luxury houses with pool for sale Huntington, United States

Direct Waterfront Estate with 300+ Ft Deep-Water Dock Built in 2006 and crafted by renowned architect Oliver Cope with landscape design by Edmund Hollander and Kean Development, this 10,000± sq. ft. waterfront estate offers 6 bedrooms, 5 full and 2 half bathrooms, and sits on 2.35 acres of prime bay front with sweeping western exposure and panoramic views over Oyster Bay and Centre Island. At the water’s edge, a private 300+ ft deep-water dock (rebuilt in 2010) provides rare direct access for boating and yachting, anchoring the property as one of the most desirable on the North Shore. Expansive bluestone patios, manicured grounds, a covered patio, and a resort-style infinity-edge pool with spa capture breathtaking sunsets that paint the bay in spectacular color each evening. Inside, every detail has been elevated — from extensive custom millwork to soaring ceiling heights. A chef’s kitchen with a massive marble center island flows into both grand entertaining spaces and intimate sitting rooms. A stunning library with cathedral ceilings opens to a large balcony and a private home office. Throughout the home you’ll find six fireplaces, smart home technology with surveillance, a full-house generator, and bedrooms with private balconies overlooking the water. The primary suite is a true retreat, offering a spa bath, radiant heated floors, and an indoor-outdoor lounge for savoring the waterfront setting. Above, a third-floor widow’s walk rooftop terrace crowns the residence, delivering the ultimate vantage point with panoramic water views and endless sunsets. The full finished lower level offers a resort-quality experience with a fitness center, sauna, steam room, cabana bath/changing room, kitchenette, and media room. A detached four-car garage completes this world-class estate — a rare offering that combines architectural pedigree, modern luxury, and unmatched direct waterfront living in one of Long Island’s most coveted bay front settings.

Nestled on two beautifully landscaped acres in the Wawapek section of Cold Spring Harbor, this classic Colonial offers a rare combination of privacy, scale, and timeless appeal. Set on a quiet cul-de-sac, the property is thoughtfully designed for both everyday living and effortless entertaining. The home features five bedrooms and five and a half baths, with expansive windows throughout that fill each space with natural light and create a seamless connection to the surrounding grounds. Meticulously maintained, the interiors are warm and inviting, with generously sized rooms and a natural flow. At the heart of the home, a beautifully updated eat-in kitchen blends classic design with modern functionality, opening to sunlit living spaces that are both comfortable and refined. The outdoor setting is equally impressive, featuring a heated in-ground Gunite pool, a Har-Tru tennis court, and mature landscaping that provides exceptional privacy and year-round beauty. A rare opportunity to own a truly special property in the heart of Cold Spring Harbor. Listed at $3,950,000 with taxes of $48,776.28 Eagle Dock beach and mooring rights with fee. Broker Open House Monday 4/13 from 11-12.

Tucked away on four spectacular acres overlooking a tranquil freshwater pond, this extraordinary Cold Spring Harbor estate offers a rare balance of complete seclusion and effortless convenience. Hidden behind a gated entrance and surrounded by nature, the property evokes the feeling of a private country retreat while remaining just moments from the charming village, harbor, acclaimed schools, and every amenity that makes Cold Spring Harbor one of Long Island's most coveted communities.nExtensively rebuilt and expanded in 2019, the residence seamlessly blends timeless architecture with sophisticated modern design. A dramatic two-story foyer welcomes you into the heart of the home, offering stunning sight lines through the residence to the resort-like pool and picturesque grounds beyond. The magnificent two-story great room is centered around an impressive floor-to-ceiling stone wood-burning fireplace and flows effortlessly into the open-concept living and dining spaces, designer kitchen, and elegant bar area. Expansive windows flood the interiors with natural light while framing breathtaking views of the surrounding landscape.nDesigned for both grand entertaining and comfortable everyday living, the home offers an exceptional collection of gathering spaces. A dedicated first-floor media room with a 4K projector delivers an immersive cinematic experience, while the inviting billiard room features its own stone fireplace, reclaimed barn wood walls and beams, creating the perfect setting for entertaining. Modern conveniences include a Sonos sound system with integrated speakers in the kitchen, great room, and pool area, providing effortless indoor-outdoor enjoyment.nThe thoughtfully designed second level showcases rich walnut flooring throughout and is highlighted by the luxurious primary suite. A private sanctuary featuring soaring vaulted ceilings, oversized walk-in closets, a private balcony, and a spa-inspired en suite bath complete with a soaking tub, sauna, and refined finishes with the addition of seasonal water views of the harbor make this retreat truly exceptional. Five additional bedrooms and a conveniently located laundry room complete the second floor. Two of the secondary bedrooms are tucked away in their own private wing, separated by an inviting sitting area and served by a private rear staircase, creating an ideal layout for guests, extended family, or multigenerational living while preserving comfort and privacy.nThe outdoor living experience is equally impressive. A saltwater Gunite pool with a sunken spa is surrounded by lush landscaping and expansive entertaining spaces, offering the ultimate setting for relaxation. Gentle natural springs wind through the property, adding a peaceful soundtrack to this remarkable setting. A breezeway with double electric entry doors enhances both convenience and security to inner courtyard and three-car garage.nFinished with a classic cedar shingle roof and crafted with exceptional attention to detail throughout, this remarkable estate presents an exceedingly rare opportunity to own one of the North Shore's most private and captivating residences. Here, the sounds of flowing springs, the beauty of the freshwater pond, and an unparalleled sense of privacy create the feeling of being a world away yet the vibrant waterfront village and everyday conveniences of Cold Spring Harbor remain just minutes from your gate. 25A to Shore Road to Spring Street

