Shelter Island Real Estate

Welcome to the Shelter Island School District, a gem nestled in the heart of Suffolk County, New York. This picturesque district is not just a place to learn; it's a community that fosters growth, creativity, and a lifelong love of education. With its stunning natural surroundings and rich local culture, Shelter Island provides an idyllic backdrop for students to thrive academically and socially.

The Shelter Island School District is committed to delivering a high-quality education that prepares students for the challenges of tomorrow. With a small student-to-teacher ratio, educators can provide personalized attention, ensuring that each child’s unique talents and needs are recognized and nurtured. The district boasts a curriculum that balances academic rigor with artistic and athletic programs, promoting a well-rounded education that encourages students to explore their passions.

Beyond the classroom, the district emphasizes community involvement and character development. Students have numerous opportunities to engage in extracurricular activities, from sports teams to arts programs, fostering teamwork and leadership skills. The supportive environment encourages students to build lasting friendships and develop a strong sense of community.

Parents and families are integral to the success of the Shelter Island School District. The district regularly hosts events and workshops, inviting families to participate in their children’s educational journey.

Living in Shelter Island means being part of a vibrant community dedicated to education, where the beauty of nature complements the pursuit of knowledge. Whether you're considering relocating or simply exploring, the Shelter Island School District is a cornerstone of this charming locale, promising a bright future for its students.

Newest Listings in Shelter Island

$749,000

1063023 MLS

Here’s a rare chance to own a private, wooded 1.1± acre lot on a quiet residential street on Shelter Island. Mature hardwoods surround the parcel, giving you the privacy and natural beauty the island is known for. It’s a blank canvas for a year-round home or a weekend getaway, so bring your architect and design the home you’ve been waiting for. Island living means sandy bay beaches, the Mashomack Preserve, kayaking, sailing and peaceful country roads. Greenport’s restaurants and Sag Harbor’s shops are a short ferry ride away. Buildable land on Shelter Island rarely comes to market, so don’t miss this one.

27 Lakeview Drive, Shelter Island

$2,800,000

1055760 MLS

Introducing the final available building parcel at Pandion, one of Shelter Island's most distinctive waterfront communities, where architectural vision, natural beauty, and thoughtful development come together to create an extraordinary residential setting along Coecles Harbor. Spanning 3.72 acres, Lot 5 offers a rare opportunity to design and build a custom residence within a neighborhood that has already established its character and caliber. The sprawling parcel features beautiful topography, allowing for water views across the harbor and out to Gardiners Bay. Since Pandion's inception, a collection of architecturally significant, high-end residences has taken shape, creating a stunning setting defined by thoughtful design, substantial investment, and an appreciation for the surrounding landscape. The Pandion subdivision consists of just five residential properties. Residents enjoy access to an exceptional collection of shared amenities, including a deep-water dock, tennis courts, boat storage, and a waterfront boathouse ideal for entertaining or returning from a day on the water. Harbor mooring privileges further enhance the boating lifestyle, with Sag Harbor, the North Fork, and the greater East End within easy reach.

2 Pandion Road, Shelter Island

$3,250,000

4 Beds ⋅ 3 Baths ⋅ 1062621 MLS

Discover a one-of-a-kind Shelter Island retreat where historic farmhouse charm meets inspired modern living. Set amid 1.8 acres of mature trees, tall privets, sun-drenched edged lawns, and open green space, this circa-1900 property offers a rare combination of character, privacy, and flexibility. The original 2-story residence showcases beautiful period details, including traditional moldings, hand-hewn beams, wood floors, and distinctive vintage glass windows. Inside, 3 bedrooms and 2 baths are complemented by comfortable living and dining rooms, a thoughtfully updated chef’s kitchen with a casual dining area, and a screened porch perfect for long summer evenings. A remarkable addition completed in 2005 is the approximately 1,300-square-foot artist’s atelier, featuring radiant-heated floors and an upper-level primary suite that opens onto a spacious rooftop deck. A detached guest cottage adds another dimension to the property, offering independent accommodations with a large bedroom, full bath, kitchen, living room, and its own garden and lawn. A charming outbuilding provides yet another opportunity, whether envisioned as a reading nook or hobby space. With its blend of historic architecture, dedicated studio space, separate guest quarters, and generous grounds, the property invites a variety of possibilities, including the potential for a swimming pool. Equally suited to relaxed summer gatherings or comfortable year-round living, this is a distinctive island sanctuary with room to create something truly your own.

