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$5,299,000
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
$3,999,000
6 Beds ⋅ 9 Baths ⋅ 1045340 MLS
Elegance redefined. 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
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 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 new 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.

11 Danton Lane N, Locust Valley
$1,395,000
5 Beds ⋅ 3 Baths ⋅ 1040284 MLS
Charming Colonial set on just over an acre of spectacular property surrounded by beautiful specimen trees. A welcoming entry foyer opens to a spacious living room with a wood-burning fireplace. The kitchen features updated appliances and a generous dining area, perfect for everyday living and entertaining. The first floor offers three bedrooms, including a large en-suite bedroom, plus two additional bedrooms that share a full hall bath. Upstairs, the private primary suite is complemented by a versatile bonus room, ideal for a home office or nursery, and a spacious full bath. An Innocenti & Webel-designed terrace extends off the first floor, creating a wonderful setting for outdoor entertaining while overlooking the picturesque grounds. Additional highlights include a large unfinished basement offering endless possibilities, attached garage, and a new septic system. A special property offering beautiful grounds, generous living space, and exceptional potential. Please note the bedrooms and foyer were virtually Staged.

84 Bayville Road, Locust Valley
$2,480,000
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
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
$1,680,000
4 Beds ⋅ 3 Baths ⋅ 1036391 MLS
Welcome to this distinctive 2004 rebuilt builder’s own home, ideally situated on a quiet cul-de-sac and offering four finished levels, including the main level, second floor, legally finished attic, and fully finished basement. With approximately 4,071 sq. ft. of living space, 4 bedrooms, 3 bathrooms, a private swimming pool, and a brand-new roof, gas generator. The dramatic main living area features approximately 17-foot ceilings and oversized floor-to-ceiling windows that fill the home with natural light. Expansive second-floor windows overlook the pool and enhance the bright, open atmosphere. The versatile four-level layout provides excellent separation between living areas, ideal for entertaining, working from home, hosting guests, or creating additional private spaces. The spacious kitchen features an extra-large center island with generous workspace and ample room for cooking, casual dining, and gathering. Outside, enjoy a private swimming pool with a newly replaced liner, creating an inviting setting for summer relaxation and entertaining. Exceptional storage throughout the home provides additional convenience rarely found in comparable properties. The stone-and-siding exterior, mature landscaping, attached garage, spacious driveway, and cul-de-sac location complete this unique property. A rare opportunity to own a bright and spacious four-level home with soaring ceilings, abundant natural light, flexible living areas, excellent storage, and a private outdoor retreat. Photos have been digitally staged for visualization purposes. Price to sell, available now.

70 Nursery Street, Locust Valley
$999,999
4 Beds ⋅ 2 Baths ⋅ 1034512 MLS
Coastal charm meets endless potential in the picturesque Village of Bayville! Situated on a quiet exclusive street just steps away from a private resident-only beach, this spacious Colonial offers a peaceful retreat. Features generous living spaces and a master suite already rough-plumped for its own private bathroom- finishing this project creates a 3- bathroom home! Motivat

