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Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary. A striking stone and stucco facade with oversized black-trim windows sets a sophisticated tone upon arrival. Inside, a dramatic marble foyer with a sweeping spiral staircase unveils the heart of the home: a voluminous great room featuring soaring ceilings, a sleek gas fireplace, bespoke wet bar, and walls of glass that dissolve the boundary between indoors and out. Every inch of this residence speaks to thoughtful luxury. The chef’s kitchen is clad in two-toned cabinetry, boasts a suite of chef-grade stainless steel appliances and thick-cut stone countertops. The welcoming family room has a warm fireplace with a custom, stone mantel and beautiful natural wood built-ins. Entertain effortlessly in the formal dining room, designed to host 14+ guests, supported by a fully outfitted butler’s pantry. Designed for both grand entertaining and intimate day-to-day living, the main level also features a spacious home office with a private sitting area, two elegant powder rooms, a guest-ready first-floor bedroom suite, an elevator and a mudroom conveniently located off of the 4-car attached garage. Upstairs, the primary wing evokes the atmosphere of a five-star hotel, complete with a private lounge, dressing and vanity area, spa-like bath with an oversized rain shower and soaking tub, radiant heated floors, and multiple walk-in closets, with custom wardrobe installations. There are four additional bedrooms, four marble full-bathrooms and an expansive laundry room. The walk-out lower level is a world unto itself, beginning with a dramatic foyer framed by a floor-to-ceiling wine display wall. Details include a one-bedroom guest suite, media or den space, full bath, a state-of-the-art gym with sound system and sauna, and a full-scale golf simulator for year-round recreation. Outdoors, the resort-quality amenities continue with a covered patio with a fireplace, a built-in kitchen, and a sparkling in-ground pool and spa. A poolside cabana offers yet another luxe retreat, complete with a kitchenette, lounge, changing rooms, and full bath. Beyond the main residence, a two-story barn with a loft serves as an 8-stall equestrian facility or an extraordinary car collector's gallery, accompanied by a fully-appointed 3/4 bedroom guest house for extended stays or guest quarters. Nestled in a picturesque and ultra-private setting, this 20,000+ Sq.Ft. Old Brookville masterpiece redefines modern estate living with unmatched elegance, scale, and functionality. Located within the North Shore School District.

10 Beds ⋅ 15 Baths ⋅ 922932 MLS

Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary. A striking stone and stucco facade with oversized black-trim windows sets a sophisticated tone upon arrival. Inside, a dramatic marble foyer with a sweeping spiral staircase unveils the heart of the home: a voluminous great room featuring soaring ceilings, a sleek gas fireplace, bespoke wet bar, and walls of glass that dissolve the boundary between indoors and out. Every inch of this residence speaks to thoughtful luxury. The chef’s kitchen is clad in two-toned cabinetry, boasts a suite of chef-grade stainless steel appliances and thick-cut stone countertops. The welcoming family room has a warm fireplace with a custom, stone mantel and beautiful natural wood built-ins. Entertain effortlessly in the formal dining room, designed to host 14+ guests, supported by a fully outfitted butler’s pantry. Designed for both grand entertaining and intimate day-to-day living, the main level also features a spacious home office with a private sitting area, two elegant powder rooms, a guest-ready first-floor bedroom suite, an elevator and a mudroom conveniently located off of the 4-car attached garage. Upstairs, the primary wing evokes the atmosphere of a five-star hotel, complete with a private lounge, dressing and vanity area, spa-like bath with an oversized rain shower and soaking tub, radiant heated floors, and multiple walk-in closets, with custom wardrobe installations. There are four additional bedrooms, four marble full-bathrooms and an expansive laundry room. The walk-out lower level is a world unto itself, beginning with a dramatic foyer framed by a floor-to-ceiling wine display wall. Details include a one-bedroom guest suite, media or den space, full bath, a state-of-the-art gym with sound system and sauna, and a full-scale golf simulator for year-round recreation. Outdoors, the resort-quality amenities continue with a covered patio with a fireplace, a built-in kitchen, and a sparkling in-ground pool and spa. A poolside cabana offers yet another luxe retreat, complete with a kitchenette, lounge, changing rooms, and full bath. Beyond the main residence, a two-story barn with a loft serves as an 8-stall equestrian facility or an extraordinary car collector's gallery, accompanied by a fully-appointed 3/4 bedroom guest house for extended stays or guest quarters. Nestled in a picturesque and ultra-private setting, this 20,000+ Sq.Ft. Old Brookville masterpiece redefines modern estate living with unmatched elegance, scale, and functionality. Located within the North Shore School District.

