat, complete with a generous his and her walk-in closet and a beautifully appointed bathroom featuring a steam shower. An additional first-floor bedroom with a full bathroom provides ideal accommodations for guests or extended family. The second level features four generously proportioned guest bedrooms complemented by two full bathrooms. Additionally an expansive loft with its own balcony and full bathroom offers a versatile space ideally suited for a private office, additional lounge, or secluded retreat. Designed for recreation, wellness, and entertaining, the expansive lower level features a dramatic double-sided fireplace connecting the game room and entertainment spaces. A spacious recreation area with a wet bar provides the perfect setting for gatherings, while a substantial private gym with its own full bathroom creates a dedicated fitness retreat. Additional accommodations include a staff or guest bedroom and another full bathroom. Beyond the residence sits a remarkable private resort featuring a swimming pool, hot tub, and tennis court. A substantial poolside cabana offers a full indoor kitchen, outdoor wet bar, comfortable lounge, full bathroom, and dedicated laundry facilities. A built-in outdoor grill completes the exceptional entertaining amenities, providing an effortless transition between indoor luxury and outdoor leisure. A four-car garage further complements the estate, providing generous space for automobiles and storage. The property presents a remarkable opportunity to experience architectural distinction, privacy, and an uncompromising lifestyle.

7 Beds ⋅ 9 Baths ⋅ 1061600 MLS

Set on five magnificent acres of sprawling, level grounds along one of Long Island’s most coveted residential streets, this extraordinary contemporary estate, designed by acclaimed architectural firm Mojo Stumer, represents a sophisticated expression of modern luxury, architectural innovation, and resort-inspired living. Distinguished by dramatic proportions, soaring ceilings, expansive walls of glass, and a seamless connection between indoor and outdoor spaces, the residence offers an exceptional combination of architectural significance, privacy, and grand-scale entertaining. A grand entrance foyer introduces interiors defined by remarkable volume and natural light, leading to a breathtaking double-height great room anchored by a striking marble fireplace. Expansive windows frame picturesque views of the surrounding landscape, enhancing the home's connection to its private, park-like setting. The thoughtfully designed main level features an elegant formal dining room, spacious eat-in kitchen, inviting family room, and sophisticated lounge with a wet bar. A powder room and first-floor laundry provide additional convenience. Occupying a private wing of the main level, the luxurious first-floor primary suite offers an exceptional retreat, complete with a generous his and her walk-in closet and a beautifully appointed bathroom featuring a steam shower. An additional first-floor bedroom with a full bathroom provides ideal accommodations for guests or extended family. The second level features four generously proportioned guest bedrooms complemented by two full bathrooms. Additionally an expansive loft with its own balcony and full bathroom offers a versatile space ideally suited for a private office, additional lounge, or secluded retreat. Designed for recreation, wellness, and entertaining, the expansive lower level features a dramatic double-sided fireplace connecting the game room and entertainment spaces. A spacious recreation area with a wet bar provides the perfect setting for gatherings, while a substantial private gym with its own full bathroom creates a dedicated fitness retreat. Additional accommodations include a staff or guest bedroom and another full bathroom. Beyond the residence sits a remarkable private resort featuring a swimming pool, hot tub, and tennis court. A substantial poolside cabana offers a full indoor kitchen, outdoor wet bar, comfortable lounge, full bathroom, and dedicated laundry facilities. A built-in outdoor grill completes the exceptional entertaining amenities, providing an effortless transition between indoor luxury and outdoor leisure. A four-car garage further complements the estate, providing generous space for automobiles and storage. The property presents a remarkable opportunity to experience architectural distinction, privacy, and an uncompromising lifestyle.

18 Chestnut Hill Drive, Upper Brookville

$699,000

Welcome to 112 North Street, a charming three-bedroom ranch in the heart of Locust Valley, offering an incredible opportunity at a desirable price point. Move-in ready and filled with possibilities, this inviting home features a spacious living room with gas fireplace, dining room, eat-in kitchen, three bedrooms and two full baths, including a primary bedroom with en-suite bath. The versatile third bedroom offers direct access to the backyard and can easily serve as a home office, den or bonus space. A spacious finished basement with separate entrance and laundry provides even more room and flexibility. Outside, enjoy a private backyard with deck, perfect for relaxing or entertaining. Comfortable as-is with plenty of potential to make it your own, 112 North Street is a wonderful opportunity to put down roots in Locust Valley.

3 Beds ⋅ 2 Baths ⋅ 1054854 MLS

Welcome to 112 North Street, a charming three-bedroom ranch in the heart of Locust Valley, offering an incredible opportunity at a desirable price point. Move-in ready and filled with possibilities, this inviting home features a spacious living room with gas fireplace, dining room, eat-in kitchen, three bedrooms and two full baths, including a primary bedroom with en-suite bath. The versatile third bedroom offers direct access to the backyard and can easily serve as a home office, den or bonus space. A spacious finished basement with separate entrance and laundry provides even more room and flexibility. Outside, enjoy a private backyard with deck, perfect for relaxing or entertaining. Comfortable as-is with plenty of potential to make it your own, 112 North Street is a wonderful opportunity to put down roots in Locust Valley.

112 North Street, Locust Valley

$1,299,000

welcome to this waterfront contemporary colonial,fully renovated,this baysidewaterfront home has incredible views,great room has full wall of new sliders overlooking water, new trex decking from first and second floor decks,great roomfeatures beautiful stone fireplace,gorgeous new kitchen with center island, white shake cabinets,quartz counertops,new appliances, french doors open to lovely den,half bath,second floor has 4 all large bedrooms, master bedroom features vaulted ceilingan walls of glass overlooking serene waterfront views, an door leads out to your own private deck,master bath is breathtaking featues vaulted ceiling ,huge seperate shower ,double sinks, soaking tub with winows looking at stunning waterviews so many extras in this stunning home

4 Beds ⋅ 3 Baths ⋅ 1061133 MLS

welcome to this waterfront contemporary colonial,fully renovated,this baysidewaterfront home has incredible views,great room has full wall of new sliders overlooking water, new trex decking from first and second floor decks,great roomfeatures beautiful stone fireplace,gorgeous new kitchen with center island, white shake cabinets,quartz counertops,new appliances, french doors open to lovely den,half bath,second floor has 4 all large bedrooms, master bedroom features vaulted ceilingan walls of glass overlooking serene waterfront views, an door leads out to your own private deck,master bath is breathtaking featues vaulted ceiling ,huge seperate shower ,double sinks, soaking tub with winows looking at stunning waterviews so many extras in this stunning home

35 adams Avenue, Bayville

$1,699,000

THE CANOPY! Let the magic of The Canopy capture your heart. Set gracefully on a quiet cul-de-sac in the Hamlet of Locust Valley, this extraordinary, 11-room, four-bedroom, three-bath residence is a home defined by light, space, and an unmistakable connection to nature. From the moment the sun rises, extraordinary natural light moves throughout the home, illuminating an open and inviting floor plan and creating an atmosphere that is both sophisticated and wonderfully warm. A gracious second-story entry foyer welcomes you with an immediate sense of scale and architectural character. To one side, a turret with a custom curved wall of windows with a built-in window seat, currently enjoyed as a music room, offers a uniquely inspiring space that could equally serve as a home office, reading room, or creative retreat. Dramatic architectural details continue into the expansive living room, where a tray ceiling and a wall of glass windows draw the outdoors in and fill the room with light. The living room flows naturally into the oversized formal dining room, which may also be accessed directly from the grand foyer and kitchen, creating an effortless setting for both intimate dinners and larger gatherings. Beyond, the eat-in kitchen connects to the great room extending across the far side of the home. Custom wood-paneled built-ins with extensive display shelving and a wall-mounted television, glass doors opening to the emerald-green rear knoll make this exceptional room equally suited to relaxed everyday living and entertaining. A formal powder room, two coat closets, and laundry room with direct access to the side yard complete this level. Upstairs, a light-filled landing with double windows brings daylight to a custom built-in computer station. The principal suite is a generous private retreat, distinguished by a vaulted ceiling, and two oversized walk-in closets. The sumptuous primary bath is designed for comfort and indulgence, featuring a Jacuzzi tub, floor-to-ceiling glass-enclosed shower, and double vanity. Three additional bedrooms provide exceptional flexibility, and share a beautifully proportioned bath with a double vanity, full tub, and glass enclosure. One bedroom is enhanced by custom built-in bookshelves, a wall-mounted television, and double closets. Another echoes the distinctive curved architecture found in the music room below, with a wall of windows and custom built-in seating. It is an especially enchanting space, inviting the next owner to create a one-of-a-kind reading nook, bedroom retreat, or designer sanctuary. The lower level adds another dimension to the home with a spacious recreation room. A cedar closet, ample storage-utility room, and access to a two car garage. Outside, a generous newly paved driveway framed by Belgian block provides abundant parking for guests, with space for upwards of eight additional vehicles. Nature is quite literally part of the address. Directly across the street lies the extraordinary Coffin Woods Nature Preserve-this treasured natural setting provides a beautiful backdrop. The grassy rear knoll awaits your vision. Imagine a beautifully designed patio or deck where morning coffee can be enjoyed beneath the open sky, surrounded by the extraordinary cacophony of birds and the ever-changing colors and textures of the seasons. With its exceptional natural light, distinctive architectural details, generous proportions, thoughtful spaces for work and creativity, and a rare relationship to protected woodland, The Canopy is far more than a residence. It is a place to live beautifully, entertain effortlessly, and experience the quiet magic of Locust Valley every day. View 3D Tour and floor plan.

4 Beds ⋅ 3 Baths ⋅ 1059772 MLS

THE CANOPY! Let the magic of The Canopy capture your heart. Set gracefully on a quiet cul-de-sac in the Hamlet of Locust Valley, this extraordinary, 11-room, four-bedroom, three-bath residence is a home defined by light, space, and an unmistakable connection to nature. From the moment the sun rises, extraordinary natural light moves throughout the home, illuminating an open and inviting floor plan and creating an atmosphere that is both sophisticated and wonderfully warm. A gracious second-story entry foyer welcomes you with an immediate sense of scale and architectural character. To one side, a turret with a custom curved wall of windows with a built-in window seat, currently enjoyed as a music room, offers a uniquely inspiring space that could equally serve as a home office, reading room, or creative retreat. Dramatic architectural details continue into the expansive living room, where a tray ceiling and a wall of glass windows draw the outdoors in and fill the room with light. The living room flows naturally into the oversized formal dining room, which may also be accessed directly from the grand foyer and kitchen, creating an effortless setting for both intimate dinners and larger gatherings. Beyond, the eat-in kitchen connects to the great room extending across the far side of the home. Custom wood-paneled built-ins with extensive display shelving and a wall-mounted television, glass doors opening to the emerald-green rear knoll make this exceptional room equally suited to relaxed everyday living and entertaining. A formal powder room, two coat closets, and laundry room with direct access to the side yard complete this level. Upstairs, a light-filled landing with double windows brings daylight to a custom built-in computer station. The principal suite is a generous private retreat, distinguished by a vaulted ceiling, and two oversized walk-in closets. The sumptuous primary bath is designed for comfort and indulgence, featuring a Jacuzzi tub, floor-to-ceiling glass-enclosed shower, and double vanity. Three additional bedrooms provide exceptional flexibility, and share a beautifully proportioned bath with a double vanity, full tub, and glass enclosure. One bedroom is enhanced by custom built-in bookshelves, a wall-mounted television, and double closets. Another echoes the distinctive curved architecture found in the music room below, with a wall of windows and custom built-in seating. It is an especially enchanting space, inviting the next owner to create a one-of-a-kind reading nook, bedroom retreat, or designer sanctuary. The lower level adds another dimension to the home with a spacious recreation room. A cedar closet, ample storage-utility room, and access to a two car garage. Outside, a generous newly paved driveway framed by Belgian block provides abundant parking for guests, with space for upwards of eight additional vehicles. Nature is quite literally part of the address. Directly across the street lies the extraordinary Coffin Woods Nature Preserve-this treasured natural setting provides a beautiful backdrop. The grassy rear knoll awaits your vision. Imagine a beautifully designed patio or deck where morning coffee can be enjoyed beneath the open sky, surrounded by the extraordinary cacophony of birds and the ever-changing colors and textures of the seasons. With its exceptional natural light, distinctive architectural details, generous proportions, thoughtful spaces for work and creativity, and a rare relationship to protected woodland, The Canopy is far more than a residence. It is a place to live beautifully, entertain effortlessly, and experience the quiet magic of Locust Valley every day. View 3D Tour and floor plan.