13 Meadow Lane, Bayville
$3,480,000
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
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
$8,995,000
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
$7,800,000
7 Beds ⋅ 8 Baths ⋅ 1031122 MLS
Nestled on four rare waterfront acres in the prestigious Village of Lattingtown, this exceptional estate encompasses 6,351 square feet of luxurious living space in an idyllic North Shore setting. Surrounded by rare dual water views overlooking The Creek and the Long Island Sound, the property seamlessly blends timeless architecture with thoughtfully curated modern updates. Designed for both elegant entertaining and comfortable everyday living, the residence features seven bedrooms and eight baths. Beautifully renovated formal spaces set the tone throughout. The formal living room and dining room, each anchored by its own fireplace, provide refined settings for gatherings and special occasions. At the heart of the home, a spectacular chef's kitchen captures picturesque water views and is appointed with premium appliances and an expansive center island. An adjacent, completely remodeled family room creates a seamless flow for everyday living, while a nearby butler's pantry and wet bar elevate the home's entertaining capabilities. Tucked near the primary wing, a distinguished library with its own fireplace provides a quiet retreat. The expansive first-floor primary wing serves as a private sanctuary, where bay windows frame serene water views and create the perfect setting to enjoy your morning coffee. Complete with dual baths, dual walk-in closets, and direct access to the patio overlooking the beautifully landscaped grounds, this exceptional retreat seamlessly blends comfort, luxury, and the beauty of its waterfront setting. The renovated lower level extends the home's versatility with a spacious recreation room, a dedicated fitness and wellness area featuring a sauna and cold plunge, an additional bedroom, a full bath, cedar closet, and abundant storage. Completing the estate, an updated two-bedroom apartment above the garage provides exceptional flexibility as a private guest residence or accommodations for extended family. The resort-inspired grounds offer an extraordinary setting for relaxation and entertaining, where newly designed patios, a custom fire pit, a spectacular saltwater gunite pool, a beautifully appointed pool house, and expansive rolling lawns are perfectly positioned to capture breathtaking waterfront vistas and golden sunsets shimmering across the water. Modern comforts include geothermal heating and cooling, a whole-house water filtration system, a whole-house generator, a slate roof, and extensive landscape enhancements. Ideally situated near private clubs, beaches, fine dining, shopping, and transportation, this is a rare opportunity to own one of Lattingtown's premier waterfront estates.

2 Lands End Road, Locust Valley
$3,799,000
5 Beds ⋅ 5 Baths ⋅ 1027379 MLS
Set on two flat, beautifully landscaped acres along a low-traffic street in Brookville, yet just minutes from major highways and shopping, this classic Colonial built in 1964 offers thoughtfully updated living space throughout. An extensive renovation touched nearly every corner of the home, from all new Marvin windows and doors to central air, updated heating, and a full repaint inside and out. The kitchen underwent its own complete transformation, emerging with high end appliances, a center island, and gas cooking, ideal for anyone who loves to cook and entertain. Three fireplaces warm the home throughout, found in the den, the living room, and the sunroom, where a new gas fireplace adds year round comfort. Upstairs, five bedrooms include a primary suite with a walk-in closet and an en suite bath featuring a soaking tub, stall shower, and double vanity, while a sixth bedroom was converted into a convenient laundry room. Three full baths and two half baths serve the home's living spaces, and a full unfinished basement offers ample storage or future potential. The three car garage, expanded from its original two car footprint, sits above with a second story that shares a wall with the primary suite. Comfort continues with three zone heating and air conditioning, a 400 amp electrical service, an automatic propane generator, and a Control4 smart home system managing sound, lighting, and video throughout. Outside, mature landscaping surrounds a brand new in-ground pool, a pergola, and an outdoor kitchen with a gas BBQ, perfect for warm weather gatherings. A new thirty year asphalt roof, new driveway, and updated sprinkler system round out a home where every major system and finish has been thoughtfully addressed. Colonial in style and scaled for gracious living, 15 Dogwood Hill offers a rare combination of space, setting, and easy access to everything Long Island's North Shore has to offer.

15 Dogwood Hill, Brookville
$5,599,000
6 Beds ⋅ 7 Baths ⋅ 1026409 MLS
Introducing an Extraordinary new Construction Estate in the prestigious Village of Muttontown, Set on approximately 3 Private acres overlooking a Picturesque Golf Couse. This Exceptional 2026 built residence offers the perfect blend of Modern Luxury , Elegance, and Sophistication. Featuring Six (6) Spacious Bedrooms and 6.5 designer bathrooms, with Radiant Heated Floors. The home showcases impeccable craftsmanship and high-end finishes throughout. A Grand Entrance welcomes you into a breathtaking Great Room, with soaring ceilings, expansive windows, and abundant natural light, creating an impressive setting for both everyday living and entertaining. Designed for comfort and style, the residence includes two fireplaces- One Gas and One Electric, adding warmth and ambiance to the home's thoughtfully designed living spaces. The open and flowing floor plan seamlessly connects formal and informal areas while maximizing the stunning Golf Course Views. Nestled on a beautifully situated 3-acre property, this Magnificent estate offers privacy, tranquility, and resort-style living in one of Long Island's most sought-after communities. A rare opportunity to own a newly built luxury home in the Heart of Muttontown. (Optional pool, optional outdoor kitchen, optional elevator.)

