luxury real estate for sale Oyster Bay, United States

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.

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

Perched above Oyster Bay Harbor on 4.04 private acres in the heart of prestigious Mill Neck, resides this exceptional estate. Framed by panoramic views of Oyster Bay Harbor and Centre Island, this beautifully renovated six-bedroom residence showcases timeless design, refined craftsmanship, and curated modern updates throughout. Every space has been thoughtfully designed to celebrate its breathtaking surroundings, where expansive walls of glass blur the line between indoors and out while filling the home with natural light. Rich mahogany custom millwork, white oak inlay flooring, and elegant architectural details create an atmosphere of warmth and sophistication, while beautifully proportioned living and entertaining spaces offer both comfort and effortless elegance. At the heart of the home, the chef's kitchen is as functional as it is beautiful, featuring custom white cabinetry, striking quartzite countertops, elegant brass accents, and picturesque harbor views. A renovated sunroom, spa-inspired primary suite, radiant heat floors, updated baths, an expansive mudroom, and a summer kitchen further elevate the home's exceptional lifestyle, seamlessly extending to Brazilian IPE decks/terraces designed for outdoor entertaining. Thoughtfully modernized for today's discerning buyer, the residence features commercial-grade heating and cooling, eight-zone HVAC, over 100 new windows, a newer roof, an automatic sprinkler system, and three two car garages. Owned solar panels enhance the home's energy efficiency, while a Tesla battery backup provides reliable peace of mind with the ability to power the residence for approximately three days during an outage. Surrounded by the natural beauty of Long Island's Gold Coast and just moments from charming villages, waterfront dining, boutique shopping, beaches, and clubs, this extraordinary estate offers a rare combination of privacy, sophistication, and breathtaking water view vistas.

Discover one of North Syosset’s most exceptional new-construction residences. Privately positioned at the end of a tranquil cul-de-sac, this magnificent home is surrounded by nearly two secluded acres and backs an untouched nature preserve, offering an extraordinary combination of privacy, architectural grandeur, and modern luxury. Encompassing approximately 10,800 square feet, including a fully finished lower level, with approximately 7,800 square feet above grade, the residence has been thoughtfully designed for sophisticated entertaining and comfortable everyday living. The impressive floor plan features six bedrooms, six-and-a-half bathrooms, multiple laundry rooms, a four-car garage, and generously proportioned living spaces throughout. At the heart of the home is a spectacular, sun-filled great room where dramatic scale, refined design, and serene views of the surrounding natural landscape create an unforgettable setting. This remarkable property presents a rare opportunity to own a newly constructed estate offering exceptional space, privacy, and luxury in one of Long Island’s most sought-after communities.

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.

Set behind gated access on over 10 breathtaking acres, this extraordinary estate embodies timeless luxury, exceptional craftsmanship, and effortless livability. A sweeping drive, interlocking stone walkway, and stately covered entrance create an impressive arrival, while beautifully appointed interiors offer warmth, sophistication, and abundant natural light. Designed with both grand-scale entertaining and comfortable everyday living in mind, the residence features 8 bedrooms, 6 full baths, and 3 half baths, including a thoughtfully positioned first-floor guest wing offering privacy and convenience. Rich wood detailing, custom built-ins, marble finishes, and expansive windows are found throughout. A handsome wood-paneled library and bespoke study evoke classic old-world elegance, while gracious entertaining spaces flow seamlessly from one to the next. The beautifully appointed dining room is highlighted by a dramatic floor-to-ceiling bowed window that fills the space with an abundance of natural light. An adjoining wet bar leads seamlessly to the chefs's kitchen, where an oversized center island, breakfast bar, state-of-the-art appliances, and extensive prep areas create an exceptional setting for everything from intimate gatherings to large-scale entertaining. An impressive array of lifestyle amenities includes a custom dance and ballet studio, expansive fitness space, resurfaced tennis court, and spectacular in-ground Gunite pool surrounded by mature trees and private lounging areas. A raised stone patio provides an elegant setting for outdoor dining and entertaining, while an attached pool cabana room with its own bathroom offers exceptional convenience and a seamless connection to the pool and outdoor living areas. From spa-inspired baths and sun-filled sitting rooms to multiple garages and extensive parking, every detail of the remarkable estate has been thoughtfully considered. Sophisticated without feeling formal, the property offers exceptional privacy, gracious proportions, and resort-style amenities in a truly magnificent setting.

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.

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

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.

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.

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.

Set on a quiet cul-de-sac in desirable North Syosset, 1 Ryan Court offers an exceptional blend of space, privacy, and outdoor living. Situated on a generous quarter-acre lot within the renowned Syosset School District, this 3-bedroom, 2.5-bath residence offers an expansive multi-level layout with generously sized living spaces designed to accommodate a variety of lifestyles. Step inside to a bright and welcoming interior where natural light fills the home throughout the day. Oversized windows in the living and dining rooms create an airy atmosphere, while rich hardwood floors add warmth and timeless appeal. The thoughtfully designed floor plan offers spacious, comfortable rooms with an effortless flow, making the home equally suited for everyday living and entertaining. The well-appointed kitchen features a Sub-Zero refrigerator, professional stainless steel gas range with exhaust hood, double ovens, extensive cabinetry, and sliding glass doors leading directly outdoors. Step outside to an impressive private retreat featuring a brand-new Trex deck with multiple areas for dining, relaxing, and entertaining. The spacious backyard includes a large in-ground pool, outdoor kitchen area, and a beautiful koi pond with a cascading waterfall, creating a peaceful and distinctive outdoor oasis. Additional features include a two-car garage, dedicated laundry area, and abundant closet and storage space. Located on a quiet private court while remaining conveniently close to shopping, dining, train station, and everyday conveniences, this home offers the perfect combination of tranquility and accessibility. With its spacious interior, exceptional outdoor amenities, and highly sought-after North Syosset location, this is an opportunity not to be missed.