Few properties can evoke as many emotions as this one of a kind. Completed in 2013, set in 8 landscaped acres in the heart of the luxury enclaved of Horseshoe Road, Chateau Sur L'Etaing is Gallagher Homburger Gonzales Architects' brand new estate complete with indoor pool, elegant pond, state of the art greenhouse and six-car garage. Informed by a classic aesthetic that reaches across centuries while embracing the best of what is contemporary, Chateau over the Pond is surrounded by flowering gardens timeless splendor as gracious elegance combines with stunning architectural details and cutting edge technology within the more than 23,000 SF residence on three level of living space. The building was designed with zero deflection with steel decks, double steel beams and concrete layered on each floor. Structural walls are 16 inches of reinforced concrete, rarely seen in residential grade structures.THE CHATEAUThis remarkable home features 7 fireplaces, both gas and wood, 7 bedrooms, 9 bathrooms and 2 powder rooms. Brazilian Cherry surrounds you and your guests as you entertain in this spacious, 12 foot ceiling first floor. Two chef kitchens and a 2,000 bottle wine cellar will set the stage for any occasion, large or small.Few homes can match the level of detail that are seen in every corner. Custom cut polished marble throughout the halls, radiant heat, hydraulic elevator, Savant Smart Home Automation and Lutron Home systems operate all controls with an iPad or iPhone.The fundamentals resonate here with relaxation in mind. Steam sauna in master bedroom, imported dry sauna from Finland, electronic shades in every room, outside garden, custom grilles throughout, indoor swimming pool which can be adjusted to any temperature has walls cut from Indiana Limestone and travertine marble on the floor and Jacuzzi area. A two-story greenhouse will surely be an oasis within overlooking a pond that awaits a skipping stone on a summers' eve.The finished basement features 10 foot ceilings with the finest quality of wall and ceiling moldings. A gym, spacious cedar closet, billiard room and home theater featuring 5 flat screens and 12 reclining leather chairs with an elegant bar that has an illuminated marble counter top and popcorn machine will keep your guests entertained day or night. All staff, handyman, gardener and painters are available upon request, as well as all the furniture. A private police village security patrols is also included.The house is situated in Mill Neck with many great schools, surrounded by golf courses including the world-renowned Bethpage Golf Course. Mill Neck has easy access to NYC via train or car and the Republic Airport (state of the art executive airport) is 20 minute door-to-door. NOTE: Showings by appointment only and furniture available upon request.OTHER AMENITIES8 AcresPond6 cars heated garage with two car lifts and plenty of storage space2 GreenhousesViews of Beaver LakeThe Village of Mill Neck is located on the North Shore of Long Island in the Town of Oyster Bay. Bounded by Beaver Lake, Mill Neck and Oyster Bay Harbor, Mill Neck is a residential village with prestigious and exclusive homes and a sense of tranquility. Some of Long Island's last remaining Gold Coast estates can be found in the Village of Mill Neck. Protected nature preserves and walking trails lend bucolic ambiance.Bordering Horseshoe Rd is the 37-acre estate of Soon Mei-Ling, the wife of Nationalist Leader Chiang Kai-Shek. Soon known as Madame Chiang Kai-Shek, moved to the United States in 1975, and settle in the Lattingtown estate that her husband purchased in 1949. It is said that the late leader bought the property because of the excellent harmonic Feng Shui, also known as Geomancy, in other words excellent living harmony that evokes wealth and prosperity!