730 Remsens Lane, Muttontown
$2,599,888
7 Beds ⋅ 5 Baths ⋅ 1023664 MLS
Experience pristine living in this exquisite diamond Brookville home, offering unsurpassed value in a highly coveted location. The prestigious approach features a long circular driveway, welcoming you to a serene retreat. The exterior boasts mature specimen plantings and estate fencing encircling a country club style yard with a 20x40 Gunite gas heated pool. The flat 2 acres of entertaining backyard and brick patio, provides ample space to add tennis, pickleball or sport court. This serene oasis is perfect for relaxation and entertainment. Inside the kitchen features hardwood cabinets, complimented by gleaming hardwood flooring throughout the home. 4,717 of finished living space and an additional 1,148 of unfinished basement to create a media room, play room or entertainment cave. The architectural roof adds to the home's timeless elegance. First floor bedroom with en-suite bath and dual walk in closets, and a versatile bedroom/office with a walkout to the fabulous yard. There is so much more to this exceptional property that must be seen to be fully appreciated. Don't miss this rare opportunity to own a true retreat in a serene oasis.

15 Tappentown Lane, Brookville
$5,295,000
6 Beds ⋅ 9 Baths ⋅ 1021182 MLS
Imagine an exclusive lifestyle redefined within a private HOA gated community, where absolute security meets unparalleled luxury on a flat, beautifully landscaped 2.53-acre parcel. This masterfully constructed 7,000-square-foot estate—boasting an impressive six bedrooms and seven bathrooms, each with their own private balcony—is defined by ultra-high-quality finishes throughout, including radiant heated floors, a central vacuum system, and a private elevator servicing all levels. The crown jewel of the residence is a first floor year-round indoor wellness spa complete with a pristine indoor pool, relaxing sauna, and steam room facilities. Designed for flexible multi-generational living, the home features dual (2) primary suites with private balconies and jacuzzi baths, a media room for grand entertainment, a designer eat-in chef’s kitchen anchored by a massive island, and a beautifully finished walk-out lower level. Entertain brilliantly on the expansive rear patio with outdoor kitchen and covered pavilion. Conveniently located just 11 minutes to the Long Island Expressway, this luxury home seamlessly blends elite architecture with a truly exceptional compound experience.

5 Farmwoods Lane, Upper Brookville
$4,525,000
5 Beds ⋅ 6 Baths ⋅ 1022418 MLS
Exceptional brick estate offering 9,023 sq ft of refined living with 6bedrooms and 5.5baths on nearly two private acres in Locust Valley. Built in 2009, the home showcases custom mahogany millwork throughout, a dramatic two-story foyer with a sweeping butterfly staircase, and a great room framed by a soaring wall of arched windows. A first-floor library and dedicated meditation room offer quiet retreats. The chef's kitchen features rich custom cabinetry, coffered ceilings, an oversized center island, and a full suite of Viking appliances including a professional gas range, complemented by a butler's pantry with built-in wine storage and dual Viking wine refrigerators. The grand-scale primary suite is a wing unto itself, with a fireplace, sitting area, boutique-style dressing room, and an oversized spa bath with soaking tub and separate shower. A full-width entertainer's terrace spans the rear of the home, overlooking the manicured grounds. Below, the expansive walk-out garden level opens to the lawn through a graceful arched loggia — ideal for recreation, gym, or guest space. A rare blend of scale, craftsmanship, and privacy moments from Locust Valley village.

