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Surrounded by tranquil waters separating the town from the rest of Suffolk County, Shelter Island sits at the far eastern end of Long Island, nestled between the North and South Forks. This 8,000-acre island, accessible only by boat or private plane, offers a rich history, laid-back vibe, scant traffic, and gentler real estate prices.

A uniquely blended quirky, artsy, rural, and cosmopolitan community, Shelter Island offers an indescribable beauty where breathtaking ocean and wilderness views form the backyards of grand historic homes and charming seaside cottages. The town is a fantasia of Victoriana complete with an abundance of untouched land.

More than a third of the island encompasses a complete wilderness of protected woodlands, marshes, freshwater ponds, and tidal creeks, inhabited by a range of wildlife including osprey, ibis, hummingbirds, muskrats, foxes, harbor seals, and terrapins. The land is also home to several Braille, nature, and bird-watching trails.

Top beaches, golf courses, yacht clubs, and restaurants give residents a place to unwind and play after work. A vacation destination since the 1870s, Shelter Island offers 70 boat landings including ample opportunity for boating, golfing, fishing, and hiking. The Yacht Club remains a social center for summer families today.

Many residents have deep family roots dating back to the Colonial period. Summer residents are fifth generation visitors. Wary of overdevelopment, the town board recently passed measures to regulate short-term rentals, preventing a freewheeling Airbnb-style tourist culture from overtaking the quiet charm residents and visitors love.

Contact Team Rita today to schedule viewings for homes in Shelter Island, New York. Call to schedule a free consultation with one of our real estate agents.


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  1. 5 Beds,  5.5 Baths
    4,040 sqft   lot 3.44 ac
    MLS 849374
    4 Days on Market
  2. 3 Beds,  2 Baths
    3,170 sqft   lot 1.04 ac
    MLS 842082
    16 Days on Market
  3. 4 Beds,  3.5 Baths
    3,800 sqft   lot 39,640 sqft
    MLS 838795
    28 Days on Market
  4. 6 Beds,  4 Baths
    4,949 sqft   lot 1.04 ac
    MLS 834105
    38 Days on Market
  5. 5 Beds,  3.5 Baths
    3,325 sqft   lot 43,560 sqft
    MLS 811480
    94 Days on Market
  6. 4 Beds,  4.5 Baths
    5,300 sqft   lot 39,814 sqft
    MLS L3592958
    145 Days on Market
  7. 3 Beds,  2 Baths
    1,500 sqft   lot 22,957 sqft
    MLS L3590276
    161 Days on Market
  8. 4 Beds,  3 Baths
    3,420 sqft   lot 1.89 ac
    MLS L3577201
    224 Days on Market
  9. 6 Beds,  4.5 Baths
    4,957 sqft   lot 2.01 ac
    MLS L3567654
    270 Days on Market
  10. 4 Beds,  3 Baths
    2,600 sqft   lot 29,447 sqft
    MLS L3543543
    374 Days on Market
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