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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. 2 Beds,  2 Baths
    lot 21,780 sqft
    MLS 3545912
    4 Days on Market
  2. 4 Beds,  3 Baths
    lot 29,621 sqft
    MLS 3543543
    13 Days on Market
  3. 4 Beds,  3 Baths
    2,200 sqft   lot 1.29 ac
    MLS 3543073
    15 Days on Market
  4. 2 Beds,  1.5 Baths
    1,411 sqft   lot 1.47 ac
    MLS 3540919
    25 Days on Market
  5. 6 Beds,  7 Baths
    5,622 sqft   lot 2.16 ac
    MLS 3539613
    32 Days on Market
  6. 4 Beds,  4.5 Baths
    5,300 sqft   lot 40,076 sqft
    MLS 3536906
    43 Days on Market
  7. 3 Beds,  2.5 Baths
    2,380 sqft   lot 1.06 ac
    MLS 3532284
    66 Days on Market
  8. 3 Beds,  2.5 Baths
    lot 26,572 sqft
    MLS 3523302
    112 Days on Market
  9. 4 Beds,  3.5 Baths
    3,800 sqft   lot 39,640 sqft
    MLS 3521653
    127 Days on Market
  10. 3 Beds,  1 Bath
    1,443 sqft   lot 37,898 sqft
    MLS 3520840
    132 Days on Market
  11. 5 Beds,  5 Baths
    6,000 sqft   lot 2.00 ac
    MLS 3513979
    174 Days on Market
  12. 3 Beds,  2 Baths
    1,161 sqft   lot 21,780 sqft
    MLS 3513923
    174 Days on Market
  13. 4 Beds,  4.5 Baths
    3,689 sqft   lot 27,008 sqft
    MLS H6276020
    175 Days on Market
  14. 3 Beds,  2.5 Baths
    1,795 sqft   lot 43,560 sqft
    MLS 3508513
    202 Days on Market
  15. 4 Beds,  5 Baths
    lot 8.12 ac
    MLS 3508407
    202 Days on Market
  16. 3 Beds,  2.5 Baths
    1,637 sqft   lot 39,640 sqft
    MLS 3498830
    249 Days on Market
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