Southampton Homes with Pool

Welcome to Southampton, New York, a picturesque gem nestled in the heart of Suffolk County. Renowned for its stunning beaches, charming downtown, and vibrant arts scene, Southampton offers a perfect blend of coastal living and suburban charm. This idyllic town is not just a summer retreat; it boasts year-round appeal with its rich history, delightful shops, and exquisite dining options. Whether you’re strolling along the scenic waterfront or exploring the lush landscapes, Southampton is a place where every moment feels like a vacation.

One of the most sought-after features in Southampton real estate is the presence of homes with pools. Imagine stepping into your backyard oasis, where a sparkling pool invites you to relax and unwind. These homes with pools provide the perfect setting for entertaining friends and family, hosting summer barbecues, or simply enjoying a quiet afternoon under the sun. With a variety of architectural styles, from charming cottages to luxurious estates, there’s a home for everyone in Southampton.

Living in Southampton means you’re never far from the beauty of nature. The area is dotted with parks, nature preserves, and, of course, the stunning Atlantic Ocean. Whether you’re a beach lover, a boating enthusiast, or someone who enjoys outdoor activities, Southampton has something to offer.

Investing in a home with a pool in Southampton not only elevates your lifestyle but also enhances the value of your property. Dive into the Southampton experience—where every day feels like a getaway, and your home is your personal paradise.

Newest Southampton Homes with Pool

$2,170,000

3 Beds ⋅ 3 Baths ⋅ 1028965 MLS

Thoughtfully renovated Southampton property set behind an electric gated entrance and newly asphalted driveway on nearly one-acre of mostly cleared property, this 3/3 contemporary light-filled home offers nearly 3,000 square feet of finished living space across two well designed levels. The main level features a master bedroom with ensuite double vanity bathroom, two additional bedrooms with shared full bathroom, vaulted high ceilings, a wood-burning fireplace and a brand-new modern kitchen, while a dedicated dining room and separate den or home office provide flexibility for both everyday living and entertaining. A spacious lower level significantly expands the home's living space with a full double vanity bathroom and additional living/dining areas, easily accommodating a fourth bedroom if desired. The property offers two distinct outdoor settings. A tranquil landscaped pond with a gentle waterfall creates a peaceful, Zen-like arrival, while the rear of the home features a wraparound deck and a spacious bluestone patio leading up to a new 18x48 heated pool, providing exceptional privacy for entertaining or relaxing. The attached two-car garage completes the property's outdoor appeal. Designed for today's lifestyle, the home features comprehensive smart home automation, allowing remote access and full control of the sliding gate, garage doors, indoor/outdoor lighting, Honeywell thermostats, irrigation system, pool equipment and other major systems at the touch of a button. Offered fully furnished and ideally positioned for easy access to and from New York City, this move-in-ready home offers the opportunity to begin enjoying the Hamptons from day one or immediately generate rental income as an exceptional Hamptons retreat.

138 Longview Road, Southampton

$2,175,000

4 Beds ⋅ 4 Baths ⋅ 1022236 MLS

SOUTHAMPTON HOME, GREAT ENTERTAINING SPACES! This custom-built Hamptons retreat is designed for those who appreciate home comforts with great spaces for entertaining. The house is being sold "as is" with its furniture and furnishings and gym equipment, excluding only its artwork, tools, and personal items, enhancing the opportunity to immediately move in and start enjoying all that the Hamptons have to offer. The large entry foyer leads to a light-filled, double-height great room, measuring 22' x 21', combining a chef's kitchen, dining area, and spacious living room. There are four bedrooms and four full bathrooms, including the first floor primary and junior-primary bedroom suites. Also located on the first floor is an office, a family room, the laundry area, and a third full bath. Beautiful solid oak flooring, stained a beachy coastal white, was recently installed on the first level. Upstairs, two generously sized bedrooms share a hallway bath. The basement has a full poured concrete foundation and includes the garage. The large, unfinished basement can be finished for multiple uses and currently has a home gym set-up that is included in the sale. The backyard is a highlight. Three sliding glass doors from the great room open onto an expansive rear deck set up for dining and leisure. The 20' x 40' heated pool has an electric cover to retain the pool water's warmth during cool summer nights. The property also features a two-story pavilion with outdoor seating and an alfresco dining area by the pool. Additional amenities include a large wood burning fireplace in the great room, central vacuum, an awning on the rear deck, and an electric car charger in the garage. The Solar Voitaic system is fully paid for and are tied into the PSEG grid, creating extremely low monthly electric bills. Located just west of Southampton Village in the Highlands subdivision of Shinnecock Hills, this home offers convenient access to world-class beaches, shopping, and restaurants.