53 Simonson Road, Old Brookville

$5,490,000

Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable. From the moment you step inside, you’re swept into a world of high style and high impact. The soaring ceilings set the stage, while bold architectural details and designer finishes bring a sense of drama to every room. The custom chef’s kitchen is as functional as it is stunning—perfect for hosting everything from cozy family dinners to glamorous cocktail parties. Every detail was designed to delight. The pink laundry room will make you smile every time you walk in, and the sleek, sophisticated man bar is party-ready for unforgettable nights with friends. Every corner of this home tells a story of creativity, luxury, and fun. Step outside and it only gets better. The grounds are your private resort: a sparkling pool glistening in the sun, a full tennis court for a quick match, and beautifully landscaped gardens that feel like your own private park. Whether you’re entertaining on a grand scale or enjoying quiet evenings under the stars, this property delivers it all.

6 Beds ⋅ 6 Baths ⋅ 845880 MLS

Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable. From the moment you step inside, you’re swept into a world of high style and high impact. The soaring ceilings set the stage, while bold architectural details and designer finishes bring a sense of drama to every room. The custom chef’s kitchen is as functional as it is stunning—perfect for hosting everything from cozy family dinners to glamorous cocktail parties. Every detail was designed to delight. The pink laundry room will make you smile every time you walk in, and the sleek, sophisticated man bar is party-ready for unforgettable nights with friends. Every corner of this home tells a story of creativity, luxury, and fun. Step outside and it only gets better. The grounds are your private resort: a sparkling pool glistening in the sun, a full tennis court for a quick match, and beautifully landscaped gardens that feel like your own private park. Whether you’re entertaining on a grand scale or enjoying quiet evenings under the stars, this property delivers it all.

89 Pound Hollow Road, Old Brookville

$5,250,000

Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase welcomes you into beautifully appointed interiors designed for both grand-scale entertaining and comfortable everyday living. The thoughtfully designed floor plan offers expansive formal and informal living spaces, including a gracious living room that flows seamlessly into the inviting den. At the heart of the home is an exceptional chef’s kitchen, thoughtfully designed with premium appliances, custom cabinetry, expansive workspace, and a generous center island. The kitchen opens effortlessly to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. Step outside to your own private resort, where multiple stone patios, a fully equipped outdoor kitchen, sparkling in-ground pool, and beautifully appointed pool house provide the ultimate setting for entertaining or quiet relaxation, all surrounded by meticulously landscaped grounds and unmatched privacy. The luxurious primary suite serves as a private retreat, complete with a large dressing room and a spa-inspired bath featuring a soaking tub, oversized shower, and refined finishes. Five additional spacious bedrooms, along with seven full bathrooms and three half bathrooms, provide exceptional accommodations. The finished lower level is designed for both recreation and relaxation, offering a custom wine cellar, state-of-the-art home theater, fitness center, expansive recreation room, and abundant storage. Perfectly blending timeless design with modern luxury, this remarkable estate offers an unparalleled lifestyle in one of Old Brookville’s most sought-after locations, where privacy, sophistication, and exceptional entertaining come together in a truly extraordinary setting.

6 Beds ⋅ 10 Baths ⋅ 1031994 MLS

Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase welcomes you into beautifully appointed interiors designed for both grand-scale entertaining and comfortable everyday living. The thoughtfully designed floor plan offers expansive formal and informal living spaces, including a gracious living room that flows seamlessly into the inviting den. At the heart of the home is an exceptional chef’s kitchen, thoughtfully designed with premium appliances, custom cabinetry, expansive workspace, and a generous center island. The kitchen opens effortlessly to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. Step outside to your own private resort, where multiple stone patios, a fully equipped outdoor kitchen, sparkling in-ground pool, and beautifully appointed pool house provide the ultimate setting for entertaining or quiet relaxation, all surrounded by meticulously landscaped grounds and unmatched privacy. The luxurious primary suite serves as a private retreat, complete with a large dressing room and a spa-inspired bath featuring a soaking tub, oversized shower, and refined finishes. Five additional spacious bedrooms, along with seven full bathrooms and three half bathrooms, provide exceptional accommodations. The finished lower level is designed for both recreation and relaxation, offering a custom wine cellar, state-of-the-art home theater, fitness center, expansive recreation room, and abundant storage. Perfectly blending timeless design with modern luxury, this remarkable estate offers an unparalleled lifestyle in one of Old Brookville’s most sought-after locations, where privacy, sophistication, and exceptional entertaining come together in a truly extraordinary setting.

