luxury real estate for sale Oyster Bay, United States

Enjoy a relaxed, resort-style lifestyle at the exclusive Goldwynn Residences. This impeccably appointed 3-bedroom, 3-bathroom oceanfront residence is positioned along the pristine shoreline of Goodman’s Bay, offering breathtaking views over the infinity pool and the glistening turquoise waters beyond. Seamlessly blending elegance and comfort, this refined retreat embodies the essence of coastal sophistication in one of Nassau’s most coveted addresses. Signature Features • Prime oceanfront location overlooking Goodman’s Bay • Three spacious bedrooms, each with a private ensuite bathroom • Open-concept kitchen, dining, and living area with panoramic ocean views • Three private balconies offering sweeping vistas of the sea • Master suite with walk-in custom closet and oceanfront terrace • Separate laundry and utility room for convenience and function • Expansive covered patio ideal for alfresco dining and entertaining • Access to exclusive rooftop pool, gym, spa, and concierge services • On-site restaurant and take-out dining options • Undercover parking and 24/7 security Living & Dining Spaces The heart of the residence is its open-plan living, kitchen, and dining area—designed for modern luxury and effortless entertaining. Framed by floor-to-ceiling glass doors that open onto a sweeping oceanview balcony, this space invites natural light and gentle sea breezes. Whether hosting guests or enjoying a quiet morning, the ambiance is one of refined tranquility. Gourmet Kitchen The sleek, fully equipped kitchen is both functional and stylish, featuring high-end appliances, modern cabinetry, and seamless flow into the dining and living areas. Designed with both culinary enjoyment and social connection in mind, it’s the perfect centerpiece for island living. Bedrooms & Private Retreats Each of the three bedrooms is generously proportioned and elegantly finished, complete with its ensuite bathroom for ultimate privacy. The master suite is a sanctuary of its own, boasting a walk-in custom closet and direct access to a private oceanfront balcony—an idyllic spot to begin or end your day. Outdoor Living From the expansive covered patio, indulge in alfresco dining while taking in the vibrant hues of the ocean. The three private balconies throughout the residence offer multiple vantage points to enjoy the ever-changing seascape, from sunrise to sunset. Goldwynn Residences Amenities Living at Goldwynn means enjoying an exceptional array of private amenities. Residents have access to a rooftop pool and relaxation terrace, a state-of-the-art fitness center, a tranquil spa, a coffee lounge, and an oceanview restaurant. Whether dining downstairs or enjoying take-out in your residence, every day feels like a luxurious escape. This residence is offered in US$.

Welcome to 43 Highwood Road! A warm and welcoming 4 Bedroom, 4 Bath home, situated in the heart of East Norwich. This residence has been meticulously cared for with thoughtful improvements. In addition to an exceptional primary bedroom with ensuite and an expansive walk in closet, there are 3 generous sized bedrooms. The house highlights soaring vaulted ceilings and skylights, enhancing the open floor layout. The L-shaped living room and dining room features an inviting wood burning fireplace. The kitchen, complete with stainless steel appliances, boasts custom cabinetry and beautiful granite counters and backsplash. The inviting family room offers a wet bar for entertaining and sliders to the outdoor patio. The outdoor space is a tranquil retreat to take in the picturesque golf course views. Additional features include an attached one car garage, new driveway with ample parking, and a 4 zone in ground sprinkler system. Ideally located near historic Oyster Bay, boutiques, dining, beaches, park, and LIRR.

Beautifully renovated, this Farm Ranch with a lovely cedar exterior and octagonal covered porch is nestled on 2.77 magnificent acres. Featuring 4 bedrooms and 3 full bathrooms, this phenomenal residence boasts an expansive, bright and airy chef’s kitchen with a heated terracotta floor, pantry, quartz counters, farm sink, stainless-steel appliances with a pro-style range, large peninsula with seating, and a spacious dining area with a picture window overlooking the bucolic property. Relax in the adjacent family room that has a vaulted ceiling and rustic wood beams, a fireplace, and a built-in bar, ideal for entertaining. The master suite is spacious and has 2 walk-in closets, plenty of room for a home gym/office or a reading nook, 2 Juliet balconies, and a master bath with designer fixtures and fittings that offers a double vanity, soaking tub, and large shower. Additional bedrooms have plenty of natural light with ample closet space - 2 with vaulted ceilings and heated floors. The hall bathroom is updated with new tile and features a double vanity. Outside is tailor-made for entertaining with a large patio and charming porch. This extraordinary home is complete with radiant heat throughout the first floor, 5-zone heat, 2-zone air-conditioning, and Oyster Bay Cove deeded beach and mooring rights. Convenient to the Long Island Railroad, historic Oyster Bay's restaurants and shopping, as well as local parks and beaches which offer a myriad of boating options.