3 Chivas Court, Southampton

$8,800,000

9 Beds ⋅ 11 Baths ⋅ 1027277 MLS

A rare opportunity to own one of Southampton’s most distinctive private compounds. Situated on approximately 5 acres, this extraordinary contemporary estate features two architecturally striking residences with a combined living area of approximately 10,500 square feet, dual swimming pools, exceptional privacy, and remarkable future potential. Experience exceptional luxury and privacy on this remarkable 5-acre Southampton estate featuring two contemporary residences, each with its own heated swimming pool. The main residence offers approximately 7,500 SF of thoughtfully designed living space with 5 spacious bedrooms, 6 full bathrooms, soaring ceilings, dramatic walls of glass, custom finishes, expansive entertaining areas, and seamless indoor-outdoor living. A separate 3,000 SF guest residence features 4 bedrooms and 3 full bathrooms, providing the perfect accommodation for extended family, guests, or private retreats. Surrounded by mature trees for complete privacy, the property showcases expansive terraces, resort-style outdoor spaces, and beautifully landscaped grounds. A private on-site well supplies the property’s water, contributing to exceptionally low annual property taxes of approximately $10,000. An additional approximately 3 acres offer outstanding future potential, subject to buyer verification and municipal approvals, for possible subdivision, additional development, recreational amenities, or other permitted uses. Ideally located just minutes from Southampton Village, world-renowned ocean beaches, championship golf courses, fine dining, wineries, and upscale shopping. This rare compound presents an exceptional opportunity as a year-round residence, luxury vacation retreat, or multigenerational estate in one of the Hamptons’ most desirable locations.

87 Castle Hill Court, Southampton

$4,000,000

4 Beds ⋅ 4 Baths ⋅ 1025348 MLS

Discover a pristine home in Southampton that embodies modern design and decor, exuding both luxury and comfort. Upon arrival, high ceilings and a wall of windows greet you, filling the space with natural light and showcasing views of the beautifully landscaped backyard. The spacious living room features a gas fireplace complemented by built-in shelving, while the gourmet kitchen and open dining area create a generous open floor plan, perfect for hosting and celebrating. For more intimate gatherings, the step-down lounge offers privacy while maintaining connectivity with the main floor. The primary suite, located on the main floor, includes a spa-inspired bathroom and ample closet space. Upstairs, across the catwalk, you'll find a second junior ensuite and two additional bedrooms. Additional bonus space can be personalized as a gym, office, or library. The outdoor area is designed for entertaining, complete with a heated gunite pool, a deck with a pergola, an outdoor kitchen, and a side yard. This home is conveniently located near Southampton Village, providing a variety of dining and shopping options, along with easy access to beautiful ocean beaches, golf courses, and equestrian fields.

22 Summer Drive, Southampton

$3,250,000

3 Beds ⋅ 3 Baths ⋅ 1023422 MLS

Bright and Spacious Summer Home A rare combination of privacy and convenience, this sun-filled three-bedroom, 2.5-bath home is set on a generous 0.49-acre property in Southampton Village, featuring an expansive, beautifully landscaped backyard designed for seclusion and year-round enjoyment. Mature plantings and thoughtful landscaping create a peaceful retreat, ideal for both quiet relaxation and entertaining. Inside, the home offers well-proportioned bedrooms and elegant marble bathrooms, along with a custom modern white eat-in chef's kitchen featuring quartz and Glassos countertops and stainless steel appliances. The inviting living room is anchored by a wood-burning fireplace, adding warmth and character. Outdoors, a bluestone patio extends from the home to a heated 40x18 gunite pool, complemented by a dedicated outdoor dining area-perfect for hosting or unwinding in a private setting. Ideally located near both the Village center and renowned ocean beaches-including Coopers Beach, often ranked among America's best-this property offers the perfect balance of privacy, space, and accessibility.

770 Hill Street, Southampton

$7,950,000

6 Beds ⋅ 6 Baths ⋅ 1022948 MLS

Set in the heart of Southampton Village, this award-winning Victorian traditional has long been celebrated for its old world charm — wide-plank wood floors, exquisite tilework, and stately proportions that speak to a more gracious era of Hamptons living. Nearly 6,500 square feet of living space unfolds across a home that has been meticulously and recently restored to its finest expression, with European designer finishes and a soft, refined palette that makes every room feel both elevated and effortlessly livable. Six bedrooms and 6 marble bathrooms, are thoughtfully arranged to offer flexibility — privacy when desired, connection when needed. The primary suite and sitting area function as a sanctuary unto themselves, while a picturesque stand-alone garden cottage provides an additional private retreat alongside the classic in-ground pool and manicured English Garden. The chef's kitchen anchors the home with a massive central island, two oversized refrigerators, a professional range with dual ovens and griddle, and multiple dining configurations that make hosting feel natural rather than effortful. Wrap terraces front and back — newly furnished with European modern classics — extend the living space outdoors in a way that feels seamless rather than seasonal. A well-appointed lower level and a magical, tucked-away third floor complete this singular Southampton retreat. Please give 24 hour notice for showings.