10 Matinecock Court, Locust Valley

$2,250,000

Welcome to 116 Valley Avenue, a beautifully renovated 4-bedroom ranch set on a private just shy half-acre in the heart of Lattingtown Village. Completely updated from top to bottom and presented in mint condition, this home offers a seamless blend of luxury, comfort, and effortless one-level living. The bright, open-concept interior features generously sized bedrooms, including a spacious primary suite with a walk-in closet. The custom kitchen is designed for both everyday living and entertaining, with a large centre island and quartz countertops, Viking appliances, a quick-touch faucet, and elegant finishes throughout. Coffered ceilings, radiant heat, and built-in speakers throughout the interior and exterior further elevate the home’s comfort and functionality. A finished basement provides additional flexible living space, while the attached two-car heated garage offers year-round convenience. The home is also equipped with exterior security cameras for added peace of mind. Outside, the property truly shines. The expansive backyard features open lawn, mature private landscaping, an in-ground heated pool, outdoor kitchen, extensive paver patios, and multiple areas for entertaining, relaxing, and enjoying the outdoors. Located within Lattingtown Village with access to a private beach and close proximity to the elementary school, this exceptional home is also just minutes from Locust Valley’s parks, country clubs, beaches, local shops, restaurants, and LIRR station. Turnkey, beautifully finished, and offering an outstanding indoor-outdoor lifestyle, 116 Valley Avenue is a rare opportunity in one of the North Shore’s most desirable communities.

4 Beds ⋅ 3 Baths ⋅ 1058290 MLS

Welcome to 116 Valley Avenue, a beautifully renovated 4-bedroom ranch set on a private just shy half-acre in the heart of Lattingtown Village. Completely updated from top to bottom and presented in mint condition, this home offers a seamless blend of luxury, comfort, and effortless one-level living. The bright, open-concept interior features generously sized bedrooms, including a spacious primary suite with a walk-in closet. The custom kitchen is designed for both everyday living and entertaining, with a large centre island and quartz countertops, Viking appliances, a quick-touch faucet, and elegant finishes throughout. Coffered ceilings, radiant heat, and built-in speakers throughout the interior and exterior further elevate the home’s comfort and functionality. A finished basement provides additional flexible living space, while the attached two-car heated garage offers year-round convenience. The home is also equipped with exterior security cameras for added peace of mind. Outside, the property truly shines. The expansive backyard features open lawn, mature private landscaping, an in-ground heated pool, outdoor kitchen, extensive paver patios, and multiple areas for entertaining, relaxing, and enjoying the outdoors. Located within Lattingtown Village with access to a private beach and close proximity to the elementary school, this exceptional home is also just minutes from Locust Valley’s parks, country clubs, beaches, local shops, restaurants, and LIRR station. Turnkey, beautifully finished, and offering an outstanding indoor-outdoor lifestyle, 116 Valley Avenue is a rare opportunity in one of the North Shore’s most desirable communities.

116 Valley Avenue, Locust Valley

$2,395,000

Bright, beautifully updated, and completely turn-key, this sophisticated five-bedroom, five-and-a-half-bath residence offers modern luxury, thoughtful design, and effortless indoor-outdoor living. The open-concept interior features a gracious great room with living and dining areas, a fireplace, separate family room, and private study. A chef’s kitchen with marble countertops anchors the home, while the great room opens through two sets of French doors to the patio and pool area. All five bedrooms are en suite, including a private first-floor primary suite. Smart home technology and extensive updates ensure truly turn-key living. Outside, a heated pool, generous entertaining terrace, and fully equipped outdoor kitchen create an inviting setting for gatherings and relaxed weekends at home. Ideally located in the heart of Locust Valley, this exceptional residence offers modern amenities, elegant living spaces, and in a coveted neighborhood.

5 Beds ⋅ 6 Baths ⋅ 1057004 MLS

Bright, beautifully updated, and completely turn-key, this sophisticated five-bedroom, five-and-a-half-bath residence offers modern luxury, thoughtful design, and effortless indoor-outdoor living. The open-concept interior features a gracious great room with living and dining areas, a fireplace, separate family room, and private study. A chef’s kitchen with marble countertops anchors the home, while the great room opens through two sets of French doors to the patio and pool area. All five bedrooms are en suite, including a private first-floor primary suite. Smart home technology and extensive updates ensure truly turn-key living. Outside, a heated pool, generous entertaining terrace, and fully equipped outdoor kitchen create an inviting setting for gatherings and relaxed weekends at home. Ideally located in the heart of Locust Valley, this exceptional residence offers modern amenities, elegant living spaces, and in a coveted neighborhood.

2 Wood Lane, Locust Valley

$8,000,000

12.6 Acres of Prime Land for Sale –Can be Planned for 4 Homes – 3-Acre Zoning – Cul-de-Sac Access (PLANS NOT APPROVED) A rare development opportunity awaits with this 12.6-acre parcel of land, ideally situated at the end of a peaceful cul-de-sac. Zoned for 3-acre minimum lots, this property comes with a concept plan for 4 single-family homes, making it perfect for a small subdivision, custom home build. This is a perfect opportunity for developers, builders, or investors looking for a manageable project with strong potential and desirable zoning. With all entrances planned from the cul-de-sac, this layout ensures privacy, safety, and minimal traffic—ideal for a quiet residential enclave.

1057857 MLS

12.6 Acres of Prime Land for Sale –Can be Planned for 4 Homes – 3-Acre Zoning – Cul-de-Sac Access (PLANS NOT APPROVED) A rare development opportunity awaits with this 12.6-acre parcel of land, ideally situated at the end of a peaceful cul-de-sac. Zoned for 3-acre minimum lots, this property comes with a concept plan for 4 single-family homes, making it perfect for a small subdivision, custom home build. This is a perfect opportunity for developers, builders, or investors looking for a manageable project with strong potential and desirable zoning. With all entrances planned from the cul-de-sac, this layout ensures privacy, safety, and minimal traffic—ideal for a quiet residential enclave.

5694 Northern Boulevard, Muttontown

$839,500

Set in the heart of Locust Valley Village, this charming three-bedroom home offers an inviting combination of character, space and an exceptional village lifestyle. Hardwood floors flow throughout generously proportioned rooms, while the home's solid construction and versatile layout create a wonderful canvas to customize and make your own. Three bedrooms and one-and-a-half baths are complemented by a large walk-up attic and full unfinished basement, offering abundant additional space and possibilities. Outdoors, a private backyard, long driveway and detached garage complete the property. Just moments from Locust Valley's favorite shops, restaurants, cafes and the LIRR, this is an opportunity to enjoy the ease of village living with the beauty and character that make Locust Valley such a special place to call home.

3 Beds ⋅ 2 Baths ⋅ 1057033 MLS

Set in the heart of Locust Valley Village, this charming three-bedroom home offers an inviting combination of character, space and an exceptional village lifestyle. Hardwood floors flow throughout generously proportioned rooms, while the home's solid construction and versatile layout create a wonderful canvas to customize and make your own. Three bedrooms and one-and-a-half baths are complemented by a large walk-up attic and full unfinished basement, offering abundant additional space and possibilities. Outdoors, a private backyard, long driveway and detached garage complete the property. Just moments from Locust Valley's favorite shops, restaurants, cafes and the LIRR, this is an opportunity to enjoy the ease of village living with the beauty and character that make Locust Valley such a special place to call home.

24 Bella Vista Street, Locust Valley

$3,390,000

Luxurious estate in a private gated neighborhood in the Village of Upper Brookville! This exceptional estate offers a rare combination of expansive acreage, generous living space, and resort-style amenities. Set on more than two acres, the 5,063-square-foot residence features six bedrooms, five full and one-half baths, and an inviting layout designed for both refined everyday living and effortless entertaining. Soaring ceilings, expansive windows, and an open-concept design create a light-filled sense of volume throughout the home. The majority of the living spaces are thoughtfully arranged on the main level, while generously proportioned rooms provide flexibility for both intimate gatherings and larger-scale entertaining. Walls of windows frame serene views of the beautifully landscaped grounds and bring the surrounding setting into the home. Beyond the interiors, the property unfolds as a private outdoor retreat. A sparkling in-ground pool and full tennis court provide an exceptional setting for recreation, relaxation, and summer entertaining, while the expansive grounds offer both privacy and room to enjoy the estate to its fullest. A three-car garage and distinguished circular drive enhance the property's impressive arrival and everyday convenience. A distinctive opportunity to enjoy privacy, scale, and an exceptional collection of amenities in one of Long Island's most sought-after North Shore settings

6 Beds ⋅ 6 Baths ⋅ 1056792 MLS

Luxurious estate in a private gated neighborhood in the Village of Upper Brookville! This exceptional estate offers a rare combination of expansive acreage, generous living space, and resort-style amenities. Set on more than two acres, the 5,063-square-foot residence features six bedrooms, five full and one-half baths, and an inviting layout designed for both refined everyday living and effortless entertaining. Soaring ceilings, expansive windows, and an open-concept design create a light-filled sense of volume throughout the home. The majority of the living spaces are thoughtfully arranged on the main level, while generously proportioned rooms provide flexibility for both intimate gatherings and larger-scale entertaining. Walls of windows frame serene views of the beautifully landscaped grounds and bring the surrounding setting into the home. Beyond the interiors, the property unfolds as a private outdoor retreat. A sparkling in-ground pool and full tennis court provide an exceptional setting for recreation, relaxation, and summer entertaining, while the expansive grounds offer both privacy and room to enjoy the estate to its fullest. A three-car garage and distinguished circular drive enhance the property's impressive arrival and everyday convenience. A distinctive opportunity to enjoy privacy, scale, and an exceptional collection of amenities in one of Long Island's most sought-after North Shore settings