250 Oyster Bay Road, Locust Valley
$2,995,000
6 Beds ⋅ 5 Baths ⋅ 1019700 MLS
- Low Taxes - $36,000 -Locust Valley Schools - Village of Muttontown, located on the north side of Northern Boulevard/25A, bordering Upper Brookville - 3,900 Sq Ft Colonial - 2 Acres - All Upstairs Bathrooms Fully Renovated with high end finishes - Kitchen features Carrara Marble with new Wolf and Sub-Zero Appliances - Bluestone Patio with fully equipped outdoor kitchen featuring DCS Gas Grill, Lynx Pizza Oven, Lynx Refrigerator, Lynx Ice Maker, Lynx Warming Drawer, Gas Fireplace & Outdoor TV - Heated Saltwater Gunite Pool - Locust Valley SD Set on two beautifully landscaped private acres bordering Upper Brookville, 855 Orchard Lane offers a rare combination of refined interiors, exceptional outdoor living and true move-in-ready luxury. This beautifully renovated five/six-bedroom, four-and-a-half-bath Colonial has been thoughtfully updated for sophisticated everyday living and effortless entertaining. The kitchen pairs Carrara marble with Wolf and Sub-Zero appliances, while gracious living spaces feature custom millwork, rich natural materials and a gas fireplace accented in Imperial Danby marble. The primary suite provides a serene retreat with a spa-inspired Calacatta Gold marble bath and Waterworks fixtures. Each additional bath has been individually renovated with designer stone, fixtures and finishes, creating a consistent level of quality throughout the home. Outside is where 855 Orchard Lane truly distinguishes itself. A sprawling Bluestone terrace extends the living space into a private resort-like setting, with retractable awnings, a fully equipped outdoor kitchen featuring a DCS grill, Lynx pizza oven, refrigerator, ice maker and warming drawer, plus a separate outdoor living area centered around a gas fireplace and television. Beyond the terrace, a heated saltwater Gunite pool with waterfall is surrounded by beautiful lawns and mature landscaping, creating an exceptional backdrop for summer afternoons, intimate dinners and large-scale entertaining. With five/six bedrooms, approximately 3,848 square feet, two-car attached garage and full-house generator, the property delivers substantial amenities without the scale or maintenance demands of an oversized estate. Located in the Village of Muttontown on the north side of Northern Boulevard/25A and bordering Upper Brookville, 855 Orchard Lane offers privacy, acreage and a beautifully finished North Shore lifestyle—all ready to enjoy.

855 Orchard Lane, Muttontown
$3,195,000
5 Beds ⋅ 5 Baths ⋅ 1020514 MLS
Down a long, private driveway canopied by mature trees, 17 Danton Lane is a modern 5-bedroom, 4.5-bath home that spans approximately 7,000 square feet on over 4 acres, in one of Locust Valley's most coveted beach enclaves, just a stroll from a private beach. A striking 2 story atrium foyer welcomes you in, with glass doors beckoning straight out to the backyard. The kitchen, redesigned in 2019, features large countertops, custom cabinetry, and Viking appliances, while a newly finished basement offers a full bathroom, gym and recreational space. On the main floor, the impressively large great room is designed for entertaining with oversized windows and elegant fireplace. On the other side of the house, the two-story primary suite includes a soaking tub, walk-in closets, and an upstairs office/den. The grounds, designed by Dubner, offer layered points of interest throughout, from a sparkling gunite pool with jacuzzi to a serene koi pond, creating a series of destinations to discover rather than a single view. Clean, contemporary design meets total privacy, lush surroundings, and private beach access on over 4 acres at 17 Danton Lane.

17 Danton Lane N, Locust Valley
$799,000
3 Beds ⋅ 2 Baths ⋅ 1019915 MLS
Welcome to 15 Pershing Avenue, a charming Locust Valley residence where classic character meets modern comfort in one of the North Shore’s most beloved communities. This inviting 3-bedroom, 2-bath home offers a warm and functional layout filled with natural light, timeless appeal, and flexible living space for today’s lifestyle. A thoughtfully designed bonus room provides the perfect option for a home office, guest space, playroom, or creative studio, while the newly finished basement adds valuable additional space ideal for recreation, entertaining, fitness, storage, or extended everyday use. Set on a spacious property with a detached 2-car garage, this home offers room to gather, garden, and entertain. Perfectly located near Locust Valley’s shops, dining, parks, schools, and on Matinecock Border. 15 Pershing Avenue delivers comfort, charm, flexibility, and location in one beautiful package.

