luxury houses with terrace for sale Oyster Bay, United States

Move-in ready Colonial charm meets classic North Shore character. Outside, natural stone steps lead into a serene backyard retreat. Inside, gleaming hardwood floors run throughout, brightened by an abundance of natural light. The main level flows effortlessly from the entry into an open living space that includes a spacious living room, a dining room, and a full bathroom. The fully updated kitchen features elegant wood cabinetry, a chef’s countertop, a classic beadboard backsplash. Stainless steel appliances include a gas range, microwave, and dishwasher. Upstairs, three comfortable bedrooms and a second full bath complete a floor plan perfectly suited for everyday living. A large finished basement with laundry facilities and a full attic provide ample storage and excellent room to expand. The entire house has been fully updated and freshly painted, making it truly turn-key. Village shops, the waterfront, and Oyster Bay’s historic downtown are all within easy reach, with beautiful North Shore parks and LIRR access nearby.

Introducing 31 Chestnut Hill Drive, an extraordinary contemporary estate situated on five private acres at the end of a prestigious cul-de-sac in Upper Brookville. Originally designed by renowned architect Gary Gallagher and comprehensively reimagined from 2023 to 2026 by award-winning architect Stuart Narofsky, this exceptional residence seamlessly blends striking modern architecture with sophisticated design, cutting-edge technology, and resort-style amenities. Spanning over 10,000 square feet, the home features six bedrooms, six full and four half bathrooms, including a luxurious first-floor primary suite. Dramatic architectural details, including two custom floating staircases with glass railings, expansive walls of glass, porcelain flooring, and polished white oak floors, create a remarkable sense of openness and light. Thoughtfully designed living and entertaining spaces are complemented by a state-of-the-art chef's kitchen featuring custom cabinetry, integrated Thermador appliances, specialty quartz countertops, and an expansive center island. The home's extensive accommodations include multiple home offices, a library, and beautifully appointed guest suites. The fully finished lower level offers an exceptional collection of recreational and wellness amenities, including a Dolby Atmos home theater, custom wine room and tasting area, wet bar, fitness room, Finnish sauna, and dedicated yoga and massage space. Outdoors, the estate unfolds into a private resort-like setting, complete with a newly rebuilt heated saline pool and spa, expansive porcelain patios, and a fully renovated guest/pool house with its own kitchen. An outdoor kitchen and beautifully landscaped grounds provide an ideal setting for both intimate gatherings and large-scale entertaining. Additional highlights include a heated four-car garage, five-zone energy-efficient climate control, whole-house generator, and comprehensive smart-home technology managing lighting, security, motorized shades, and numerous additional systems. Offering exceptional privacy, architectural distinction, and an extraordinary level of modern luxury, 31 Chestnut Hill Drive represents a rare opportunity to experience contemporary estate living on Long Island's Gold Coast.

Welcome to 92 School Street, a charming three-bedroom, one-and-a-half-bath home in the heart of Oyster Bay. Pale green clapboard siding, matching shutters, and a welcoming covered porch give the move-in-ready Colonial classic North Shore character. In back, the expansive yard offers a brick patio, dog run, lawn, and a substantial shade tree. A quieter secondary yard sits just steps beyond, framed by fencing and greenery. Inside, gleaming hardwood floors run throughout, brightened by natural light. The main level flows easily from the entry into open living space that includes a living room, dining room, and half bath. The kitchen is fully updated with light wood cabinetry, chef’s counter, a beadboard backsplash, and under-cabinet lighting. Stainless appliances include a gas range, microwave, and Bosch dishwasher. Upstairs, three bedrooms and a full bath complete a floor plan well suited to everyday living. A large basement with laundry and a full attic add ample storage and room to expand. The house is move-in ready being recently painted . Village shops, the waterfront, and Oyster Bay’s historic downtown are all within easy reach, with North Shore parks and LIRR access nearby.