55 Post Crossing, Southampton

$2,495,000

5 Beds ⋅ 5 Baths ⋅ 1019304 MLS

Just completed, this beautifully renovated transitional home is the quintessential Hamptons retreat. Set on nearly 1.5 private acres and complemented by a detached accessory studio with its own private entrance, the property offers a rare combination of flexibility, exceptional privacy, and expansive level grounds. Abutting protected Southampton Town preserve, the home enjoys a peaceful natural backdrop with miles of scenic walking trails just beyond the backyard, all while being moments from Southampton Village, world-renowned ocean & beaches, boutique shopping, and acclaimed restaurants. The thoughtfully redesigned residence features five spacious bedrooms, 4- of which are en-suite, and five full bathrooms. Bright, open living spaces are filled with natural light, flowing seamlessly between the living room, dining area, and beautifully appointed kitchen. Contemporary finishes, refined craftsmanship, and timeless design create a sophisticated yet welcoming atmosphere throughout. Designed for effortless indoor-outdoor living, the expansive backyard is a private oasis featuring a sparkling swimming pool, generous patio space, mature landscaping, and a sprawling lawn ideal for entertaining or relaxing. The detached accessory studio provides exceptional flexibility as a home office, fitness studio, creative workspace. Combining a just-completed custom renovation, nearly 1.5 private acres, a detached accessory studio, a two-car garage, and an exceptional Southampton setting, this turnkey property offers the very best of Hamptons living.

1579 N Sea Road, Southampton

$2,695,000

4 Beds ⋅ 4 Baths ⋅ 1019371 MLS

Welcome to this newly renovated, New England-inspired colonial home in Southampton, situated on a shy 1.5 acres at the entrance to the Hamptons. Upon arrival, the residence is set back on the property, providing a great deal of privacy. As you enter the home, you are greeted by high ceilings and a spacious foyer. The open floor plan is filled with natural light and seamlessly connects the living and dining areas. The kitchen features custom white cabinetry and stainless steel appliances, along with a casual dining island. Two sets of sliding doors provide easy access to the private backyard, accessing the pool and spacious entertaining patio. Additionally, the side yard offers ample space for curating a garden or outdoor lounge. On the main floor, you will find an office, a full bathroom with laundry facilities, and a lounge that opens to the backyard, making it an inviting space to gather and enjoy the pool. Upstairs, wide hallways lead to a loft space and four bedrooms. The primary suite includes a spa-inspired bathroom with a soaking tub, while the junior ensuite bedroom offers lovely views of the backyard. The two additional generously sized bedrooms share a full bathroom. The full, unfinished lower level provides versatile options, whether you envision it as a recreation room, gym, or home theater. Enjoy convenient access to picturesque beaches, golf courses, equestrian fields, and the charming village, where you can indulge in shopping, dining, and nightlife options.

148 Hills Station Road, Southampton

$1,699,000

3 Beds ⋅ 3 Baths ⋅ 1019081 MLS

Property is occupied. Please do not disturb the tenant. The property is being sold as-is, subject to the bank's approval. Interior access is not available at this time. Drive-by only until bank approval is obtained.

