luxury houses with pool for sale Southold, United States

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

Discover a rare and compelling offering on Shelter Island where historic character and modern sophistication exist in perfect harmony. 7 Stearns Point Road presents a unique opportunity to live expansively-either as a private family compound or as an owner-occupied five-bedroom Bed & Breakfast. The residence is set on 0.70 acres in the heart of Shelter Island Heights, just moments from Crescent Beach and Sunset Beach. Spanning approximately 5,838 square feet, with an additional 2,588-square-foot full-height basement, the home seamlessly blends timeless architectural details with contemporary comfort. Arranged across two distinct structures connected by a covered breezeway, the property's nine bedrooms and nine bathrooms are thoughtfully distributed between the original Annex-offering seven bedrooms-and a recently completed extension featuring two additional ensuite bedrooms. The new wing is further distinguished by a dramatic double-height living area and a dedicated wellness room, equally suited for private residential use or boutique hospitality. Generous entertaining spaces include two living rooms and a well-equipped kitchen designed to accommodate both intimate gatherings and larger-scale hosting. Outdoors, the grounds evoke a private resort atmosphere, featuring a heated 40' x 18' gunite pool, mature landscaping, and multiple areas for relaxation and entertaining. Two separate driveways provide added convenience and privacy for owners and guests alike. With zoning and approvals allowing for an owner-occupied five-bedroom Bed & Breakfast, along with the benefit of an existing liquor license for guest use, the property offers a rare level of versatility. Whether envisioned as a legacy family retreat, a refined island escape, or a boutique hospitality venture, the possibilities are both flexible and compelling.

Architecturally distinctive and deeply connected to its coastal setting, 126 South Midway Road is a private compound that captures the spirit of Shelter Island's artistic legacy. A private sanctuary comprising a four-bedroom main residence, a dedicated large art studio, and an independent two-bedroom casita, the property is thoughtfully arranged to maximize natural light, privacy, and sweeping water views. The architecture recalls relaxed modernism of iconic beach houses, an approach rooted in simplicity, creativity, and a fluid relationship with the landscape. Clean lines, a sleek pool and an intuitive indoor-outdoor flow create spaces that feel both intentional and effortlessly livable, ideal for a design-minded coastal lifestyle. The separate studio enhances the compound's creative sensibility, offering a quiet, light-filled environment for work or reflection, while the two-bedroom casita provides comfortable, private accommodations for guests or extended stays. Together, the structures form a cohesive yet flexible retreat, equally suited to intimate living and hosting. Comprised of 3,400 sq. feet living space across 3 levels in the main house plus additional storage, an expansive art studio of 1,400 sq. ft and 2-bedroom Casita living 1,140 sq feet with multiple decks and outdoor entertaining spaces this incredible compound is moments from Wades Beach. The property offers a rare combination of architectural character and proximity to one of Shelter Island's most celebrated shorelines. Longtime Shelter Island residents David Rankin OAM and Lily Brett OAM, both internationally recognized for their contributions to the visual arts and literature, have stewarded the home with a deep appreciation for creativity and place. (OAM denotes the Order of Australia Medal, a national honor recognizing distinguished contribution.) A compelling offering for those drawn to thoughtful design, privacy, and coastal modernism, 126 South Midway Road is a singular Shelter Island retreat.