Privately set on more than two beautifully landscaped acres and perfectly situated at the end of a quiet cul-de-sac, in the coveted enclave of Oyster Bay Cove, within the Syosset School District. This exceptional Tutor residence embodies the elegance, craftsmanship, and timeless appeal of Gold Coast living. Framed by mature landscaping and expansive grounds, the property offers an extraordinary private retreat with an in-ground heated saltwater pool, tennis court, and an expansive mahogany deck, creating an idyllic setting for both grand-scale entertaining and relaxed summer living. Inside, refined architectural details and custom craftsmanship define the gracious interiors. Rich custom molding complements the home's distinctive Tudor character, while two impressive stone fireplaces anchor the living spaces. The elegant living room is enhanced by a dramatic cathedral ceiling and stone fireplace, while the sophisticated den features custom built-in cabinetry and its own handsome fireplace, creating an inviting retreat for quiet evenings or intimate gatherings. The spectacular chef's kitchen is both beautifully appointed and designed for entertaining, showcasing custom black oak cabinetry, a stone farm sink with Waterworks brass faucets, and brass pot filler, and a substantial center island with a dramatic waterfall edge, quartz countertops, a professional Thermador gas range, and an additional double wall oven. The adjacent banquet-size formal dining room provides an elegant backdrop for hosting memorable occasions. The second floor is devoted to comfort and privacy. The luxurious primary suite features cherrywood hardwood flooring, two oversized outfitted closets, and an expansive marble bath with radiant-heated floors, a French provincial-style double-sink vanity, and a sculptural freestanding copper soaking tub. Three additional bedrooms, two bedrooms that share an adjoining full bath with a central shower and separate vanity, sink and toilet area on either side, plus an additional hall bathroom complete the second floor. Beyond the interiors, the grounds unfold as a private resort-like sanctuary. The expansive mahogany deck features a comfortable pergola with an outdoor television, creating an inviting outdoor living space for al fresco dining, entertaining, and relaxed summer evenings overlooking the pool and beautifully landscaped grounds. A private tennis court extends the resort-like amenities, offering enjoyment well into the evening. A three-car garage, full basement, and a Generac whole-house generator complete this offering. Featuring six bedrooms, four full and two half bathrooms, exceptional architectural character, and an array of indoor and outdoor amenities, this remarkable home presents a rare opportunity to experience the allure of Long Island at its finest. Located close to transportation, shopping, fine dining, and all the North Shore has to offer. Syosset School District | Berry Hill Elementary | South Woods MS.

Set on a gentle knoll and approached by a circular driveway, this expansive Farm Ranch offers exceptional privacy, beautifully appointed interiors, and resort-style outdoor amenities. A vaulted Entry Foyer with marble flooring opens to Formal Living and Dining Rooms featuring detailed molding, hardwood floors, large windows, and tray ceiling . The inviting Family Room boasts a natural sandstone wood-burning fireplace, beamed cathedral ceiling, three skylights, and French doors flanking the fireplace leading to the outdoor patio. The Eat-In-Kitchen features white cabinetry, wood floors, Carrera marble countertops, and a six-burner Thermador cooktop. A convenient pantry area leads to laundry space and garage access. A luxurious Guest Suite includes a spacious Bedroom, recently tiled private Bath, and a large Living Room. The Primary Suite offers Brazilian cherry floors, double closets, a walk-in closet and a spa-like porcelain bath with river rock shower, double vanity and soaking tub. Two additional Bedrooms share a large hall bath. The second floor adds a spacious bedroom, full bath and expansive Media Room with vaulted and beamed ceiling and skylight. The serene private grounds feature a heated vinyl pool, outdoor covered service area with refrigerator and ice maker, expansive decking and patio - create an exceptional setting for entertaining and relaxed summer living.

This magnificent Hamptons-style shingle and stone Center-Hall Colonial sits on 2 professionally landscaped acres, offering refined luxury and seamless indoor-outdoor living. The spectacular 2-story foyer with a curved staircase leads to formal spaces—a stately dining room with a butler’s pantry and wine refrigeration, and an elegant living room featuring a coffered ceiling, fireplace, and bay window. The heart of the home is the spacious great room, anchored by a fireplace with built-in shelving and sliding doors to the patio. French doors reveal a private study with rich wood paneling. The stunning chef’s kitchen features bespoke inset cabinetry, a premium designer backsplash, and a massive marble island. Professional-grade appliances from Thermador, Wolf, and Sub-Zero ensure peak performance, complemented by a walk-in pantry, breakfast area, laundry room, and 2 tastefully appointed powder rooms. The expansive master suite is a tranquil sanctuary boasting a tray ceiling, an incredible walk-in dressing room with a custom closet system, and a spa-inspired bath with a freestanding soaking tub, large shower, and radiant-heated floors. The remaining bedrooms offer private en-suites and convenient Jack-and-Jill layouts, all with generous closets. A beautifully finished bonus space complete with an additional bedroom and full bath is ideal for guest stays. The finished walk-out lower level is an entertainer's dream with high ceilings, a full secondary kitchen serving the pool, a recreation room, home gym, temperature-controlled wine cellar, state-of-the-art movie theater, game room, and full bath. Outside, resort-style grounds feature a sparkling pool and multi-level bluestone patios. Modern comfort is ensured by a 6-zone HVAC, security system, and central vacuum. Near the historic towns of Cold Spring Harbor, Oyster Bay, and Huntington, this home is close to upscale shopping, fine dining, the LIRR, and the Oyster Bay Cove Residents' Beach. Entirely turnkey, this Gold Coast estate masterfully blends timeless character with today’s amenities.

