Top 5 Southampton Homes for Sale with Epic Pools

1860 Meadow Lane, Southampton
1860 Meadow Lane, Southampton, Photo: Courtesy Sotheby’s International Realty

Try finding a premier Hamptons home without a pool. They’re almost nonexistent. And as the summer sun bears down and entertaining becomes a priority, why wouldn’t you want to dive in and cool off in your own backyard? This week, we celebrate the swimming and splashing season with our top five Southampton homes for sale with epic pools.

595 Captain's Neck Lane, Southampton
595 Captain’s Neck Lane, Southampton, Photo: Courtesy Sotheby’s International Realty

595 Captain’s Neck Lane, Southampton

With almost 5 acres bordering a 31-acre reserve, expansive water-frontage and western views across Shinnecock Bay, this Southampton estate is truly something special. Behind a gated entrance and down a long drive, the Traditional-style residence, built in 1914, has retained original details, all indicative of the early 20th century. It has 10 bedrooms, 7 baths, powder room, living room, den, formal dining room, sunroom, covered patio, chefs and service kitchens, plus staff quarters in its 6,500 square feet of living space. Outside it feature tennis, a beautifully curvy swimming pool with patio, Jacuzzi spa, cutting gardens and a path with footbridge over a picturesque pond. A covered carport and caretaker sheds round out the storybook setting. Sotheby’s International Realty

1860 Meadow Lane, Southampton aerial
1860 Meadow Lane, Southampton, Photo: Sotheby’s IR

1860 Meadow Lane, Southampton

This custom-built oceanfront contemporary boasts dramatic 360-degree views of the Atlantic and Shinnecock Bay with over 200 feet of direct ocean frontage on over five acres. The property includes a north/south tennis court, specimen trees, slate outdoor barbecue area and extensive decking. The interior of the 4-bedrooms, 6-bath house features a spacious master suite with separate baths and closets, private walkout decks, fireplace and office/sitting area. The combination sunken living room with fireplace and dining area with second floor decking allows for spectacular views, and the updated kitchen offers state-of-the-art equipment, dumbwaiter and a second-floor deck. Arguably one of the most exciting amenities, a 40- by 20-foot indoor heated pool has a connecting pool house and sauna, and entertaining area with its own kitchen. Sotheby’s International Realty

237 Gin Lane, Southampton
237 Gin Lane, Southampton, Photo: Courtesy Sotheby’s International Realty

237 Gin Lane, Southampton

On the market for the first time, this magnificent and meticulously detailed home is sited on 2 acres of magical, park-like grounds on Southampton Village’s legendary Gin Lane. The gracious floor plan, perfect for entertaining, includes a large formal living room with fireplace, paneled library with fireplace, sunroom, formal dining room and an oversized kitchen/family room—all accessing the gardens, covered dining porch, red brick patio and lengthy pool. There are 9 family bedrooms, 9 full baths and 2 half baths, including a master suite with dramatic architectural details and an ocean view. Additionally, the home has a staff wing, 2-car garage accessed through a stone courtyard and tennis outside. Sotheby’s International Realty

60 Herrick Road, Southampton

Offering 6,500 square feet of luxury on three levels, the ideal layout of this 6-bedroom, 9.5-bath beauty includes a gym, media room and lower level with surprises, such as a second living room with fireplace and access to lower level spa. A smart home Control4 system brings the house to life with a single touch inside, while the grounds include a pool house with kitchenette and full bath. The fabulous in-ground pool and spa fit snugly alongside a covered porch in the crook of the house, while mature plantings—not limited to the 18-foot arborvitae—encase the property leaving it extremely private. A detached 2-car garage with full basement and outdoor shower complete the picture. Corcoran Group

99 Bay Street, Southampton
99 Bay Street, Southampton, Photo: Douglas Elliman

99 Bay Street, Southampton

Perched high on the bluffs overlooking Little Peconic Bay, this stunning Mediterranean-inspired beachfront home includes 3 bedrooms, 2 baths and 1,760 square feet of luxurious waterfront living. The house, with bay views from almost every room and a state of the art, eat-in chef’s kitchen, is designed to take full advantage of its incredible natural surroundings and breathtaking bay-front vistas. It features a beautifully landscaped backyard with gunite infinity pool and spa right above the bay. Multiple private sundecks, personal beach access and the surrounding nature preserve make this North Sea Beach Colony property a true treasure. It feels secluded and private, yet it’s just 10 minutes from downtown Southampton. This home has a perfect blend of luxurious convenience and waterfront serenity. Douglas Elliman

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