Shelter Island, NY Homes

• 

  

  

  /8

  $1,375,000

  $125K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  20 Crescent Way, Shelter Island, NY 11964

  This lovely home is nicely sited ona shy acre close to Menhaden LaneBeach and Golf. Hard wood floors throughout.Spaciousliving room with cathedral ceiling, fireplace andsliders which open onto a large deck and yard beyond. Three nice sized bedrooms, two full baths, formal dining room, chef's kitchen with gas stove, Den/potential media roomwith egress, two-car garage+.Yard is fenced with plenty of

  Melina Wein M WEIN REALTY INC

  20 Crescent Way, Shelter Island, NY 11964
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• 

  Est $1,593,390

  Not Listed For Sale

  1 Deer Park Ln, Shelter Island, NY 11964

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

  1 Deer Park Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 52% Above List Price
  • $427/SF
  • 153 Days On Market

  • Last Sold Price $1,050,000
  • Jan 24, 2025

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
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  /4

  $995,000

  $100K PRICE DROP

  • Land
  • 27,878 Sq Ft
  • $1,554,688 per Acre

  12 Hilo Dr, Shelter Island, NY 11964

  .64 Acres on Shelter Island, adjacent to cumminty dock. Room fof house and pool

  Brian Buckhout Compass

  12 Hilo Dr, Shelter Island, NY 11964
• 

  Not Listed For Sale

  18 Dickerson Dr, Shelter Island, NY 11786

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft
  • Built 1973

  18 Dickerson Dr, Shelter Island, NY 11786

  Last Sold Summary

  • $901/SF
  • 16 Days On Market

  • Last Sold Price $2,500,000
  • Feb 11, 2025

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate
• 

  

  

  /19

  $1,175,000

  • 3 Beds
  • 3 Baths
  • 1,950 Sq Ft

  16 Shelterlands Path, Shelter Island, NY 11964

  This island classic is truly a home for all seasons. The bright and open floor plan is beautifully complemented by the natural surroundings of Shelter Island, creating an inviting atmosphere throughout the year. The spacious living room and dining room feature sliding doors that open onto surrounding decks, making summer relaxation a breeze. A cozy fireplace offers comfort on the chilliest autumn

  Mary Elizabeth Galle Corcoran

  16 Shelterlands Path, Shelter Island, NY 11964
• 

  Est $1,222,000

  Not Listed For Sale

  169 N Ferry Rd, Shelter Island, NY 11964

  169 N Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 69% Above List Price
  • 14 Days On Market

  • Last Sold Price $725,000
  • Apr 18, 2024

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
• 

  

  /27

  $1,995,000

  $355K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,484 Sq Ft

  23 Osprey Rd, Shelter Island, NY 11964

  Situated in the desirable Sherwood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes

  Kieran Brew SERHANT.

  23 Osprey Rd, Shelter Island, NY 11964
• 

  Est $1,600,162

  Not Listed For Sale

  5 Country Club Dr, Shelter Island, NY 11964

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

  5 Country Club Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 28% Above List Price
  • $525/SF
  • 304 Days On Market

  • Last Sold Price $1,250,000
  • Feb 07, 2025

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sotheby's
• 

  

  /46

  $6,945,000

  Pending

  • 8 Beds
  • 7.5 Baths

  55 & 70 Peconic Ave, Shelter Island, NY 11964

  Presenting a rare and compelling joint offering at 55 & 70 Peconic Avenue-a modern compound opportunity in one of Shelter Island's most coveted waterfront enclaves. Together, these two distinct yet complementary properties deliver scale, privacy, and irreplaceable southwest-facing water views across the Peconic toward Southampton-creating a legacy estate unlike anything else on the market. 55

  Jack Richardson SERHANT.

  55 & 70 Peconic Ave, Shelter Island, NY 11964
• 

  Est $2,086,000

  Not Listed For Sale

  3 Bevan Place, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft
  • Built 1979

  3 Bevan Place, Shelter Island, NY 11964

  Last Sold Summary

  • 16% Below List Price
  • $1,379/SF
  • 307 Days On Market

  • Last Sold Price $2,475,000
  • Oct 02, 2024

  Last Listing Agent Mary Elizabeth Galle Corcoran
• 

  

  /28

  $4,445,000

  $450K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 5,622 Sq Ft

  100 S Ferry Rd, Shelter Island, NY 11964

  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 with their own en-suite, and two additional half-baths, this residence effortlessly blends style

  Christine Beckwith Douglas Elliman Real Estate

  100 S Ferry Rd, Shelter Island, NY 11964
• 

  Est $2,697,315

  Not Listed For Sale

  44 Saint Mary's Rd, Shelter Island, NY 11964

  • 3 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1985

  44 Saint Mary's Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 23% Below List Price
  • $1,085/SF
  • 28 Days On Market