A masterful blend of timeless character and elevated modern luxury, this designer-renovated Shelter Island residence delivers a curated living experience across more than an acre of lush, private grounds. Every space has been thoughtfully reimagined with bespoke finishes, high-end materials, and a refined aesthetic that feels both effortless and elegant.nStep inside to sun-filled interiors with clean lines, wide-plank flooring, and a seamless flow ideal for year-round living and entertaining. The designer kitchen serves as the heart of the home, featuring premium appliances, custom cabinetry, and a sophisticated palette that complements the homes heritage. The adjacent dining and living spaces offer an inviting atmosphere, with natural light and tasteful detailing enhancing every moment.nFive beautifully appointed bedrooms and three spa-inspired bathrooms provide comfort and privacy for guests or full-time residents. Each room reflects a balance of luxury and warmth, from serene color schemes to thoughtfully selected fixtures and finishes. A luxurious primary suite includes a spa-style bathroom and walk-in closet, creating a private retreat within the home.nOutdoors, resort-style living comes to life. A heated gunite pool, expansive bluestone patio, and multiple lounging and dining areas create a truly elevated summer retreat. Manicured gardens, mature landscaping, and a serene pond offer tranquil views and exceptional privacy, while the acre+ setting provides ample space for recreation, entertaining, or simply enjoying the natural beauty of Shelter Island. The property also includes an outdoor kitchen, fire pit, and multiple shaded seating areas, perfect for alfresco dining and gatherings.nAdditional amenities include a state-of-the-art HVAC system, smart home features, and ample storage throughout. The propertys layout and orientation maximize natural light, cross-ventilation, and the surrounding scenic vistas.nLocated moments from beaches, Mashomack Preserve, South Ferry, marinas, and local restaurants, this home captures the essence of Shelter Island livingquiet, refined, and effortlessly connected to the best of the East End. Move-in ready and finished to a designer standard, this is a rare opportunity to own one of Shelter Islands most sophisticated and lifestyle-driven offerings, where every detail has been curated for comfort, elegance, and timeless appeal.

Discover a serene sanctuary amidst the natural beauty of Shelter Island. This stunning residence offers breathtaking water views of Miss Annie's Creek, providing an unparalleled escape from the ordinary. Step onto the property and be captivated by the charm of covered porches and a heated pool, inviting you to relax and soak in the picturesque vistas. Whether you're enjoying a quiet morning coffee or hosting unforgettable gatherings, this waterfront oasis provides the perfect backdrop for every occasion. Don't miss this opportunity to own a piece of paradise in Mashomack Preserve.

Welcome to a breathtaking testament to luxury living at 1694 Millstone Rd, Sag Harbor. As you pull up the driveway, you'll immediately be struck by the grandeur of the home's cedar siding and stone exterior. The large windows allow natural light to flood the interior, showcasing the unparalleled craftsmanship and clean lines of this exceptional property. Situated on 1.85 acres, this home boasts a perfect blend of modern design and Italian/European elegance. The grand foyer welcomes you, leading to expansive living spaces adorned with the finest finishes and bespoke details. The gourmet kitchen is a chef's dream, featuring top-of-the-line Miele appliances, custom cabinetry that spans from floor to ceiling, and a large island perfect for culinary exploration. The dining area overlooks the meticulously landscaped grounds, creating the perfect setting for entertaining guests. The seven bedrooms offer a sense of comfort and luxury, each featuring an ensuite bathroom with radiant heated floors. The floor-to-ceiling windows drench the interiors with natural light, creating a seamless indoor-outdoor living experience. The estate's grounds are a true oasis, complete with a fully equipped pool house, gunite infinity pool that overlooks the private tennis court, and meticulously landscaped gardens. The lower level of the home offers a wellness center with a gym, spa, sauna, media room, and wine room - perfect for unwinding after a long day. This luxurious estate is the perfect home for the discerning buyer seeking the pinnacle of sophistication and modern living. With its unparalleled craftsmanship, elegant design, and stunning amenities, this property is a true masterpiece that will redefine luxury living in the Hamptons.

Welcome to a breathtaking testament to luxury living at 1694 Millstone Rd, Sag Harbor. As you pull up the driveway, you'll immediately be struck by the grandeur of the home's cedar siding and stone exterior. The large windows allow natural light to flood the interior, showcasing the unparalleled craftsmanship and clean lines of this exceptional property. Situated on 1.85 acres, this home boasts a perfect blend of modern design and Italian/European elegance. The grand foyer welcomes you, leading to expansive living spaces adorned with the finest finishes and bespoke details. The gourmet kitchen is a chef's dream, featuring top-of-the-line Miele appliances, custom cabinetry that spans from floor to ceiling, and a large island perfect for culinary exploration. The dining area overlooks the meticulously landscaped grounds, creating the perfect setting for entertaining guests. The seven bedrooms offer a sense of comfort and luxury, each featuring an ensuite bathroom with radiant heated floors. The floor-to-ceiling windows drench the interiors with natural light, creating a seamless indoor-outdoor living experience. The estate's grounds are a true oasis, complete with a fully equipped pool house, gunite infinity pool that overlooks the private tennis court, and meticulously landscaped gardens. The lower level of the home offers a wellness center with a gym, spa, sauna, media room, and wine room - perfect for unwinding after a long day. This luxurious estate is the perfect home for the discerning buyer seeking the pinnacle of sophistication and modern living. With its unparalleled craftsmanship, elegant design, and stunning amenities, this property is a true masterpiece that will redefine luxury living in the Hamptons., Additional information: ExterioFeatures:Tennis