6 Quail Path, Glen Head

39 Chestnut Hill Drive, Upper Brookville

$12,750,000

Built in 2001 and privately set on five pristine acres, this extraordinary estate is a residence of rare character and enduring elegance, blending old-world craftsmanship, architectural drama, and gracious modern living. From richly detailed formal rooms to expansive spaces designed for entertaining, every level reveals another layer of thoughtful design. The home makes an immediate impression with a distinguished foyer featuring classic checkered flooring, where graceful archways establish a sense of symmetry and sophistication. Beyond, the formal living room is beautifully appointed with intricate hardwood floors, a marble fireplace and mantel, and French doors opening directly to the terrace, creating an effortless connection between the interiors and gardens. A formal office boasts distinguished rich hardwood paneling, an intricately finished plaster ceiling, and its own wood-burning fireplace. The formal dining room is equally refined, framed by substantial moldings and anchored by another fireplace—an elegant setting for both intimate dinners and grand-scale entertaining. One of the home's most memorable architectural moments is a discreet curved staircase leading to the dramatic family room. Here, soaring vaulted ceilings, exposed wood beams, and a monumental stone fireplace create a remarkable sense of scale. A concealed door reveals a private wet bar, adding an unexpected and sophisticated element for entertaining. The kitchen and service areas have been conceived with both beauty and function in mind. A handsome butler's pantry features a hand-painted tile backsplash, marble countertops, and abundant preparation space. The expansive farmhouse-inspired eat-in kitchen is finished with warm terracotta floors, two porcelain farmhouse sinks, oversized chef's appliances, a substantial center island, and a sun-filled breakfast area overlooking the grounds. A pantry and discreetly positioned powder room are located just off the kitchen, while a circular rear staircase provides convenient access between levels. A separate side entrance opens to a practical mudroom with an additional service pantry, complete with sink and refrigerator. Ascending to the second floor, an oval wood architectural ceiling crowns a gracious landing overlooking the level below, creating a striking transition to the private bedroom quarters. The secondary accommodations include four generously proportioned bedrooms, one with its own loft space, each appointed with a marble en-suite bath. Near the rear-stair landing, a convenient preparation or household station with sink adds functionality, while a private office provides a dedicated workspace. The primary suite is an extraordinary private retreat. Generous in scale and beautifully secluded, it offers separate dressing rooms and walk-in closets, along with a spa-inspired bath featuring a jetted soaking tub and oversized walk-in shower. An adjoining sitting room creates a quiet sanctuary, with access to a walk-up attic offering additional possibilities. The lower level rivals the principal entertaining spaces in both scale and amenities. Remarkably high ceilings enhance an expansive den and recreation area, complemented by a powder room, full bar, billiards and game room, wine cellar, professionally matted gym, and an impressive 15-seat private theater. Two additional staff or guest rooms, supported by two full baths, complete this exceptionally versatile level. Across the estate's five pristine acres, the grounds unfold as a private resort. Expansive slate and brick terraces provide multiple settings for dining and entertaining, while covered patios framed by graceful archways offer shaded retreats overlooking the property. Beyond, a swimming pool and spa form the centerpiece of the property's recreational amenities, accompanied by a substantial, one-of-a-kind pool house that further elevates the estate's resort-like appeal.

8 Beds ⋅ 12 Baths ⋅ 1056809 MLS

Built in 2001 and privately set on five pristine acres, this extraordinary estate is a residence of rare character and enduring elegance, blending old-world craftsmanship, architectural drama, and gracious modern living. From richly detailed formal rooms to expansive spaces designed for entertaining, every level reveals another layer of thoughtful design. The home makes an immediate impression with a distinguished foyer featuring classic checkered flooring, where graceful archways establish a sense of symmetry and sophistication. Beyond, the formal living room is beautifully appointed with intricate hardwood floors, a marble fireplace and mantel, and French doors opening directly to the terrace, creating an effortless connection between the interiors and gardens. A formal office boasts distinguished rich hardwood paneling, an intricately finished plaster ceiling, and its own wood-burning fireplace. The formal dining room is equally refined, framed by substantial moldings and anchored by another fireplace—an elegant setting for both intimate dinners and grand-scale entertaining. One of the home's most memorable architectural moments is a discreet curved staircase leading to the dramatic family room. Here, soaring vaulted ceilings, exposed wood beams, and a monumental stone fireplace create a remarkable sense of scale. A concealed door reveals a private wet bar, adding an unexpected and sophisticated element for entertaining. The kitchen and service areas have been conceived with both beauty and function in mind. A handsome butler's pantry features a hand-painted tile backsplash, marble countertops, and abundant preparation space. The expansive farmhouse-inspired eat-in kitchen is finished with warm terracotta floors, two porcelain farmhouse sinks, oversized chef's appliances, a substantial center island, and a sun-filled breakfast area overlooking the grounds. A pantry and discreetly positioned powder room are located just off the kitchen, while a circular rear staircase provides convenient access between levels. A separate side entrance opens to a practical mudroom with an additional service pantry, complete with sink and refrigerator. Ascending to the second floor, an oval wood architectural ceiling crowns a gracious landing overlooking the level below, creating a striking transition to the private bedroom quarters. The secondary accommodations include four generously proportioned bedrooms, one with its own loft space, each appointed with a marble en-suite bath. Near the rear-stair landing, a convenient preparation or household station with sink adds functionality, while a private office provides a dedicated workspace. The primary suite is an extraordinary private retreat. Generous in scale and beautifully secluded, it offers separate dressing rooms and walk-in closets, along with a spa-inspired bath featuring a jetted soaking tub and oversized walk-in shower. An adjoining sitting room creates a quiet sanctuary, with access to a walk-up attic offering additional possibilities. The lower level rivals the principal entertaining spaces in both scale and amenities. Remarkably high ceilings enhance an expansive den and recreation area, complemented by a powder room, full bar, billiards and game room, wine cellar, professionally matted gym, and an impressive 15-seat private theater. Two additional staff or guest rooms, supported by two full baths, complete this exceptionally versatile level. Across the estate's five pristine acres, the grounds unfold as a private resort. Expansive slate and brick terraces provide multiple settings for dining and entertaining, while covered patios framed by graceful archways offer shaded retreats overlooking the property. Beyond, a swimming pool and spa form the centerpiece of the property's recreational amenities, accompanied by a substantial, one-of-a-kind pool house that further elevates the estate's resort-like appeal.

39 Chestnut Hill Drive, Upper Brookville

$7,250,000

Bold, sophisticated and entirely of the moment, 7 Brookville Road represents a new level of luxury. Set on 2.5+ magnificent acres in Brookville’s prestigious Estate Section, this newly constructed modern estate offers 8,700 square feet under roof. A rare opportunity to own a truly distinctive Brookville residence—thoughtfully designed for an exceptional way of life. Built and designed by Willard Holmes, the residence is dramatic in scale yet refined in every detail. Highlights include two luxurious primary suites, a spectacular chef’s kitchen with separate catering kitchen, and expansive living spaces for relaxed daily living and grand-scale entertaining. Outside, a pool and pool house complete the private retreat. For the discerning buyer seeking an elevated lifestyle, this estate offers room for everyone, with inviting spaces to gather and retreat in privacy. Equally compelling as a year-round residence or an escape from the city, it brings a sense of ease to everyday living.

6 Beds ⋅ 8 Baths ⋅ 1055002 MLS

Bold, sophisticated and entirely of the moment, 7 Brookville Road represents a new level of luxury. Set on 2.5+ magnificent acres in Brookville’s prestigious Estate Section, this newly constructed modern estate offers 8,700 square feet under roof. A rare opportunity to own a truly distinctive Brookville residence—thoughtfully designed for an exceptional way of life. Built and designed by Willard Holmes, the residence is dramatic in scale yet refined in every detail. Highlights include two luxurious primary suites, a spectacular chef’s kitchen with separate catering kitchen, and expansive living spaces for relaxed daily living and grand-scale entertaining. Outside, a pool and pool house complete the private retreat. For the discerning buyer seeking an elevated lifestyle, this estate offers room for everyone, with inviting spaces to gather and retreat in privacy. Equally compelling as a year-round residence or an escape from the city, it brings a sense of ease to everyday living.

7 Brookville Road, Brookville

$850,000

Welcome to 76 Hernan Ave, a charming and well maintained high ranch offering nearly 2000 sq ft of comfortable living space in a lovely and desirable Locust Valley neighborhood. Situated on a beautiful block near the end of a dead end street, the home enjoys a peaceful setting with water views from the street. The first floor features a spacious den along with a generously sized bedroom with en suite bathroom, perfect for those seeking convenient first floor living or for guests. A laundry room completes the first floor. Upstairs, you'll find hardwood floors, three additional bedrooms, full bathroom, eat in kitchen, dining room and a comfortable living room with water views. The property also offers the unique advantage of a small portion of the lot being located within the Village of Lattingtown, providing access to the Glen Cove Golf Course and the Village of Lattingtown Beach. Recent improvements include a brand new cesspool, new hot water heater, new roof and newer washer/ dryer. A wonderful opportunity to own a well cared for home in a charming setting, on one of Locust Valley's lovely residential blocks with water views and desirable village amenities. Close to schools, shops, & beaches. Not to be missed!

4 Beds ⋅ 2 Baths ⋅ 1054412 MLS

Welcome to 76 Hernan Ave, a charming and well maintained high ranch offering nearly 2000 sq ft of comfortable living space in a lovely and desirable Locust Valley neighborhood. Situated on a beautiful block near the end of a dead end street, the home enjoys a peaceful setting with water views from the street. The first floor features a spacious den along with a generously sized bedroom with en suite bathroom, perfect for those seeking convenient first floor living or for guests. A laundry room completes the first floor. Upstairs, you'll find hardwood floors, three additional bedrooms, full bathroom, eat in kitchen, dining room and a comfortable living room with water views. The property also offers the unique advantage of a small portion of the lot being located within the Village of Lattingtown, providing access to the Glen Cove Golf Course and the Village of Lattingtown Beach. Recent improvements include a brand new cesspool, new hot water heater, new roof and newer washer/ dryer. A wonderful opportunity to own a well cared for home in a charming setting, on one of Locust Valley's lovely residential blocks with water views and desirable village amenities. Close to schools, shops, & beaches. Not to be missed!

