Shelter Island, NY Homes

• 

  $660,000 Sold Dec 02, 2025

  8 Wheeler Rd, Shelter Island, NY 11964

  • Land
  • 1.2 Acres
  • $550,000 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 99 Days On Market

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  8 Wheeler Rd, Shelter Island, NY 11964
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• 

  Est $1,670,000 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  74 Peconic Ave, Shelter Island, NY 11964

  74 Peconic Ave, Shelter Island, NY 11964
• 

  

  

  /27

  $1,895,000

  • 4 Beds
  • 3 Baths
  • 2,296 Sq Ft

  73 N Midway Rd, Shelter Island, NY 11964

  A thoughtfully designed retreat offering peace, privacy, and understated luxury.Tucked away on a private drive in the island's center, you're close enough to bike to all of the island’s beaches or restaurants.The approach sets the tone: a winding drive reveals the house gradually. The home emerges across an expansive lawn, its clean black lines and Anderson windows throughout creating a

  JoAnn Wind Daniel Gale Sothebys Intl Rlty

  73 N Midway Rd, Shelter Island, NY 11964
• 

  $1,050,000 Sold Jan 24, 2025

  1 Deer Park Ln, Shelter Island, NY 11964

  • 3 Beds
  • 3.5 Baths
  • 2,460 Sq Ft
  • Built 1993

  Last Sold Summary

  • 40% Below List Price
  • $427/SF
  • 153 Days On Market

  Current Estimated Value $1,606,441

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  1 Deer Park Ln, Shelter Island, NY 11964
• 

  Est $3,545,000 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,350 Sq Ft

  148E N Ferry Rd, Shelter Island, NY 11964

  148E N Ferry Rd, Shelter Island, NY 11964
• 

  

  /27

  $2,650,000

  • 6 Beds
  • 4 Baths
  • 2,418 Sq Ft

  14 Freds Ln, Shelter Island, NY 11964

  Tucked away on a shy acre, this private retreat features a heated Gunite pool, fire-pit seating area, all framed by mature trees. The main house has an open floor plan with cathedral ceilings and exposed wood beams in the living room, a cook's kitchen with stainless steel appliances, island seating for 3-4, and a dining area that flows easily for entertaining. A deck off the kitchen sets the

  Melina Wein M WEIN REALTY INC

  14 Freds Ln, Shelter Island, NY 11964
• 

  $1,250,000 Sold Feb 07, 2025

  5 Country Club Dr, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft
  • Built 1986

  Last Sold Summary

  • 25% Below List Price
  • $525/SF
  • 304 Days On Market

  Current Estimated Value $1,528,841

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  5 Country Club Dr, Shelter Island, NY 11964
• 

  Est $1,561,000 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft

  10 Penny's Path, Shelter Island, NY 11964

  10 Penny's Path, Shelter Island, NY 11964
• 

  

  /29

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  4 Duvall Rd, Shelter Island, NY 11964

  Amazing 1800s house with 3 bedrooms and 2 baths. Perfectly quiet location in Shelter Island! Tennis courts directly across the street and backyard view of rolling land, minutes to the beach and a few steps to restaurants and gallery.

  Simon Harrison Simon Harrison Real Estate

  4 Duvall Rd, Shelter Island, NY 11964
• 

  Est $1,718,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft

  1 Worthy Way, Shelter Island, NY 11964

  1 Worthy Way, Shelter Island, NY 11964
• 

  

  /35

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  10 Strawberry Ln, Shelter Island, NY 11964

  Nestled on a serene .58-acre parcel just minutes from Wades Beach and Fresh Pond, this well-maintained ranch-style home offers the perfect blend of classic Shelter Island charm and modern convenience. Built in 1967 and lovingly cared for, the home features 1,340 square feet of single-level living with 3 bedrooms and 2 full baths, including a primary en-suite for added comfort and privacy. The

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  10 Strawberry Ln, Shelter Island, NY 11964
• 

  Est $1,821,919 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  6 Evans Rd, Shelter Island, NY 11964

  6 Evans Rd, Shelter Island, NY 11964
• 

  

