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| Address | Bed / Bath | Listing Price |
|---|---|---|
73 N Midway Road
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 emerg
Living Area:
2296 Sqft.
|
4
Beds,
3
Baths
|
$1,895,000 |
13 Tarkettle Road
Nestled on over an acre along Shelter Island's coveted Dickerson Creek, this Scandinavian-style waterfront cottage offers a serene escape with 100 ft. of gorgeous shoreline. Imagine waking up to breathtaking sunrises and launching your paddle board right from your backyard. Inside, discover a light-
Living Area:
1373 Sqft.
|
3
Beds,
2
Baths
|
$3,175,000 |
26 S Menantic Road
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-pla
Living Area:
1702 Sqft.
|
4
Beds,
4
Baths
|
$1,695,000 |
1 Gazon Road
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 crea
Living Area:
2618 Sqft.
|
4
Beds,
3
Baths
|
$1,295,000 |
10 Strawberry Lane
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 wi
Living Area:
1340 Sqft.
|
3
Beds,
2
Baths
|
$1,195,000 |
52 S Midway Rd
Around the bend from Turkem's Rest and a short paddle from Salt and Shipwreck, this recently renovated, 4-bedroom, circa 1908 Shelter Island farmhouse, on a shy acre, is perched above Menantic Creek with a substantial dock and profits from panoramic water views with southwestern exposure for magical
Living Area:
2200 Sqft.
|
4
Beds,
3
Baths
|
$3,750,000 |
100 S Ferry Road
A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep.
Boasting six bedrooms, each w
Living Area:
5622 Sqft.
|
6
Beds,
8
Baths
|
$4,495,000 |
68 Peconic Avenue
Shelter Island Sound water front beach house offers stunning sunsets, sandy beach, fully bulkheaded, L'Shaped dock with lift and splash boards;a waterside 50' heated Gunite pool; and expansive unobstructed views out to Robins Island. A serene retreat with a blend of comfort and coastal charm nestled
Living Area:
2061 Sqft.
|
3
Beds,
3
Baths
|
$4,900,000 |
100 Peconic
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 cat
Living Area:
1626 Sqft.
|
3
Beds,
3
Baths
|
$4,000,000 |
14 Fred's Lane
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
Living Area:
2418 Sqft.
|
6
Beds,
4
Baths
|
$2,650,000 |
15A / 15 & 13 S Menantic Road
For the first time in over a century, this extraordinary collection of generationally owned properties is being offered together as a singular and rare opportunity. Nestled along the serene and picturesque Menantic Creek, these three separate parcels combined total 4.9 acres, which have been combine
Living Area:
3944 Sqft.
|
9
Beds,
6
Baths
|
$9,955,000 |
26 Ole Buck Run
This recently renovated 3 bedroom, two bath home with wood burning fireplace is situated on .89 private acres. The home now has a: new roof, siding, and air conditioners. Newly refinished floors, painted interior, new back decks, exterior basement entry and new appliances. Turn key and ready for you
Living Area:
Sqft.
|
3
Beds,
2
Baths
|
$1,085,000 |
47L S Ferry Road
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. Sp
Living Area:
3800 Sqft.
|
4
Beds,
4
Baths
|
$9,900,000 |
90 Peconic Avenue
This Nantucket Shingle Classic with room for pool has Size, Location and Style to adorn this Rare Sunset Waterfront Green Lawns Gem. Surprisingly Bigger than it looks! Many believe the side lawn a separate lot from the spacious 5 bedroom Beach House on gorgeous Shelter Island. The only house known
Living Area:
3325 Sqft.
|
5
Beds,
4
Baths
|
$5,415,000 |
10 Sunshine Road B
Quintessential Hamptons estate in the heart of Shelter Island . Enjoy the best of both worlds at this traditional Hamptons style home, with approximately 5000sqft of immaculate living space across one level, and nearly an acre of land, it's the perfect setting for the best of year round and seamless
Living Area:
5300 Sqft.
|
4
Beds,
5
Baths
|
$2,795,000 |