Welcome to Williamsburg, an exceptional estate nestled on more than 4.8 private acres in the prestigious Village of Lattingtown. Built in 1991 and offering approximately 9,500 square feet of living space, this remarkable residence combines timeless elegance, impressive scale, and sophisticated comfort. A dramatic two-story foyer with a sweeping curved staircase introduces elegant interiors designed for both entertaining and everyday living. The home features gracious formal living and dining rooms, a spectacular family room with soaring ceilings, a private office/library, and abundant natural light throughout. Six spacious bedrooms and six-and-one-half bathrooms include a luxurious primary suite wing with a spacious bath and two oversized walk-in closets. Additional highlights include five fireplaces, including a striking double-sided fireplace shared between the living and family rooms, a wine tasting room and wine cellar, recreation room, full basement, walk-up attic, oversized attached multi-bay garage, slate roof, and 600-amp electric service. Resort-style grounds complete the offering with an in-ground gunite pool, tennis court, expansive lawns, and mature landscaping. A rare opportunity to own a distinguished North Shore estate offering exceptional privacy, scale, and lifestyle amenities.

Welcome to this spacious Colonial offering a versatile layout with 4 bedrooms and 2 baths. Set back from the road with a private frontage lane, the home enjoys added privacy and separation for additional off-road parking. A welcoming entry opens to a comfortable living room and steps up to the main family room which features a grand vaulted ceilings, hardwood floors, a brick gas fireplace, and an abundance of windows that fill the space with natural light, and an adjoining dining room perfect for everyday living and entertaining. The dining room flows seamlessly into the kitchen, complete with an Andersen sliding glass door to the backyard deck, and step down to the gracious eat-in kitchen area with a pantry closet, access to the attached garage and a side entrance to the yard. The second level features four bedrooms and a full hall bath. Additional amenities include central air conditioning, gas heat and cooking, an ADT security system, spacious one-car garage, and a basement offering laundry hookup, utilities, and storage. Set on a beautifully maintained .25-acre property, the backyard is designed for entertaining with a wood deck, cement and fieldstone patio, above-ground pool with built-in decking, 8 zone in-ground sprinkler system, and plenty of open space to enjoy. Located in the Huntington School District with low annual taxes of just $10,507.

Extraordinary Estate located in Laurel Hollow, NY! Discover unparalleled luxury and space at this one-of-a-kind estate nestled on 3.7 acres in Laurel Hollow. This magnificent 5-bedroom, 5.5-bathroom residence spans over 5,900 sq. ft. of living space, offering a seamless blend of elegance, comfort, and modern convenience. Step through the grand entrance, where a custom mural flooring sets the stage for the exquisite natural woodwork, cathedral-height ceilings, and oversized windows that flood the home with natural light. The main level boasts a sprawling eat-in kitchen, complete with abundant cabinetry, a breakfast bar, and high-end appliances, leading to a formal dining room, great room, and family room, all featuring large windows that showcase breathtaking views of the serene, expansive backyard. Whether in the kitchen, dining area, living room or great room, you’ll be surrounded by the beauty of lush landscaping, the outdoor kitchen, pergola, treehouse, playground, and Gunite pool with a diving board. A pool house and a wraparound deck further enhance the outdoor living experience, making this home an entertainer’s dream. Entertain effortlessly in the formal living room, family room, or the expansive great room, which features a balcony ideal for a library or office. A media room and two laundry rooms add to the home’s functionality. Designed for ultimate comfort and privacy, the home features a first-floor en suite bedroom, perfect for guests, while the second level hosts the grand primary suite, complete with a private office, walk-in closets, and a spa-like bathroom. Two of the additional bedrooms are unique duplex-styles on the main level, offering two levels of living space, while the fifth bedroom is also an en-suite. The walkout basement offers incredible flexibility, while the five car attached garage ensures ample parking and storage. Additional highlights include two wood-burning fireplaces, a central sound system, and extensive storage throughout. This extraordinary property is a rare find, offering a blend of sophistication, comfort, and endless possibilities. Schedule a private tour today to experience the unmatched charm of 121 Laurel Ln!

Situated within a private and prestigious community, 40 Coves Run has been thoughtfully expanded and updated by its current owners, offering exceptional space, comfort, and modern amenities. This impressive residence features 5 spacious bedrooms and 4.5 bathrooms designed for both elegant entertaining and everyday living. Upon entering, you are welcomed by a gracious living room and an expansive formal dining room. The sun-filled main living areas are open, airy, and seamlessly connected, creating an effortless flow throughout the home. At the heart of the residence is a spectacular chef’s kitchen featuring a large center island, high-end appliances, breakfast area and a walk-in pantry. The main level offers the convenience of three generously sized bedroom suites, including the luxurious primary suite. Upstairs, an open hallway overlooks the living space below and leads to two additional bedrooms, each privately situated on opposite sides of the home and featuring its own balcony. The fully finished Walk-Out lower level provides outstanding recreational space, including a game room, dance studio, recreation area, Gym, abundant storage closets, and utility space. The outdoor setting is a resort-like retreat. Enjoy a covered patio with a fully equipped outdoor kitchen, a heated in-ground salt water swimming pool, and a charming pool house and out door shower. A lit basketball court. Surrounded by lush, professionally landscaped grounds, this exceptional property offers the perfect blend of luxury, privacy, and indoor-outdoor living.

