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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. 4 Beds,  2.5 Baths
    lot 1.04 ac
    MLS 3567097
    1 Days on Market
  2. 3 Beds,  1 Bath
    lot 37,898 sqft
    MLS 3566661
    3 Days on Market
  3. 1 Bed,  1 Bath
    1,800 sqft   lot 5.50 ac
    MLS 3565240
    10 Days on Market
  4. 3 Beds,  2.5 Baths
    3,312 sqft   lot 20,038 sqft
    MLS 3564455
    12 Days on Market
  5. 2 Beds,  2 Baths
    1,472 sqft   lot 27,008 sqft
    MLS 3563528
    25 Days on Market
  6. 3 Beds,  3 Baths
    1,400 sqft   lot 1.47 ac
    MLS 3557181
    46 Days on Market
  7. Price Drop
    6 Beds,  4.5 Baths
    3,764 sqft   lot 1.30 ac
    MLS 3554498
    54 Days on Market
  8. 3 Beds,  1 Bath
    1,296 sqft   lot 20,038 sqft
    MLS 3553678
    60 Days on Market
  9. 3 Beds,  3.5 Baths
    2,460 sqft   lot 43,560 sqft
    MLS 3551800
    66 Days on Market
  10. 4 Beds,  3.5 Baths
    2,800 sqft   lot 1.08 ac
    MLS 3550758
    72 Days on Market
  11. 3 Beds,  2 Baths
    lot 21,780 sqft
    MLS 3545912
    93 Days on Market
  12. 4 Beds,  3 Baths
    2,600 sqft   lot 29,621 sqft
    MLS 3543543
    102 Days on Market
  13. 4 Beds,  4.5 Baths
    5,300 sqft   lot 40,076 sqft
    MLS 3536906
    132 Days on Market
  14. 3 Beds,  2.5 Baths
    2,380 sqft   lot 1.06 ac
    MLS 3532284
    155 Days on Market
  15. 3 Beds,  2.5 Baths
    lot 26,572 sqft
    MLS 3523302
    201 Days on Market
  16. 4 Beds,  3.5 Baths
    3,800 sqft   lot 39,640 sqft
    MLS 3521653
    216 Days on Market
  17. 5 Beds,  5 Baths
    6,000 sqft   lot 2.00 ac
    MLS 3513979
    263 Days on Market
  18. 4 Beds,  4.5 Baths
    3,689 sqft   lot 27,008 sqft
    MLS H6276020
    264 Days on Market
  19. 3 Beds,  2.5 Baths
    1,795 sqft   lot 43,560 sqft
    MLS 3508513
    291 Days on Market
  20. 3 Beds,  2.5 Baths
    1,637 sqft   lot 39,640 sqft
    MLS 3498830
    338 Days on Market
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