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luxury houses with pool for sale Suffolk County, United States (page 3)

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18

House with pool Port Jefferson (United States)

Inc Village--Drive through The Gates to Belle Terre onto Cliff road to a dead-end street near the water and discover this custom home in a Beach and Country Club community. The 1.61 acre wooded lot offers privacy with oval driveway and brick walkway to front door. Custom built by Clarendon, this 4,252 sq ft home features open spaces and lots of light for today's living and entertaining with its huge deck, in-ground pool, 6 bedrooms, 4.5 baths , plus oversize primary with renovated bath and additional room for visiting parents and /or guests on main floor. The Village of Belle Terre has been designated as a bird sanctuary, has a private beach for residents, a park with children's playground, a pickle ball court, a summer program for children, and residents are also welcome at the Port Jefferson Country Club for golf membership. Belle Terre is located adjacent to quaint Port Jefferson Village with restaurants, shops, Library, Ferry to Bridgeport, deep water mooring for boats and 2 major hospitals. Belle Terre truly is a beautiful place to live!

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$1,388,000
5bedrooms
5bathrooms
land 6,515

By Daniel Gale Sotheby's International Realty

36

House with pool Southampton (United States)

Southampton Village Luxury Real Estate Opportunity - The Polo Club Townhouse A rare chance to own an oversized luxury townhouse in Southampton Village, located in the highly sought-after Polo Club condominium community. This turn-key Hamptons home for sale offers over 3,500 sq. ft. of designer living, combining the privacy of a free-standing residence with the ease of low-maintenance, lock-and-leave Hamptons living. Step inside to a dramatic double-height entry foyer, 10-ft ceilings, extensive millwork, and a spacious open-concept living and dining area - ideal for both everyday living and entertaining. The modern chef's kitchen features stainless steel appliances and generous prep space, perfect for those seeking a luxury Southampton kitchen. This 4-bedroom Southampton Village home includes four ensuite bedrooms, each with beautifully appointed bathrooms. The second level features a serene primary suite with radiant-heated floors, along with two guest suites and a convenient laundry room. A finished lower level offers a media/den and a fourth guest suite, perfect for hosting. Enjoy your own private bluestone patio surrounded by lush Hamptons landscaping, featuring seasonal hydrangea and rose of sharon. The attached two-car garage, two fireplaces, and stand-alone privacy elevate this home far above typical Village condos. Set down a private drive, The Polo Club Southampton offers meticulously maintained grounds, a clubhouse, and a resort-style swimming pool, making it one of the most desirable Southampton Village condo communities. Conveniently located near Southampton Village shops, dining, transportation, and world-famous ocean beaches, this residence delivers the perfect blend of luxury, convenience, and Hamptons lifestyle. If you're searching for a move-in-ready Southampton Village home, a luxury Hamptons townhouse, or an investment property with premier amenities, this rare Polo Club offering stands out as one of the best opportunities on the market.

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$3,295,000
4bedrooms
5bathrooms
land 1.2ha

By Sotheby's International Realty - Southampton Brokerage

39

House with pool Southampton (United States)

On .57 acres just minutes from Southampton Village and ocean beaches, this turn-key home offers an exceptional combination of style, privacy, and space. 3 bedrooms, 3 bathrooms, an open living and dining area with wood-burning fireplace and abundant natural light. Outdoors include mature hedging, established trees, an ambient heated pool, and generous deck. Plus, expansion potential-approximately 3,600 sq. ft. of allowable gross floor area and 4,300 sq. ft. allowable lot coverage.