  /7

  $695,000

  • Land
  • 1 Acre
  • $695,000 per Acre

  1 Strawberry Ln, Shelter Island, NY 11964

  This truly magical building lot is ready for your dream home. A full acre of land with test well in place. "C" Zone which is the least restrictive residential zone on Shelter Island. A stone's throw from Fresh Pond and short distance to Wades Beach. Quiet location. Close to shops, school, library, restaurants and beaches. Exclusive: $695K

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  1 Strawberry Ln, Shelter Island, NY 11964
• 

  Est $1,618,000 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,098 Sq Ft

  27 Terry Dr, Shelter Island, NY 11964

  27 Terry Dr, Shelter Island, NY 11964
• 

  

  /48

  $5,875,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,504 Sq Ft

  21 Thompson Rd, Shelter Island, NY 11964

  Perched 59 feet above sea level for commanding views and peace of mind, this exceptional contemporary estate—designed by noted architect Kenton van Boer—rests on 9.4 private acres, of which 2.7 acres are buildable, and offers 561 feet of premier waterfront on Smiths Cove. Sweeping panoramic vistas of the Sound and the tranquil yacht anchorage set the scene for direct beachfront access and creek

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  21 Thompson Rd, Shelter Island, NY 11964
• 

  Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 2,978 Sq Ft

  8 Margaret's Dr, Shelter Island, NY 11964

  8 Margaret's Dr, Shelter Island, NY 11964
• 

  

  /48

  $1,695,000

  • 4 Beds
  • 3.5 Baths
  • 1,702 Sq Ft

  26 S Menantic Rd, Shelter Island, NY 11964

  Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  26 S Menantic Rd, Shelter Island, NY 11964
• 

  Est $1,766,003 Not Listed For Sale

  2 Dering Woods Rd, Shelter Island, NY 11964

  2 Dering Woods Rd, Shelter Island, NY 11964
• 

  

  /35

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,618 Sq Ft

  1 Gazon Rd, Shelter Island, NY 11964

  This enchanting Shelter Island home feels like a true getaway. Tucked into a peaceful setting, it offers a sense of calm and ease the moment you arrive. The house has a warm and welcoming atmosphere, with open, airy spaces that invite you to slow down and unwind. A large living room and kitchen create the heart of the home, centered by a wood-burning fireplace - perfect for gathering with friends

  Kristy Naddell Douglas Elliman Real Estate

  1 Gazon Rd, Shelter Island, NY 11964
• 

  Est $996,142 Not Listed For Sale

  29 St Marys Rd, Shelter Island, NY 11964

  29 St Marys Rd, Shelter Island, NY 11964
• 

  

  /20

  $4,000,000

  • 3 Beds
  • 3 Baths
  • 1,626 Sq Ft

  100 Peconic Ave, Shelter Island, NY 11964

  Infinite Views over Shelter Island Sound and extensive bulk-headed sandy beach front make for perfect, summer days and sunset filled nights spent enjoying the beauty and tranquility of this property. Charming interior with beautiful wood floors and touches of wainscoting, living room with beamed cathedral ceiling, picture window and wood burning fireplace, cooks kitchen with dining alcove, two

  Melina Wein M WEIN REALTY INC

  100 Peconic Ave, Shelter Island, NY 11964
• 

  Est $1,462,484 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,672 Sq Ft

  9 S Midway Rd, Shelter Island, NY 11964

  9 S Midway Rd, Shelter Island, NY 11964
• 

  

  /17

  $3,995,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  47B S Ferry Rd, Shelter Island, NY 11964

  Discover a secluded paradise on Shelter Island, nestled within the expansive 2,350-acre Mashomack Nature Preserve. Tucked away at the end of a private road lies a unique opportunity: 1.74 acres of picturesque land featuring a charming 1,800 square-foot home with three bedrooms. Enjoy breathtaking water vistas from every window, 150 feet of direct water frontage, and the convenience of a private

  Hedgerow Exclusive Team Hedgerow Exclusive Properties

  47B S Ferry Rd, Shelter Island, NY 11964
• 

  Est $1,785,000 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,200 Sq Ft

  58 Country Club Dr, Shelter Island, NY 11964

  58 Country Club Dr, Shelter Island, NY 11964
• 

  