Minutes from the bustle and charm of Sag Harbor Village, set on an exceedingly private and gated acre-plus flag lot with mature hedges, this immaculate 7 bedroom, 6500 square foot traditional checks all the boxes of a quintessential Hamptons summer home with a heated, gunite pool and spa, exceptional outdoor spaces, lined with hydrangeas, built-in BBQ grill kitchen, and an expansive finished lower level. Through the automated gate, a tree-lined approach leads to the handsome, white, shingled traditional with an attached 2-car garage. Adorned with shiplap, the bright, full height foyer creates a dramatic first impression. With lovely indoor and outdoor flow, the open concept floor plan offers a gourmet eat-in kitchen with an adjacent living room with fireplace and sitting area, with two sets of French door leading to the covered porch overlooking the pool area and rear grounds. A formal dining room with passthrough wet bar and wine storage serves the kitchen. A guest bedroom suite, pool full bath, foyer powder bath, expansive mud room, laundry room, and two-car garage completes the main level. Upstairs has a generous primary suite with luxurious bath including a freestanding tub and floating dual vanity. Three spacious en suite guest bedrooms supplement. The finished lower level features a gym, recreation area, and two bedrooms. Unique opportunity to own a turnkey home of excellent quality on a private acre-plus flag lot with a heated, gunite pool and spa and outdoor spaces fit for summer in the Hamptons.

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature. Spanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise to sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level. The upper level reveals the home's most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor-outdoor lifestyle experience. The living room, dining area, and gourmet chef's kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range. Designed for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six person barrel sauna and cold plunge. Beautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

Newly built cedar-shake estate on approximately 2.37 acres overlooking Fresh Pond and Sag Harbor Bay. in coveted North Haven. Offering 8,030± SF of living space, this traditional-style residence blends classic Hamptons architecture with modern scale, just minutes from Sag Harbor Village, marinas, beaches, and dining. The home features 7 bedrooms, 7 full and 2 half bathrooms, with wide-plank white oak floors, tray ceilings, and a wood-burning fireplace anchoring the main living spaces. Walls of sliding glass doors create seamless indoor-outdoor flow and enhance natural light throughout. An eat-in chef's kitchen with premium appliances serves as the heart of the home, complemented by a first-floor office/den. Multiple living and dining areas provide flexibility for everyday living and entertaining. Upstairs includes a beverage center, spacious bedroom suites, and two rear balconies with pond and bay outlooks. The layout is designed for comfort, scale, and easy living. Outdoor amenities include a 20' x 50' heated pool with bluestone patio, covered dining and lounge areas, and a fireplace-centered outdoor living room for year-round enjoyment. A rare highlight is the opportunity to add a 2,500± SF guest house, offering exceptional flexibility for future expansion. A refined North Haven offering with water views, privacy, and timeless design close to Sag Harbor Village.

Newly built modern estate on approximately 3.65 acres overlooking Fresh Pond and Sag Harbor Bay. Located in coveted North Haven, less than one mile from Sag Harbor Village, this 8,960± SF residence offers privacy, scale, and proximity to beaches, marinas, and dining. The home features 8 bedrooms and 8.5 bathrooms, with expansive glass walls, a double-height foyer, and open-concept living areas designed to maximize natural light and water views. The chef's kitchen includes Sub-Zero and Wolf appliances, marble countertops, an oversized island, and a full butler's pantry. Indoor-outdoor living is emphasized with multiple covered porches, terraces, and retractable glass doors. The main level includes a junior primary suite with spa-like bath and sitting room, along with additional living, dining, and service spaces. The upper level offers a water-view primary suite with dual walk-in closets and a luxury bath, plus five ensuite guest bedrooms and a secondary lounge with wet bar and terrace access. Outdoor amenities include a 20' x 50' heated gunite infinity-edge saltwater pool with spa, limestone patios, mahogany terraces, and a 320± SF pool house with kitchenette and firepit. The property also allows space for a future pickleball or padel court. A refined North Haven offering combining modern design, privacy, and convenient access to Sag Harbor Village.

Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ˜ 6,100-square-foot coastal estate that redefines luxury through the lens of effortless living. Set on a sprawling 0.92-acre parcel with captivating winter water views of Gardiners Bay, this masterfully designed home offers a seamless daily rhythm, beginning in the light-filled foyer where exquisite millwork meets glass doors that open to the expansive grounds. Designed for both high-end entertaining and absolute ease, the flowing main level connects a stately firelit living room to a magnificent chef's kitchen—complete with a professional cooktop, a walk-in pantry, and dual dishwashers for effortless cleanup—before transitioning outside to a resort-style pool featuring an electric safety cover and direct cabana-bath access. A sanctuary of personal wellness, the second floor boasts a marble-clad primary suite with a private water-view office overlooking the bay, alongside three generous guest rooms and two laundry rooms configured for ultimate convenience. Below, the fully finished lower level serves as a private wellness and entertainment pavilion, featuring a home gym, media room, and a temperature-controlled wine cellar, balanced by an abundant bulk-provisioning storage room and an attached garage for your water toys. Situated just steps from the pristine sands of Menhaden Lane Beach and moments from the island’s premier marinas, boutiques, and acclaimed dining, this estate offers a turnkey, worry-free island lifestyle where every modern luxury is already perfectly in place.

Huge potential. This turn of the 20th century gem was the residence of a single family through generations since its inception! A Queen Anne style house with its classic front gable and massive covered front porch invokes grandeur of times past as it sits prominently on prestigious Lumber Lane. Much of the original detail has been maintained including millwork, windows, doors, staircase, siding, structure, and the bones of this grand dame appear of high integrity. Collectors often favor a little patina over a flurry of modifications de jour. Such is the case with this roughly 2,100 sf residence, currently configured as two-family home, offering 4 bedrooms, 2 baths, 2 kitchens, 8’8” first floor and 8’4” second floor ceiling heights. In addition, the “1/2 story” attic with four dormers adorned with large leaded glass windows facing in each direction of the compass can stir one’s imagination of what it could become. 119 Lumber Ln located in the heart of Bridgehampton is a short distance from Main St, the LIRR station, numerous beaches, all other Hamptons hamlets, and provides over 5,000 sf of allowable lot coverage: ample space to accommodate expansion of the primary structure as well as various accessory structures and swimming pool/spa, or build a magnificent new home.

Rare 1.07-Acre Coastal Compound on The StrandnSet along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach non-buildable parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

Set along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach non-buildable parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

Recently constructed by renowned builder Farrell, this beautifully designed Sag Harbor home offers the perfect balance of luxury, comfort, and convenience just moments from the village, nearby marinas, and the ocean beaches of Bridgehampton. Thoughtfully designed across three finished levels, the residence features 7 bedrooms and 6.5 exceptional baths with sophisticated, current finishes and beautifully curated design throughout. The first-floor primary suite is a private retreat complete with its own office and direct access to the backyard patio and pool area. Upstairs, four ensuite guest bedrooms share access to a private terrace, while a conveniently located laundry room adds everyday ease. The heart of the home is the expansive open living space where a wood-burning fireplace anchors the great room, flowing seamlessly into the dining area and gourmet eat-in kitchen outfitted with top-of-the-line appliances and premium finishes. Oversized glass doors open beautifully to the resort-style backyard, creating an effortless connection between indoor and outdoor living. Designed for entertaining and relaxation alike, the outdoor space features a heated gunite pool, outdoor shower, grilling station, and multiple patios for dining and lounging. The finished lower level offers exceptional additional living space including a gym, media lounge, and recreation/game area, along with two additional bedrooms and a full bath. A staircase leading directly from the pool area to the lower level provides convenient access to the indoor gym after a swim or workout. Additional highlights include a mud room, 2-car garage, central vacuum system, and abundant storage throughout. Crafted with the quality, craftsmanship, and attention to detail synonymous with a Farrell-built home, this turnkey property is ideally positioned near the restaurants, boutiques, waterfront, and marinas of Sag Harbor Village while only minutes to the renowned ocean beaches of Bridgehampton. Sophisticated, stylish, and move-in ready, this is Hamptons living at its finest.