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$3,500,000
3bedrooms
3bathrooms
land 2,307

By Sotheby's International Realty - Bridgehampton Brokerage

45
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House with pool Southampton (United States)

This beautiful classic white shingled 3-story house with 6 bedrooms, 6 full & two 1/2 baths, gorgeous backyard, heated pool and spa is a perfect summer residence in Southampton Village. Enter the large foyer and experience the spacious nature and high ceilings that exist throughout the house. The main floor offers an elegant and spacious living room that opens onto the patio and gardens, a wonderful bright sunroom, and a den with fireplace that opens onto a west-facing furnished porch to catch the golden hour. In addition, there is a state-of-the-art eat-in kitchen with stone and stainless steel counters that opens to a covered porch for informal dining, as well as indoor formal dining room and mudroom. Almost every room on the first floor opens to a porch. Up the wide staircase and onto the second floor, the large primary bedroom suite offers two large walk-in closets/dressing rooms, two separate bathrooms, a beautiful covered porch and study/office. In addition, there are two guest bedrooms with ensuite bathrooms, and second floor laundry room all accessed from the large landing with sitting area. The third floor has three more large guest bedrooms and two more bathrooms as well as an additional sitting area. The indoor/outdoor living is what makes this house so special with the multiple covered porches, heated Gunite pool, spa, pool house with changing room and bathroom, outdoor shower and heated 3-car garage surrounded by special mature landscaping. The 2300 sq.ft. lower level, with high ceilings offers a superb opportunity for expansion to include a gym, theater and lounge with bar and billiard table. All this and just one mile to Main Street and beautiful Old Town and Wyandanch beaches.

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$11,995,000
6bedrooms
8bathrooms
land 3,723

By Sotheby's International Realty - Southampton Brokerage

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41
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House with pool Southampton (United States)

In the heart of Southampton Village, this newly constructed 2024 masterpiece by acclaimed architect Douglas C. Wright brings together the best of traditional Southampton elegance and modern luxury living. Set on an expansive 0.85-acre south-facing lot, the estate is ideally positioned just moments from the Village's world-renowned ocean beaches, boutiques, and restaurants. Designed with meticulous craftsmanship and an elevated lifestyle in mind, the six-bedroom, seven-and-a-half-bath residence features a heated gunite pool, spa, detached garage, and a beautifully appointed pool house, all wrapped in lush mature landscaping for total privacy and serenity. A grand entryway ushers you inside, where refined architectural details unfold in every direction. The double-height living room, framed by floor-to-ceiling UV-protected windows, intricate moldings, and crisp wainscoting, establishes an atmosphere of timeless sophistication. The chef's kitchen offers both beauty and functionality with state-of-the-art appliances, custom cabinetry, and an expansive pantry. A ground-floor bedroom suite provides extra flexibility for guests, staff, or multi-generational living. Upstairs, the primary suite serves as a private sanctuary with a spa-inspired bathroom, generous closets, and French doors leading to a Juliet terrace overlooking the picturesque grounds. Three additional en-suite bedrooms complete the second level, each designed with exceptional comfort and privacy. The fully finished lower level dramatically expands the home's footprint, offering soaring 12-foot ceilings, a state-of-the-art gym, a dedicated golf room outfitted with the Foresight GC Hawk Golf Simulator, and a cozy living and play area anchored by a fireplace. Two additional en-suite bedrooms provide even more room for hosting or extended stays. Outdoor living is equally impressive, with wide wrap-around porches, mature landscaping, and the 20x50 heated pool complemented by a climate-controlled pool house featuring accordion-style doors for effortless indoor-outdoor enjoyment. Built with an unwavering commitment to quality and efficiency, the home includes 10 HVAC zones, a geothermal closed-loop system, and Mermaid Water Solutions filtration for pristine water throughout. Technology is seamlessly integrated with a Lutron lighting system, a seven-camera security setup, hidden built-in speakers, and a centralized smart hub that controls the entire property wirelessly. Exterior materials-from the hand-cut Alaskan white cedar siding to the pressure-treated cedar shingles and UV-protected thermal pane windows-reflect thoughtful design and enduring craftsmanship. A true Southampton Village treasure, this newly built estate represents the pinnacle of Hamptons living: sophisticated, innovative, and timeless, all situated in one of the most desirable and prestigious locations on the East End.

