Shelter Island, NY Homes

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  /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 Shorewood 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
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• 

  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

  • 16 Days On Market

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate
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  /26

  $2,700,000

  • 6 Beds
  • 3 Baths
  • 5,900 Sq Ft

  2 Prospect Ave, Shelter Island, NY 11964

  A rare opportunity to own a legacy compound on Shelter Island, this offering brings together three income-producing historic cottages and a separate buildable lot, all just moments from the water. Positioned at 2 Prospect Avenue and 38 Rock Point Road, the properties are offered as one cohesive investment, blending immediate revenue with exceptional future potential. Each of the three cottages

  Marco Maida Compass Greater NY LLC

  2 Prospect Ave, Shelter Island, NY 11964
• 

  Est $1,064,000

  Not Listed For Sale

  169 N Ferry Rd, Shelter Island, NY 11964

  169 N Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
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  /5

  $1,375,000

  • 3 Beds
  • 2 Baths

  20 Crescent Way, Shelter Island, NY 11964

  Tucked on nearly an acre in a quiet, established neighborhood, this 2,175 sq. ft. home offers the rare combination of privacy, location, and room to grow. The light-filled upper level features a cathedral-ceiling living room with fireplace and sliders to an entertainment deck, a primary suite, and three bedrooms in all. Easy access to Menhaden Lane Beach and golf. A fully enclosed yard with room

  Melina Wein Compass

  20 Crescent Way, Shelter Island, NY 11964
• 

  Est $1,695,408

  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

  • 304 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
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  /28

  $3,850,000

  New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,985 Sq Ft

  8 Hilo Dr, Shelter Island, NY 11964

  This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail,

  Enzo Morabito Douglas Elliman Real Estate

  8 Hilo Dr, Shelter Island, NY 11964
• 

  Est $2,731,570

  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

  • 28 Days On Market

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate
• 

  

  /25

  $2,595,000

  • 4 Beds
  • 2.5 Baths
  • 1,994 Sq Ft

  11 Prospect Ave, Shelter Island, NY 11964

  Shelter Island Heights IconGracefully positioned in the heart of Shelter Island Heights, this timeless residence has been thoughtfully renovated and restored to honor its original character while seamlessly incorporating today's modern comforts. Rich in architectural charm and classic detail, the home offers an elegant blend of historic beauty and refined living. A gracious, oversized covered

  Donna Walker Douglas Elliman Real Estate

  11 Prospect Ave, Shelter Island, NY 11964
• 

  Est $2,137,405

  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

  • 73 Days On Market

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

  

  /45

  $1,850,000

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

  4 Irene Ln, Sag Harbor, NY 11963

  Discover a serene sanctuary amidst the natural beauty of Shelter Island. This stunning residence offers breathtaking water views of Miss Annie's Creek, providing an unparalleled escape from the ordinary. Step onto the property and be captivated by the charm of covered porches and a heated pool, inviting you to relax and soak in the picturesque vistas. Whether you're enjoying a quiet morning

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  4 Irene Ln, Sag Harbor, NY 11963
• 

  Est $3,736,000

  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

  • 79 Days On Market

  Last Listing Agent Bridget Elkin Compass Greater NY LLC
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  /28

  $4,295,000

  New Construction $600K 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 $1,812,000

  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

  • 47 Days On Market

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

  

  /18

  $4,000,000

  • 3 Beds
  • 3 Baths

  100 Peconic Ave, Shelter Island, NY 11964

  This waterfront is classic Shelter Island. Set on more than half an acre with 153 feet of private, bulkheaded sandy beach, this 1952 cottage keeps its head turned to the water from nearly every room. A fireplace and hardwood floors anchor the living room, the primary suite wakes to the Bay, and a covered waterside patio waits for the long part of the evening. Wooden steps lead down to your own

  Melina Wein Compass

  100 Peconic Ave, Shelter Island, NY 11964
• 

  Est $1,230,506

  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

  • 86 Days On Market

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

  