15 Pershing Avenue, Locust Valley
$4,998,000
5 Beds ⋅ 7 Baths ⋅ 1018743 MLS
The most discerning will appreciate the unparalleled architectural details and sublime luxury that abounds in this hilltop Classic Contemporary Estate. Renovated top to bottom in 2018 by a professional builder for his personal residence, only the finest European structural and design elements were utilized. "Hilltop" offers a beautiful setting for comfortable living and gracious entertaining. The Open Concept interior floor plan, with floor to ceiling windows and breath-taking sweeping views of the landscape, flows seamlessly to the exterior Ipe deck and patio. Nestled in the Lattingtown Harbor Community, residents enjoy the private beach and clubhouse with mooring rights. All this awaits, a mere 30 Miles from Manhattan and less than 2 miles from downtown Locust Valley with charming shops, fine dining and public transportation. LHPOA Fees approx. $2500/yrly Private Carting., Additional information: Appearance:MINT+++,Interior Features:Marble Bath

8 Frost Creek Drive, Locust Valley
$2,675,000
4 Beds ⋅ 4 Baths ⋅ 1015612 MLS
A rare opportunity to own brand-new direct waterfront construction with private beach access and sweeping views of the Long Island Sound in the heart of Bayville. Perched atop a bluff overlooking the water, this exceptional residence offers the perfect blend of coastal living and modern luxury. Featuring 4 bedrooms and 3.5 bathrooms, the home is thoughtfully designed with an open-concept layout and abundant natural light throughout. The expansive family room is anchored by a gas fireplace and opens through sliding glass doors to the backyard, where breathtaking water views create a stunning backdrop for everyday living and entertaining. The beautifully appointed eat-in kitchen flows seamlessly into the main living spaces, while the private bedroom suites offer their own tranquil retreats. Private balconies off the bedrooms capture panoramic, crystal-clear views of the Long Island Sound, stretching to the Connecticut shoreline and all the way to the New York City skyline. From spectacular sunrises over the water to the twinkling lights of the city in the distance, the views are nothing short of extraordinary. Additional highlights include a 2-car garage, a full basement with high ceilings offering endless possibilities, and direct access to a private beach just steps away. Set within the highly regarded Locust Valley School District, this is a truly unique opportunity to own brand-new waterfront construction and experience coastal living at its finest.

33A Bayville Avenue, Bayville
$2,490,000
4 Beds ⋅ 4 Baths ⋅ 1016868 MLS
Amazingly LOW Taxes & TWO (2) meticulously landscaped acres with salt water POOL, this exceptional Brookville residence showcases refined design, expansive living spaces, and resort-style outdoor amenities. Elegant stone patio with gazebo and outdoor kitchen equipped with a barbecue, refrigerator, and sink. A dramatic entry opens to soaring ceilings with skylights and impressive window walls that flood the home with natural light. The spacious floor plan includes a sprawling living room/dining room, two inviting dens, and a recently renovated eat-in kitchen designed for both daily living and entertaining. Four beautifully updated bedrooms (1 separate bedroom suite with backyard access for second generation) and three-and-a-half baths provide comfortable accommodations throughout. The finished ground level offers versatile additional living space, while the seamless connection between indoor and outdoor areas enhances the home's exceptional functionality and appeal. Move-in ready and thoughtfully updated. Ideally situated near transportation, shopping, dining, parks, universities, golf and tennis facilities, this is a remarkable offering in Brookville.