In a class by itself, New to Market, exquisite Malibu Style Modern Contemporary perfectly suited on a meticulously well-kept shy 2-acre parcel with Pool and Tennis offering the Ultimate in Hamptons Resort Style Summer living. Magnificently positioned and perched high above is where you'll find this exceptional Hamptons 4 level Modern bathing in full privacy and greenery with its commanding views of the full-sized North/South Tennis and its oversized 50x18 heated Saltwater Gunite Pool. Here summer never ends with its pool and jacuzzi wrapped in white marble and sprawling green lawns which take center stage all summer long. Boasting 6725 ft of luxurious open and modern resort style living spaces on 4 levels which feature soaring ceiling heights, an abundance of natural light and its expansive sliding glass doors which magically blend the indoor and outdoor spaces effortlessly creating the ultimate Hamptons entertaining space. Guests of all ages will enjoy the well-appointed 4 Guest ensuite beds found on 2 private levels plus the additional private Owners Suite which occupies the entire 3rd floor, complete with Resort Style Spa bath and breathtaking views. For the discerning Chef, a fully outfitted Chefs Kitchen with its professional high-end stainless-steel appliances and large center island sit ready and waiting to deliver the ultimate dining experience while enjoying marvelous Tennis and Poolside views. A whole range of amenities are available on level 1that enliven this unequaled Hamptons Summer Getaway, and include a Cinema room, Fitness center, and sprawling lounge and well-furnished wet bar. While serenity enwraps this captivating Hamptons retreat, it lies in superbly convenient proximity to world renowned Sag Harbor, Bridgehampton and Southampton shopping districts and its beloved Ocean Beaches.

Located in a serene neighborhood at the end of a quiet cul-de-sac, this 3000+/- sq. ft. residence offers the perfect blend of privacy, comfort, and opportunity. Set on 1.3 beautifully landscaped acres, the property features mature trees, manicured lawns, and vibrant garden beds that frame a luxurious 50' x 20' heated gunite pool and spa, surrounded by classic flagstone. The home's first floor provides multiple common living areas, with a formal dining room, living room, large den, and open-concept kitchen that flows seamlessly into the inviting family room with a fireplace, along with a laundry room and full bath. Situated upstairs are a large primary ensuite bedroom, a hallway full bath, and three spacious bedrooms. The covered front porch offers a quiet spot to relax. The expansive rear porch, with a fixed awning running the length of the house, provides the perfect shady spot to gaze at the grounds and gorgeous pool, or dine and entertain. Whether you choose to renovate, expand or build anew, this exceptional property presents a rare opportunity to create your dream Hamptons retreat. The Water Mill location offers a tranquil lifestyle with the convenience of nearby farm stands accessible by bike, and ocean beaches just to the south. The communities of Southampton Village, Bridgehampton and Sag Harbor - with its marinas and bay beaches - are all within easy reach. A true sanctuary with endless potential.

Set beyond a private gate, this stunning estate offers expansive acreage and breathtaking farm field vistas, creating a rare retreat in the heart of Water Mill. Thoughtfully designed for both gracious entertaining and quiet relaxation, this six-bedroom, six-bathroom home is filled with natural light and beautifully appointed spaces. A grand double-height foyer welcomes you into an open and airy layout, where the great room with soaring ceiling and a fireplace flows seamlessly into the gourmet kitchen. Outfitted with top-tier Wolf and Sub-Zero appliances, a spacious center island with a second sink, quartz countertops, and a dedicated coffee station, this kitchen is both stylish and functional. A chic entertainer's bar, complete with a sink, dishwasher, refrigerator, ice maker, and wine cooler, enhances the home's effortless flow. The first floor features a private wing with the expansive primary suite, offering a spa-like bath with an air tub, radiant heated floors, and a loft space perfect for an office or library. Three additional first-floor bedroom optons provide comfortable accommodations for guests. Upstairs, two more ensuite bedrooms open to multiple decks overlooking the scenic farmland. The fully finished lower level offers endless possibilities, including an entertainment/TV area, gym, cedar wine storage, full bath, and private guest quarters. An oversized heated garage accommodates three vehicles, and a whole-home generator ensures uninterrupted comfort. Outside, discover a true Hamptons oasis, where a heated swimming pool with a brick patio is surrounded by lush English-style gardens and striking art sculptures. The outdoor kitchen is a chef's dream, featuring a brick pizza oven imported from Italy, a bar with hot/cold running water, two refrigerators, a smoker grill, and a two-burner stove with granite countertops. A water feature seating area and a two-season firepit with seating for 10+ complete the multiple outdoor entertaining spaces. Surrounded by horse pastures and scenic farm fields, this exceptional retreat blends luxury, privacy, and natural beauty, offering the ultimate Hamptons lifestyle.

