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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.

Source: OneKey MLS, MLS#: 1016035

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  • Property Type
    Residential
  • Lot
    0.92 acres

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Owning this Home

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

Life at 55 Island Creek Road


Schools


School data courtesy of LiveBy, Inc.
Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date Event Value Agent
6/19/2026Source: OneKey MLS Added to Database
June 19, 2026
Listing provided courtesy of CorcoranEvan F. Church- MLS# 1016035MLS ProviderContact Information: 917-684-0663