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$16,750,000
6bedrooms
10bathrooms
land 3,440

By Sotheby's International Realty - Southampton Brokerage

Contract pending
43

Property with pool Stony Brook (United States)

Discover the perfect blend of charm, comfort, and convenience in this beautifully maintained 4-bedroom, 2.5-bath Center Hall Colonial, ideally positioned on a serene 0.60-acre property off a cul-de-sac in Old Stony Brook’s sought-after Quaker Hill neighborhood. This inviting home offers an exceptional lifestyle both inside and out. Step through the welcoming foyer into sun-filled living spaces, including a spacious living room, elegant formal dining room with butler’s pantry, and a warm, character-rich den featuring a wood-burning stove/fireplace, an ideal setting for cozy evenings or effortless entertaining. The open kitchen serves as the heart of the home, boasting quartz countertops, stainless steel appliances, and a charming breakfast nook that overlooks the property. The expansive, fully fenced backyard is your private retreat, complete with a wood deck and sparkling salt water in-ground pool—perfect for summer gatherings, relaxation, and outdoor enjoyment. A full basement provides abundant storage and flexible recreation space. Located just minutes from local shops, SUNY Stony Brook, West Meadow Beach, and the train station, this home offers unmatched convenience in one of the area’s most desirable settings. Classic architecture, modern updates, and a prime location come together to create a truly exceptional opportunity.

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$1,075,000
4bedrooms
3bathrooms
land 2,428

By Daniel Gale Sotheby's International Realty

47

House with pool Sag Harbor (United States)

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.

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$5,495,000
7bedrooms
7bathrooms
land 1,983

By Sotheby's International Realty - Bridgehampton Brokerage

Contract pending
36

House with pool Southampton (United States)

Brand new listing for sale in a sought-after Southampton Village area. This home is perfectly positioned in a quiet cul de sac conveniently located close to the village and ocean beaches. The property features: estate like landscaping, a majestic pool area with extensive decking and complete privacy. There are three bedrooms, two and a half baths, and an open dining/ living room areas. Attached is a two car garage. Enjoy this home as is or a fabulous renovation project!

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$4,300,000
3bedrooms
3bathrooms
land 1,902

By Sotheby's International Realty - Southampton Brokerage

Contract pending
32

Property with pool East Islip (United States)

GREAT OPPOUTUNITY! Four bedroom, 2 full Bath Colonial with attached in-law suite or legal rental apartment. Set on resort-style property boasting in ground heated salt water pool with waterfall, hot tub and large Patio with wood Awning. The pool house has full bath and washer /dryer and second floor storage. Main house has Living room, formal dining room, oversized family room, eat in Kitchen, full bath and 1st floor laundry room. Four bedrooms and new full bath complete the second floor. Separate in-law suite or legal apartment with separate entrance, eat in kitchen, sun drenched dining room/living room and full Bath with sliding doors to deck. 3 Zone Gas heat, 2 zone CAC, circular driveway and much more.

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$969,000
4bedrooms
2bathrooms
land 1,538

By Daniel Gale Sotheby's International Realty

22

House with pool East Hampton (United States)

Located in the Hansom Hills neighborhood on a quiet cul-de-sac, this custom-built, single-story East Hampton residence offers an unique blend of privacy, comfort, and future expansion potential. The front foyer leads to a spacious, double-height great room with living and dining areas, enhanced by a wood-burning fireplace and by windows and sliding doors that frame picturesque views of the rear yard. The kitchen, featuring stainless steel appliances and a breakfast nook, is adjacent to a dedicated mudroom and laundry area with multiple storage options. The primary suite is generously sized and accented by a vaulted ceiling. Its ensuite bath is thoughtfully designed with a soaking tub, a large walk-in shower, and a well-appointed walk-in closet with custom built-in shelving. A second bedroom also offers a walk-in closet and is conveniently served by a full bath that functions as both an ensuite and hallway bathroom for guests. Outside, the property is enriched by mature deciduous trees, select specimen plantings, and ample lawn areas. The 18' x 36' swimming pool is surrounded by a classic brick patio, and an elevated deck provides a serene spot to dine al fresco. The home offers excellent expansion possibilities, such as adding two more bedrooms, a full bath, and upgrading the current carport to a two-car garage, making it a rare opportunity to own a Hamptons home with both immediate appeal and exceptional potential, all within moments of the renowned Hamptons ocean beaches and the vibrant Villages of East Hampton and Sag Harbor.

