Shelter Island, NY Homes

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  /16

  $1,999,999

  $350K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,777 Sq Ft

  5 Marc St, Shelter Island, NY 11964

  Welcome to your dream getaway where modern luxury meets laid-back coastal charm. This Newly renovated 4 Bedroom 3.5 Bathroom home offers perfect blend of style & tranquility, just moments from beaches, marinas and all that island has to offer. Designer Kitchen with Quartz countertops. custom soft close cabinetry with center island & high end appliances. Located on first floor Primary Bedroom with

  Anthony Guidice RE/MAX Signature Real Estate

  5 Marc St, Shelter Island, NY 11964
• 

  Est $3,752,922

  Not Listed For Sale

  6 Cave Way, Shelter Island, NY 11964

  • 3 Beds
  • 4 Baths
  • 2,117 Sq Ft
  • Built 1973

  6 Cave Way, Shelter Island, NY 11964

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
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  /35

  $8,500,000

  • 3 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  3 Bevan Place, Shelter Island, NY 11964

  Set along the quiet shoreline of Pipers Cove Bay in Shelter Island Heights, this west-facing waterfront retreat is tucked at the end of a private drive and has been thoughtfully reimagined by Heiberg Cummings, whose signature approach to layered design transforms the home into something both sophisticated and deeply connected to its surroundings. Every room on both levels is oriented toward the

  Stacey Cohen The Agency Hamptons

  3 Bevan Place, Shelter Island, NY 11964
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  Not Listed For Sale

  78 Peconic Ave, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 2,504 Sq Ft
  • Built 1962

  78 Peconic Ave, Shelter Island, NY 11964

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
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  /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 $1,795,515

  Not Listed For Sale

  15 S Midway Rd, Shelter Island, NY 11964

  • 4 Beds
  • 2.5 Baths
  • 2,144 Sq Ft
  • Built 1975

  15 S Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Christine Beckwith Douglas Elliman Real Estate
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  /6

  $825,000

  $70K PRICE DROP

  • Land
  • 36,590 Sq Ft
  • $982,143 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 $1,424,775

  Not Listed For Sale

  9 S Midway Rd, Shelter Island, NY 11964

  • 4 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • Built 1948

  9 S Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 309 Days On Market

  Last Listing Agent Karen Connolly Karen O Connolly
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  /18

  $6,999,000

  Pending

  • 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 $1,852,000

  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

  • 224 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
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  /33

  $2,239,000

  $246K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 3,413 Sq Ft

  14 Freds Ln, Shelter Island, NY 11964

  Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  14 Freds Ln, Shelter Island, NY 11964
• 

  Est $1,028,739

  Not Listed For Sale

  10 N Midway Rd, Shelter Island, NY 11964

  • 2 Beds
  • 1 Bath
  • 976 Sq Ft
  • Built 1955

  10 N Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 171 Days On Market

  Last Listing Agent Linda Mccarthy Daniel Gale Sothebys Intl Rlty
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  /34

  $2,495,000

  $200K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,000 Sq Ft

  3 Conrad Rd, Shelter Island, NY 11964

  Set on a quiet street in the Montclair Colony section of Shelter Island, this newly renovated four-bedroom, four-bath combines the ease of single-story living with the feel of a private retreat. The turn-key residence is surrounded by mature hedges on a flat, manicured 0.70-acre lot, providing an exceptional setting for an immediate indoor-outdoor lifestyle and seamless entertaining. Inside, the

  Matthew Breitenbach Compass

  3 Conrad Rd, Shelter Island, NY 11964
• 

  Est $1,682,409

  Not Listed For Sale

  4 Sleepy Hollow Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,451 Sq Ft
  • Built 1990

  4 Sleepy Hollow Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Annmarie Seddio Atlas Sales Realty
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  /13

  $3,750,000

  • Land
  • 1 Acre
  • $3,750,000 per Acre

  14B Heron Ln, Shelter Island, NY 11964

  SHELTER ISLAND WATERFRONTThis one acre waterfront building offers unobstructed views and breathtaking sunsets overlooking Noyac Bay. Sandy beach waterfront is perfect for swimming

  Theodore Damiecki Brown Harris Stevens Hamptons

  14B Heron Ln, Shelter Island, NY 11964
• 

  Est $3,216,611

  Not Listed For Sale

  133 S Midway Rd, Shelter Island, NY 11964

  • 3 Beds
  • 1 Bath
  • 1,510 Sq Ft
  • Built 1955

  133 S Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Linda Mccarthy Daniel Gale Sothebys Intl Rlty
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  /39

  $5,000,000

  $395K PRICE DROP

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

  9 Margarets Dr, Shelter Island, NY 11964

  AIA Award-winning 9 Margarets Drive is a modern Shelter Island retreat where architecture, landscape, and natural light come together with exceptional clarity. Designed by Lacuna Architecture Atelier, the approximately 5,530-square-foot residence, including a substantial finished lower level, offers four en-suite bedrooms, five full baths, and one half bath, with a design centered on a seamless

