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Shelter Island Real Estate for Sale
A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique ...
- ACTIVE Status
- 5 Beds
- 4 Baths
- 1029569 MLS
Listing courtesy of Listing Agent: Christine M. Beckwith (christine.beckwith@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Brand new in one of Shelter Island's premier enclaves along Gardiners Bay, this custom 5,535 +/- SF, south-facing residence developed by Juno Homes presents a refined ble...
- ACTIVE Status
- 5 Beds
- 7 Baths
- 1027086 MLS
Listing courtesy of Listing Agent: Kristy B. Naddell (kristy.naddell@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Private Retreat with Separate Studio & Pool Potential Tucked away on Shelter Island's coveted southern peninsula, 5 Osprey Lane offers a rare combination of privacy, flex...
- ACTIVE Status
- 4 Beds
- 5 Baths
- 1023936 MLS
Listing courtesy of Listing Agent: Justin P. Stolarczyk (justins@bhsusa.com) from Listing Office: Brown Harris Stevens Hamptons.
Shelter Island Heights Icon Gracefully positioned in the heart of Shelter Island Heights, this timeless residence has been thoughtfully renovated and restored to honor it...
- ACTIVE Status
- 4 Beds
- 3 Baths
- 1022345 MLS
Listing courtesy of Listing Agent: Donna L. Walker (donna.walker@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Rare opportunity to own a charming early-1900s Victorian farmhouse in the historic Heights. Set on a quiet road, this inviting home features an extra-large yard perfect f...
- ACTIVE Status
- 4 Beds
- 2 Baths
- 1017824 MLS
Listing courtesy of Listing Agent: Tina Marika Kaasik (marikakaasik@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
This quiet community known as Long View acres is the perfect place to build your Shelter Island dream home. Located just minutes from Bootleggers Alley Beach which is kno...
- ACTIVE Status
- 1016620 MLS
Listing courtesy of Listing Agent: Tina Marika Kaasik (marikakaasik@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtak...
- ACTIVE Status
- 5 Beds
- 5 Baths
- 1016596 MLS
Listing courtesy of Listing Agent: Tina Marika Kaasik (marikakaasik@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Pool Possible- subject to Permits and approvals.
- ACTIVE Status
- 2 Beds
- 2 Baths
- 1015995 MLS
Listing courtesy of Listing Agent: Erica Lancellotti (erica.lancellotti@serhant.com) from Listing Office: Serhant East End LLC.
Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ˜ 6,100-square-foot coastal estate that redefines luxury through the...
- ACTIVE Status
- 5 Beds
- 5 Baths
- 1012419 MLS
Listing courtesy of Listing Agent: Mackenzie Needham (mackenzieneedham@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and bouti...
- ACTIVE Status
- 3 Beds
- 2 Baths
- 1013318 MLS
Listing courtesy of Listing Agent: Debra L. Von Brook Binder CBR (debravonbrookbinder@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of ...
- ACTIVE Status
- 5 Beds
- 4 Baths
- 1007669 MLS
Listing courtesy of Listing Agent: Elizabeth Melichar (elizabethmelichar@serhant.com) from Listing Office: Serhant East End LLC.
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 ju...
- ACTIVE Status
- 6 Beds
- 3 Baths
- 1005789 MLS
Listing courtesy of Listing Agent: Marco L. Maida (marco.maida@compass.com) from Listing Office: Compass Greater NY LLC.
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 unpar...
- ACTIVE Status
- 4 Beds
- 3 Baths
- 1003398 MLS
Listing courtesy of Listing Agent: Debra L. Von Brook Binder CBR (debravonbrookbinder@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal ...
- ACTIVE Status
- 3 Beds
- 3 Baths
- 1001893 MLS
Listing courtesy of Listing Agent: Debra L. Von Brook Binder CBR (debravonbrookbinder@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
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 & tranqui...
- ACTIVE Status
- 4 Beds
- 4 Baths
- 991700 MLS
Listing courtesy of Listing Agent: Anthony L. Guidice (real694@aol.com) from Listing Office: RE/MAX Signature Real Estate.
An architecturally significant modern retreat set on two private acres within coveted Shelter Island Heights owners association. Floor-to-ceiling glass dissolves the boun...
- ACTIVE Status
- 4 Beds
- 6 Baths
- 990118 MLS
Listing courtesy of Listing Agent: Benjamin P. Dixon (benjamin.dixon@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Welcome to Shelter Island — a place where time slows down and nature takes center stage. Accessible only by ferry, this rare island community offers a level of peace, pr...
- ACTIVE Status
- 4 Beds
- 4 Baths
- 981046 MLS
Listing courtesy of Listing Agent: Ron Moschetta (ronmoschetta77@gmail.com) from Listing Office: Keller Williams Realty Greater.
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...
- ACTIVE Status
- 6 Beds
- 4 Baths
- 978923 MLS
Listing courtesy of Listing Agent: Debra L. Von Brook Binder CBR (debravonbrookbinder@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront ass...
- ACTIVE Status
- 5 Beds
- 5 Baths
- 977439 MLS
Listing courtesy of Listing Agent: Debra L. Von Brook Binder CBR (debravonbrookbinder@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
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 commun...