  • Last Sold Price $3,500,000
  • Feb 11, 2025

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate
• 

  

  /27

  $1,845,000

  $50K PRICE DROP

  • 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
• 

  Est $1,418,000

  Not Listed For Sale

  74 Peconic Ave, Shelter Island, NY 11964

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1953

  74 Peconic Ave, Shelter Island, NY 11964

  Last Sold Summary

  • 29% Below List Price
  • $1,543/SF
  • 73 Days On Market

  • Last Sold Price $2,000,000
  • Sep 12, 2024

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
• 

  

  /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 $3,692,000

  Not Listed For Sale

  148E N Ferry Rd, Shelter Island, NY 11964

  • 3 Beds
  • 3 Baths
  • 2,350 Sq Ft
  • Built 1990

  148E N Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 30% Above List Price
  • $1,213/SF
  • 79 Days On Market

  • Last Sold Price $2,850,000
  • Sep 13, 2023

  Last Listing Agent Bridget Elkin Compass Greater NY LLC
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  /35

  $1,195,000

  $100K PRICE DROP Pending

  • 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 $1,591,000

  Not Listed For Sale

  10 Penny's Path, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft
  • Built 1980

  10 Penny's Path, Shelter Island, NY 11964

  Last Sold Summary

  • 22% Above List Price
  • $573/SF
  • 47 Days On Market

  • Last Sold Price $1,300,000
  • Aug 17, 2023

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
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  /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 $1,446,000

  Not Listed For Sale

  1 Worthy Way, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft
  • Built 1980

  1 Worthy Way, Shelter Island, NY 11964

  Last Sold Summary

  • 35% Above List Price
  • $883/SF
  • 86 Days On Market

  • Last Sold Price $1,075,000
  • Sep 11, 2023

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
• 

  

  /21

  $499,000

  Open Sat 11AM - 1PM

  • 1 Bed
  • 1 Bath
  • 39,964 Sq Ft

  13 Winthrop Rd Unit 24, Shelter Island, NY 11964

  Discover effortless living in this beautifully renovated one-bedroom, one bath co-op on Shelter Island. The apartment is set within a serene and private eight-acre community. Thoughtfully updated, the residence features a modern kitchen and bath, with Bosch appliances, including an in-unit washer anddryer for ultimate convenience. The home opens to a private deck-perfectly suited for outdoor

  Elizabeth Wohl Brown Harris Stevens Hamptons

  13 Winthrop Rd Unit 24, Shelter Island, NY 11964
• 

  Est $1,856,231

  Not Listed For Sale

  6 Evans Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1986

  6 Evans Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 12% Above List Price
  • $635/SF
  • 267 Days On Market

  • Last Sold Price $1,650,000
  • Dec 20, 2023

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sotheby's
• 

  

  /31

  $4,479,000

  Pending

  • 4 Beds
  • 4.5 Baths

  70 Peconic Ave, Shelter Island, NY 11964

  Introducing 70 Peconic Avenue-an irreplaceable, one-of-a-kind waterfront estate commanding sweeping southwest views across the Peconic toward Southampton. With four fully finished levels, nearly every room framed by water, and private shoreline access, this is the kind of property that simply does not come back to market. From the moment you enter the front foyer, the view stops you in your

  Jack Richardson SERHANT.

  70 Peconic Ave, Shelter Island, NY 11964
• 

  Est $1,657,000

  Not Listed For Sale

  27 Terry Dr, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,098 Sq Ft
  • Built 1974

  27 Terry Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 66% Above List Price
  • $477/SF
  • 186 Days On Market

  • Last Sold Price $999,999
  • Jun 28, 2023

  Last Listing Agent Annmarie Seddio Atlas Sales Realty
• 

  

  /46

  $1,595,000

  $200K PRICE DROP

  • 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
• 

  Not Listed For Sale

  8 Margaret's Dr, Shelter Island, NY 11964

  • 6 Beds
  • 4.5 Baths
  • 2,978 Sq Ft
  • Built 1973

  8 Margaret's Dr, Shelter Island, NY 11964

  Last Sold Summary

  • $672/SF
  • 247 Days On Market

  • Last Sold Price $2,000,000
  • May 31, 2023

  Last Listing Agent Marianne Collins Brown Harris Stevens N Fork
• 

  

  /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 $1,853,955

  Not Listed For Sale

  2 Dering Woods Rd, Shelter Island, NY 11964

  2 Dering Woods Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 69% Above List Price
  • 373 Days On Market

  • Last Sold Price $1,100,000
  • Aug 22, 2024

  Last Listing Agent Annmarie Seddio Atlas Sales Realty
• 

  

  /6

  $895,000

  • Land
  • 36,590 Sq Ft
  • $1,065,476 per Acre

  9 Hillside Dr, Shelter Island, NY 11964

  First time listed is this mostly cleared (+/-) .84 acre in Hilo Shores. The building site has 85'-95' of elevation (per GIS attached) and offers a possible water view. The Hilo Shores Association has a community dock and racks for kayaks, paddle boards and other small personal water craft.