Welcome to 279 Hillcrest Lane — A Rare Gold Coast Retreat on Over 2 Private Acres Nestled in the prestigious Village of Upper Brookville on New York's storied North Shore, 279 Hillcrest Lane is a beautifully updated modified ranch offering the perfect blend of timeless elegance, thoughtful modern upgrades, and exceptional outdoor living. Set on over 2 park-like acres (87,133 sq ft) of lush, professionally landscaped grounds, this distinctive residence delivers the privacy, scale, and lifestyle that define Gold Coast living at its finest. Turnkey Peace of Mind. Major capital improvements have been recently completed, including a brand-new GAF Timberline HDZ roof with ice-and-water shield, new synthetic felt underlayment, new pipe flanges, hips, ridge, and re-counterflashed chimneys — backed by a 10-year workmanship guarantee and 30-year material warranty. A new above-ground oil tank rounds out the mechanical upgrades, offering efficiency and long-term confidence for the discerning buyer. Sophisticated Interiors. A grand living room with soaring ceilings and a stately wood-burning fireplace sets an impressive tone upon entry. The renovated kitchen features brand-new stainless steel appliances and flows seamlessly into the dining area and a sun-drenched great room, where expansive windows frame serene views of the manicured grounds. A versatile home office or den — complete with its own fireplace — offers a refined space for focused work or quiet retreat. Effortless Main-Floor Living. The main-floor primary suite is a true sanctuary, featuring a peaceful sitting area and a thoughtfully appointed ensuite with a double vanity and walk-in shower. A second full bathroom and laundry are also conveniently located on the main level. Upstairs, three generously proportioned bedrooms and a full bath provide comfortable accommodations for family or guests. An Outdoor Oasis. Step outside to a fully fenced backyard designed for both relaxation and entertaining. An in-ground pool, charming gazebo, and spacious circular driveway with ample guest parking create the perfect backdrop for warm-weather gatherings. A working garden with a rustic barn adds a distinctive, pastoral character — ideal for storage, hobbies, or imaginative use. Location. Situated minutes from top-rated schools, premier equestrian facilities, world-class golf and country clubs, fine dining, boutique shopping, and convenient access to major transportation routes into Manhattan. This is North Shore living at its very best. A rare opportunity to own a turnkey estate in one of Long Island's most sought-after enclaves — where privacy, prestige, and natural beauty converge.

Dam House is a magnificent 8.66-acre waterfront estate presiding over brilliant sunsets and water views of Beaver Lake. Completed in 1926, the masterfully designed six - bedroom Colonial residence has a refined elegance and timeless charm. It is complemented by expansive bluestone and red-brick patios, a four-bedroom cottage, a one-bedroom pool house, a sparkling swimming pool and a hard surface tennis court. Shade, specimen and flowering trees proliferate the captivating gardens. Manicured shrubs and flowering perennials add to the landscaped beauty. Additional amenities include an irrigation system, an outdoor fireplace, a vegetable garden, a root cellar and two enclosed dog runs with shelter. Full house generator for the main residence and a separate generator services the cottage. Attached two-bay garage and detached four-car garage. This property offers a luxurious lifestyle, in an idyllic waterfront setting.

273 Sugar Toms Lane, East Norwich, NY 11732

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

*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.