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$1,650,000
2bedrooms
2bathrooms
land 3,157

By Sotheby's International Realty - Bridgehampton Brokerage

21

House with pool Sag Harbor (United States)

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.

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$10,990,000
7bedrooms
9bathrooms
land 9,591

By Sotheby's International Realty - Southampton Brokerage

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House with pool Sag Harbor (United States)

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.

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$15,995,000
8bedrooms
9bathrooms
land 1.5ha

By Sotheby's International Realty - Southampton Brokerage

Contract pending
26

House with pool Jamesport (United States)

Welcome to your North Fork escape in the heart of Jamesport—where relaxed coastal living meets effortless entertaining. This sprawling 3-bedroom, 3 full bath ranch is designed for both comfort and style, featuring hardwood floors throughout, cathedral ceilings, skylights, decorative beams, and two wood-burning fireplaces that create a warm, inviting atmosphere year-round. This home boasts light filled principal rooms, open flow living and tons of storage or flex living space. This home is also equipped with owned solar panels, enhancing efficiency and long term value. Step outside and experience a true entertainer’s paradise. Set on .6 acre with sweeping, unspoiled farmland views, the backyard offers a private resort-like setting complete with an in-ground heated saltwater pool, hot tub, outdoor shower, tiki bar, and fire pit, perfect for hosting or unwinding under the stars. Too many updates to list but highlights include, full bath, HW heater, roof, outdoor shower, hot tub, pool heater and fence. Ideally located moments from the beach, this home is at the center of everything the North Fork is known for, renowned vineyards, charming farm stands, and exceptional local dining, all while maintaining a peaceful, rustic ambiance. Whether you’re seeking a full-time residence or the perfect weekend retreat, this property offers the best of North Fork living and an opportunity to truly enjoy your next chapter.

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$1,075,000
3bedrooms
3bathrooms
land 2,388

By Daniel Gale Sotheby's International Realty

32

House with pool Southampton (United States)

Breathtaking Meadow Lane estate offering expansive ocean and bay views across +/- 9.75 acres of lush, landscaped grounds. The property features expansive lawns, an oceanside gunite pool, and an Omni tennis court. A sophisticated blend of modern and Mediterranean-inspired architecture delivers soaring ceilings and grand open spaces throughout. Designed with state-of-the-art, high-end finishes, the residence includes an ultramodern chef's kitchen with quartz countertops and premium stainless steel appliances. Both the living room and family room showcase water views, fireplaces, and wet bars, with a dramatic two-story coffered dining room positioned adjacent. The second-floor primary suite captures sweeping ocean vistas and offers a fireplace and spa-caliber bath. All six bedrooms feature automatic shades and newly renovated contemporary bathrooms. Additional amenities include an elevator and a full catering kitchen. Created for exceptional indoor-outdoor living, the home provides multiple terraces on both levels framing panoramic ocean and bay vistas. A raised boardwalk leads toward the shoreline, offering elevated, breathtaking perspectives of the surrounding waters. Approved plans are in place to capture an additional +/- 1,000 sq. ft. of living space and rework the existing indoor-outdoor floor plan to further modernize and balance the layout. Inquire today to arrange a confidential showing of this world-class property.