Situated on a cul-de-sac, 12 Bob White Drive offers a rare blend of privacy, timeless design, and proximity to everything that makes the Hamptons lifestyle so desirable. As you approach, you'll pass wide open fields and estate homes with panoramic views of the countryside -- setting the tone for this tranquil Water Mill retreat. Sited on a landscaped acre, the classic shingled traditional home was recently renovated and expanded for a modern lifestyle. The interiors are filled with natural light, with hardwood floors throughout and a gracious floor plan that balances open-concept living with relaxed spaces. The renovated chef's kitchen is equipped with premium Wolf/Sub-Zero appliances and flows easily into the great room with windows on three sides. The formal dining area connects to an expansive rear deck that is perfect for indoor/outdoor entertaining. Outside, mature landscaping frames a heated pool, a charming gazebo, and a sun deck that looks over the backyard. Whether entertaining or enjoying a quiet weekend, the setting exudes Hamptons charm. A formal den area with gas fireplace and vaulted ceilings compliments the open concept with a more intimate space. Rounding out the 1st floor is a powder room, laundry closet and one of the two primary suites. Upstairs are three additional bedrooms including the 2nd primary suite. The finished lower-level includes additional guest rooms, with potential for up to 6 total bedrooms if one desired. Ample rec space and sliding glass doors connect the lower-level to the pool area creating great indoor/outdoor flow. Located just minutes from the villages of Bridgehampton, Sag Harbor, and Southampton, and a short drive to ocean and bay beaches, this property is ideally situated for year-round or seasonal living.

Perfectly curated, fully renovated, and thoughtfully designed, this exceptional Hamptons retreat offers a rare combination of sophisticated modern design, comfort, and resort-caliber amenities. Set down a long driveway and behind professionally manicured landscaping, the property makes an immediate impression with its expanded designer interior and seamless indoor-outdoor living. Major renovations and additions completed in recent years by HGTV host elevate the home with a refined, magazine-worthy aesthetic throughout. Inside, an expansive family room serves as the heart of the home, featuring a fireplace, bar area, dedicated TV lounge, and an adjoining recreation room or library. A more intimate sitting area with an additional fireplace flows effortlessly into the open-concept chef's kitchen, complete with high-end appliances, counter seating, and a spacious dining area, all enhanced by abundant natural light streaming through oversized picture windows and glass doors. The home features four beautifully appointed en-suite bedrooms, including a luxurious primary suite with distant water views, a private walk-out balcony, fireplace, and spa-inspired bath with a generous soaking tub. Laundry on both the second floor and lower level adds everyday convenience. Designed for both entertaining and private relaxation, the outdoor setting feels like a true resort retreat, highlighted by a heated saltwater pool, spa, outdoor shower, updated decking, and multiple dining and lounge areas surrounded by lush landscaping and exceptional privacy. A rare turnkey offering that captures the very best of modern Hamptons living.