33 Chicken Valley Road, Old Brookville

$4,150,000

Old Brookville with choice of North Shore or Locust Valley Schools. 2 Acre Property Welcome to 17 Hunt Court, nestled within the coveted Pheasant Chase section of Old Brookville and tucked behind the area's renowned equestrian center. This exceptional brick colonial blends timeless architecture with beautifully updated interiors, resort-inspired outdoor living, and the peaceful surroundings that define the quintessential Old Brookville lifestyle. A tranquil wrap-around porch welcomes your arrival before double entry doors open to an impressive 18-foot foyer, highlighted by a sweeping wrapped staircase and gracious proportions that set the tone throughout the home. Designed for both refined entertaining and comfortable everyday living, the main level offers a formal living room anchored by a wood-burning fireplace, an elegant formal dining room connected to the kitchen through a butler's pantry, and a spacious family room featuring tray ceilings, a second wood-burning fireplace, and French doors opening seamlessly to the backyard. The beautifully appointed chef's kitchen serves as the heart of the home, thoughtfully designed with a breakfast nook, built-in office area, Sub-Zero refrigerator and freezer, refrigerator drawers, two dishwashers, a wine refrigerator, built-in Miele coffee system, television nook, and a gas range with pot filler, creating an inviting space for gathering and entertaining. A country club-inspired mudroom offers exceptional functionality with direct access to the backyard, second level, and attached three-car garage. Completing the first floor is a home office which can also be used as a first-floor bedroom. The second level is highlighted by a luxurious primary suite featuring hidden laundry, an expansive spa-inspired bathroom with dual vanities, a soaking tub overlooking the beautifully landscaped grounds, water closet, beverage refrigerator, oversized walk-in shower, generous walk-in closet, and a private retreat designed for comfort and relaxation. Four additional bedrooms and two recently renovated full bathrooms complete the upper level. The finished lower level expands the home's exceptional living and entertaining space, offering a wet bar, dedicated fitness room, expansive recreation area, and direct outdoor access to the backyard. Outdoors, the property has been extensively transformed into a private resort-inspired retreat. An expansive patio surrounds the heated gunite pool and fully equipped outdoor kitchen, creating an exceptional setting for entertaining while overlooking meticulously maintained landscaping and sprawling lawns. The shared common green space beyond enhances the sense of privacy and openness, further contributing to the quiet, secluded setting that makes this neighborhood so desirable. Offering six bedrooms, beautifully curated indoor and outdoor living spaces, and an exceptional location within one of the North Shore's most sought-after communities, 17 Hunt Court presents a rare opportunity to experience the very best of Gold Coast living in the heart of Old Brookville.

6 Beds ⋅ 6 Baths ⋅ 1034020 MLS

Old Brookville with choice of North Shore or Locust Valley Schools. 2 Acre Property Welcome to 17 Hunt Court, nestled within the coveted Pheasant Chase section of Old Brookville and tucked behind the area's renowned equestrian center. This exceptional brick colonial blends timeless architecture with beautifully updated interiors, resort-inspired outdoor living, and the peaceful surroundings that define the quintessential Old Brookville lifestyle. A tranquil wrap-around porch welcomes your arrival before double entry doors open to an impressive 18-foot foyer, highlighted by a sweeping wrapped staircase and gracious proportions that set the tone throughout the home. Designed for both refined entertaining and comfortable everyday living, the main level offers a formal living room anchored by a wood-burning fireplace, an elegant formal dining room connected to the kitchen through a butler's pantry, and a spacious family room featuring tray ceilings, a second wood-burning fireplace, and French doors opening seamlessly to the backyard. The beautifully appointed chef's kitchen serves as the heart of the home, thoughtfully designed with a breakfast nook, built-in office area, Sub-Zero refrigerator and freezer, refrigerator drawers, two dishwashers, a wine refrigerator, built-in Miele coffee system, television nook, and a gas range with pot filler, creating an inviting space for gathering and entertaining. A country club-inspired mudroom offers exceptional functionality with direct access to the backyard, second level, and attached three-car garage. Completing the first floor is a home office which can also be used as a first-floor bedroom. The second level is highlighted by a luxurious primary suite featuring hidden laundry, an expansive spa-inspired bathroom with dual vanities, a soaking tub overlooking the beautifully landscaped grounds, water closet, beverage refrigerator, oversized walk-in shower, generous walk-in closet, and a private retreat designed for comfort and relaxation. Four additional bedrooms and two recently renovated full bathrooms complete the upper level. The finished lower level expands the home's exceptional living and entertaining space, offering a wet bar, dedicated fitness room, expansive recreation area, and direct outdoor access to the backyard. Outdoors, the property has been extensively transformed into a private resort-inspired retreat. An expansive patio surrounds the heated gunite pool and fully equipped outdoor kitchen, creating an exceptional setting for entertaining while overlooking meticulously maintained landscaping and sprawling lawns. The shared common green space beyond enhances the sense of privacy and openness, further contributing to the quiet, secluded setting that makes this neighborhood so desirable. Offering six bedrooms, beautifully curated indoor and outdoor living spaces, and an exceptional location within one of the North Shore's most sought-after communities, 17 Hunt Court presents a rare opportunity to experience the very best of Gold Coast living in the heart of Old Brookville.