Stately Postmodern Brick Colonial, Tall Oaks, Oyster Bay Cove. Poised on two exquisitely manicured acres within the storied enclave of Tall Oaks, this majestic almost 6,200 sq.ft brick colonial stands as a masterwork of scale and sophistication, gracefully sited within the coveted Cold Spring Harbor School District. A dramatic two-story entry foyer sets the tone, opening onto a sun-drenched, free-flowing floor plan where oversized rooms and soaring floor-to-ceiling windows frame the surrounding landscape like living art. Rich hardwood floors unfurl throughout six sumptuous bedrooms and six-and-a-half baths, each detail composed with quiet refinement. The main-floor primary suite is a study in indulgent privacy — a serene retreat appointed with a spa-caliber bath offering both soaking tub and glass-enclosed shower, with direct access to the pool and grounds beyond, and an adjoining annex effortlessly adaptable as a nursery, study, or private fitness room. Five additional en-suite bedrooms lend graceful accommodation to family and guests, while a mezzanine level reveals its own secluded en-suite bedroom paired with a generous sitting room - an inspired retreat for extended stays. Beyond, the grounds unfold in quiet splendor: an inground saltwater pool, sweeping patios, and a built-in BBQ set the stage for effortless, elegant entertaining amid lush, professionally curated gardens. Below, a capacious finished lower level opens through full sliders to the side yard, with additional unfinished space affording abundant storage. An extraordinary residence, distinguished by pedigree and place, in one of the North Shore's most rarefied addresses. Taxes $36,582 including Village

Built in 2001 and privately set on five pristine acres, this extraordinary estate is a residence of rare character and enduring elegance, blending old-world craftsmanship, architectural drama, and gracious modern living. From richly detailed formal rooms to expansive spaces designed for entertaining, every level reveals another layer of thoughtful design. The home makes an immediate impression with a distinguished foyer featuring classic checkered flooring, where graceful archways establish a sense of symmetry and sophistication. Beyond, the formal living room is beautifully appointed with intricate hardwood floors, a marble fireplace and mantel, and French doors opening directly to the terrace, creating an effortless connection between the interiors and gardens. A formal office boasts distinguished rich hardwood paneling, an intricately finished plaster ceiling, and its own wood-burning fireplace. The formal dining room is equally refined, framed by substantial moldings and anchored by another fireplace—an elegant setting for both intimate dinners and grand-scale entertaining. One of the home's most memorable architectural moments is a discreet curved staircase leading to the dramatic family room. Here, soaring vaulted ceilings, exposed wood beams, and a monumental stone fireplace create a remarkable sense of scale. A concealed door reveals a private wet bar, adding an unexpected and sophisticated element for entertaining. The kitchen and service areas have been conceived with both beauty and function in mind. A handsome butler's pantry features a hand-painted tile backsplash, marble countertops, and abundant preparation space. The expansive farmhouse-inspired eat-in kitchen is finished with warm terracotta floors, two porcelain farmhouse sinks, oversized chef's appliances, a substantial center island, and a sun-filled breakfast area overlooking the grounds. A pantry and discreetly positioned powder room are located just off the kitchen, while a circular rear staircase provides convenient access between levels. A separate side entrance opens to a practical mudroom with an additional service pantry, complete with sink and refrigerator. Ascending to the second floor, an oval wood architectural ceiling crowns a gracious landing overlooking the level below, creating a striking transition to the private bedroom quarters. The secondary accommodations include four generously proportioned bedrooms, one with its own loft space, each appointed with a marble en-suite bath. Near the rear-stair landing, a convenient preparation or household station with sink adds functionality, while a private office provides a dedicated workspace. The primary suite is an extraordinary private retreat. Generous in scale and beautifully secluded, it offers separate dressing rooms and walk-in closets, along with a spa-inspired bath featuring a jetted soaking tub and oversized walk-in shower. An adjoining sitting room creates a quiet sanctuary, with access to a walk-up attic offering additional possibilities. The lower level rivals the principal entertaining spaces in both scale and amenities. Remarkably high ceilings enhance an expansive den and recreation area, complemented by a powder room, full bar, billiards and game room, wine cellar, professionally matted gym, and an impressive 15-seat private theater. Two additional staff or guest rooms, supported by two full baths, complete this exceptionally versatile level. Across the estate's five pristine acres, the grounds unfold as a private resort. Expansive slate and brick terraces provide multiple settings for dining and entertaining, while covered patios framed by graceful archways offer shaded retreats overlooking the property. Beyond, a swimming pool and spa form the centerpiece of the property's recreational amenities, accompanied by a substantial, one-of-a-kind pool house that further elevates the estate's resort-like appeal.

This beautifully reimagined Colonial blends historic Oyster Bay character with the comfort and sophistication of extensive modern updates.Thoughtfully renovated throughout, the home features comprehensive interior and exterior improvements while preserving the warmth and character of its original architecture. Wood floors flow throughout the home, complemented by Andersen windows that bring in abundant natural light. The beautifully updated kitchen is appointed with Viking stainless steel appliances, custom cabinetry and designed for both everyday living and entertaining. With four bedrooms and three full baths, the home offers a flexible and well-proportioned layout suited to today’s lifestyle. A newly fully fenced backyard, landscaping and patio are an ideal setting for outdoor dining, entertaining, or simply relaxing at home. Sprinklers throughout the property. A rare opportunity to enjoy the character of a classic Oyster Bay Colonial with the benefit of extensive modern updates, all within one of Long Island’s most storied villages.

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.

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.

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.