Discover the perfect blend of comfort, style, and functionality in this exceptional expanded Ranch, where a charming front porch welcomes you home and sets the stage for the warm, inviting living spaces within, all located in the Syosset School District. Thoughtfully designed with spacious sun-filled interiors, soaring ceilings, skylights, and dramatic walls of windows. An open layout connecting the dining and living room spaces features an impressive cathedral ceiling, exposed wood beam accents, custom built-ins and expansive windows. Filled with natural light and timeless architectural details, this inviting space is perfect for everyday living and entertaining. The gourmet eat-in kitchen is the heart of the home, featuring premium appliances, granite countertops, a generous center island, and abundant workspace for gathering with family and friends. The luxurious first-floor primary suite provides a private retreat with a cozy fireplace, spa-inspired bath, oversized room size closet, home office, and direct access to the backyard deck. Three additional bedrooms and two full baths complete the main level, while a private, spacious second-floor guest suite/playroom with its own bath offers the perfect space for extended family or visitors. The finished lower level expands the living space with a media room featuring a fireplace, fitness area, full bath, and outside entrance, creating endless possibilities for work, recreation, or multi-generational living. Designed for year-round comfort, this home also includes radiant heat, a whole-house generator, and a heated two-car garage with epoxy flooring. Step outside to your own backyard retreat with an expansive deck overlooking the heated inground gunite pool, surrounded by mature landscaping that provides beauty and privacy. Offering an incredible combination of space, quality, and amenities in one of Long Island’s most sought-after communities, this is an exceptional opportunity to own a truly special home just minutes from shopping, parks, transportation, and everything Syosset has to offer.

*527 Split Rock Road is a beautiful custom-built brick and stucco Colonial home set on 2 professionally landscaped, tranquil acres in the Syosset SD. Situated on a private road (off Split Rock Rd), the park-like lush property boasts a 250' driveway in a serene, private quiet setting. This approximately 5500 sq. ft house is set between the shops of downtown Syosset and the waterfront of Oyster Bay. The property is phenomenal, a year-round wonderland that offers spectacular sunrises in the backyard -- and picturesque sunsets glowing over the front lawn. Designed with an open floor plan, the heart of the house features a spacious country kitchen complete with Sub-zero refrigerator and high-end appliances, plus an adjacent multi-windowed dining area overlooking the stunning property. First floor includes formal dining room, bedroom, full bath, living room, grand foyer with soaring ceilings and sweeping staircase, den with cozy fireplace, luxurious powder room, laundry room and convenient back staircase for easy access to second floor. The second floor features a tremendous 2nd family room and additional room with French doors, perfect for another bedroom or office. 4 second level bedrooms include an expansive primary with a private balcony overlooking the grounds. This serene retreat includes a sitting area, dressing area, walk-in-closets and elegant, oversized, ensuite bath with soaking tub and spacious shower. 3 additional bedrooms share 2 well-appointed baths. The home features custom moldings, pristine hardwood floors and bespoke closets. The resort-like property features a spectacular 44'x22' saltwater, heated, gunite swimming pool with automatic retractable pool cover, expansive paver patios, lush specimen plantings, covered pergola BBQ area and additional deck off the kitchen/den. Unfinished basement with walk-out steps awaiting your design. The home is in the coveted Syosset School District, including Berry Hill Elementary School.

