55 Island Creek Road • Southampton, NY 11968

$3,895,000 Beds: 4 • Baths: 3 full • Sq. Feet: 2215 • MLS ID: 1016035 • Subdivision:School Dist: Southampton
Southampton Retreat with Two Story AnnexNestled 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 environmen View this listing at: http://josephpiscitello.laffey.com/mls=1016035

Property Features

  • Garage: 3
  • Taxes: $5,199
  • Basement: Yes
  • Swimming Pool: Yes
  • Exterior: Frame
  • Special View Info: Trees/Woods
  • Lot Size: 0.92 Acres
  • Heating: Baseboard
  • Cooling: Central Air
  • Year Built: 1996
  • Water: Public
  • Sewer: Septic Tank
  • On Market Date: 2026-06-19
  • Appliances: Convection Oven,Cooktop,Dishwasher
  • Basement: Storage Space,Unfinished,Walk-Out Access
  • Building Area Total: 3171
  • GarageY/N: Yes
  • Interior Features: First Floor Bedroom,First Floor Full Bath,Ceiling Fan(s),High Ceilings,Open Kitchen
  • Number Of Kitchens: 1
  • Parcel Number: 0900-092-00-03-00-028-000
  • Parking Features: Heated Garage,Oversized,Private,Storage
  • Patio And Porch: Deck,Porch,Terrace
  • Property Attached Y/N: 1
  • Rental Term: Monthly
  • Rooms Total: 10
  • Utilities: Cable Available,Electricity Connected,Water Connected
  • Waterfront Features: Water Access

School Information

  • High School: Southampton High School
  • Middle School: Southampton Intermediate School
  • Elementary School: Tuckahoe School
  • School District: Southampton
Printed June 29, 2026


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