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$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
$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
$1,699,000
869782 MLS
Sunrise, sunsets! Finished, ready-to-go 1.04 acre building lot - one of the last full-acre properties available in Southampton, just waiting for your creative design. Backs up to wooded, Town-owned parkland. Private cul-de-sac neighborhood, finished with Belgian block curbs. More than enough space for house of your dreams, with room for garage, pool, patio and gardens;; possibly tennis. Underground water, electric, cable and Verizon in place now at curb. Quick bike ride to swimming, canoeing, freshwater fishing at Elliston Park, Big Fresh Pond (Lake Missapogue). Close to boating, saltwater fishing and other water sports at Scallop Pond and beautiful Peconic Bay. Minutes to ocean beaches, dining and shopping in Southampton Village, Water Mill, and Sag Harbor.

8 Lois Lane, Southampton

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.