Welcome to 1007 West Shore Rd, Mill Neck, an extraordinary waterfront estate where timeless Neo-Classical architecture meets exceptional craftsmanship, with panoramic harbor views from nearly every room. Perched high above the waterfront on Long Island’s prestigious Gold Coast, this residence draws inspiration from the grand estates of ancient Greece and Rome. Defined by its striking symmetry, stately full height columns, elegant proportions, and refined architectural detailing, the home embodies a level of sophistication and permanence rarely found in today’s luxury market. A magnificent double height foyer welcomes you with soaring 12 foot ceilings and an impressive dual curved mahogany staircase, setting the tone for the grandeur that unfolds throughout this remarkable residence. Rich mahogany craftsmanship is showcased in every detail from the custom doors, staircases, intricate moldings, and built-ins to the distinguished executive library, complete with handcrafted millwork, a window seat, and exquisite 24-karat gold gilded details. Designed for both elegant entertaining and comfortable everyday living, the residence offers 8 bedrooms and 5 and a half luxurious custom marble bathrooms. The grand formal living room and oversized formal dining room are framed by breathtaking harbor views, while the dining room is enhanced by custom mahogany built-ins and hand-applied 24 karat gold leaf detailing. The spacious eat-in chef’s kitchen opens to a private deck and front balcony, creating the perfect setting to enjoy morning coffee while overlooking the sparkling waterfront. The inviting family room, executive library, powder room, and thoughtfully designed entertaining spaces complete the main level. The luxurious primary suite serves as a private sanctuary, featuring spectacular panoramic water views, generous walk-in closets including a cedar closet, and a spa-inspired marble bathroom complete with a steam shower, Jacuzzi tub, and refined finishes. The upper level offers 4 bedrooms, including the primary suite, with 3 bedrooms enjoying private en-suite marble bathrooms. An elegant sitting area overlooking the harbor and a secondary spiral staircase provide both beauty and convenience. The fully finished walk out lower level expands the home’s exceptional living space, offering 4 additional bedrooms, a full bathroom, an expansive recreation and living area, and direct access to the patio overlooking the picturesque English gardens and tranquil waterfront beyond. Every full bathroom is beautifully appointed with luxurious marble finishes, Jacuzzi tubs, and steam showers, reflecting the uncompromising attention to detail found throughout the home. Brazilian hardwood flooring, custom Marvin windows, smart thermostats, and a whole house AquaSure water filtration system further enhance both comfort and quality. Outside, the estate continues to impress with beautifully landscaped grounds inspired by traditional English gardens, multiple terraces and outdoor entertaining spaces, an oversized driveway capable of accommodating numerous guests, and an attached 3 car garage. Completed in 1993 and designed by a renowned Manhattan architect, 1007 West Shore Road is more than a home, it’s a legacy estate. Combining timeless Neo-Classical architecture, extraordinary craftsmanship, and one of Mill Neck’s most captivating waterfront settings, this is a rare opportunity to own a residence of enduring elegance, distinction, and unmatched beauty.

Enter the wrought iron gates 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.

Welcome to this pristine location in the heart of Oyster Bay Cove (GLENDALE ESTATES) where tranquility and privacy await on a spectacular 2.01-acre property. Surrounded by nature and mature landscaping, this spacious 5 bedroom, 3.5 bath residence offers endless potential to create the home of your dreams. Featuring generously sized rooms throughout, this home boasts a large primary suite complete with an oversized full bath, spacious secondary bedrooms, abundant closet space, and hardwood flooring. The inviting family room is highlighted by a stunning stone fireplace, creating the perfect gathering place for family and friends. Step outside to the expansive wood decking overlooking the peaceful backyard, ideal for entertaining or simply enjoying the serene surroundings. A full unfinished basement provides additional storage and possibilities for future living space. Being sold AS IS, this is a wonderful opportunity for buyers with vision to bring their personal touches and TLC to a home in one of North Shore's most desirable locations. Make this exceptional property your own and enjoy the lifestyle Oyster Bay Cove has to offer. OPEN HOUSE CANCELLED!