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$33,000,000
6bedrooms
7bathrooms
land 4ha

By Sotheby's International Realty - East Hampton Brokerage

27

House with pool Water Mill (United States)

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.

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$3,599,000
4bedrooms
5bathrooms
land 4,047

By Sotheby's International Realty - Bridgehampton Brokerage

28

House with pool Bridgehampton (United States)

Less than one mile from the ocean, in one of Bridgehampton South's most treasured estate settings, this offering unites two already subdivided parcels totaling two and one half acres. It is a rare opportunity to secure a presence of meaningful scale in the Hamptons, where the serenity of the present and the promise of the future come together in a way seldom available. For those seeking an estate that can evolve gracefully across generations, this property stands apart Anchoring the offering is a gracious residence that is traditional in feel and thoughtfully positioned amid mature, beautifully composed landscaping. The home provides approximately six thousand square feet of interior space with more than six bedrooms, five full bathrooms, two half bathrooms, expansive living and dining areas, three fireplaces, a heated swimming pool, tennis, and a recently added guest suite with private exterior access. The atmosphere is refined and serene, capturing the timeless character that defines the most beloved Hamptons estates. The adjoining parcel, which forms part of the total acreage, is a meaningful asset in its own right. It offers the ability to create a substantial additional residence that would complement the existing home and elevate the estate for future generations. Whether envisioned as a retreat for extended family or planned thoughtfully over time, the possibilities are exceptional and increasingly rare in this coveted location. With village shops and restaurants close at hand and the ocean less than one mile away, the setting offers tranquility, convenience, and enduring appeal. This is an offering designed for those who appreciate beauty, privacy, and the promise of a legacy that can unfold over many years.

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$17,500,000
6bedrooms
7bathrooms
land 1ha

By Sotheby's International Realty - Bridgehampton Brokerage

28
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House with pool Shelter Island (United States)

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.

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$3,995,000
9bedrooms
9bathrooms
land 2,833

By Sotheby's International Realty - East Hampton Brokerage

50
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House with pool Shelter Island (United States)

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.

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$3,100,000
6bedrooms
6bathrooms
land 3,642

By Sotheby's International Realty - East Hampton Brokerage

35

House with pool Southampton (United States)

Set on just over an acre in a waterfront community, this inviting home offers both comfort and room to grow. Built in 2005 with an interior renovation in 2018. The first floor features a fully renovated kitchen, a dining area, and a living room with beautiful built-ins and a fireplace. Three sets of glass doors open seamlessly to the outdoors, creating a bright, airy flow. A den/office, a renovated powder room, a laundry room, and a two-car attached garage complete this level. The second floor offers a large sitting area with room for a large sectional sofa and TV. The vaulted-ceiling primary suite includes a generous bath and walk-in closets. Two additional guest bedrooms, that share a large bath, provide plenty of space, while a generous junior primary offers its own ensuite bath. A 1,300± sq. ft. unfinished basement provides opportunity for additional living or recreation space. Outdoors, mature specimen trees and flowering gardens surround the property, creating a serene setting. The backyard features a patio with a pergola for outdoor dining, a pool with a hedge-lined lounge area and bluestone patio, a koi pond, a firepit area, outdoor lighting, and a gazebo. With no clearing restrictions, there is ample room for expansion to the house and the potential to add a pool house. Low taxes add to the appeal, and the location is moments from Bullhead Yacht Club and a boat launch, making boating, kayaking, and paddleboarding especially convenient. Just minutes from Southampton Village and ocean beaches, this home is perfectly positioned for year-round living or summer enjoyment.