19 Tappentown Lane, Brookville
$12,250,000
7 Beds ⋅ 10 Baths ⋅ 1017340 MLS
This is an exclusive opportunity to own a turn-key Modern Mansion, perfectly positioned on 5 manicured acres on the Gold Coast of Long Island. Constructed in 2022, this designer residence showcases oversized windows, 12ft ceilings, multiple marble gas fireplaces, pocket doors, glass railings and more. Both captivating and secluded, this residence offers the warmth of a traditional home with a contemporary flair. The first floor has a two story foyer, spacious formal living and dining rooms, an office and a lounge with a built-in bar and billiards area. The state-of-the-art modern kitchen is outfitted with top-of-the-line Viking appliances, Neo Marble countertops, numerous pantries and a sweeping center island with bar seating. Off of the kitchen is a beautiful light-filled eating area, with doors leading out to the backyard, an inviting family room and a bespoke homework area/ work space. The main house boasts 6 vast bedrooms, all with en-suite bathrooms and large closets. The Primary Wing is on the first floor and is outfitted with a private sitting room, 2 patios, a laundry area, 'His and Her' spa-like bathroom with a stand-alone tub and two glass enclosed showers, as well as 2 custom walk-in closets, one totaling over 3,000 Sq.Ft. of storage space. Upstairs also features a playroom with a media center, a crafts room, a matted fitness area and a massive flex room over the 8 car attached garage. Additional interior details include 4 stylish powder rooms, an elevator, 2 full service laundry rooms, a whole-house Smart Camera and Alarm System, a central vacuum system, surround sound speakers and an unfinished basement, with an indoor sports court, spanning the entire length of the home. The exterior is fashioned with a gated entry, a long blue stone and pebble driveway, a solid stucco facade, steel windows and decorative metal gutters. The property is elegantly landscaped and has a 60ft x 25ft Saltwater Heated Pool and Hot Tub, a Cabana with a Kitchenette, a fenced-in Dog Run and a covered patio with an outdoor lounge area, great for entertaining. In proximity to The Village of Locust Valley, the LIRR, charming local beaches and some of Long Island's most prominent Country/Golf Clubs. Zoned for the acclaimed Locust Valley Central School District.

199 Lattingtown Road, Locust Valley
$4,998,000
6 Beds ⋅ 7 Baths ⋅ 1010689 MLS
A Private Oasis in Upper Brookville. Timeless elegance prevails in this custom-built, majestic brick 6-bedroom, 6.5-bath manor home in Upper Brookville. Masterfully set at the end of a cul-de-sac, a private driveway leads to a spacious courtyard and impressive, stately residence set on 6 prime, serene acres. For a qualified buyer, this is an exceptional opportunity. Many many features include: a two-story entryway, a luxurious primary suite on the main level, a free-form inground heated gunite pool with a waterfall, a covered outdoor kitchen, and a 3-car garage. Luxurious living with hidden privacy and easy access.

7 Fairway Court, Upper Brookville
$8,975,000
6 Beds ⋅ 9 Baths ⋅ 1011822 MLS
A Legacy Estate of Uncommon Distinction — Buttonball Hill Conceived in 1929 for Vanderbilt heir Aldred Coster Schermerhorn, Buttonball Hill is a masterwork of Georgian architecture set amid sweeping manicured grounds. The classic red brick and clapboard exterior — crowned by a slate roof and crisp black shutters — announces itself with quiet authority. Inside, a double-height foyer with hand-carved moldings and a gracefully curved staircase sets the tone. Soaring ceilings and a natural flow make the principal rooms equally suited to intimate daily living and grand entertaining. The formal living room opens through French doors into a sun-filled solarium; the chestnut-paneled library and cozy den each offer their own fireplace and garden access. The chef’s kitchen is a true centerpiece — expansive and impeccably appointed, with top-of-the-line appliances, custom cabinetry, and generous counter space designed for serious cooking and effortless hosting. Multiple seating areas make it the natural heart of the home: a sun-drenched breakfast nook overlooking the gardens, a sprawling island ideal for casual dining, and a comfortable sitting area perfect for gathering with family and guests. The primary suite is a sanctuary: sitting room, two ensuite baths, fireplace, and a private balcony with sweeping estate views. Outside, a heated pool, Har-Tru tennis court, and beautifully landscaped gardens round out the resort-caliber grounds. A superbly maintained estate where historic soul meets modern ease — minutes from top schools, village amenities, and convenient rail access to the city.