Steeped in architectural pedigree and timeless elegance, this extraordinary Muttontown estate, on 3.84 bucolic acres, was designed by renowned architect Marion Sims Wyeth, celebrated for his iconic work on Mar-a-Lago in Palm Beach. Privately tucked behind an impeccably landscaped half mile-long drive off Route 106, the property unfolds as a secluded North Shore sanctuary of exceptional beauty and distinction. Set amidst sweeping lawns, manicured gardens, and picturesque equestrian grounds, the stately brick residence, crowned with a slate roof and introduced by a charming courtyard entry, exudes enduring sophistication. Inside, grand formal entertaining rooms showcase exquisite millwork, original hardwood floors, dramatic wrought-iron railings, and an abundance of French doors that flood the interiors with natural light while seamlessly connecting the home to its breathtaking surroundings. Offering five bedrooms and five-and-a-half baths, the home masterfully balances grandeur with comfort. The formal living room, complete with a fireplace and built-in wet bar, creates an inviting setting for entertaining, while the sunlit breakfast turret and updated chef’s kitchen, appointed with premium professional-grade appliances, provide effortless everyday functionality. A spacious family room and elegant powder room complete the main living spaces. The first-floor primary suite serves as a luxurious private retreat, featuring dual full baths, a fireplace, expansive walk-in closets, and an intimate sitting room. The upper level offers two generously proportioned bedrooms and a beautifully appointed full bath with a thoughtfully separated vanity and shower area. Completing the space is an expansive unfinished attic, presenting exceptional potential for storage or future customization. Additional highlights include a walk-out finished lower level with laundry, bedroom with full bathroom and direct access to the attached two-car garage. Designed for both gracious living and sophisticated entertaining, the residence boasts expansive slate terraces spanning the length of the home, overlooking the stone courtyard driveway, private gardens, charming pergola, and in-ground gunite pool - evoking the romance and refinement of a storybook North Shore estate. A true horse property, the fully fenced equestrian amenities are equally exceptional, featuring a pristine multi-stall barn built-by Morton, thoughtfully designed grazing paddocks, and scenic walking trails woven throughout the grounds. A truly rare offering, this remarkable estate presents an unparalleled opportunity to own a significant piece of Long Island history, all within the esteemed Syosset Central School District.

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!

660 Chicken Valley Road , Locust Valley, Long Island Gold Coast Positioned within the most coveted enclave of Locust Valley on Long Island’s historic Gold Coast, 660 Chicken Valley Road is not merely a residence—it is a private estate of enduring significance, designed for a highly discerning buyer who values legacy, discretion, and uncompromising quality. Set across approximately 5.33 acres of secluded, manicured grounds and encompassing nearly 16,500 square feet of interior living space, the estate embodies a rare combination of architectural integrity, refined craftsmanship, and long-term asset strength—an offering seldom available in today’s market. Architectural Integrity & Engineering Excellence The residence far exceeds conventional residential standards, delivering exceptional structural durability and long-term stability. Every element—from roofing systems to drainage engineering, from acoustic insulation to thermal efficiency—has been executed to a near commercial-grade level, ensuring the property performs as beautifully as it presents over time. A fully integrated geothermal heating system, paired with advanced climate and humidity control, provides year-round comfort while preserving fine art, furnishings, and materials at an optimal level. Smart home integration allows full remote operation globally, supported by central vacuum, multi-zone climate control, and a whole-house generator—ensuring seamless living without compromise. Security and privacy are paramount, with dual gated access, an extended private drive, and discreet contingency features that elevate the estate to a level of true residential security. Interiors , Bespoke Craft, Quiet Luxury The interior experience is defined not by excess, but by precision. From hand-finished hardwood floors to finely executed crown moldings, each detail reflects a commitment to craftsmanship that is increasingly rare. The kitchen and service areas are appointed with best-in-class appliances—including Wolf, Sub-Zero, and Miele—integrated with custom millwork and carefully selected stone surfaces. These spaces function equally as a private culinary environment and a sophisticated setting for entertaining. The primary suite is conceived as a private retreat, featuring a fireplace, a fully appointed dressing room, and a spa-caliber bathroom with radiant heated floors, a freestanding soaking tub, and a multi-function shower system—delivering a daily experience of understated indulgence. Technology is seamlessly embedded throughout the home, integrating lighting, climate, and security into a unified system that supports effortless, modern living while preserving warmth and timeless character. Grounds , A Private Landscape of Distinction The estate grounds offer a level of scale and privacy rarely achieved. A defining feature is the approximately 2,000-foot cherry blossom-lined drive, creating a seasonal spectacle that transforms the approach into an experience of quiet grandeur—both cinematic and deeply personal. The landscape unfolds with expansive lawns, mature trees, and curated outdoor environments designed for both solitude and large-scale entertaining. Recreational amenities further enhance the lifestyle offering, positioning the estate as a true private resort. Location & Investment Perspective Locust Valley remains one of the most tightly held and supply-constrained markets on the Gold Coast. Properties of this caliber—combining land scale, construction quality, and privacy—are increasingly rare. This offering represents not only a primary or secondary residence, but a strategic long-term asset with strong preservation of value and generational appeal. 660 Chicken Valley Road is not defined by square footage alone, but by what it represents. It is a residence for those who understand that true luxury is not declared—it is recognized. Here, ownership is not simply acquired. It is inherited forward.