Tucked behind a private gated drive and set across over eight pristine acres, this iconic 1916 manor estate has been comprehensively restored and strategically enhanced to meet the expectations of today’s most discerning buyer. Historic architecture remains intact, while modern systems, technology, and amenities have been elevated to a truly exceptional level. Grand formal living and dining rooms feature museum-quality moldings and millwork, offering a refined backdrop for both intimate gatherings and large-scale entertaining. The gourmet kitchen is designed for serious cooking and seamless hosting, flowing naturally into the home’s main living spaces. A striking paneled library with wood-burning fireplace provides a moody, private retreat, while the showstopping 23’ x 44’ great room by Smiros & Smiros commands attention with 16-foot ceilings and a dramatic stone fireplace—engineered for memorable entertaining. The primary suite functions as a true private residence within the home, complete with a separate sitting room, coffee bar, and half bath, a spa-caliber marble bathroom with radiant heated floors, and dual dressing rooms. Five additional en-suite bedrooms, including a fully ADA-accessible suite, along with an office overlooking the gardens, complete the second level. Amenities rival those of a private resort, including a paneled elevator, indoor endless lap pool, catering kitchen, dog spa, a fully refreshed gym, and a discreet panic room / walk-in vault offering an elevated level of security. For the automotive collector, the estate delivers rare flexibility: a heated three-car garage with soaring ceiling heights designed to accommodate lifts for up to six vehicles, complemented by two additional single-car garages. The grounds are equally intentional. A new slate roof, heated gunite pool, Har-Tru tennis court with lighting (recently resurfaced and fenced), putting green, English gardens, playhouse, and curated outdoor lighting create a private, park-like setting designed for year-round enjoyment. Extensive masonry restoration, irrigation repair, landscape clearing, and exterior upgrades have been executed at scale. Behind the scenes, the home has undergone substantial systems modernization, including new and serviced HVAC, complete attic insulation, comprehensive electrical upgrades, restored fireplaces, upgraded pool infrastructure, a fully serviced gate and telecom system, and enterprise-grade security with AI-enabled cameras and property-wide WiFi coverage. The interior has been fully refreshed with newly painted finishes, refinished hardwood floors, custom window screens throughout, and exterior trim replaced with durable Azek for longevity. This is not simply a restored estate—it is a fully realized modern compound, where legacy architecture meets forward-thinking execution

Welcome to this exceptional 1893 architectural masterpiece -- the embodiment of Long Island's renowned Gold Coast. Once part of the historic Weir estate that encompassed multiple acres, this estate, now on just over 2 acres, and tucked away on a secluded hilltop sanctuary, offers the elegance of yesteryear, but with the updated amenities we all need today. Located in one of the North Shore's most charming and coveted neighborhoods, this stunning six-bedroom, six-bathroom residence offers more than 6,300 sq. ft of thoughtfully designed living space with a strong emphasis on privacy, comfort, and outdoor enjoyment. The cedar shake home features a slate roof and fieldstone accents that attest to its architectural heritage. Enter the home through a magnificent wood door enhanced with beautiful leaded windows into a spacious foyer with herringbone oak floors. The main level features a large Living Room with a fireplace and multiple sitting areas, as well as access to a patio beyond. A formal Dining Room, also with a fireplace, as well as a coffered ceiling, anaglypta wainscoting, elegant crown moldings and a hardwood floor sits on the other side of the foyer. The china pantry features wood cabinets that can hold numerous sets of china. The cozy Library will enchant with its floor-to-ceiling wall of bookcases. Beyond the Library one enters the updated and modern kitchen, which has green granite counters, and an abundance of efficient cabinets. Only the most modern appliances will be found here - a Wolf range, and a Fisher Paykel dishwasher, for example. Just beyond the kitchen proper, you'll find a climate-controlled wine room, as well as a large space for in - kitchen eating. The main floor also includes a sunroom off the Living Room, a Den with another fireplace off the Kitchen, and a Conservatory beyond that. The upstairs is reserved for sleeping. The Primary bedroom is the ultimate sanctuary, with a fireplace, an elegant marble bath, as well as a hallway of closets and a dressing room. Beyond that, there are five more bedrooms and four more baths, as well as a Craft Room. From the moment you arrive, the outdoor spaces command your attention with an almost theatrical flourish. Sweeping grounds unfold in every direction, offering a verdant tapestry of manicured gardens, and sun-drenched expanses that blur the boundary between curated landscape and natural splendor. This is not merely a yard -- it is a private domain designed for al fresco entertaining. Whether languishing by the heated saltwater pool, or reading a book by the firepit while overlooking the sumptuous grounds, there's a sense of calm and peace. And for those who love whimsey, the elevated tree house with its expansive decks and the charming playhouse offer additional pleasures. Beyond the property's own boundaries the surrounding community adds immeasurable dimension. The home sits across the street from the renowned Creek Club, and Bailey Arboretum is just down the street. The nearby village of Locust Valley offers a multitude of acclaimed restaurants and enchanting shops and the proximity to the LIRR ensures seamless connectivity to Manhattan. Families appreciate the convenience of acclaimed educational institutions situated just moments away reinforcing the neighborhood's reputation for discerning households who refuse to compromise on quality of life. This is Locust Valley at its most compelling -- where the prestige of a historic Gold Coast address converges with the warmth of a true family home.