52 Piping Rock Road, Locust Valley
$1,149,000
4 Beds ⋅ 3 Baths ⋅ 1010411 MLS
Welcome to 6 Cedar Ave, nestled in the tranquil and private locale of Locust Valley, NY, is a delightful 4-bedroom, 3-bathroom center hall colonial home. Constructed in 1988, this residence spans a generous 2,538 square feet and is situated on approximately 7000 square foot lot. The home exudes a blend of classic colonial style with modern upgrades, featuring a cozy fireplace and a combination of tile, carpet, and hardwood flooring. Recent updates include a charming deck and pergola, which provide a perfect setting for outdoor gatherings while overlooking the yard. The property also offers ample space to accommodate an inground pool, enhancing the outdoor living experience. Inside, the home is warmed by baseboard heating with oil and cooled by new 2024 Central Air Conditioning. Additional conveniences include an attached garage for parking and essential appliances like a dishwasher, dryer, freezer, microwave, range/oven, refrigerator, and washer, making it an ideal family retreat with both comfort and privacy. First Floor Windows approx. 12 Years, Most of the 2nd floor windows were replaced 2026, New Oven, Dishwasher, Refrigerator 3 years old, CAC 3 Years. New Front railing is being installed. New estate fencing in the yard.

6 Cedar Avenue, Locust Valley
$5,888,000
6 Beds ⋅ 6 Baths ⋅ 1001932 MLS
Discover unparalleled luxury in the heart of Muttontown at 2 Chelmsford Drive, a striking post-modern custom-designed new construction set on a breathtaking 2-acre country club setting. Surrounded by specimen plantings and professionally curated landscaping, this extraordinary estate offers exceptional craftsmanship, sophisticated design, and resort-style amenities throughout. A dramatic custom pivot front door opens to a grand paneled foyer with soaring ceilings ranging from 14 to 20 feet, creating an impressive first impression. Wide-plank white oak floors and custom Pella windows enhance the home's warm, contemporary elegance. The state-of-the-art chef’s kitchen is a true showpiece, featuring rich walnut cabinetry, stunning black quartzite countertops, and a full suite of premium Wolf appliances, including double ovens, a six-burner cook top with griddle, microwave, built-in coffee system, separate ice maker, beverage refrigerator drawers and subzero refrigerator. The formal dining room offers soaring ceilings and walls of glass that open to an outdoor entertaining terrace complete with a full kitchen, pizza oven, and fireplace. The spectacular living room features a double-sided gas fireplace and a custom plaster ceiling. The luxurious primary suite boasts a dramatic 20-foot ceiling, built-in designer headboard feature wall, private deck overlooking the expansive grounds, two custom walk-in closets, and a designer spa bath. Three additional bedrooms are conveniently located on the main level. A stunning illuminated floating staircase leads to the lower level, where you will find additional guest bedrooms, a private gym with adjoining sauna and bath, a large movie theater, and an oversized recreation room with wet bar and glass doors opening directly to the backyard oasis. Designed for ultimate outdoor enjoyment, the country club-inspired grounds feature an oversized heated saltwater Gunite pool with spa, an elegant cabana with outdoor kitchen, and a separate pool house for storage. Automobile enthusiasts will appreciate the extraordinary garage capacity for up to 10 vehicles, including two car lifts, along with a circular paved driveway that completes this one-of-a-kind estate. 2 Chelmsford Drive is a masterfully designed residence that seamlessly blends architectural excellence, luxury amenities, and unparalleled lifestyle living.