  Jennifer Friedberg Compass

  9 Margarets Dr, Shelter Island, NY 11964
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  Est $1,507,907

  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

  • 72 Days On Market

  Last Listing Agent Mike Carroll RE/MAX Best
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  /29

  $1,275,000

  $75K PRICE DROP

  • 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 $1,486,071

  Not Listed For Sale

  70 S Ferry Rd, Shelter Island, NY 11964

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1832

  70 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
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  Not Listed For Sale

  149 Ram Island Dr, Shelter Island, NY 11964

  • 6 Beds
  • 7 Baths
  • 5,518 Sq Ft
  • Built 2003

  149 Ram Island Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 201 Days On Market

  Last Listing Agent Andrea Ackerman Brown Harris Stevens Hamptons
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  Not Listed For Sale

  1 Wheeler Rd, Shelter Island, NY 11964

  • 6 Beds
  • 5.5 Baths
  • 3,700 Sq Ft
  • Built 1962

  1 Wheeler Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 91 Days On Market

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

  Est $3,148,851

  Not Listed For Sale

  13 Tarkettle Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Built 1950

  13 Tarkettle Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 71 Days On Market

  Last Listing Agent Andrew Spina HomeSmart Premier Living Rlty
• 

  Est $2,325,174

  Not Listed For Sale

  4 Wheeler Rd, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft
  • Built 2021

  4 Wheeler Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 129 Days On Market

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

  Est $2,489,399

  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

  • 451 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
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  Est $1,162,553

  Not Listed For Sale

  84 N Cartwright Rd, Shelter Island, NY 11964

  • 2 Beds
  • 1 Bath
  • 1,350 Sq Ft
  • Built 1940

  84 N Cartwright Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 157 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
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  Est $2,498,493

  Not Listed For Sale

  82 N Cartwright Rd, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,104 Sq Ft
  • Built 1920

  82 N Cartwright Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 157 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
• 

  Est $3,227,749

  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

  • 14 Days On Market

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

  Est $3,416,146

  Not Listed For Sale

  24 S Midway Rd, Shelter Island, NY 11964

  • 5 Beds
  • 5 Baths
  • 4,475 Sq Ft
  • Built 1940

  24 S Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 251 Days On Market

  Last Listing Agent Peter Humphrey Douglas Elliman Real Estate
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  Est $10,553,737

  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

  • 17 Days On Market

  Last Listing Agent Deborah Pirro Daniel Gale Sothebys Intl Rlty
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  Not Listed For Sale

  5 Tuthill Dr, Shelter Island, NY 11964

  5 Tuthill Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 316 Days On Market

  Last Listing Agent Linda Mccarthy Daniel Gale Sothebys Intl Rlty
• 

  

  /3

  Est $3,059,000

  Not Listed For Sale

  31A Dickerson Dr, Shelter Island, NY 11964

  • 4 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1994

  31A Dickerson Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Lisa Pullini Pullini Realty Corp.
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  Est $1,196,532

  Not Listed For Sale

  42 Brander Pkwy, Shelter Island, NY 11964

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • Built 1959

  42 Brander Pkwy, Shelter Island, NY 11964

  Last Sold Summary

  • 180 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
• 

  Est $668,400

  Not Listed For Sale

  3 Quail Hedge Ln, Shelter Island, NY 11964

  3 Quail Hedge Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 100 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
• 

  Est $4,166,946

  Not Listed For Sale

  28 Merkel Ln, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,760 Sq Ft
  • Built 1984

  28 Merkel Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 150 Days On Market

  Last Listing Agent Linda Mccarthy Daniel Gale Sothebys Intl Rlty
• 

  Est $2,645,255

  Not Listed For Sale

  87 N Ferry Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,544 Sq Ft
  • Built 1980

  87 N Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 371 Days On Market

  Last Listing Agent Mary Elizabeth Galle Corcoran
• 

  Est $2,305,878

  Not Listed For Sale

  9 Wheeler Rd, Shelter Island, NY 11964

  • 5 Beds
  • 3.5 Baths
  • 2,371 Sq Ft
  • Built 2003

  9 Wheeler Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 237 Days On Market

  Last Listing Agent John Klupka Douglas Elliman Real Estate
• 

  Est $3,797,248

  Not Listed For Sale

  28 S Menantic Rd, Shelter Island, NY 11964

  • 4 Beds
  • 6 Baths
  • 4,174 Sq Ft
  • Built 1888

  28 S Menantic Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Janet Markarian Daniel Gale Sothebys Intl Rlty
• 

  Est $2,319,735

  Not Listed For Sale

  6 Quail Hedge Ln, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 3,054 Sq Ft
  • Built 1999

  6 Quail Hedge Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 363 Days On Market

  Last Listing Agent Linda Mccarthy Daniel Gale Sothebys Intl Rlty
• 

  Est $1,632,263

  Not Listed For Sale

  20 Terry Dr, Shelter Island, NY 11964

  • 4 Beds
  • 2.5 Baths
  • 2,644 Sq Ft
  • Built 1984

  20 Terry Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 94 Days On Market

  Last Listing Agent Linda Mccarthy Daniel Gale Sothebys Intl Rlty

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