Welcome to 55 Pershing Avenue, ideally situated in the heart of Locust Valley. This charming two-story home offers a rare opportunity to own a piece of the North Shore's rich history while enjoying thoughtful modern updates throughout. The home features a newly renovated kitchen and updated bath, along with a spacious living room that flows seamlessly into the dining room, creating an inviting setting for both everyday living and entertaining. The lower level provides versatile bonus space, offering endless possibilities for a home office, gym, recreation room, or additional storage. Step outside to a fully fenced backyard oasis showcasing beautifully maintained gardens, a variety of mature roses, including modern, historical, and rare, hard-to-find varieties, and an abundance of perennial flowering shrubs. A detached garage provides exceptional flexibility and can serve as a workshop, hobby space, studio, or private office—an uncommon and valuable feature. Located within the highly regarded Locust Valley School District, this home is just moments from the village's charming boutiques, fine dining, beaches, arboretums, and the Long Island Rail Road, providing a convenient commute to Manhattan. A wonderful blend of character, comfort, and location, 55 Pershing Avenue is ready to welcome its next owner.

Spectacular Waterfront Retreat on 2 Verdant Acres This extraordinary 2-acre waterfront retreat is where privacy, elegance, and natural beauty come together in perfect harmony. Designed by Brian Shore, it extends over 360 feet of waterfront and was built to take advantage of the panoramic views of Cold Spring Harbor and the Long Island Sound. This magnificent Post Modern boasts seamless indoor-outdoor living with high ceilings and a spacious open floor plan filled with abundant natural light that streams through expansive windows. The great room has a vaulted ceiling with beams, a fireplace, and wall-to-wall windows framing incredible water views. Adjacent is the dining room and an open kitchen with professional-grade Wolf and Sub-Zero appliances, an ocean-hued backsplash, and nautical-inspired fixtures, forming the perfect coastal backdrop for the stunning vistas. Off the great room, there is a generous composite deck that spans the entire length of the house. The tranquil master suite has equally exquisite views and features 3 walk-in closets and an expansive master bath. On the walk-out lower level, a water-view family room is complemented by a study, two bedrooms, a full bath, a laundry room, and a beach shower. Property highlights include hardwood floors throughout the main floor, central vacuum, sprinklers, 4-Zone air-conditioning, a 3-car garage, and park-like property. Close to dining, shopping, beaches, parks, and LIRR. Whether enjoying sunrise views over the water, relaxing on the beach, or entertaining against a backdrop of spectacular scenery, this remarkable estate presents a rare opportunity to own a truly special waterfront property.

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.

Perched atop 3 magnificently landscaped acres in the prestigious waterfront enclave of Mill Neck, this extraordinary custom-built estate seamlessly blends timeless architecture, exceptional craftsmanship, and modern luxury. Built in 2014, the residence was thoughtfully designed to capture breathtaking panoramic water views of Oyster Bay Harbor, Cove Neck, Centre Island, and the Long Island Sound from nearly every room. Approached through a private gated entrance, the property is surrounded by lush manicured lawns, specimen trees, vibrant gardens, and an impressive collection of fruit-bearing trees, creating a serene estate like setting. The exterior showcases stunning Mediterranean travertine stone, Marvin storm rated windows with rich mahogany interiors, handcrafted imported Italian doors and hardware, a custom curved “Artistic” mahogany entry door, and a Ludowici terra cotta roof. Constructed on oversized Mat Foundations a superior structural system rarely found in residential construction, the home reflects an exceptional level of quality and engineering. Inside, soaring 25-foot ceilings, Brazilian cherry flooring, custom Wenge oak doors imported from Italy, exquisite Murano glass lighting, and walls of glass create an atmosphere of sophistication and grandeur. A magnificent one-piece custom made curved staircase serves as a striking architectural centerpiece, while every principal room is positioned to maximize the spectacular waterfront vistas. The chef’s kitchen is beautifully appointed with custom mahogany cabinetry, a spacious center island, premium appliances including Bosch, Wolf, BlueStar, Liebherr, and Sub-Zero, and a fully equipped butler’s pantry. Designed for both intimate gatherings and large scale entertaining, the home offers elegant formal and informal living spaces that flow seamlessly onto expansive terraces and wrap-around balconies overlooking the water. The residence features five spacious bedrooms and six bathrooms, including four full baths and two powder rooms. The first-floor primary suite serves as a private sanctuary with water views, a luxurious spa bath, radiant heated floors, and custom California Closets. Each additional bedroom is ensuite and enjoys its own private balcony, creating a unique retreat for family and guests alike. The walk-out lower level is an entertainer’s dream, featuring a custom wet bar with Sub-Zero refrigeration, ice maker, dishwasher, gas fireplace, temperature-controlled 1,200-bottle wine cellar with integrated cigar humidor, private guest suite, second laundry room, library, multiple storage rooms, and direct access to an oversized patio overlooking the serene waterfront setting. This smart home is equipped with Control4 automation, Lutron lighting, Sonos audio throughout all three levels and outdoor spaces, VMS security, intercom system, HEPA air filtration, whole-house dehumidification, nine-zone heating, nine-zone cooling, radiant heated bathroom floors, 400-amp electrical service, natural gas, irrigation supplied by a private well, greenhouse, copper gutters with dry wells, French drains, and a whole-house Cummins generator backup. Rarely does a residence combine such extraordinary construction quality, resort-style amenities, spectacular water views, and unmatched privacy. Located just 45 minutes from Manhattan, this exceptional Gold Coast estate represents a truly rare offering in one of Long Island’s most coveted waterfront communities.