  /18

  $6,999,000

  • Land
  • 6 Acres
  • $1,166,500 per Acre

  3a/3b Pandion Rd Unit 3a/3b, Shelter Island, NY 11964

  In a market where exceptional land opportunities are scarce, this rare property on Shelter Island presents the chance to create your ultimate Hamptons waterfront compound. With 875 feet of water frontage, this six-acre, two-parcel offering along Coecles Harbor comes with architectural plans fully approved by both the Suffolk County Department of Health Services and the Department of Environmental

  Breitenbach Advisory Team Compass

  3a/3b Pandion Rd Unit 3a/3b, Shelter Island, NY 11964
• 

  Est $1,079,502 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 976 Sq Ft

  10 N Midway Rd, Shelter Island, NY 11964

  10 N Midway Rd, Shelter Island, NY 11964
• 

  

  /36

  $1,850,000 Pending

  • 3 Beds
  • 2 Baths
  • 3,170 Sq Ft

  27 Country Club Dr, Shelter Island, NY 11964

  Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant custom home was lovingly crafted by a local artist in 2011 and spans 3,170 square feet. Designed to maximize natural light, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. The home features 21' vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  27 Country Club Dr, Shelter Island, NY 11964
• 

  Est $1,472,857 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,250 Sq Ft

  98 S Ferry Rd, Shelter Island, NY 11964

  98 S Ferry Rd, Shelter Island, NY 11964
• 

  

  /38

  $9,900,000

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  47L S Ferry Rd, Shelter Island, NY 11964

  Discover unparalleled privacy and serenity within the heart of the 2,350-acre Mashomack Nature Preserve, a rare and cherished enclave. At the culmination of a secluded, winding drive, this newly constructed architectural gem unveils itself, a testament to modern design and uncompromising quality. Spanning 3,800 square feet, this residence is a symphony of light and space, framed by walls of glass

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  47L S Ferry Rd, Shelter Island, NY 11964
• 

  Est $2,587,834 Not Listed For Sale

  • 8 Beds
  • 4.5 Baths
  • 3,098 Sq Ft

  101 S Ferry Rd, Shelter Island, NY 11964

  101 S Ferry Rd, Shelter Island, NY 11964
• 

  Est $1,621,921 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  7 Marc St, Shelter Island, NY 11964

  7 Marc St, Shelter Island, NY 11964
• 

  Est $3,414,529 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,137 Sq Ft

  47 Peconic Ave, Shelter Island, NY 11965

  47 Peconic Ave, Shelter Island, NY 11965
• 

  Est $10,039,104 Not Listed For Sale

  • 6 Beds
  • 10 Baths
  • 9,230 Sq Ft

  29 Winthrop Rd, Shelter Island, NY 11964

  29 Winthrop Rd, Shelter Island, NY 11964
• 

  Est $902,215 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  68 S Ferry Rd, Shelter Island, NY 11964

  68 S Ferry Rd, Shelter Island, NY 11964
• 

  Est $1,509,598 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft

  63 N Midway Rd, Shelter Island, NY 11964

  63 N Midway Rd, Shelter Island, NY 11964
• 

  Est $1,033,674 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,546 Sq Ft

  57 N Midway Rd, Shelter Island, NY 11964

  57 N Midway Rd, Shelter Island, NY 11964
• 

  Est $1,566,618 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  5 Emerson Ln, Shelter Island, NY 11964

  5 Emerson Ln, Shelter Island, NY 11964
• 

  Est $5,654,079 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  6 Club Dr, Shelter Island, NY 11964

  6 Club Dr, Shelter Island, NY 11964
• 

  Est $1,402,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,860 Sq Ft

  1 Behringer Ln, Shelter Island, NY 11964

  1 Behringer Ln, Shelter Island, NY 11964
• 

  Est $4,226,355 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,680 Sq Ft

  6 Cave Way, Shelter Island, NY 11964

  6 Cave Way, Shelter Island, NY 11964

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