17 Hunt Court, Old Brookville

$3,100,000

Built by the renowned Farrell Building Company in 1996, whose homes are recognized among Long Island’s finest for their exceptional quality and enduring craftsmanship, this exceptional brick Gold Coast estate blends timeless architecture with today’s luxury amenities, offering over 5,480 square feet of elegantly appointed living space on two private acres in the heart of prestigious Old Brookville. Designed for both grand entertaining and comfortable everyday living, the home showcases five bedrooms, five full baths, two powder rooms, grandly scaled interiors, rich hardwood floors, custom solid wood built-ins, abundant natural light, and four fireplaces that add warmth and character throughout. At the heart of the home is a beautifully appointed eat-in kitchen featuring granite countertops, a large center island, double ovens, two dishwashers, and generous dining space. The kitchen flows seamlessly into the inviting family room with custom built-ins and a dramatic stone wood-burning fireplace. Formal living and dining rooms, a private study, a spacious laundry room, and a cabana bath with direct access to the backyard complete the thoughtfully designed main level. The luxurious primary suite is a private retreat, offering a gas fireplace, a spa-inspired bath with radiant heated floors, dual vanities, a double shower, and extraordinary walk-in closets. A rare walk-out lower level, entirely move grade offering an additional 1,800 square feet of finished living space, thoughtfully designed to function as an extension of the home. This level includes a spacious a recreation room, fireplace, gym, guest suite with an en-suite bath, powder room, and direct access to the backyard. Designed for exceptional outdoor living, the resort-inspired grounds feature a heated saltwater gunite pool, an outdoor fireplace, a built-in barbecue, expansive bluestone patios, a gazebo and mature landscaping, creating an exceptionally private setting. Additional highlights include a heated four-car garage with hot and cold water, a private driveway accommodating over 10 cars and a whole-house generator. Perfectly positioned near waterfront dining, Long Island Sound beaches, championship golf courses, nature preserves, and the charming villages of Roslyn, Oyster Bay, and Locust Valley, this is a rare opportunity to own a timeless Gold Coast estate where exceptional craftsmanship, refined living, and today’s comforts come together in one extraordinary residence.

5 Beds ⋅ 7 Baths ⋅ 969013 MLS

Built by the renowned Farrell Building Company in 1996, whose homes are recognized among Long Island’s finest for their exceptional quality and enduring craftsmanship, this exceptional brick Gold Coast estate blends timeless architecture with today’s luxury amenities, offering over 5,480 square feet of elegantly appointed living space on two private acres in the heart of prestigious Old Brookville. Designed for both grand entertaining and comfortable everyday living, the home showcases five bedrooms, five full baths, two powder rooms, grandly scaled interiors, rich hardwood floors, custom solid wood built-ins, abundant natural light, and four fireplaces that add warmth and character throughout. At the heart of the home is a beautifully appointed eat-in kitchen featuring granite countertops, a large center island, double ovens, two dishwashers, and generous dining space. The kitchen flows seamlessly into the inviting family room with custom built-ins and a dramatic stone wood-burning fireplace. Formal living and dining rooms, a private study, a spacious laundry room, and a cabana bath with direct access to the backyard complete the thoughtfully designed main level. The luxurious primary suite is a private retreat, offering a gas fireplace, a spa-inspired bath with radiant heated floors, dual vanities, a double shower, and extraordinary walk-in closets. A rare walk-out lower level, entirely move grade offering an additional 1,800 square feet of finished living space, thoughtfully designed to function as an extension of the home. This level includes a spacious a recreation room, fireplace, gym, guest suite with an en-suite bath, powder room, and direct access to the backyard. Designed for exceptional outdoor living, the resort-inspired grounds feature a heated saltwater gunite pool, an outdoor fireplace, a built-in barbecue, expansive bluestone patios, a gazebo and mature landscaping, creating an exceptionally private setting. Additional highlights include a heated four-car garage with hot and cold water, a private driveway accommodating over 10 cars and a whole-house generator. Perfectly positioned near waterfront dining, Long Island Sound beaches, championship golf courses, nature preserves, and the charming villages of Roslyn, Oyster Bay, and Locust Valley, this is a rare opportunity to own a timeless Gold Coast estate where exceptional craftsmanship, refined living, and today’s comforts come together in one extraordinary residence.