  /27

  $1,845,000

  $50K PRICE DROP Pending

  • 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 $2,020,680

  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

  • 267 Days On Market

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

  

  /29

  $1,500,000

  Pending

  • 5 Beds
  • 2.5 Baths
  • 2,845 Sq Ft

  5 Spring Garden Ave, Shelter Island, NY 11964

  Steeped in history and timeless architectural charm, this rare circa-1872 Gothic Revival cottage is located within the historic district of Shelter Island Heights, listed on both the National and New York State Registers of Historic Places. Beautifully preserved and largely unchanged since its original design, the home is a remarkable example of the picturesque residential style created by

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  5 Spring Garden Ave, Shelter Island, NY 11964
• 

  Est $1,887,829

  Not Listed For Sale

  2 Dering Woods Rd, Shelter Island, NY 11964

  2 Dering Woods Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 373 Days On Market

  Last Listing Agent Annmarie Seddio Atlas Sales Realty
• 

  

  /29

  $2,295,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  100 S Midway Rd, Shelter Island, NY 11964

  A stone's throw from popular Wades Beach this spacious contemporary is situated on an acre of park like grounds. Four bedrooms, three baths. Living room with vaulted ceilings and wood burning fireplace. Chef's kitchen with open floor plan. Lower level walkout with library/family room and wet bar. Large decks overlooking a heated gunite swimming pool with park like grounds. Exclusive: $2.295M

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  100 S Midway Rd, Shelter Island, NY 11964
• 

  Est $915,585

  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

  • 215 Days On Market

  Last Listing Agent Richard Connelly Douglas Elliman Real Estate
• 

  

  /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 $1,691,116

  Not Listed For Sale

  5 Wade Rd, Shelter Island, NY 11964

  • 3 Beds
  • 3 Baths
  • 1,854 Sq Ft
  • Built 1967

  5 Wade Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Rosanna Piazza Signature Premier Properties
• 

  

  /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 $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
• 

  

  /21

  $499,000

  • 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 $1,720,562

  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

  • 103 Days On Market

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

  

  /41

  $6,495,000

  Pending

  • 4 Beds
  • 6 Baths
  • 3,863 Sq Ft

  28 S Menantic Rd, Shelter Island, NY 11964

  Built in 1888 and thoughtfully renovated by acclaimed architect Lee H. Skolnick in 1988, this storied Shelter Island estate represents a rare convergence of architectural pedigree, cultural history, and timeless design. Set on two exquisitely landscaped acres with gardens designed by celebrated landscape designer Jeff Mendoza, the property has long served as a retreat for notable creative

  Stacey Cohen The Agency Hamptons

  28 S Menantic Rd, Shelter Island, NY 11964
• 

  Est $907,625

  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

  • 287 Days On Market

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

  

  /35

  $3,795,000

  • 5 Beds
  • 5 Baths
  • 3,072 Sq Ft

  5 Sea Gull Rd, Shelter Island, NY 11964

  Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  5 Sea Gull Rd, Shelter Island, NY 11964
• 

  Est $1,782,170

  Not Listed For Sale

  63 N Midway Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft
  • Built 1920

  63 N Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Linda Mccarthy Daniel Gale Sothebys Intl Rlty
• 

  

  /8

  $2,350,000

  • 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 $1,504,839

  Not Listed For Sale

  5 Emerson Ln, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 2016

  5 Emerson Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Dawn Watson Serhant East End LLC
• 

  

  /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
• 

  Est $5,078,611

  Not Listed For Sale

  6 Club Dr, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • Built 1973

  6 Club Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Edward Mulderrig Compass Greater NY LLC
• 

  

  /46

  $1,450,000

  $345K PRICE DROP Pending

  • 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 $1,333,225

  Not Listed For Sale

  105 S Ferry Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2.5 Baths
  • 1,726 Sq Ft
  • Built 1977

  105 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 177 Days On Market

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

  

  /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 $1,437,068

  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

  • 186 Days On Market

  Last Listing Agent Annmarie Seddio Atlas Sales Realty

Showing Results 41 - 80, Page 2 of 18