76 Hernan Avenue, Locust Valley

$13,250,000

La Reserve - A Legendary Gold Coast Estate of Rare Provenance Perched atop one of the North Shore's most commanding elevations, at the end of a mile-long private drive overlooking the iconic Cleft Road Causeway, La Reserve serve stands among the most significant surviving estates of Long Island's storied Gold Coast. Originally commissioned in 1922 by Arthur Vining Davis - financier, industrialist, chairman of the Aluminum Company of America, and once ranked among the wealthiest men in the United States - this extraordinary residence embodies a level of craftsmanship, scale, and historical significance that is virtually impossible to replicate today. Designed by renowned architect Guy Lowell in the Italian Renaissance style, the estate was originally conceived as a grand country retreat for one of America's most influential business titans. The interiors were executed by the celebrated design firm Wm. H. Baumgarten & Co., while the grounds were masterfully designed by legendary landscape architects Ellen Biddle Shipman and Ferruccio Vitale. Their collective vision created a rare synthesis of architecture and landscape that remains remarkably intact and continues to shape the character of the estate today. The property boasts multiple auxiliary structures that provide exceptional flexibility for guests, staff, and extended family. A substantial four-bedroom guest residence offers luxurious accommodations complete with expansive entertaining rooms, a gourmet kitchen, and private wellness amenities. Above the home's five-car garage is a newly redesigned apartment, featuring a seamless open-concept living space with a large great room, two bedrooms, and two full bathrooms. Set amidst nearly 18 acres of meticulously maintained grounds, the cream-colored stucco main residence is crowned by a classic red terracotta tile roof, its elegant proportions recalling the great villas of Northern Italy. Broad rear verandas overlook rolling lawns that descend gracefully toward seasonal water views of Mill Neck Creek and Beaver Lake, creating a serene backdrop of natural beauty and privacy. Encompassing more than 10,000 square feet and comprehensively reimagined approximately 20 years ago, this exceptional residence unfolds across multiple levels of impeccably detailed living space. Rich millwork, marble flooring, intricate hardwood floors, hand-forged iron window details, marble fireplace mantels, Juliet balconies and numerous sets of French doors speak to the extraordinary level of craftsmanship throughout. The first floor features a grand formal living room, a distinguished library/study, and an elegant bar salon designed for refined entertaining. A more recent renovation introduced a spectacular chef's kitchen centered around two massive marble-clad islands and outfitted with a suite of premium Wolf and Sub-Zero appliances, two oversized farmhouse sinks, and limestone tile flooring. The space flows seamlessly into a sunlit breakfast area and adjoining den. The main residence offers seven bedrooms, including private staff quarters, with most bedrooms featuring generous closets, wood-burning fireplaces, and en-suite baths. Beneath the residence lies one of the estate's most remarkable features: a two-level walkout lower level originally created for the enjoyment of one of America's great industrial magnates. The first level includes a richly appointed mahogany bar, kitchenette, game room, screening room, spa facilities, barber shop, gym, map room, vault room and support spaces. Descending further reveals an astonishing private casino complete with its own discreet escape tunnel - a rare and captivating reminder of the estate's glamorous past. The grounds are equally compelling. A gated entrance, extensive stone walls, formal gardens, fountains, comprehensive security systems, and whole-house generators ensure effortless modern living.

10 Beds ⋅ 15 Baths ⋅ 1048378 MLS

La Reserve - A Legendary Gold Coast Estate of Rare Provenance Perched atop one of the North Shore's most commanding elevations, at the end of a mile-long private drive overlooking the iconic Cleft Road Causeway, La Reserve serve stands among the most significant surviving estates of Long Island's storied Gold Coast. Originally commissioned in 1922 by Arthur Vining Davis - financier, industrialist, chairman of the Aluminum Company of America, and once ranked among the wealthiest men in the United States - this extraordinary residence embodies a level of craftsmanship, scale, and historical significance that is virtually impossible to replicate today. Designed by renowned architect Guy Lowell in the Italian Renaissance style, the estate was originally conceived as a grand country retreat for one of America's most influential business titans. The interiors were executed by the celebrated design firm Wm. H. Baumgarten & Co., while the grounds were masterfully designed by legendary landscape architects Ellen Biddle Shipman and Ferruccio Vitale. Their collective vision created a rare synthesis of architecture and landscape that remains remarkably intact and continues to shape the character of the estate today. The property boasts multiple auxiliary structures that provide exceptional flexibility for guests, staff, and extended family. A substantial four-bedroom guest residence offers luxurious accommodations complete with expansive entertaining rooms, a gourmet kitchen, and private wellness amenities. Above the home's five-car garage is a newly redesigned apartment, featuring a seamless open-concept living space with a large great room, two bedrooms, and two full bathrooms. Set amidst nearly 18 acres of meticulously maintained grounds, the cream-colored stucco main residence is crowned by a classic red terracotta tile roof, its elegant proportions recalling the great villas of Northern Italy. Broad rear verandas overlook rolling lawns that descend gracefully toward seasonal water views of Mill Neck Creek and Beaver Lake, creating a serene backdrop of natural beauty and privacy. Encompassing more than 10,000 square feet and comprehensively reimagined approximately 20 years ago, this exceptional residence unfolds across multiple levels of impeccably detailed living space. Rich millwork, marble flooring, intricate hardwood floors, hand-forged iron window details, marble fireplace mantels, Juliet balconies and numerous sets of French doors speak to the extraordinary level of craftsmanship throughout. The first floor features a grand formal living room, a distinguished library/study, and an elegant bar salon designed for refined entertaining. A more recent renovation introduced a spectacular chef's kitchen centered around two massive marble-clad islands and outfitted with a suite of premium Wolf and Sub-Zero appliances, two oversized farmhouse sinks, and limestone tile flooring. The space flows seamlessly into a sunlit breakfast area and adjoining den. The main residence offers seven bedrooms, including private staff quarters, with most bedrooms featuring generous closets, wood-burning fireplaces, and en-suite baths. Beneath the residence lies one of the estate's most remarkable features: a two-level walkout lower level originally created for the enjoyment of one of America's great industrial magnates. The first level includes a richly appointed mahogany bar, kitchenette, game room, screening room, spa facilities, barber shop, gym, map room, vault room and support spaces. Descending further reveals an astonishing private casino complete with its own discreet escape tunnel - a rare and captivating reminder of the estate's glamorous past. The grounds are equally compelling. A gated entrance, extensive stone walls, formal gardens, fountains, comprehensive security systems, and whole-house generators ensure effortless modern living.

100 Horseshoe Road, Mill Neck

$4,200,000

Welcome to 10 Laurel Woods Drive, an expansive 8,000+ square-foot residence privately situated on 5.45 park-like acres in Upper Brookville. Set behind wrought iron gates at the end of a quiet, tree-lined cul-de-sac, this impressive expanded ranch offers exceptional scale, privacy, and a true estate-like setting. The home features six bedrooms and eight bathrooms, including a spacious first-floor primary suite. Generously proportioned interiors are designed for both everyday living and large-scale entertaining, with formal living and dining rooms, a sitting room, and an expansive great room, all enhanced by new flooring. A newly renovated, state-of-the-art chef’s kitchen serves as the heart of the home, thoughtfully equipped with both gas and electric cooking stations. Just beyond, a dedicated mudroom provides direct access to the four-car garage, offering exceptional space for car enthusiasts, collectors, or additional storage. The fully finished lower level provides extensive additional living and entertaining space, complete with a dedicated theater room, wet bar, gym, and ample room for recreation, gatherings, and flexible use. Outside, the property unfolds as a private retreat. A newly repaved tennis court, updated gunite swimming pool with new equipment, and dedicated pool house are surrounded by sweeping lawns and mature landscaping. Meandering walking paths extend throughout the grounds, complemented by a fire pit and garden, creating numerous spaces to relax, entertain, and enjoy the remarkable natural setting. Offering substantial interior space, extensive amenities, and more than five acres of beautifully established grounds, 10 Laurel Woods Drive presents a rare opportunity to enjoy estate living in one of the North Shore’s most desirable villages

6 Beds ⋅ 8 Baths ⋅ 1043804 MLS

Welcome to 10 Laurel Woods Drive, an expansive 8,000+ square-foot residence privately situated on 5.45 park-like acres in Upper Brookville. Set behind wrought iron gates at the end of a quiet, tree-lined cul-de-sac, this impressive expanded ranch offers exceptional scale, privacy, and a true estate-like setting. The home features six bedrooms and eight bathrooms, including a spacious first-floor primary suite. Generously proportioned interiors are designed for both everyday living and large-scale entertaining, with formal living and dining rooms, a sitting room, and an expansive great room, all enhanced by new flooring. A newly renovated, state-of-the-art chef’s kitchen serves as the heart of the home, thoughtfully equipped with both gas and electric cooking stations. Just beyond, a dedicated mudroom provides direct access to the four-car garage, offering exceptional space for car enthusiasts, collectors, or additional storage. The fully finished lower level provides extensive additional living and entertaining space, complete with a dedicated theater room, wet bar, gym, and ample room for recreation, gatherings, and flexible use. Outside, the property unfolds as a private retreat. A newly repaved tennis court, updated gunite swimming pool with new equipment, and dedicated pool house are surrounded by sweeping lawns and mature landscaping. Meandering walking paths extend throughout the grounds, complemented by a fire pit and garden, creating numerous spaces to relax, entertain, and enjoy the remarkable natural setting. Offering substantial interior space, extensive amenities, and more than five acres of beautifully established grounds, 10 Laurel Woods Drive presents a rare opportunity to enjoy estate living in one of the North Shore’s most desirable villages

10 Laurel Woods Drive, Upper Brookville

$480,000

Tucked away on the North Shore of Long Island in Bayville, just a short stroll from the Creek beach, is a 2 story, 2 bedroom cottage on a 50 x 100 lot. Use your imagination to renovate or reconstruct in this seaside village which offers boating, swimming, kayaking, tennis/pickle ball courts. Enjoy the many wonderful shops & restaurants.

2 Beds ⋅ 1 Baths ⋅ 1040651 MLS

Tucked away on the North Shore of Long Island in Bayville, just a short stroll from the Creek beach, is a 2 story, 2 bedroom cottage on a 50 x 100 lot. Use your imagination to renovate or reconstruct in this seaside village which offers boating, swimming, kayaking, tennis/pickle ball courts. Enjoy the many wonderful shops & restaurants.

6 Cross Road, Bayville

$3,875,000

A rare modernist residence designed by noted architect George Nemeny, with interiors by pioneering architect Debora Reiser. Featured in House & Garden shortly after construction, this spectacular, lovingly maintained modern work of art is situated on five private estate acres in the heart of Matinecock, less than 1.5 miles from downtown Locust Valley. The home was harmoniously designed around the historic formal gardens of the former J.D. Lyons estate, originally planned by the renowned firm Delano & Aldrich. The owner, a botanist, further enhanced the grounds with arboretum-quality specimen plantings, creating a truly magical, one-of-a-kind landscape. A striking outdoor sculpture is positioned at the edge of a sweeping grassland meadow garden framed by tranquil walking paths. Further enriching the property's provenance is the historic "Piping Rock," a geological landmark tied to local Matinecock Native American lore. Fully intact, the interiors showcase soaring 19-foot ceilings and expansive walls of glass overlooking the grounds. Floor-to-ceiling sliding glass doors in every room flood the space with natural light, treating the seasonal changes outdoors as living art. The main living spaces are conveniently configured on a single level, complemented by a cozy library perched above the dining room and accessed via an elegant spiral staircase. This property represents a unique opportunity to acquire an architecturally significant, undisturbed modernist home and arboretum-like garden, cherished and preserved by its original owners.

4 Beds ⋅ 4 Baths ⋅ 1046678 MLS

A rare modernist residence designed by noted architect George Nemeny, with interiors by pioneering architect Debora Reiser. Featured in House & Garden shortly after construction, this spectacular, lovingly maintained modern work of art is situated on five private estate acres in the heart of Matinecock, less than 1.5 miles from downtown Locust Valley. The home was harmoniously designed around the historic formal gardens of the former J.D. Lyons estate, originally planned by the renowned firm Delano & Aldrich. The owner, a botanist, further enhanced the grounds with arboretum-quality specimen plantings, creating a truly magical, one-of-a-kind landscape. A striking outdoor sculpture is positioned at the edge of a sweeping grassland meadow garden framed by tranquil walking paths. Further enriching the property's provenance is the historic "Piping Rock," a geological landmark tied to local Matinecock Native American lore. Fully intact, the interiors showcase soaring 19-foot ceilings and expansive walls of glass overlooking the grounds. Floor-to-ceiling sliding glass doors in every room flood the space with natural light, treating the seasonal changes outdoors as living art. The main living spaces are conveniently configured on a single level, complemented by a cozy library perched above the dining room and accessed via an elegant spiral staircase. This property represents a unique opportunity to acquire an architecturally significant, undisturbed modernist home and arboretum-like garden, cherished and preserved by its original owners.