10 Overbrook Lane, Old Brookville

$2,799,000

Tucked at the end of a quiet cul-de-sac, this timeless contemporary sits on two perfectly level acres offering exceptional privacy and a deep, usable yard. The property features an in-ground heated pool with a waterfall and beautiful outdoor space ideal for gatherings or relaxation. Inside, the home provides plenty of opportunity with its dramatic ceilings and walls of glass that create a bright, open feel throughout. The sunken living room flows into a dining area with a wet bar. The first floor includes a spacious primary suite, a dedicated home office, and both formal and casual living areas—all thoughtfully laid out and generously proportioned. With its solid foundation and impressive architectural details, this home offers an incredible opportunity to update and customize to your personal style.

5 Beds ⋅ 4 Baths ⋅ 938081 MLS

Tucked at the end of a quiet cul-de-sac, this timeless contemporary sits on two perfectly level acres offering exceptional privacy and a deep, usable yard. The property features an in-ground heated pool with a waterfall and beautiful outdoor space ideal for gatherings or relaxation. Inside, the home provides plenty of opportunity with its dramatic ceilings and walls of glass that create a bright, open feel throughout. The sunken living room flows into a dining area with a wet bar. The first floor includes a spacious primary suite, a dedicated home office, and both formal and casual living areas—all thoughtfully laid out and generously proportioned. With its solid foundation and impressive architectural details, this home offers an incredible opportunity to update and customize to your personal style.

7 Pin Oak Court, Old Brookville

$2,199,999

Sprawling Brick Expanded Ranch in Prestigious Old Brookville! Welcome to this impressive custom-expanded ranch, rebuilt in 2001 and nestled on 2.2 flat acres in the heart of Old Brookville. Offering over 5,100 sq ft of living space, this 6-bedroom, 3.5-bath home combines generous scale with a versatile open floor plan—perfect for both everyday living and entertaining. Highlights include a large living room with fireplace that flows seamlessly into the gourmet kitchen featuring a center island with seating for 8 , Wolf stove, and Sub-Zero refrigerator. A beautifully crafted library with custom mahogany millwork and a second fireplace adds warmth and sophistication. A spacious laundry room with double washers and dryers adds convenience. The primary suite includes a walk-in closet and a roughed-in en-suite bath awaiting your vision to complete. Upstairs offers a large bonus room with a full bath and ample storage—ideal for guests, office, or recreation. Outside, enjoy a peaceful, private setting with a vinyl in-ground pool, expansive patio, and lush grounds. The home also has a partial unfinished basement. Endless potential.

6 Beds ⋅ 4 Baths ⋅ 959191 MLS

Sprawling Brick Expanded Ranch in Prestigious Old Brookville! Welcome to this impressive custom-expanded ranch, rebuilt in 2001 and nestled on 2.2 flat acres in the heart of Old Brookville. Offering over 5,100 sq ft of living space, this 6-bedroom, 3.5-bath home combines generous scale with a versatile open floor plan—perfect for both everyday living and entertaining. Highlights include a large living room with fireplace that flows seamlessly into the gourmet kitchen featuring a center island with seating for 8 , Wolf stove, and Sub-Zero refrigerator. A beautifully crafted library with custom mahogany millwork and a second fireplace adds warmth and sophistication. A spacious laundry room with double washers and dryers adds convenience. The primary suite includes a walk-in closet and a roughed-in en-suite bath awaiting your vision to complete. Upstairs offers a large bonus room with a full bath and ample storage—ideal for guests, office, or recreation. Outside, enjoy a peaceful, private setting with a vinyl in-ground pool, expansive patio, and lush grounds. The home also has a partial unfinished basement. Endless potential.

9 Chicken Valley Road, Old Brookville

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