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$3,100,000
4bedrooms
4bathrooms
land 4,047

By Sotheby's International Realty - Southampton Brokerage

Contract pending
50
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House with pool Southampton (United States)

Set behind a stately brick pillared gated entrance, a striking crushed red lava rock driveway framed by mature specimen trees creates a dramatic approach to this exceptional Southampton Village estate on 1.2 acres, set in a coveted location offering a seamless balance of privacy and proximity to the ocean and village. The property evokes a refined Hollywood meets Hamptons sensibility, where classic architecture and curated landscaping define a sense of timeless elegance. An elegant entry foyer opens to a dramatic double height great room, anchored by an intricate marble fireplace and framed by French doors that lead seamlessly to the rear patio and gardens. The home's thoughtfully designed layout balances formal entertaining with relaxed living, featuring a gourmet marble kitchen with an adjacent grilling station, a formal dining room with direct access to a covered pavilion and trellised outdoor dining area, and an additional great room with a stone fireplace and French doors opening to the grounds. Across three levels, six bedrooms offer exceptional scale and privacy. The second floor landing creates a striking architectural moment and leads to the primary suite, a true retreat complete with its own fireplace and a Juliet balcony overlooking the estate at sunset. A private library extends from the suite and opens to its own balcony, creating a secluded indoor outdoor escape. Discreetly accessed through the library, a separate third floor study provides a quiet, tucked away space ideal for work or retreat. On the second level, one of the guest bedrooms is set apart with its own private terrace, offering a rare sense of independence for visitors. A privately positioned suite above the garage, complete with a full bath and dedicated office area, provides additional flexibility for guests, staff, or extended stays. On the first floor, a junior primary suite with French doors to the patio offers comfort and convenience, while an additional bedroom or office adds further versatility. Marble bathrooms throughout underscore the home's elevated finish. A lower level offers additional storage with convenient exterior access, ideal for seasonal use. A five car garage outfitted with lifts presents a rare offering for automotive enthusiasts. Outdoors, the grounds are designed for both entertaining and leisure. A heated gunite pool with spa and waterfall overflow serves as the centerpiece, complemented by a fully equipped pool house with bar and bath. Beyond, a rose covered trellis and mature landscaping create a backdrop reminiscent of a more glamorous era, while an expansive lawn offers space for gatherings, lawn games, or relaxed afternoons. A rare offering in Southampton Village, this property combines scale, privacy, and a timeless aesthetic in one of the area's most desirable settings.

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$7,200,000
6bedrooms
6bathrooms
land 4,775

By Sotheby's International Realty - Bridgehampton Brokerage

Contract pending
18

House with pool Water Mill (United States)

Picture-perfect five bedroom traditional on a quiet cul-de-sac, south of the highway in Water Mill. A classic wraparound porch with columns sets the tone, evoking the charm of a true Hamptons farmhouse, while inside the flow is open and easy. With three levels of above ground living this home is generous yet manageable in scale . The main floor offers living room and formal dining, both with fireplaces, along with a recently renovated chef's kitchen that opens to a casual sitting area, also anchored by a fireplace. A wall of French doors leads out to a screened porch that spans the entire back of the house, creating a seamless indoor-outdoor setup that is as suited to quiet moments as it is to full-scale entertaining. Upstairs, a graciously wide hallway leads to the primary suite which overlooks beautifully landscaped grounds and features a fireplace, private porch, and a newly completed spa-like bath. Two additional en suite guest rooms are also on this level. The legal third floor adds two more bright, skylit bedrooms that share a bath, ideal for overflow or flexible use. Outside, the grounds are lush and thoughtfully designed, with bluestone patios, a heated pool, outdoor shower, firepit, and large lawn all framed by mature landscaping. The detached three-car garage includes unfinished space above, offering potential for pool house or studio. Set among substantial estates, this is a turnkey property and fabulous investment that has been lovingly maintained and recently upgraded, including brand new cedar shake roof. Close to farm stands, ocean beaches, and perfectly central to all the Hamptons has to offer.

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$5,795,000
5bedrooms
5bathrooms
land 3,723

By Sotheby's International Realty - Bridgehampton Brokerage

28

House with pool Water Mill (United States)

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.