An exceptional blend of modern luxury, chic design, and thoughtful functionality on 2+ spectacular acres. Featuring a 2-story foyer clad in crisp white millwork, this tastefully renovated Colonial boasts an expansive floor plan that includes an elegant formal dining room with a butler’s pantry and an airy formal living room with a lovely Palladian window and a fireplace. The layout is ideal for everyday living and entertaining, with an easy flow between the comfortable family room that features a vaulted ceiling with a 2nd fireplace and a chef-inspired kitchen that offers an oversized island, professional-grade stainless-steel appliances, designer tile, and a sunny breakfast area. A guest room, full bath, office/bedroom, gorgeous powder room with classic marble hex flooring, and laundry/mudroom are all conveniently located on the main floor. The 2nd floor houses a stunning master suite with a sitting area, 2 walk-in closets, a dressing space, and a spa-like bath with a soaking tub, plus there are 3 additional spacious bedrooms and 2 beautifully appointed full baths with premium fixtures and fittings. The finished lower level has high-coffered ceilings and offers extra space for a gym, recreation room, and plenty of storage. Surrounded by estate fencing, this resort-style backyard is a sanctuary designed with a heated saltwater pool, bluestone patio, a built-in BBQ and fridge, and a bar with seating. Just minutes to the Residents' Only Laurel Hollow Beach that offers kayak storage and mooring rights (with fee) and close to historic Oyster Bay and Cold Spring Harbor village parks, beaches, dining, and shopping. This exceptional smart home is complete with a brand-new 2-zone HVAC, whole-house UV air filtration system, central vac, myQ garage door openers, smart door access, Ring camera security system, sprinklers, a new well, and a 3-car garage. Easy access to NYC via the LIRR and centrally located to all major highways. An extraordinary setting and exquisite residence make this magnificent property the epitome of Gold Coast living.

Tucked away on Mill Neck Creek, the tranquil setting is a perfect place to enjoy the beauty of the waterfront landscape around this classic six bedroom brick residence with fabulous architectural details and woodwork throughout. Beginning in the resplendent Foyer, the expansive floor plan shows the sun-filled rooms polished to perfection. Gracious principal rooms such as the Living Room, Sun Room, Den and Dining Room provide the ambiance to entertain in large scale. The main floor primary suite with fireplace and views of the water offer two baths and a large dressing room. Two additional bedrooms are on the main floor with three bedrooms are located on the second floor. The eat-in kitchen marries form and function with a fabulous prep kitchen with top of the line appliances. Brick walled patios, bluestone walkways, vibrant gardens and an outdoor fireplace surround the home for enjoyment throughout the seasons. Off the Mudroom is an oversized three car garage. In warm weather, there is a heated pool with a brick patio enclosed by estate fencing. A separate two bedroom cottage and one car garage are a delightful bonus.