347 Duck Pond Road, Matinecock

$2,675,000

Located within a picture perfect community of pristine properties, this striking sprawling Ranch Residence is set on 2 acres of rolling green lawns, professional gardens, and mature evergreens. This Gracious Home welcomes Guests through the handsome Double Door Entry to an Expansive Reception Foyer where classic Wrought Iron Railings line a Circular Staircase. Ideal for Grand Entertaining, the generously proportioned Formal Living Room opens to Formal Dining and Den with Breathtaking Stone Wall Fireplace and Sliding Door to Patio. The Eat In Kitchen is a Chef's Delight with oversized Center Island and separate Breakfast Area. A Mud Room with outside access, Laundry Rm, Full Bath and Spacious Bedroom are set off of the Kitchen with entry to the Garage. On the opposite side of the Grand Foyer is a Guest Powder Room and the Bedroom Wing. The Primary Bedroom is an oversized retreat with 2 separate walk-in Closets, Full Private Bath, floor to ceiling Windows and Sliding Door to Patio and Pool. 3 Large Bedrooms and Full Bath complete the first floor. The Lower Level is entered from a dramatic curved stairway to a second Foyer lined with a striking Stone Wall. The enormous open floor plan features Media Room with Brick Wall Fireplace, Gym Area and Full Bath. The opposite side of the Lower Level is an unfinished storage area with second staircase to first floor Mud Room. A beautiful large deck spans the rear of the homes parklike property, leading to the sparkling In-Ground Pool, Tennis and Pond. Driveway Enters from Dorchester, passing the 2.5 Car Garage and exits on Chelmsford giving ample parking for larger gatherings. Locust Valley SD. By Appointment

5 Beds ⋅ 5 Baths ⋅ 1045194 MLS

Located within a picture perfect community of pristine properties, this striking sprawling Ranch Residence is set on 2 acres of rolling green lawns, professional gardens, and mature evergreens. This Gracious Home welcomes Guests through the handsome Double Door Entry to an Expansive Reception Foyer where classic Wrought Iron Railings line a Circular Staircase. Ideal for Grand Entertaining, the generously proportioned Formal Living Room opens to Formal Dining and Den with Breathtaking Stone Wall Fireplace and Sliding Door to Patio. The Eat In Kitchen is a Chef's Delight with oversized Center Island and separate Breakfast Area. A Mud Room with outside access, Laundry Rm, Full Bath and Spacious Bedroom are set off of the Kitchen with entry to the Garage. On the opposite side of the Grand Foyer is a Guest Powder Room and the Bedroom Wing. The Primary Bedroom is an oversized retreat with 2 separate walk-in Closets, Full Private Bath, floor to ceiling Windows and Sliding Door to Patio and Pool. 3 Large Bedrooms and Full Bath complete the first floor. The Lower Level is entered from a dramatic curved stairway to a second Foyer lined with a striking Stone Wall. The enormous open floor plan features Media Room with Brick Wall Fireplace, Gym Area and Full Bath. The opposite side of the Lower Level is an unfinished storage area with second staircase to first floor Mud Room. A beautiful large deck spans the rear of the homes parklike property, leading to the sparkling In-Ground Pool, Tennis and Pond. Driveway Enters from Dorchester, passing the 2.5 Car Garage and exits on Chelmsford giving ample parking for larger gatherings. Locust Valley SD. By Appointment

10 Dorchester Drive, Muttontown

$5,299,000

Set on two private acres in the heart of Brookville and located within the Locust Valley School District, 63 Fruitledge Road offers refined luxury living on Long Island’s prestigious Gold Coast. This newly completed 6,880 Sq ft residence features a striking modern Colonial exterior with expansive windows and 10-foot ceilings throughout, creating an airy, light-filled atmosphere and large-scale rooms ideal for both everyday living and entertaining. A grand foyer introduces the home’s elegant flow. The formal living room includes a fully equipped custom marble wet bar, while the open-concept den is framed by floor-to-ceiling windows overlooking the backyard and anchored by a marble fireplace.The custom kitchen opens seamlessly to the formal dining room and is complimented by thoughtful storage cabinetry, a large center island, Gaggenau gas appliances, double Bosch dishwashers, and a Sub-Zero refrigerator/freezer. Upstairs, all five bedrooms are en suite, offering privacy and comfort for guests alike. The extra-large primary suite serves as a private retreat, featuring dual outfitted custom walk-in closets and a luxurious marble bath with a steam shower, soaking tub, and two vanities. A spacious laundry room is conveniently located on this level. A well-designed service area beyond the kitchen includes a mudroom, a walk-in pantry, a full bath, and convenient access to the three-car garage, back staircase, and steps leading to the basement. The main level also features a generously sized bedroom, ideal for guests or extended stays. Radiant heated floors are featured in all bathrooms and the mudroom. The outdoor space is equally impressive, featuring a heated 40' x 20' Gunite saltwater pool, paver patio, and outdoor kitchen—perfect for entertaining or enjoying the serene, private grounds.

6 Beds ⋅ 7 Baths ⋅ 1044684 MLS

Set on two private acres in the heart of Brookville and located within the Locust Valley School District, 63 Fruitledge Road offers refined luxury living on Long Island’s prestigious Gold Coast. This newly completed 6,880 Sq ft residence features a striking modern Colonial exterior with expansive windows and 10-foot ceilings throughout, creating an airy, light-filled atmosphere and large-scale rooms ideal for both everyday living and entertaining. A grand foyer introduces the home’s elegant flow. The formal living room includes a fully equipped custom marble wet bar, while the open-concept den is framed by floor-to-ceiling windows overlooking the backyard and anchored by a marble fireplace.The custom kitchen opens seamlessly to the formal dining room and is complimented by thoughtful storage cabinetry, a large center island, Gaggenau gas appliances, double Bosch dishwashers, and a Sub-Zero refrigerator/freezer. Upstairs, all five bedrooms are en suite, offering privacy and comfort for guests alike. The extra-large primary suite serves as a private retreat, featuring dual outfitted custom walk-in closets and a luxurious marble bath with a steam shower, soaking tub, and two vanities. A spacious laundry room is conveniently located on this level. A well-designed service area beyond the kitchen includes a mudroom, a walk-in pantry, a full bath, and convenient access to the three-car garage, back staircase, and steps leading to the basement. The main level also features a generously sized bedroom, ideal for guests or extended stays. Radiant heated floors are featured in all bathrooms and the mudroom. The outdoor space is equally impressive, featuring a heated 40' x 20' Gunite saltwater pool, paver patio, and outdoor kitchen—perfect for entertaining or enjoying the serene, private grounds.

63 Fruitledge Road, Brookville

$1,325,000

New Construction built in 2026 !!! welcome to an exceptional water view residence overlooking the serene waters of Mill Neck Creek. This beautifully appointed colonial blends timeless architectural details with sophisticated modern finishes, creating an elegant yet inviting home. A dramatic entrance foyer with a soaring 20-foot ceiling sets the tone upon arrival. Throughout the residence, 9-foot ceilings and rich wide oak hardwood floors add warmth and scale. The gracious living room features crown and base moldings throughout, custom electric window shades, recessed lighting throughout. The elegant dining room is enhanced by a striking custom chandelier. The chef’s kitchen is designed for both entertaining and everyday living, featuring quartz countertops, custom cabinetry and fixtures, and a farmhouse sink a marble backsplash, stainless steel appliances, Electric shades throughout the first floor. A generous center island is illuminated by two stylish pendant lights. Sliding glass doors open directly to the patio, creating an effortless transition to outdoor dining and entertaining. Adjacent to the kitchen, the inviting den provides a relaxing retreat with a fireplace and an abundance of natural sunlight. 4 Bedrooms 2 full baths and a powder room, The Primary suite with vaulted ceilings, electric shades, custom Huntington closet, primary spa bath with large shower and soaking tub, laundry on the second floor. Sprinkler system, full basement with high ceilings and outdoor entrance. Thoughtfully designed with comfort, style, and entertaining in mind, this exceptional residence offers a sophisticated Gold Coast coastal haven lifestyle. Not located in a flood zone. Locust Valley School District. Ideally situated in close proximity to beaches, shopping, dining, and transportation. Turnkey.

4 Beds ⋅ 3 Baths ⋅ 1037944 MLS

New Construction built in 2026 !!! welcome to an exceptional water view residence overlooking the serene waters of Mill Neck Creek. This beautifully appointed colonial blends timeless architectural details with sophisticated modern finishes, creating an elegant yet inviting home. A dramatic entrance foyer with a soaring 20-foot ceiling sets the tone upon arrival. Throughout the residence, 9-foot ceilings and rich wide oak hardwood floors add warmth and scale. The gracious living room features crown and base moldings throughout, custom electric window shades, recessed lighting throughout. The elegant dining room is enhanced by a striking custom chandelier. The chef’s kitchen is designed for both entertaining and everyday living, featuring quartz countertops, custom cabinetry and fixtures, and a farmhouse sink a marble backsplash, stainless steel appliances, Electric shades throughout the first floor. A generous center island is illuminated by two stylish pendant lights. Sliding glass doors open directly to the patio, creating an effortless transition to outdoor dining and entertaining. Adjacent to the kitchen, the inviting den provides a relaxing retreat with a fireplace and an abundance of natural sunlight. 4 Bedrooms 2 full baths and a powder room, The Primary suite with vaulted ceilings, electric shades, custom Huntington closet, primary spa bath with large shower and soaking tub, laundry on the second floor. Sprinkler system, full basement with high ceilings and outdoor entrance. Thoughtfully designed with comfort, style, and entertaining in mind, this exceptional residence offers a sophisticated Gold Coast coastal haven lifestyle. Not located in a flood zone. Locust Valley School District. Ideally situated in close proximity to beaches, shopping, dining, and transportation. Turnkey.

9 Hickory Road, Bayville

$3,999,000

Perfect Multi-Generational Compound with 2 Master Suites, one on the 1st and one on the 2nd floor. Additional Guest Suites with Separate Entrance that is Perfect for Home Office or Music/Art Studio. This fully gated extraordinary Upper Brookville estate seamlessly blends mid-century modern design with contemporary sophistication, set on two lush, gated acres. Soaring 30-foot ceilings, dramatic windows, rich wood architectural elements, clean lines, and sculptural details create a striking sense of tranquility. Palatial in scale yet thoughtfully designed for comfortable living and entertaining, this residence offers remarkable versatility with resort-style amenities. A true architectural masterpiece where Zen-inspired design meets glamour and beauty, creating a luxurious lifestyle. The expansive great room features floor-to-ceiling windows, warm wood accents, and a dramatic stone fireplace soaring through the space, evoking a sense of Western grandeur. Bold color and modern materials add a sophisticated edge, balancing timeless mid-century character with contemporary elegance. The over 1,000-square-foot first-floor primary suite is exquisitely designed and decorated as a private retreat. The expansive floor plan offers six bedrooms, seven full baths, and two half baths, along with multiple separate guest suites with private entrances. One additional space can easily be converted to a private music studio or creative space, providing exceptional flexibility for a variety of living arrangements. Over $500,000 in recent renovations and improvements include the renovated kitchen and bathrooms, upgraded flooring, and enhancements to the outdoor pool and pool deck. Additional amenities include a private tennis court (TLC), multiple heating and air-conditioning zones, luxury window coverings, a full pool cabana with bath, and a three-car garage.