10 Kerrie Court, Southampton

$3,895,000

4 Beds ⋅ 3 Baths ⋅ 1016035 MLS

Southampton Retreat with Two Story Annex Nestled within nearly an acre of lushly landscaped grounds and surrounded by 20 acres of serene Southampton preserve, 55 Island Creek Road presents a rare and compelling opportunity in the heart of East End’s coveted Southampton. This enchanting retreat offers a harmonious blend of natural beauty, privacy, and modern-day convenience—creating a true storybook setting for the discerning buyer. This estate features two distinct structures: a charming 2400SF one-and-a-half-story 4 bed 3 bath residence and a 960 SF Incredible Versatile Legal Separate (2) two-story annex building, currently used as an Artists Studio—that literally opens a 10 x 10 gated door out and onto the late-great artist Shimon Okshteyn’s personal sculpture garden (included in sale). The two structures are uniquely separated by a pool built into the deck, offering a refreshing outdoor retreat and a wonderful opportunity for the new owner to personalize and make their own. The secondary structure is ideally suited for today’s evolving lifestyle—perfect as a sophisticated home office, creative studio, or an entrepreneurial workspace. This mind-blowing unique live/work configuration of the two structures is an increasingly sought-after asset, particularly for professionals and business owners seeking to seamlessly balance productivity with the peace and tranquility of a Hamptons retreat. Strategically located, the property offers remarkable accessibility. Just minutes from Southampton Village and with convenient access to major roadways and the Long Island Railroad, commuting to New York City is both practical and efficient—allowing residents to enjoy the best of both worlds: the vibrancy of Manhattan and the peaceful luxury of the Hamptons. The surrounding area is rich in amenities and lifestyle attractions. Within just a few miles are some of the most prestigious and celebrated golf courses in the country, including Shinnecock Hills Golf Club, The National Golf Links of America, Sebonack Golf Club and Southampton Golf Club. This property has access to Bullhead Bay and Great Peconic Bay. Additionally, the pristine ocean beaches that define the Hamptons lifestyle are only minutes away, along with easy access to bays, marinas, and water-based recreation—offering endless opportunities for relaxation and outdoor enjoyment. The grounds themselves are a standout feature—beautifully integrated into their natural surroundings, offering privacy, scenic views, and a deep spiritual like environment and connection to the local ecosystem. Mature landscaping enhances the atmosphere, creating a peaceful sanctuary that feels both expansive and intimate. 55 Island Creek boast super-low taxes and the undeniable charm that defines its character. From its idyllic setting to its flexible living spaces, 55 Island Creek Road represents a unique opportunity to own a residence that effortlessly combines elegance, functionality, and lifestyle. This is more than a home—it is a rare offering for the discerning purchaser seeking inspiration, convenience, and enduring value in one of Long Island’s most prestigious locations.

55 Island Creek Road, Southampton

$1,650,000

3 Beds ⋅ 1 Baths ⋅ 1011323 MLS

Build, Expand, or Enjoy in Southampton Village New to the market, this Southampton Village property presents a rare opportunity to own in one of the Hamptons' most sought-after locations. Set on .38± acre, the property offers immediate enjoyment with significant future potential. The existing cottage is rich in character, featuring original wide-plank pine floors, a welcoming living room, separate dining room, kitchen, and full bath on the first floor. Upstairs are three bedrooms, offering comfortable accommodations for summer living or year-round use. Outside, a heated gunite pool, spa, and detached garage/storage building create a private setting for relaxation and entertaining. For those looking to expand, the property can accommodate a new residence of approximately 3,500± square feet on two levels, with additional space possible in the lower level, garage, and pool house. Whether updating, expanding, or building new, this is an exceptional opportunity to secure a Village address and create lasting value. Conveniently located near Southampton Village shops, restaurants, cultural attractions, the train station, and Hampton Luxury Liner stop. Enjoy as is, reimagine, or build new in the heart of Southampton Village.

98 Powell Avenue, Southampton

$2,850,000

4 Beds ⋅ 5 Baths ⋅ 1010175 MLS

SOUTHAMPTON | PICTURE PERFECT POST MODERN Set down a long private country drive, this beautifully maintained Post Modern home offers the ideal Hamptons retreat, blending comfortable living with exceptional indoor and outdoor entertaining spaces. A dramatic double-height foyer welcomes you into the light-filled interior, where an open-concept layout seamlessly connects the great room with fireplace, dining area, and a well-appointed kitchen featuring premium appliances and a breakfast bar perfect for casual dining and gathering. The generous first-floor primary suite serves as a private sanctuary with an en-suite bath and easy access to the home's indoor-outdoor lifestyle. The second level offers an open loft overlooking the main living area along with three additional guest bedrooms, including a junior en-suite bedroom. The finished lower level provides additional recreational and lifestyle space, complete with a workout area, game room, lounge, laundry room, and custom wine storage. Designed for effortless entertaining, the outdoor spaces are a standout feature. Expansive decking overlooks the heated freeform pool and hot tub, all surrounded by mature Barry Block-designed landscaping that creates a private, resort-like setting. Multiple lounge areas, a covered outdoor dining space, grilling station, and bar area provide the perfect backdrop for summer gatherings. A conveniently located powder room functions as a cabana bath with direct access from the pool area. Completing the property is a detached two-car garage and beautifully landscaped grounds that invite relaxation and enjoyment throughout the season. A Hamptons home offering privacy, comfort, and a seamless connection between indoor living and outdoor entertaining.

20 Spinnaker Way, Southampton

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.