- ACTIVE Status
- 1 Beds
- 1 Baths
- 976321 MLS
Listing courtesy of Listing Agent: Elizabeth Wohl (ewohl@bhsusa.com) from Listing Office: Brown Harris Stevens Hamptons.
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...
- ACTIVE Status
- 4 Beds
- 6 Baths
- 962070 MLS
Listing courtesy of Listing Agent: Enzo Morabito (Enzo.morabito@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the perfect blend of luxury, comfort and privacy. Hidden at the end of a long drivew...
- ACTIVE Status
- 4 Beds
- 7 Baths
- 930022 MLS
Listing courtesy of Listing Agent: Annmarie Seddio (annmarie@atlasrealty.us) from Listing Office: Atlas Sales Realty.
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...
- ACTIVE Status
- 6 Beds
- 8 Baths
- 864101 MLS
Listing courtesy of Listing Agent: Christine M. Beckwith (christine.beckwith@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This information is not verified for authenticity or accuracy and is not guaranteed and may not reflect all real estate activity in the market. ©2026 The Real Estate Board of New York, Inc. All rights reserved.
Shelter Island Real Estate for Sale
Shelter Island Homes for Sale: Your Gateway to Exclusive Island Living
Nestled between the North and South Forks of Long Island, Shelter Island homes for sale offer a rare opportunity to own property in one of New York's most coveted destinations. This pristine 8,000-acre island community provides the perfect escape from metropolitan life while maintaining convenient access to Manhattan and the Hamptons. With its protected harbors, pristine beaches, and commitment to conservation, Shelter Island represents the pinnacle of Shelter Island Long Island real estate.
See Shelter Island Listings
Shelter Island Homes for Sale: Your Gateway to Exclusive Island Living
Nestled between the North and South Forks of Long Island, Shelter Island homes for sale offer a rare opportunity to own property in one of New York's most coveted destinations. This pristine 8,000-acre island community provides the perfect escape from metropolitan life while maintaining convenient access to Manhattan and the Hamptons. With its protected harbors, pristine beaches, and commitment to conservation, Shelter Island represents the pinnacle of Shelter Island Long Island real estate.
Distinctive Property Types on Shelter Island
The Shelter Island real estate market features an impressive array of luxury properties designed for discerning buyers:
- Spectacular waterfront estates with private beaches and deep-water docks
- Historic colonial homes and restored 18th-century properties
- Contemporary architectural masterpieces with panoramic water views
- Charming cottages and traditional shingle-style residences
- Exclusive gated compounds with guest houses and resort-style amenities
Shelter Island Real Estate Market Insights
The Shelter Island Long Island real estate market is characterized by its exclusivity and limited inventory, making each property acquisition a strategic investment. With strict zoning laws protecting the island's natural beauty and character, new construction is carefully regulated, ensuring property values remain strong. The island's year-round population of approximately 2,400 residents swells during summer months, creating a dynamic seasonal rental market for investment-minded buyers.
Essential Tips for Buying Shelter Island Properties
Purchasing Shelter Island homes for sale requires specialized knowledge of island-specific considerations. Ferry schedules, waterfront rights, and conservation restrictions all play crucial roles in property selection. Buyers should consider proximity to the ferry terminals, understand septic and well systems common to island properties, and evaluate potential for dock permits if waterfront access is desired. Working with agents familiar with Shelter Island's unique regulations and community dynamics is essential for successful transactions.
The Edify Real Estate Advantage on Shelter Island
When exploring Shelter Island real estate opportunities, partnering with Edify Real Estate provides access to exclusive listings and insider market knowledge. Our team understands the nuances of island property ownership, from navigating conservation easements to identifying properties with the greatest appreciation potential. We provide comprehensive support throughout the buying process, connecting clients with trusted local professionals including marine contractors, environmental specialists, and island-based service providers essential for property ownership on Shelter Island.
Shelter Island Real Estate Market Statistics
Stay ahead of the latest trends in Shelter Island's real estate market in Long Island. Edify Real Estate provides the insight, data, and local expertise you need to navigate buying or selling in Shelter Island with confidence. Contact us today for a personalized market report.
Market data is being compiled for Shelter Island
Please contact us for a personalized market report.
Buy or Sell Shelter Island Real Estate with Confidence
Explore exceptional real estate opportunities in Shelter Island, Long Island and beyond with Edify Real Estate. Whether you're searching for your dream home, a modern condo, or preparing to sell your current property, our team brings sharp market insight, accurate valuations, and a refined negotiation strategy tailored to today's market.
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Edify Real Estate: Your Shelter Island Specialists
At Edify Real Estate, we recognize that Shelter Island Long Island real estate represents more than just property ownership—it's an investment in an exclusive lifestyle and pristine natural environment. Our deep understanding of Shelter Island's unique market dynamics, from waterfront regulations to ferry logistics, ensures our clients make informed decisions when purchasing island properties. We maintain close relationships with the Shelter Island community, providing insider access to off-market opportunities and emerging listings before they reach the general market.
Our commitment to excellence in Shelter Island real estate extends beyond the transaction itself. We guide clients through every aspect of island property ownership, from understanding conservation restrictions to connecting with trusted local contractors and service providers. Whether you're seeking a summer retreat, year-round residence, or investment property on this coveted Long Island destination, Edify Real Estate delivers the specialized expertise and personalized service essential for success in Shelter Island's exclusive real estate market.