6 Beds ⋅ 9 Baths ⋅ 1045340 MLS

Perfect Multi-Generational Compound with 2 Master Suites, one on the 1st and one on the 2nd floor. Additional Guest Suites with Separate Entrance that is Perfect for Home Office or Music/Art Studio. This fully gated extraordinary Upper Brookville estate seamlessly blends mid-century modern design with contemporary sophistication, set on two lush, gated acres. Soaring 30-foot ceilings, dramatic windows, rich wood architectural elements, clean lines, and sculptural details create a striking sense of tranquility. Palatial in scale yet thoughtfully designed for comfortable living and entertaining, this residence offers remarkable versatility with resort-style amenities. A true architectural masterpiece where Zen-inspired design meets glamour and beauty, creating a luxurious lifestyle. The expansive great room features floor-to-ceiling windows, warm wood accents, and a dramatic stone fireplace soaring through the space, evoking a sense of Western grandeur. Bold color and modern materials add a sophisticated edge, balancing timeless mid-century character with contemporary elegance. The over 1,000-square-foot first-floor primary suite is exquisitely designed and decorated as a private retreat. The expansive floor plan offers six bedrooms, seven full baths, and two half baths, along with multiple separate guest suites with private entrances. One additional space can easily be converted to a private music studio or creative space, providing exceptional flexibility for a variety of living arrangements. Over $500,000 in recent renovations and improvements include the renovated kitchen and bathrooms, upgraded flooring, and enhancements to the outdoor pool and pool deck. Additional amenities include a private tennis court (TLC), multiple heating and air-conditioning zones, luxury window coverings, a full pool cabana with bath, and a three-car garage.

5 Carol Lane, Upper Brookville

$3,599,000

Located within the exclusive Lands End community in the Village of Lattingtown, this exceptional all-brick Colonial estate offers an extraordinary combination of timeless architecture, refined interiors, resort-style amenities and 4 beautifully landscaped acres. Locust Valley is widely regarded as the crown jewel of the historic Gold Coast - this magnificent property offers close proximity to Manhattan while enjoying the very best of North Shore living, including nearby beaches, renowned arboretums, Planting Fields State Park, boutique shopping, acclaimed dining, premier golf, tennis and boating clubs and a close sense of community. Custom built with an emphasis on quality craftsmanship and generous scale, the approximately 8,242-square-foot residence plus full basement provides an elegant yet comfortable setting for sophisticated living and grand-scale entertaining. A long paver driveway leads to a gracious courtyard and impressive portico entrance, creating a memorable arrival. Inside, a dramatic two-story foyer with a sweeping double bridal staircase introduces beautifully proportioned living spaces filled with natural light. The magnificent double-height great room serves as the centerpiece of the home, complemented by a richly appointed den with fireplace, formal dining room, and elegant library/study. The updated chef’s kitchen is designed for both everyday living and entertaining, featuring updated appliances, an expansive island, and a breakfast area overlooking the spectacular grounds and outdoor entertaining spaces. The home offers exceptional flexibility with luxurious primary suite options on both the first and second floors, as well as a private guest wing. In total, the residence offers 7 bedrooms and 6.5 baths. The outdoor experience is truly exceptional. Expansive terraces, park-like grounds and a sparkling swimming pool and spa, highlighted by a beautiful waterfall feature. A fully equipped pool house creates a private resort-like retreat, while the additional bonus sports court provides space for recreational activities. Locust Valley School District and nearby private schools including Friends Academy and Portledge, this extraordinary property defines North Shore luxury living. Photos are virtually staged in this listing.

7 Beds ⋅ 7 Baths ⋅ 1044858 MLS

Located within the exclusive Lands End community in the Village of Lattingtown, this exceptional all-brick Colonial estate offers an extraordinary combination of timeless architecture, refined interiors, resort-style amenities and 4 beautifully landscaped acres. Locust Valley is widely regarded as the crown jewel of the historic Gold Coast - this magnificent property offers close proximity to Manhattan while enjoying the very best of North Shore living, including nearby beaches, renowned arboretums, Planting Fields State Park, boutique shopping, acclaimed dining, premier golf, tennis and boating clubs and a close sense of community. Custom built with an emphasis on quality craftsmanship and generous scale, the approximately 8,242-square-foot residence plus full basement provides an elegant yet comfortable setting for sophisticated living and grand-scale entertaining. A long paver driveway leads to a gracious courtyard and impressive portico entrance, creating a memorable arrival. Inside, a dramatic two-story foyer with a sweeping double bridal staircase introduces beautifully proportioned living spaces filled with natural light. The magnificent double-height great room serves as the centerpiece of the home, complemented by a richly appointed den with fireplace, formal dining room, and elegant library/study. The updated chef’s kitchen is designed for both everyday living and entertaining, featuring updated appliances, an expansive island, and a breakfast area overlooking the spectacular grounds and outdoor entertaining spaces. The home offers exceptional flexibility with luxurious primary suite options on both the first and second floors, as well as a private guest wing. In total, the residence offers 7 bedrooms and 6.5 baths. The outdoor experience is truly exceptional. Expansive terraces, park-like grounds and a sparkling swimming pool and spa, highlighted by a beautiful waterfall feature. A fully equipped pool house creates a private resort-like retreat, while the additional bonus sports court provides space for recreational activities. Locust Valley School District and nearby private schools including Friends Academy and Portledge, this extraordinary property defines North Shore luxury living. Photos are virtually staged in this listing.

11 Danton Lane N, Locust Valley

$1,850,000

Welcome to 8 Hilltop, Bayville a masterfully reimagined coastal retreat where timeless elegance, modern luxury, and effortless resort style living converge. Nestled within an exclusive 44 home association, this exceptional residence offers the rare privilege of private mooring rights while requiring no flood insurance, delivering both an unparalleled waterfront lifestyle and lasting peace of mind. At the end of the quiet cul-de-sac, private steps lead directly to the beach, allowing you to enjoy the very best of Bayville's coveted coastal setting. Completely transformed in 2020 with uncompromising attention to detail, this exquisite home features 4 bedrooms, 3 bathrooms, and a seamless blend of sophisticated craftsmanship and contemporary comfort. At its center, a dramatic double-sided glass fireplace creates an architectural statement, elegantly connecting the home's beautifully appointed living spaces. a Spectacular chef's kitchen, thoughtfully designed for both everyday living and grand scale entertaining. Anchored by an oversized island with seating, the space is complemented by premium finishes, a dedicated coffee bar, and a built-in wine refrigerator. The luxurious primary suite serves as a private sanctuary, complete with a secluded balcony, expansive walk in closets, and a spa inspired en suite bath. Every inch of the home has been thoughtfully curated, from radiant heated floors extending throughout the residence to individually zoned thermostats in every room, ensuring personalized comfort in every season. Designed for effortless entertaining, the outdoor setting rivals a private resort. A saltwater inground pool, enhanced with a new liner and is surrounded by lush, maintenance free turf, creating an idyllic setting for sun soaked afternoons and elegant evening gatherings. A full sprinkler system further enhances the beautifully maintained grounds. Adding exceptional flexibility is a legal bonus home office above the garage an ideal executive workspace, private studio, or guest retreat. The home's remarkable lower level is truly a standout feature, offering high basement ceilings, a full basement, and an additional sub basement with a private outside entrance leading directly to the backyard and pool. Whether envisioned as a fitness studio, recreation lounge, or additional living space, the possibilities are endless. A tandem two car garage provides deep parking for two vehicles, complemented by an expansive driveway with ample additional parking for family and guests. Complete with a thoughtfully designed mudroom, dedicated laundry room, abundant storage, and exceptional indoor-outdoor living spaces, this extraordinary residence is located within the prestigious Locust Valley School District and embodies the refined sophistication of the Hamptons with the charm, privacy, and convenience of Bayville. Experience the essence of luxury coastal living where every detail has been elevated, every finish carefully considered, and every day feels like a vacation.

4 Beds ⋅ 3 Baths ⋅ 1026599 MLS

Welcome to 8 Hilltop, Bayville a masterfully reimagined coastal retreat where timeless elegance, modern luxury, and effortless resort style living converge. Nestled within an exclusive 44 home association, this exceptional residence offers the rare privilege of private mooring rights while requiring no flood insurance, delivering both an unparalleled waterfront lifestyle and lasting peace of mind. At the end of the quiet cul-de-sac, private steps lead directly to the beach, allowing you to enjoy the very best of Bayville's coveted coastal setting. Completely transformed in 2020 with uncompromising attention to detail, this exquisite home features 4 bedrooms, 3 bathrooms, and a seamless blend of sophisticated craftsmanship and contemporary comfort. At its center, a dramatic double-sided glass fireplace creates an architectural statement, elegantly connecting the home's beautifully appointed living spaces. a Spectacular chef's kitchen, thoughtfully designed for both everyday living and grand scale entertaining. Anchored by an oversized island with seating, the space is complemented by premium finishes, a dedicated coffee bar, and a built-in wine refrigerator. The luxurious primary suite serves as a private sanctuary, complete with a secluded balcony, expansive walk in closets, and a spa inspired en suite bath. Every inch of the home has been thoughtfully curated, from radiant heated floors extending throughout the residence to individually zoned thermostats in every room, ensuring personalized comfort in every season. Designed for effortless entertaining, the outdoor setting rivals a private resort. A saltwater inground pool, enhanced with a new liner and is surrounded by lush, maintenance free turf, creating an idyllic setting for sun soaked afternoons and elegant evening gatherings. A full sprinkler system further enhances the beautifully maintained grounds. Adding exceptional flexibility is a legal bonus home office above the garage an ideal executive workspace, private studio, or guest retreat. The home's remarkable lower level is truly a standout feature, offering high basement ceilings, a full basement, and an additional sub basement with a private outside entrance leading directly to the backyard and pool. Whether envisioned as a fitness studio, recreation lounge, or additional living space, the possibilities are endless. A tandem two car garage provides deep parking for two vehicles, complemented by an expansive driveway with ample additional parking for family and guests. Complete with a thoughtfully designed mudroom, dedicated laundry room, abundant storage, and exceptional indoor-outdoor living spaces, this extraordinary residence is located within the prestigious Locust Valley School District and embodies the refined sophistication of the Hamptons with the charm, privacy, and convenience of Bayville. Experience the essence of luxury coastal living where every detail has been elevated, every finish carefully considered, and every day feels like a vacation.