Maison Blanche: An Architectural Icon in Upper BrookvillenExperience the pinnacle of ultra-modern luxury at 31 Chestnut Hill Drive. Set on five flat, private acres at the crest of a premier cul-de-sac, this architectural sanctuary was originally designed by the renowned architect Gary Gallagher and redesigned by award-winning FAIA architect Stuart Narofsky, leading to an extensively renovated (20232026) masterpiece.nnThe residence features six bedrooms with en-suite bathrooms, four additional half-baths, to include an expansive first-floor primary suite. Architectural highlights include two custom floating staircases with glass railings, porcelain and white oak floors, and frameless full-bodied Belldinni doors. The chefs kitchens in the main and guest houses are equipped with Wi-Fi-controlled Thermador appliances and specialty quartz islands.nnUniquely designed for wellness and entertainment, the second-floor features 3 bedrooms and a private gym and Finnish sauna, while the lower level boasts a Dolby-Atmos theater, wine tasting room, a yoga/massage spa, and a wet bar. Outside, a heated saline pool and spa are framed by a porcelain patio and an unobstructing glass railing, and an outdoor wet kitchen.nnApp-controlled for the modern age, the estate features smart management of the custom steel entry gate, five-zone HVAC, motorized shades, security, and a whole-house generator. This is the new standard of Gold Coast living. GPS. Off of Chicken Valley Rd.

Surrounded by the Long Island Sound on three sides, this extraordinary waterfront compound has defined the southern tip of Shippan Point for more than a century. Set on a private peninsula, it offers the rare privilege of watching the sun rise over the Sound and set back into the water with the Manhattan skyline shimmering in the distance. Designed by Hunt & Hunt Architects and completed in 1914 for inventor Thomas Robins, the main residence has been thoughtfully renovated and modernized throughout, including new electrical and plumbing systems, an expanded eat-in chef's kitchen, and beautifully reimagined open living and dining spaces designed for both grand entertaining and everyday living. Exceptional fixtures, finishes, and craftsmanship complement the home's historic pedigree, while every room is carefully oriented to capture sweeping panoramic water views. The main level is further enhanced by a stunning solarium with fireplace, offering a year-round retreat immersed in the surrounding waterfront landscape. The second floor is anchored by a newly improved primary suite featuring a private balcony with panoramic views across the gardens and Long Island Sound, a luxurious spa-inspired bath, and an expansive dressing room. Three additional bedrooms, a private office, and a versatile bonus room complete this level, providing exceptional flexibility for family living, guests, and work-from-home needs. A charming gatehouse with guest quarters above welcomes guests to the gated and professionally landscaped 1.67± acre property, where prominent rock outcroppings, manicured lawns, walking paths, and specimen trees create a spectacular waterfront setting. Private waterfront access accommodates kayaks and paddleboards, while a staircase on the opposite side of the property leads directly into the Long Island Sound, offering an exceptional setting for open-water swimming. Resort-inspired outdoor amenities are equally inviting, centered around a saltwater pool, pool bath, and a waterfront spa positioned to capture sweeping views in every direction. This remarkable estate offers an unparalleled lifestyle and endless opportunities for recreation, entertaining, and enjoying one of the most extraordinary settings on the Connecticut coastline.

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.nnHidden 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 Islands 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.nnThe 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.nnDesigned 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.nnOutdoor 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 estates serene natural surroundings.nnRarely does a property offer this level of acreage, architectural integrity, historical significance, and lifestyle versatility within one of the North Shores most coveted enclaves. Applewood Estate is not simply a home it is a private world crafted for legacy living, grand entertaining, and timeless retreat.

Picture Perfect in the Heart of North Syosset! Welcome to this extraordinary new construction set on a private acre in one of North Syosset's most desirable tree-lined neighborhoods. This Hampton-style Center Hall Colonial blends timeless architecture with today's most sought-after luxury amenities. A dramatic two-story foyer creates a stunning first impression, while the custom stone and shake exterior delivers exceptional curb appeal. Inside sun-filled spaces, soaring ceilings, wide-plank White Oak floors, custom millwork, and designer finishes showcase impeccable craftsmanship throughout. The heart of the home is a banquet-sized chef's kitchen featuring premium appliances, spacious walk-in pantry and seamless flow into the spectacular great room with a modern linear gas fireplace flanked by floating built-ins. Designed for both entertaining and everyday living, the thoughtfully crafted floor plan offers five en-suite bedrooms all with walk-in closets, including a first-floor guest suite with private terrace access. The luxurious primary retreat features a spa-inspired bath with two premium custom walk-in closets. Step outside to your private resort-style backyard, complete with an infinity terrace, heated pool and spa, sun shelf, and automatic retractable cover. Additional highlights include designer bathrooms, large mudroom, three-car garage, and a 10-foot basement with endless possibilities for customization. Located in the award-winning Syosset School District and just minutes from golf clubs, fine dining, shopping, and transportation, this exceptional residence offers the ultimate blend of luxury, comfort, and convenience! (virtually staged)

Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless elegance with modern comforts. A truly iconic Georgian estate nestled in the heart of Upper Brookville, this 17,587 square feet of total living space, this sprawling residence features 9 bedrooms, 9.555+ bathrooms, 10 wood-burning fireplaces, and exquisite architectural details, including vintage millwork, antique hand-painted wallpaper, and Samuel Yellin wrought-iron gates from the JP Morgan estate. Designed in 1924 by renowned architect James W. O’Connor and landscape architect Robert Ludlow Fowler, Gray Horse Farm is where classic architecture meets nearly 9 acres of pristine, equestrian-ready grounds. Perfectly suited for multigenerational living, the estate includes three separate guest/staff quarters (two 1-bedrooms and one 3-bedroom), offering privacy while staying connected. For those who love to entertain and enjoy the outdoors, the estate features a 20' x 55' heated saltwater pool with a pool house that's fully equipped, tennis and basketball courts, and a secret meditation garden you don't want to miss. For the car enthusiast there's a 7-car garage. Equestrian enthusiasts will appreciate the 3-stall stable, multiple paddocks, and run-in horse shed, all designed for top-tier country living. Additional highlights include a whole-house generator, —all just 27 miles from Manhattan. Whether you're seeking a premier equestrian retreat or an expansive generational compound, Gray Horse Farm delivers an unmatched lifestyle of luxury, privacy, and prestige. A rare offering close to top universities,marinas, beaches, golf, museums and americana shopping!

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.

Welcome to waterfront living at its finest in sought-after Dolphin Cove. Perfectly positioned on the Long Island Sound, this beautifully renovated 4-bedroom, 3.5-bath residence offers a rare blend of coastal elegance, modern luxury, and resort-style amenities. Extensively updated throughout, the home features a stunning custom kitchen with Sub-Zero, Wolf, Bosch, and Thermador appliances, custom cabinetry, designer finishes, and an open-concept layout ideal for entertaining. The first floor has been completely reimagined with new flooring, custom millwork, a bespoke bar with wine refrigeration, updated lighting, a redesigned fireplace feature wall, and enhanced sight-lines capturing water views from the moment you enter. The luxurious primary suite was fully renovated and includes a s inspired bath, custom closets, tray ceiling with lighting, marble shower, designer tilework, and refined finishes throughout. Additional improvements include new HVAC, interior and exterior paint, updated bathrooms, upgraded electrical systems, new front entry, landscaping enhancements, sprinkler system upgrades, and countless thoughtful upgrades throughout the home.

Some homes are built for the market. Others are built for a legacy. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering, and execution, where every material, finish, and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a façade clad in premium Thermory wood siding beneath a Spanish slate roof, an exterior that feels both grounded and enduring. Walls of Aluprof glass dissolve the boundary between interior and Long Island Sound, drawing light deep into nearly every principal room. The result is a seamless connection to the water, with unobstructed views that are impossible to replicate. Inside, large-scale radiant-heated Porcelanosa tiles grace the main and lower levels, setting a warm, modern foundation. At the heart of the home, a statement kitchen delivers both performance and presence, featuring custom Vimora cabinetry, top-of-the-line Gaggenau appliances, and a fully equipped secondary prep kitchen designed for effortless entertaining at scale. Upstairs, European white oak introduces warmth, while radiant heat continues throughout all main spaces and baths, reinforcing a consistent commitment to comfort and precision. The primary suite is conceived as a private retreat, oriented entirely toward the water. A fireplace anchors the space, while a private deck leads directly to the heated pool below. The bath offers a spa-like experience, featuring a sculptural soaking tub positioned toward the view and a separate steam shower. Custom Italian wardrobes complete the suite, incorporating bespoke detailing, opaque glass, and integrated features throughout. Additional bedrooms on this level are all en suite, each perfectly positioned to capture water views. The lower level opens into a fully realized entertaining environment featuring a wine room, fitness center with sauna, guest accommodations, and a dramatic lounge anchored by an illuminated marble bar and a 162-inch screen. A concealed underground car gallery, accessed by hydraulic lift, offers a discreet and highly engineered space designed for discerning collectors. Outdoors, an expansive terrace and heated waterfront pool overlook the cove, creating a setting defined by privacy and open water. Minutes from Tod's Point, Metro North, and the village of Old Greenwich, the property occupies that rare overlap of seclusion and convenience. With five bedrooms, five baths, and two powder rooms, every element has been resolved with intention. This is a rare chance to own a crown jewel waterfront property that stands in a league of its own. A defining waterfront residence where design, setting, and permanence align at the highest level.