2 Chelmsford Drive, Muttontown
$4,500,000
6 Beds ⋅ 5 Baths ⋅ 1003784 MLS
MAJOR PRICE ADJUSTMENT: Enter the wrought iron gates, crowned with classic gas lanterns that cast a warm, welcoming glow and along a private drive, Rolling Meadows reveals itself with the quiet authority of architecture built without haste -a classic brick Georgian residence with stately columns and a slate roof, set amid nine-plus acres of gracious formal gardens and mature specimen trees. Inside, wide plank oak floors create genuine character. A sweeping staircase rises from the entry foyer; the living room and imported Filipino mahogany-paneled library each offer wood-burning marble fireplaces; the formal dining room features a distinct china showcase; and the chef’s kitchen — with its substantial center island and adjoining breakfast room — is designed for both daily living and entertaining. The principal suite is positioned on the main floor, offering exceptional privacy, generous dressing, and a unique ensuite bath. A first-floor guest suite, three additional second floor bedrooms, a substantial bonus room and a three-car attached garage complete the residence. The grounds are as fully realized as the interiors. An Innocenti and Webel pool and dedicated pool house provide an effortless setting for outdoor entertaining. The equestrian facility comprises a seven-stall barn, multiple paddocks and on-site staff quarters. The serious equestrian infrastructure is complemented by a three-car attached garage. There are two additional outdoor garages on the estate. Rolling Meadows is that increasingly rare proposition: a fully equipped country estate where architectural pedigree, equestrian infrastructure, and the warmth of a well-appointed home meet without compromise. A property of this character is best understood in person.

550 Chicken Valley Road, Locust Valley
$25,000,000
13 Beds ⋅ 17 Baths ⋅ 1001064 MLS
Experience Applewood Estate — a generational North Shore compound where timeless architecture, historic provenance, and resort-caliber living unfold across more than 35 secluded acres in the esteemed Village of Upper Brookville. Once an operating apple orchard in the early 1900s and later owned by renowned American artist Montague Flagg, this extraordinary estate carries a legacy as rich as the land itself. Hidden behind a gated, tree-lined approach, the property reveals a breathtaking landscape of rolling lawns, mature specimen trees, formal gardens, peaceful water features, and open meadows designed to evoke the grandeur of Long Island’s historic Gold Coast estates. Inspired by Tudor Cotswold architecture, the compound is a masterclass in cohesive design, blending old-world craftsmanship with modern luxury across multiple residences and lifestyle amenities. The centerpiece is a magnificent custom-built Manor residence encompassing approximately 13,000 square feet of refined living space. Constructed in 2005 with slate, brick, and stone, the home showcases extraordinary craftsmanship through onyx marble accents, oversized parquet flooring, handcrafted iron fireplaces, detailed millwork, and dramatic entertaining spaces throughout. A grand foyer anchored by a sweeping staircase introduces interiors defined by warmth and scale, including a soaring ballroom with 23-foot coffered ceilings, an elegant library loft, meditation room, billiards lounge with wet bar, and a sun-filled eat-in kitchen with breakfast room overlooking the estate grounds. Designed as a true multi-structure compound, Applewood Estate includes several additional residences and guest accommodations, including a beautifully renovated barn residence with attached two-bedroom cottage, an additional two-bedroom cottage, a two-bedroom pool house, a one-bedroom studio, and a meticulously reconstructed circa-1914 stone barn now transformed into a luxurious retreat. Outdoor living is equally exceptional. The estate features a heated swimming pool and spa pavilion, built-in outdoor kitchen, resurfaced tennis court, separate sports court, expansive paddocks, and formal equestrian facilities complete with horse stables and a training ring. Additional highlights include a six-car detached garage, maintenance barn, commercial-grade 150kW generator, and secure gated entry, all thoughtfully integrated into the estate’s serene natural surroundings. Rarely does a property offer this level of acreage, architectural integrity, historical significance, and lifestyle versatility within one of the North Shore’s most coveted enclaves. Applewood Estate is not simply a home — it is a private world crafted for legacy living, grand entertaining, and timeless retreat.

1 Applewood Estate, Upper Brookville

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.