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$2,750,000
4bedrooms
3bathrooms
land 5,261

By Sotheby's International Realty - Bridgehampton Brokerage

39

House with pool Southampton (United States)

Experience timeless Hamptons elegance at this gated eight-bedroom Southampton Estate Section compound, a 2.8-acre sanctuary with a tennis court, heated Gunite pool, spa, and separate guest house set among lush, meticulously curated grounds. Originally built in 2012 and designed by esteemed architect John David Rose, this 10,800-square-foot shingle-style residence offers refined luxury across three expansive levels, combining architectural sophistication with a warm sense of livable comfort. From the moment you enter, the home reveals a rich tapestry of detail-hand-painted murals, five fireplaces, and dramatic interiors including a double-height living room and a formal dining room that opens through French doors to a sun-filled glass-enclosed room. The custom chef's kitchen is equipped with premier appliances and anchored by a charming, window-wrapped breakfast nook that embodies classic Hamptons living. The main level flows beautifully with a paneled library, an inviting game room, and a dedicated pool lounge that opens directly to the outdoor amenities. Upstairs, the primary suite serves as a luxurious private retreat with its own balcony, dual walk-in closets, and an elegant spa-inspired bathroom. Three additional en-suite bedrooms continue the home's commitment to comfort and privacy, while the upper-level turreted office offers a whimsical and inspiring workspace. The finished lower level extends the home's appeal with a climate-controlled wine cellar, gym, laundry room, and a private guest suite complete with its own entrance and outdoor sitting area-ideal for long-term visitors or staff. Beyond the impressive interiors, the grounds are truly breathtaking. A rhythm of blooming flowers and mature landscaping creates a sense of beauty throughout all four seasons, thoughtfully designed to offer year-round color and serenity. At the edge of the cobblestone parking court sits the detached two-car garage, which includes a one-bedroom, one-and-a-half-bath guest apartment, adding another layer of luxury and functionality to this rare compound. With ocean breezes drifting across the property and the close proximity to Southampton Village shops, dining, and world-famous beaches, this estate embodies the finest qualities of Southampton luxury real estate. It is a true sanctuary-balanced, gracious, and masterfully executed, offering unparalleled living inside and out.

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$19,995,000
8bedrooms
10bathrooms
land 1.1ha

By Sotheby's International Realty - Southampton Brokerage

33
Video

House with pool East Hampton (United States)

Tucked away on a quiet cul-de-sac near town and the bay, this beautiful traditional home sits within a private oasis. Designed by landscape architect W. Dean Gamolka, the grounds feature mature specimen trees, lush plantings, and a serene setting centered around a heated gunite pool-perfect for relaxing or entertaining. A garden path leads to the home, where thoughtful design and warm character abound. Inside, a mudroom with built-ins provides an easy transition from outdoors. The double-height living room is filled with natural light from expansive windows and opens to a deck, seamlessly blending indoor and outdoor living. A wood-burning stove adds comfort and charm, while the open layout connects the living and dining areas. An addition by architect Erica Broberg features a stunning eat-in kitchen with Caesarstone countertops, custom cabinetry, and high-end appliances. Quality finishes and built-ins throughout the home enhance both elegance and durability. The first floor includes a primary bedroom suite, while the second floor offers a cozy den, two additional bedrooms, and a full bath. The lower level provides flexible living space with a media area, gym, third bathroom, and ample storage. Outdoors, enjoy multiple gathering spaces, an outdoor shower, a service entrance, and a shed, all designed for privacy and ease. This is not a spec home, but a thoughtfully crafted residence, carefully designed and lovingly maintained, a rare offering to be enjoyed for years to come.

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$2,835,000
3bedrooms
3bathrooms
land 1,538

By Sotheby's International Realty - East Hampton Brokerage

30

Farmhouse with pool Shelter Island (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.

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$2,950,000
5bedrooms
5bathrooms
land 2,023

By Daniel Gale Sotheby's International Realty

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