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Four Plus Bedroom Homes for Rent in Shelter Island, NY

(1 - 15 of 626)
  1. Southampton Village Four Bedroom with Pool and Pool House This Southampton Village, south of the highway, boasts an impeccable home on a beautiful lane that sits back from the road and is hedged on a shy half-acre property. It is only 2+/- miles f...
    Brenda Giufurta ·5 hours ago on RealtyWW
  2. Nestled in the beautiful Bay View Oaks private community, this charming 4 bedroom home boasts playful and chic design on lush grounds with a heated gunite pool. With private beach access with sunset views at the end of the street and centrally loc...
    Hedgerow Exclusive Team ·3 hours ago on RealtyWW
  3. Summer in Southampton in this pristine rental. Thoughtfully decorated and expanded with light-filled sun room, eat in kitchen, and warm family room with fireplace. Formal dining room and living room are simply but elegantly furnished, and a large ...
    Robert C (rc) Atlee-hodgson ·7 hours ago on RealtyWW
  4. Welcome to 14 Sebonac Road, Southampton - an outstanding example of contemporary architecture set on a generous entrance down a private tree-lined driveway. Designed for easy entertaining, this six-bedroom, six-bath mini-estate invites you into a ...
    Christian Lipp ·5 hours ago on RealtyWW
  5. Recently renovated, in 2021 and new heated swimming pool with expansive mahogany decking and large electric awning. This stunning loft-like barn is in the Rawson Estates bay front community with a private beach and water views. The 5, 000 square f...
    Deborah Koster ·6 hours ago on RealtyWW
  6. Located in one of Southamptons sought after waterfront communities, Southampton Cove, is this newly renovated and fully outfitted 5 bedroom, 4 bath summer house. Easily accessible from New York City and a few minutes drive to Southampton, Bridgeha...
    Jeremy Dunham ·6 hours ago on RealtyWW
  7. Experience quintessential Wainscott living at this stunning beach compound that is one of the very few original multi-generational Wainscott properties. Nestled close to one of the most private beaches, and abutting reserve, this historic property...
    The Breitenbach Advisory Team ·4 hours ago on RealtyWW
  8. Perfectly located south of the highway in the fabled Southampton estate section, this classic residence offers easy access to both village amenities and ocean beaches. With a rare combination of timeless elegance and modern comforts, the home has ...
    Nancy D. Grady ·9 hours ago on RealtyWW
  9. Located south of the highway and sited on a flag lot, this Southampton Village classic cedar Saltbox style home, is surrounded by lush gardens allowing for complete privacy and peacefulness. Within close proximity to Jobs Lane and Coopers Beach, t...
    Ryan Gleason ·6 hours ago on RealtyWW
  10. LOCATION! Leave your car at home at this immaculate summer cottage that is close to Main Street shopping and restaurants, train station and everything Southampton Village has to offer. The 4-bedroom, 3-bath home was renovated in 2021 with brand ne...
    Adriel A. Reboh ·6 hours ago on RealtyWW
  11. This Southampton Village home underwent a ground-up renovation and expansion in 2015 and has been tastefully decorated embracing the current owner's exquisite taste and vision. The beautifully maintained grounds and pool are extremely private and ...
    The Breitenbach Advisory Team ·5 hours ago on RealtyWW
  12. This traditional shingled home with views of Dering Harbor, on almost 3 acres offers privacy and recreation in a beautiful setting. With natural light, tasteful decor a memorable vacation is waiting for you. The living room has a fireplace with vi...
    M. Wein Realty Inc. ·12 hours ago on LinkURealty
  13. Iconic oceanfront home situated in the heart of Southampton Village's historic estate section majestically presides over 220 feet of pristine beach frontage. Designed to capture the essence of beachfront living, the 8, 000+/- square foot home feat...
    The Breitenbach Advisory Team ·8 hours ago on RealtyWW
  14. This beautiful Traditional has just been given a stylish update in time for you to enjoy this summer. Located on Cove Neck Lane in Southampton, this spacious 4300sf home, borders acres of preserved land. Offering 5 Bedrooms, including a sunny 1st ...
    Alyra Hoffman ·4 hours ago on RealtyWW
  15. Introducing a recently renovated Southampton residence nestled on a serene cul-de-sac, boasting six bedrooms and five-and-a-half bathrooms. Spanning approximately 7, 000 square feet across three levels, the home's modern open floor plan is tailore...
    Hedgerow Exclusive Team ·6 hours ago on RealtyWW
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