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Five Bedroom Homes for Rent in Shelter Island, NY Between $36,000 and $61,000

(1 - 15 of 29)
  1. Step inside this beautiful Hamptons home and enjoy the modern yet comfortable feeling. This immaculately kept home is the (large) space to getaway from the real world! Nestled into this quiet neighborhood you can enjoy your private time while stil...
    Fallon A Nigro ·1 day ago on RealtyWW
  2. In Southampton at the end of a private road sits KISMET, a modern waterfront oasis prominently situated on Wooley Pond with open access to Peconic Bay. Also offers your own boat dock for all your water recreation. Built by the expert team of Caval...
    Thomas Cavallo ·1 day ago on RealtyWW
  3. Drive up to the gates of your 1.1 acre estate in East Hampton Village. Pull into the large circular driveway, with room for multiple cars and enter the 3, 300 square foot 5-bedroom and 5.5-bathroom estate with indoor fireplace. The expansive and m...
    John Caulfield ·3 days ago on RealtyWW
  4. Rustic luxury on the North Fork! Located within a waterfront enclave in Mattituck and close to all creature comforts, this renovated barn will not disappoint. 5 bedrooms, 3.5 bathrooms, heated pool, large EIK and den, views of Mattituck Inlet and ...
    Sheri Winter Clarry ·4 days ago on RealtyWW
  5. Enjoy this stunning home on a third of an acre just outside East Hampton Village. Providing over 3, 850+/- sq. ft. of living on 3 levels, this light-filled residence boasts five en-suite bedrooms and a powder room. The first floor flows easily fro...
    Sarah B Minardi ·1 week ago on RealtyWW
  6. Classic Southampton traditional in a quiet residential community with a private beach. This 5 bedroom 5.5 bath house has a beautiful flow and stylish decor. The first floor has a relaxing den with tv and full bathroom. A formal dining room which s...
    Ann Marie Horan ·2 weeks ago on RealtyWW
  7. Also Available: Aug 3 - Sep 2 $45K This NEW 4-5-bedroom home offers 5.5 baths and 3800 SF of impeccably designed living. A generous open floor plan, with walls of sliding glass doors and floor-to-ceiling windows, allows natural light to fill the i...
    Posted on RealtyWW
  8. Most stylish traditional offering five bedrooms, 5.5 baths, 2 fireplaces, cac, gourmet kitchen, living room and den, all on 2.50+/- maturely landscaped park-like acres with pool house and heated gunite pool. Close to shops and restaurants. Also av...
    Posted on RealtyWW
  9. The five-bedroom house enjoys a prime location on a very quiet and private residential cul de sac, while conveniently close to ocean beaches and Southampton Village. This beautiful home sits atop 2 +/- acre property is nicely landscaped. Grounds h...
    Posted on RealtyWW
  10. Stunning new construction with 110' of Long Island Sound front and private stairs to your beach. 10ft ceilings throughout the first floor, open floor plan with panoramic views. The living room has an oversized fireplace, built in cabinets and coff...
    Posted on RealtyWW
  11. Stunning Waterfront shingle style home overlooking Long Island Sound. Private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bed...
    Posted on RealtyWW
  12. This 5 bedroom home on a secluded cul de sac has all of the bells and whistles. Mature landscaping provides privacy for entertaining around the sparkling pool and bocce court. The home has CAC, cozy dining and living areas, and a finished lower le...
    Posted on RealtyWW
  13. Enjoy a classic traditional on a spectacular property where you can hear the ocean waves while you sit in utter privacy by the heated Gunite pool and spa. The sunny terrace off the kitchen and large bedroom create a wonderful flow from inside to o...
    Posted on RealtyWW
  14. This three-story, five-bedroom home has been completely renovated with breathtaking attention to detail. Two stone pillars welcome you to a winding path leading to beautifully landscaped 2+ acres that boasts a 20x40' Gunite pool as well as basketb...
    Posted on RealtyWW
  15. This five bedroom, four and one half bath home is a launching pad for a summer to remember! A long driveway takes you past a separately fenced pool area complete with flowering shrubs and generous patios that frame a heated saltwater gunite pool. ...
    Posted on RealtyWW
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