  Dickinson Baker Saunders & Associates

  9 Hillside Dr, Shelter Island, NY 11964
• 

  Est $917,241

  Not Listed For Sale

  29 St Marys Rd, Shelter Island, NY 11964

  • Built 1955

  29 St Marys Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 7% Below List Price
  • $688/SF
  • 215 Days On Market

  • Last Sold Price $990,000
  • Dec 11, 2023

  Last Listing Agent Richard Connelly Douglas Elliman Real Estate
• 

  

  /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

  Matthew Breitenbach Compass

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

  Est $1,741,000

  Not Listed For Sale

  58 Country Club Dr, Shelter Island, NY 11964

  • 4 Beds
  • 5 Baths
  • 3,200 Sq Ft
  • Built 2023

  58 Country Club Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 20% Below List Price
  • $680/SF
  • 224 Days On Market

  • Last Sold Price $2,175,000
  • Jun 28, 2023

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
• 

  

  /35

  $5,395,000

  Open Sat 12PM - 2PM

  • 4 Beds
  • 5.5 Baths
  • 4,250 Sq Ft

  9 Margarets Dr, Shelter Island, NY 11964

  Originally conceived as the Laguna Project, 9 Margarets is an AIA award-winning modern residence on Shelter Island that brings together architecture, light, and exceptional indoor-outdoor living across ~5,530± SF of thoughtfully designed space, including a substantial finished lower level. Offering 4 en-suite bedrooms, 5 full baths, and 1 half bath, the home is defined by vaulted, light-filled

  Jennifer Friedberg Compass

  9 Margarets Dr, Shelter Island, NY 11964
• 

  Est $1,377,560

  Not Listed For Sale

  98 S Ferry Rd, Shelter Island, NY 11964

  • 3 Beds
  • 1.5 Baths
  • 1,250 Sq Ft
  • Built 1880

  98 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 157% Above List Price
  • $428/SF
  • 72 Days On Market

  • Last Sold Price $535,000
  • Jul 16, 2023

  Last Listing Agent Mike Carroll RE/MAX
• 

  

  /28

  $1,350,000

  Open Sat 11AM - 12:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,564 Sq Ft

  11 Mimosa Place, Shelter Island, NY 11964

  This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining.A large, inviting living room with a wood-burning

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  11 Mimosa Place, Shelter Island, NY 11964
• 

  Est $2,730,299

  Not Listed For Sale

  101 S Ferry Rd, Shelter Island, NY 11964

  • 8 Beds
  • 4.5 Baths
  • 3,098 Sq Ft
  • Built 1975

  101 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 71% Above List Price
  • $516/SF
  • 451 Days On Market

  • Last Sold Price $1,600,100
  • Aug 03, 2023

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
• 

  Est $1,483,640

  Not Listed For Sale

  7 Marc St, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1966

  7 Marc St, Shelter Island, NY 11964

  Last Sold Summary

  • 13% Below List Price
  • $1,417/SF
  • 103 Days On Market

  • Last Sold Price $1,700,000
  • Sep 27, 2024

  Last Listing Agent Rachel Rushforth-Worrell Sothebys Int'l Realty Hamptons
• 

  Est $3,120,774

  Not Listed For Sale

  47 Peconic Ave, Shelter Island, NY 11965

  • 3 Beds
  • 3.5 Baths
  • 3,137 Sq Ft
  • Built 1970

  47 Peconic Ave, Shelter Island, NY 11965

  Last Sold Summary

  • 13% Above List Price
  • $877/SF
  • 14 Days On Market

  • Last Sold Price $2,752,518
  • Jul 28, 2023

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
• 

  Est $9,469,899

  Not Listed For Sale

  29 Winthrop Rd, Shelter Island, NY 11964

  • 6 Beds
  • 10 Baths
  • 7,781 Sq Ft
  • Built 1888

  29 Winthrop Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 8% Above List Price
  • $1,125/SF
  • 17 Days On Market

  • Last Sold Price $8,750,000
  • May 12, 2023

  Last Listing Agent Deborah Pirro Daniel Gale Sotheby's
• 

  Est $873,577

  Not Listed For Sale

  68 S Ferry Rd, Shelter Island, NY 11964

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1960

  68 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 23% Above List Price
  • $789/SF
  • 287 Days On Market

  • Last Sold Price $710,000
  • Nov 07, 2023

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's

Showing Results 41 - 80, Page 2 of 18