Set on nearly 1 acre in a prime Hamptons location, this pre-completion new construction offers approximately 6,000 sq. ft. of thoughtfully designed living space across three levels, with completion anticipated in 2027. Designed for modern luxury living and seamless indoor-outdoor flow, this residence combines scale, sophistication, and functionality. A dramatic double-height foyer welcomes you into an expansive open-concept layout featuring a sun-filled great room, designer kitchen, and breakfast area-ideal for both everyday living and entertaining. A flexible den off the main living space provides the perfect setting for a home office, media room, or lounge. The first floor also includes a private en-suite guest bedroom with coffered ceilings and a walk-in closet, along with a two-car garage accessed through a well-appointed mudroom. The second level is anchored by a luxurious primary suite complete with multiple walk-in closets, a spa-like bath, and access to a private terrace. Three additional en-suite bedrooms complete the upper level, offering comfort and privacy for family and guests alike. The fully finished lower level is designed for lifestyle and wellness, featuring a spacious recreation room, enclosed gym, additional guest bedroom, and full bathroom. Outdoor living is equally impressive, with sliding glass doors opening to a covered porch, patio, and built-in barbecue area. A brand-new gunite heated pool is set within beautifully landscaped grounds, complemented by expansive lawn space for relaxation and entertaining. Ideally located just minutes from both Bridgehampton and Sag Harbor villages, this exceptional new build offers convenient access to world-class beaches, dining, shopping, and all the Hamptons has to offer.

Built in 2005 and gracefully sited on 1.18 acres overlooking North Sea Harbor's peaceful Fish Cove, this 5,100± sq. ft. residence captures the essence of Hamptons waterfront living. Expansive glass windows and French doors fill the interiors with natural light and frame serene harbor views from nearly every room. The main level offers a gracious entry foyer, a generous kitchen with premium appliances, and open dining and living areas designed for gatherings that flow seamlessly outdoors. A sunroom, a living room with a fireplace, and a family room with a fireplace create inviting spaces to relax, while an en-suite guest room and three-car garage complete the first floor. Upstairs, two oversized and sunny primary suites each open to private sundecks, accompanied by two additional ensuite bedrooms. Outside, a spacious mahogany deck leads down to a bluestone patio that surrounds a 40'x20' heated gunite pool, nestled among expansive lawns and mature landscaping-perfect for entertaining or enjoying peaceful mornings by the pool and water. Adding tremendous versatility is a 2,400± sq. ft. unfinished lower level with 11-foot ceilings, offering abundant space for future recreation, media, or fitness rooms. Included with the property is a separate 1.3-acre waterfront parcel with a private dock, providing direct access to boating on Peconic Bay, and making this a total of 2.48 waterfront acres. With panoramic harbor and cove views, indoor-outdoor living, and rare dual parcels, this 2005-built North Sea Harbor retreat embodies the best of the Hamptons lifestyle-minutes from Southampton Village and ocean beaches.

Built in 2014, this exceptional residence at Barn & Vine Bridgehampton showcases a timeless interpretation of one of the Hamptons’ most iconic architectural styles. Designed through a collaboration between Continental Pinewood Development Partners and renowned McDonough & Conroy Architects, the home blends classic gambrel architecture with enduring design elements that feel just as relevant today. Spanning three levels, the home offers approximately 6,257 +/- sq. ft. of living space, including 4,373 +/- sq. ft. above grade and an additional 1,884 +/- sq. ft. in the finished lower level, with 6 bedrooms, 6 full bathrooms, and 3 fireplaces throughout. The thoughtfully designed floor plan includes a junior en-suite primary bedroom on the main level, ideal for guests or flexible first-floor living. Upstairs, four additional bedrooms provide ample accommodations, including the primary suite. The bright, open-concept main living spaces are designed for both everyday comfort and entertaining, featuring expansive gathering areas and a chef’s kitchen lined with French doors that create a seamless indoor-outdoor connection. The kitchen is appointed with custom cabinetry, stone countertops, and top-tier appliances from Wolf, Sub-Zero, and Miele. The finished lower level adds exceptional lifestyle amenities with an additional guest bedroom, expansive entertainment space, and a private golf simulator. Modern conveniences include integrated ceiling speakers throughout the home, outdoor speakers for seamless entertaining, a full security system monitored by 24/7 operators, and built-in exterior cameras for added peace of mind. Outside, enjoy a covered porch, expansive patio, and a 20' x 40' heated gunite pool surrounded by professionally designed landscaping—creating a private setting for entertaining or unwinding. Complete with a two-car garage and ideally positioned just minutes from Bridgehampton Village and the Hamptons’ world-class ocean beaches, this property offers timeless Hamptons living with lasting appeal.