Introducing An Unparalleled Masterpiece Of Luxury Living On Estate Suited For A Celebrity. This Prestigious And Exclusive Private Brick Compound Situated On 7 Acres Of Lush, Sprawling Grounds In Upper Brookville Offers A Lifestyle That Seamlessly Combines Timeless Elegance With Modern Luxury. Vaulted Ceilings, Creating A Sense Of Openness. Oversized Windows With An Abundance Of Natural Light & Panoramic Views Of The Property. 6 Oversized Bedrooms W/En-Suite Baths, 7 1/2 baths, Large EIK With Generous Counter Space & Storage. For The Car Lover Enthusiast W/10 Car Garage, Top-Of-The-Line Car Lifts & Car Port. Entertainers Exclusive Front & Backyard. Custom-Designed 22,000 Gallon Koi Pond With Thoughtfully Placed Stone Work, Fountains & Lighting. Newly Resurfaced Har-Tru Tennis Court, Gunite Heated Pool, 8 Person Hot Tub, Pool House W/Kitchenette, Full Bath & Changing Room. Custom Outdoor Kitchen, Premium Speaker System Both Inside & Out. Embrace A Lifestyle In Your Private Sanctuary! Google Maps, Waze

Set on five flat, impeccably landscaped acres at the end of a quiet cul-de-sac, this stately Georgian brick estate represents one of the most private and desirable settings within Upper Brookville’s prestigious gated Colonial Drive enclave. Positioned on a private road of distinguished luxury estates and further enhanced by its own secondary gated entrance, the property offers a rare double gated level of security and exclusivity. A grand double height foyer welcomes you, anchored by a magnificent Baccarat chandelier, immediately setting a tone of timeless elegance. The home is thoughtfully designed for both grand scale entertaining and comfortable everyday living, featuring 4 fireplaces, a formal living room, elegant dining room, refined library, and a luxury bar area. The main level includes two bedrooms with two full bathrooms nearby, ideal for guests or extended living, along with a fully equipped laundry room. At the heart of the home, the sun-drenched chef’s kitchen is enhanced by skylights and oversized custom windows, creating a bright and inviting atmosphere. Completed with premium appliances including a double wall Wolf oven, Wolf gas cooktop, and two Bosch dishwashers, breakfast nook and two pantries. The space seamlessly connects to the main living areas and opens to the patio, where retractable awnings provide effortless indoor to outdoor living. Upstairs, four spacious en-suite bedrooms include a luxurious primary suite featuring its own fireplace and a spa-inspired bath, offering a true private retreat. A Juliet balcony giving a view of serene front outdoor space. A finished attic adds a versatile open space suitable for a variety of lifestyle needs. The outdoor grounds are equally exceptional, showcasing expansive flat land, a heated gunite pool, tennis court, and multiple areas for entertaining and al fresco dining, all set within one of the most picturesque locations on Colonial Drive. Additional highlights include a finished basement with extra high ceilings, a whole house surround sound system, a recently updated roof (approximately 4 years old), and newer windows (approximately 1 year old). Updated Kitchen and bathrooms. Custom-made furnishings imported from Italy are included, further elevating the home’s refined aesthetic. This extraordinary estate seamlessly blends classic Georgian architecture with modern upgrades, offering unparalleled privacy, scale, and sophistication in one of the North Shore’s most coveted locations.

Idyllic Coastal Retreat on a Private Road Nestled on a private road in a serene and picturesque setting, this beautifully renovated four-bedroom, three-bath home offers the perfect blend of tranquility and convenience. Extensively updated in 2021, this move-in-ready residence features a spacious and light-filled primary suite with soaring cathedral ceilings, a comfortable sitting area, custom closets, and a luxurious new spa-inspired bath. Its generous layout also makes it ideal for a home office. Designed for both everyday living and entertaining, the home offers an open-concept eat-in kitchen, dining room, and living room centered around a wood burning fireplace. An adjacent sunroom provides a warm and inviting space to relax and enjoy the changing seasons. A first-floor guest bedroom with a private en-suite bath completes the lower level, offering comfort and privacy for visitors or multigenerational living. Two additional well-scaled bedrooms share a well-appointed bath, while the flexible floor plan delivers comfort and functionality throughout. Step outside to your private backyard featuring a beautiful swimming pool and bluestone patio — perfect for summer enjoyment and effortless entertaining. A rare opportunity to own a peaceful retreat with water views, modern updates, and an exceptional location.