8 Hilltop Drive, Bayville

$2,398,000

Set on two flat, quiet and bucolic acres surrounded by beautiful park-like plantings, mature specimen trees and colorful perennials, this renovated four-bedroom Center Hall Colonial offers serene country setting with exceptional convenience for commuting. A dramatic and elegant entry hall welcomes you with marble flooring and a striking staircase with decorative wrought-iron banister. Just off the foyer is a beautifully appointed full bath featuring custom, high-end porcelain and marble finishes. At the heart of the home is the sleek and stunning eat-in kitchen, thoughtfully designed with two sinks, two dishwashers and a quartzite waterfall center island with seating. GE Café appliances, a French oven and porcelain farmhouse sink complete the sophisticated space. Recessed ceiling lighting and motion-activated floor lighting provide both ambiance and effortless nighttime navigation. Radiant heat adds an additional level of comfort. The spacious formal living room features a wood-burning fireplace with marble surround and an abundance of natural light fro a wall of windows and French doors opening to the bluestone rear patio-ideal for seamless indoor-outdoor entertaining. The sunny formal living room showcases beautiful new wood floors and flows into a private office/den with French doors opening to a covered concrete patio. Upstairs are four bright bedrooms, including a spacious primary en-suite. All bathrooms have been custom designed with luxurious European finishes, including Grohe fixtures, heated towel bars and radiant heat. Outside, the spectacular, level property creates a truly dreamy setting. Expansive lawns, established perrenials and magnificent mature specimen trees surround a fenced, heated Gunite in-ground pool, offering exceptional privacy and a resort-like atmosphere. Numerous recent improvements include new Pella windows throughout, an updated cesspool, roof and plumbing, a new boiler and a full-house generator. Smart-home features allow heating, cooling, washer and dryer functions to be conveniently controlled from your phone. A beautifully renovated home combining timeless elegance, modern amenities and magnificent grounds in an exceptionally peaceful setting. Radiant heat where there's marble tile floors; bathrooms and kitchen and entry hall.

4 Beds ⋅ 3 Baths ⋅ 1039187 MLS

Set on two flat, quiet and bucolic acres surrounded by beautiful park-like plantings, mature specimen trees and colorful perennials, this renovated four-bedroom Center Hall Colonial offers serene country setting with exceptional convenience for commuting. A dramatic and elegant entry hall welcomes you with marble flooring and a striking staircase with decorative wrought-iron banister. Just off the foyer is a beautifully appointed full bath featuring custom, high-end porcelain and marble finishes. At the heart of the home is the sleek and stunning eat-in kitchen, thoughtfully designed with two sinks, two dishwashers and a quartzite waterfall center island with seating. GE Café appliances, a French oven and porcelain farmhouse sink complete the sophisticated space. Recessed ceiling lighting and motion-activated floor lighting provide both ambiance and effortless nighttime navigation. Radiant heat adds an additional level of comfort. The spacious formal living room features a wood-burning fireplace with marble surround and an abundance of natural light fro a wall of windows and French doors opening to the bluestone rear patio-ideal for seamless indoor-outdoor entertaining. The sunny formal living room showcases beautiful new wood floors and flows into a private office/den with French doors opening to a covered concrete patio. Upstairs are four bright bedrooms, including a spacious primary en-suite. All bathrooms have been custom designed with luxurious European finishes, including Grohe fixtures, heated towel bars and radiant heat. Outside, the spectacular, level property creates a truly dreamy setting. Expansive lawns, established perrenials and magnificent mature specimen trees surround a fenced, heated Gunite in-ground pool, offering exceptional privacy and a resort-like atmosphere. Numerous recent improvements include new Pella windows throughout, an updated cesspool, roof and plumbing, a new boiler and a full-house generator. Smart-home features allow heating, cooling, washer and dryer functions to be conveniently controlled from your phone. A beautifully renovated home combining timeless elegance, modern amenities and magnificent grounds in an exceptionally peaceful setting. Radiant heat where there's marble tile floors; bathrooms and kitchen and entry hall.

897 Ripley Lane, Muttontown

$5,950,000

Set amid mature, beautifully landscaped grounds in the coveted Village of Matinecock, this distinguished brick North Shore residence, built in 2006, offers an exceptional combination of scale, craftsmanship, privacy, and resort-inspired living. Rich hardwood floors, substantial millwork, designer wallcoverings, and thoughtfully updated interiors create a home that is at once impressive and inviting. A dramatic, columned double-height foyer with graceful bridal staircases sets an elegant tone upon arrival. The formal dining room is distinguished by a coffered ceiling, while a handsome wood-burning fireplace anchors the spacious den. French doors extend the living spaces to an expansive slate-and-brick terrace overlooking the lush grounds. Designed for both everyday living and effortless entertaining, the eat-in chef’s kitchen features custom cabinetry extending to the ceiling, marble countertops, an oversized center island, generous pantry storage, wine refrigeration, and professional-grade Thermador stainless steel appliances. The first floor primary suite is a private retreat, entered through double doors and appointed with a fireplace, sitting den, two closets, substantial moldings, and an en-suite bath. A formal living room, sunroom with terracotta floors, beautifully appointed laundry room with abundant storage, an elegant powder room, and a bedroom with an attached full bath complete the first floor. Outdoors, the residence unfolds as a private North Shore oasis. The fully fenced 2.06-acre property is framed by mature landscaping and enhanced by multiple fountains and water features. An inviting saltwater swimming pool with an electric cover is framed by handsome slate terraces, while a built-in spa with a cascading waterfall flowing into the pool enhances the resort-like setting. A beautifully designed teak outdoor shower and playset complete an environment equally suited to sophisticated entertaining and leisurely summer days. For the automobile enthusiast or collector, an extraordinary combination of attached and detached garaging accommodates up to eight vehicles - a rare and remarkably versatile offering. Additional amenities include radiant heat beneath tiled areas, central vacuum, whole-house water filtration, natural gas, a generator, integrated audio, Lutron lighting system, seamless speaker systems, and an electric privacy gate at the entrance to the property. The expansive unfinished lower level, with tall ceilings and concrete floors, includes a matted fitness area, provides direct access to the attached garage, and offers substantial storage along with exciting potential for future recreation, wine, or entertainment spaces. Private yet welcoming, refined yet eminently livable, this exceptional Matinecock residence captures the enduring appeal of North Shore estate living, with gracious interiors, expansive grounds, resort-like amenities, and an extraordinary setting designed to be enjoyed in every season. Located within the esteemed Locust Valley Central School District.

6 Beds ⋅ 5 Baths ⋅ 1036864 MLS

Set amid mature, beautifully landscaped grounds in the coveted Village of Matinecock, this distinguished brick North Shore residence, built in 2006, offers an exceptional combination of scale, craftsmanship, privacy, and resort-inspired living. Rich hardwood floors, substantial millwork, designer wallcoverings, and thoughtfully updated interiors create a home that is at once impressive and inviting. A dramatic, columned double-height foyer with graceful bridal staircases sets an elegant tone upon arrival. The formal dining room is distinguished by a coffered ceiling, while a handsome wood-burning fireplace anchors the spacious den. French doors extend the living spaces to an expansive slate-and-brick terrace overlooking the lush grounds. Designed for both everyday living and effortless entertaining, the eat-in chef’s kitchen features custom cabinetry extending to the ceiling, marble countertops, an oversized center island, generous pantry storage, wine refrigeration, and professional-grade Thermador stainless steel appliances. The first floor primary suite is a private retreat, entered through double doors and appointed with a fireplace, sitting den, two closets, substantial moldings, and an en-suite bath. A formal living room, sunroom with terracotta floors, beautifully appointed laundry room with abundant storage, an elegant powder room, and a bedroom with an attached full bath complete the first floor. Outdoors, the residence unfolds as a private North Shore oasis. The fully fenced 2.06-acre property is framed by mature landscaping and enhanced by multiple fountains and water features. An inviting saltwater swimming pool with an electric cover is framed by handsome slate terraces, while a built-in spa with a cascading waterfall flowing into the pool enhances the resort-like setting. A beautifully designed teak outdoor shower and playset complete an environment equally suited to sophisticated entertaining and leisurely summer days. For the automobile enthusiast or collector, an extraordinary combination of attached and detached garaging accommodates up to eight vehicles - a rare and remarkably versatile offering. Additional amenities include radiant heat beneath tiled areas, central vacuum, whole-house water filtration, natural gas, a generator, integrated audio, Lutron lighting system, seamless speaker systems, and an electric privacy gate at the entrance to the property. The expansive unfinished lower level, with tall ceilings and concrete floors, includes a matted fitness area, provides direct access to the attached garage, and offers substantial storage along with exciting potential for future recreation, wine, or entertainment spaces. Private yet welcoming, refined yet eminently livable, this exceptional Matinecock residence captures the enduring appeal of North Shore estate living, with gracious interiors, expansive grounds, resort-like amenities, and an extraordinary setting designed to be enjoyed in every season. Located within the esteemed Locust Valley Central School District.

898 Chicken Valley Road, Matinecock

$3,480,000

Step away from the everyday and into this gracious, light-filled ranch, where every room feels like an invitation to relax. Sun-drenched and spacious, the interconnected living areas create an effortless flow — warm, welcoming, and made for both quiet mornings and lively gatherings. Built for entertaining, the home features a gourmet kitchen ready for your next dinner party, a formal dining room anchored by a cozy fireplace, a comfortable den, and an oversized living room with sweeping views of the beautifully landscaped grounds. The private wing offers four bedrooms — two with en-suite baths — plus a shared full bathroom and a relaxed, informal den for everyday living. On the opposite side of the home, two additional bedrooms and a full bath offer flexibility and privacy for guests, family, or a home office setup. Outside, the property is nothing short of breathtaking. A long, winding driveway sets the tone, leading past a charming gazebo, rolling lawns, and a private Gunite pool complete with a tranquil koi pond and cascading waterfall. The pool house rounds it all out with showers, a full bathroom, and a recreation room — perfect for summer days that never have to end. This is more than a home — it's a lifestyle.

6 Beds ⋅ 5 Baths ⋅ 1033074 MLS

Step away from the everyday and into this gracious, light-filled ranch, where every room feels like an invitation to relax. Sun-drenched and spacious, the interconnected living areas create an effortless flow — warm, welcoming, and made for both quiet mornings and lively gatherings. Built for entertaining, the home features a gourmet kitchen ready for your next dinner party, a formal dining room anchored by a cozy fireplace, a comfortable den, and an oversized living room with sweeping views of the beautifully landscaped grounds. The private wing offers four bedrooms — two with en-suite baths — plus a shared full bathroom and a relaxed, informal den for everyday living. On the opposite side of the home, two additional bedrooms and a full bath offer flexibility and privacy for guests, family, or a home office setup. Outside, the property is nothing short of breathtaking. A long, winding driveway sets the tone, leading past a charming gazebo, rolling lawns, and a private Gunite pool complete with a tranquil koi pond and cascading waterfall. The pool house rounds it all out with showers, a full bathroom, and a recreation room — perfect for summer days that never have to end. This is more than a home — it's a lifestyle.

24 Winding Lane, Upper Brookville

$2,895,000

Beautifully renovated, this elegant classic Colonial is nestled in the heart of Locust Valley, offering timeless charm and exceptional modern amenities. Set on five breathtaking acres with sweeping lawns and a picturesque spring-fed pond, this one-of-a-kind estate is a true North Shore retreat. The home features a stunning state-of-the-art eat-in kitchen, beautifully updated bathrooms, and thoughtfully designed living spaces that blend classic elegance with contemporary comfort. Designed for both everyday living and entertaining, the property includes an exceptional pool house complete with an old-fashioned parlor, full kitchen, sauna, gym, and game room. Additional highlights include a spacious one-bedroom guest cottage, a charming playhouse, in-ground pool (not being represented, needs to be completed), creating the ultimate compound. Offering unparalleled privacy, beauty, and resort-style amenities, this extraordinary estate is located in one of the North Shore's most sought-after communities—a rare opportunity to own a truly exceptional property in Locust Valley.

7 Beds ⋅ 9 Baths ⋅ 1033116 MLS

Beautifully renovated, this elegant classic Colonial is nestled in the heart of Locust Valley, offering timeless charm and exceptional modern amenities. Set on five breathtaking acres with sweeping lawns and a picturesque spring-fed pond, this one-of-a-kind estate is a true North Shore retreat. The home features a stunning state-of-the-art eat-in kitchen, beautifully updated bathrooms, and thoughtfully designed living spaces that blend classic elegance with contemporary comfort. Designed for both everyday living and entertaining, the property includes an exceptional pool house complete with an old-fashioned parlor, full kitchen, sauna, gym, and game room. Additional highlights include a spacious one-bedroom guest cottage, a charming playhouse, in-ground pool (not being represented, needs to be completed), creating the ultimate compound. Offering unparalleled privacy, beauty, and resort-style amenities, this extraordinary estate is located in one of the North Shore's most sought-after communities—a rare opportunity to own a truly exceptional property in Locust Valley.

450 Oyster Bay Road, Matinecock

$980,000

NOT YOUR TYPICAL BAYVILLE HOME. Tucked away on an intimate dead-end street shared by just four homes, 3 Finnin Place is a distinctive carriage house offering character, privacy, incredible versatility, and the relaxed coastal lifestyle that makes Bayville so special. Inside the home immediately feels different. Dramatic vaulted ceilings, exposed beams, and a wood-burning fireplace create a warm, open atmosphere, while the flowing living, dining, and (updated) kitchen spaces make entertaining effortless. The updated primary suite features a private en-suite bath, with two additional bedrooms and flexible spaces that allow the home to adapt to the way you live. And then there’s the garage. Far more than ordinary garage space, the oversized, fully heated garage features approximately 12-foot ceilings, oversized doors, 220V electrical capability, generous clearance, and potential for a vehicle lift, subject to proper installation and applicable requirements. It’s an incredible find for the car collector or enthusiast—but equally appealing for anyone craving serious space for a workshop, studio, equipment, hobbies, storage, or simply a garage unlike almost anything else on the market. Outside your door, enjoy everything that makes Bayville one of Long Island’s special North Shore communities—beaches, boating, waterfront recreation, parks, restaurants, shops, and the unmistakable charm of coastal living. 3 Finnin Place isn’t a cookie-cutter house—and that’s precisely the point. It’s a home for the buyer looking for something with character, something with possibilities, and something they won’t find everywhere else. Come experience it in person. This one deserves a closer look.

3 Beds ⋅ 3 Baths ⋅ 1022597 MLS

NOT YOUR TYPICAL BAYVILLE HOME. Tucked away on an intimate dead-end street shared by just four homes, 3 Finnin Place is a distinctive carriage house offering character, privacy, incredible versatility, and the relaxed coastal lifestyle that makes Bayville so special. Inside the home immediately feels different. Dramatic vaulted ceilings, exposed beams, and a wood-burning fireplace create a warm, open atmosphere, while the flowing living, dining, and (updated) kitchen spaces make entertaining effortless. The updated primary suite features a private en-suite bath, with two additional bedrooms and flexible spaces that allow the home to adapt to the way you live. And then there’s the garage. Far more than ordinary garage space, the oversized, fully heated garage features approximately 12-foot ceilings, oversized doors, 220V electrical capability, generous clearance, and potential for a vehicle lift, subject to proper installation and applicable requirements. It’s an incredible find for the car collector or enthusiast—but equally appealing for anyone craving serious space for a workshop, studio, equipment, hobbies, storage, or simply a garage unlike almost anything else on the market. Outside your door, enjoy everything that makes Bayville one of Long Island’s special North Shore communities—beaches, boating, waterfront recreation, parks, restaurants, shops, and the unmistakable charm of coastal living. 3 Finnin Place isn’t a cookie-cutter house—and that’s precisely the point. It’s a home for the buyer looking for something with character, something with possibilities, and something they won’t find everywhere else. Come experience it in person. This one deserves a closer look.

3 Finnin Place, Bayville

$8,995,000

A long driveway opens to a large courtyard with a classic fountain, revealing a magnificent Château-style Mansion on 2.03 acres of verdant property on a private cul-de-sac. Custom built for grand entertaining and everyday living, this incredible residence masterfully blends old-world European charm with modern luxury. A majestic 2-story entry foyer features a stunning domed-vaulted ceiling with a curved staircase, showcasing antiqued mirrored panels and an ornate wrought iron railing. Through a series of exquisite arches, the foyer leads to an expansive formal living room with a detailed ceiling and wall-to-wall windows as well as a palatial-sized dining room with a butler’s pantry that offers a wet bar and additional storage. The comfortable family room has a unique curved wall and a marble fireplace flanked by marble goddesses. Adjacent is a sitting room with a floor-to-ceiling built-in display wall and a cozy hexagonal built-in bay window seating area. Next door, an elegant study offers a productive place to work from home. A spectacular chef-inspired kitchen boasts a large breakfast area, dual islands, marble counters, a beautiful ILVE range with a show-stopping backsplash, Wolf, Miele and Sub-Zero appliances, plus an additional service kitchen to ensure effortless hosting. An opulent master suite retreat has a private sitting room with a fireplace, a convenient wet bar with refrigeration, 2 sets of French doors to front and rear balconies, and 2 walk-in closets – both with custom closet systems and one with a generous center island with storage – and features an incredible spa-like bath with a steam shower and a magnificent stand-alone soaking tub. All additional en-suite bedrooms are comfortable with ample walk-in closets and tastefully appointed baths with showers. The lower level is designed with a home gym, expansive recreation space, games area, raised stage, and handsome tufted leather doors leading to a state-of-the-art movie theater. An additional bonus space also offers a bedroom, closet, and a full bath with a shower. Flowing seamlessly outdoors, the lush, park-like property features an expansive bluestone terrace anchored by an outdoor fireplace and a gourmet summer kitchen equipped with a premium built-in grill, integrated refrigeration, and an artisanal pizza oven. Alongside the sparkling heated pool and large sun deck, a gorgeous cabana with a full bath and laundry provides an open yet covered space to relax, while dramatic torches illuminate the pool area at night, creating a resort-caliber experience. This exceptional smart home is complete with a Generac generator, central vacuum, Crestron security system, interior/exterior sound system, sprinkler system, radiant flooring, 3 fireplaces, fine millwork, and a 3-car garage. Just 27 miles from NYC, this French-inspired masterpiece of 5 bedrooms and 8 full baths/4 half baths, offers a tranquil retreat for the discerning buyer who appreciates a Gold Coast luxury lifestyle.

5 Beds ⋅ 12 Baths ⋅ 1031340 MLS

A long driveway opens to a large courtyard with a classic fountain, revealing a magnificent Château-style Mansion on 2.03 acres of verdant property on a private cul-de-sac. Custom built for grand entertaining and everyday living, this incredible residence masterfully blends old-world European charm with modern luxury. A majestic 2-story entry foyer features a stunning domed-vaulted ceiling with a curved staircase, showcasing antiqued mirrored panels and an ornate wrought iron railing. Through a series of exquisite arches, the foyer leads to an expansive formal living room with a detailed ceiling and wall-to-wall windows as well as a palatial-sized dining room with a butler’s pantry that offers a wet bar and additional storage. The comfortable family room has a unique curved wall and a marble fireplace flanked by marble goddesses. Adjacent is a sitting room with a floor-to-ceiling built-in display wall and a cozy hexagonal built-in bay window seating area. Next door, an elegant study offers a productive place to work from home. A spectacular chef-inspired kitchen boasts a large breakfast area, dual islands, marble counters, a beautiful ILVE range with a show-stopping backsplash, Wolf, Miele and Sub-Zero appliances, plus an additional service kitchen to ensure effortless hosting. An opulent master suite retreat has a private sitting room with a fireplace, a convenient wet bar with refrigeration, 2 sets of French doors to front and rear balconies, and 2 walk-in closets – both with custom closet systems and one with a generous center island with storage – and features an incredible spa-like bath with a steam shower and a magnificent stand-alone soaking tub. All additional en-suite bedrooms are comfortable with ample walk-in closets and tastefully appointed baths with showers. The lower level is designed with a home gym, expansive recreation space, games area, raised stage, and handsome tufted leather doors leading to a state-of-the-art movie theater. An additional bonus space also offers a bedroom, closet, and a full bath with a shower. Flowing seamlessly outdoors, the lush, park-like property features an expansive bluestone terrace anchored by an outdoor fireplace and a gourmet summer kitchen equipped with a premium built-in grill, integrated refrigeration, and an artisanal pizza oven. Alongside the sparkling heated pool and large sun deck, a gorgeous cabana with a full bath and laundry provides an open yet covered space to relax, while dramatic torches illuminate the pool area at night, creating a resort-caliber experience. This exceptional smart home is complete with a Generac generator, central vacuum, Crestron security system, interior/exterior sound system, sprinkler system, radiant flooring, 3 fireplaces, fine millwork, and a 3-car garage. Just 27 miles from NYC, this French-inspired masterpiece of 5 bedrooms and 8 full baths/4 half baths, offers a tranquil retreat for the discerning buyer who appreciates a Gold Coast luxury lifestyle.

7 Covey Court, Upper Brookville

$675,000

Welcome to 8 5th Street, Bayville, NY—a charming and move-in-ready three-bedroom, two-bath home ideally located just moments from the waterfront and the heart of Bayville. This well-maintained home features numerous recent updates, including new siding, new air conditioning units, and a new boiler, new stainless steel kitchen appliances, offering comfort and peace of mind for years to come. Inside, you'll find a bright and inviting layout with spacious living areas, three comfortable bedrooms, and two full bathrooms. Step outside to enjoy the outdoor deck, the perfect space for relaxing, entertaining, or dining al fresco. Ideally situated close to Bayville's beautiful beaches, waterfront parks, local shops, restaurants, and all the village has to offer, this home combines modern updates with an unbeatable coastal lifestyle. Whether you're looking for a year-round residence or a weekend getaway, 8 5th Street is a wonderful opportunity to enjoy the very best of Bayville living. Welcome to 8 5th Street, Bayville, NY—a charming and move-in-ready three-bedroom, two-bath home ideally located just moments from the waterfront and the heart of Bayville. This well-maintained home features numerous recent updates, including new siding, new air conditioning units, and a new boiler, offering comfort and peace of mind for years to come.

3 Beds ⋅ 2 Baths ⋅ 1031519 MLS

Welcome to 8 5th Street, Bayville, NY—a charming and move-in-ready three-bedroom, two-bath home ideally located just moments from the waterfront and the heart of Bayville. This well-maintained home features numerous recent updates, including new siding, new air conditioning units, and a new boiler, new stainless steel kitchen appliances, offering comfort and peace of mind for years to come. Inside, you'll find a bright and inviting layout with spacious living areas, three comfortable bedrooms, and two full bathrooms. Step outside to enjoy the outdoor deck, the perfect space for relaxing, entertaining, or dining al fresco. Ideally situated close to Bayville's beautiful beaches, waterfront parks, local shops, restaurants, and all the village has to offer, this home combines modern updates with an unbeatable coastal lifestyle. Whether you're looking for a year-round residence or a weekend getaway, 8 5th Street is a wonderful opportunity to enjoy the very best of Bayville living. Welcome to 8 5th Street, Bayville, NY—a charming and move-in-ready three-bedroom, two-bath home ideally located just moments from the waterfront and the heart of Bayville. This well-maintained home features numerous recent updates, including new siding, new air conditioning units, and a new boiler, offering comfort and peace of mind for years to come.

8 5th Street, Bayville