20 Baldwin Road, Shelter Island

$1,999,999

4 Beds ⋅ 4 Baths ⋅ 1060077 MLS

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 en-suite, cathedral ceiling and french doors to balcony. 3 additional Bedrooms each with an en-suite. Sunken Den, Sitting Room & office. 5" White Oak hardwood flooring throughout first and second level. Recessed lighting, Level 5 finished walls. Central air, Gas propane heat. Hardie Board siding. Upgraded 200 amp electric. 1 Car garage. Inground gunite pool ( optional ) .50 acre. Experience the best of island living in this beautiful renovated coastal retreat. Completion date October 2026. Still time to pick your colors and more

5 Marc, Shelter Island

$2,230,000

5 Beds ⋅ 4 Baths ⋅ 1058792 MLS

Set on a well-proportioned acre in one of Shelter Island’s most sought-after neighborhoods, this 1850s farmhouse offers charm, generous living space, and an exceptional location, with room for a pool. The main level features a spacious living room with a wood-burning fireplace, a dining room with a second wood-burning fireplace, and a bright sunroom. The open kitchen offers two exterior doors leading to side porches, providing an inviting connection to the outdoors and an ideal setting for entertaining. Upstairs are five generously sized bedrooms and three full bathrooms. A full basement and attic provide ample storage and utility space. Just a stone’s throw from Coecles Harbor Marina, this property presents an opportunity to enjoy the tranquility of Shelter Island.

61 N Cartwright Road, Shelter Island

2 Bayview Avenue, Shelter Island Heights

$3,895,000

4 Beds ⋅ 7 Baths ⋅ 1059229 MLS

Welcome to 2 Bayview Ave, a stunning modern home nestled in the serene, walkable streets of Shelter Island Heights, NY. This corner lot property boasts an expansive acre of bucolic land, offering a tranquil escape. The exterior of the home features large front and back porches with ample overhangs for three season comfort. Mahogany decking, porcelain tiles, integrated speakers and overhead fans enhance the enjoyment of picturesque surroundings. The raised backyard is a very private sanctuary of its own with a 16 x 40 gunite pool, a cozy cabana and lush greenery, creating an oasis for relaxation or entertaining. Step inside to a spacious open floor plan accentuated by 10-foot ceilings and a stunning 15ft x 20ft custom window wall that bathes the home in natural southern light. Wide-plank light oak flooring and a cohesive palette of contrasting trim elements evoke a Nordic design language throughout. The custom kitchen is a chef's dream, complete with an oversized quartz island, copious storage, a Thermador appliance suite, and a convenient walk-in pantry. The home is designed for comfortable everyday living and effortless entertaining. Down a windowed hall and separated from the entertaining areas of the home, the primary suite on the main level is a haven of comfort, featuring a large walk-in closet and a luxurious bathroom with double sinks on a floating vanity, a private toilet room and multi-fixture wet room. The main level also houses a convenient laundry room, a powder room, extra closets and a versatile bonus space with its own rear-patio entrance and an attached full bathroom. Upstairs, a cozy, windowed loft space overlooks the main living area. A bright hall joins three additional en-suite bedrooms, including a junior primary suite. Each bath boasts fine fixtures and marble work. The finished lower level provides valuable additional space for recreation, a home gym, media room or overflowing living with a full bathroom and walk-out level access to a private covered patio offers endless potential for customization. The property also includes a 3-car garage – a true rarity in Shelter Island Heights – elegantly situated below the sightlines of the home’s main living areas, thus preserving views of the beautifully landscaped surroundings. A secondary driveway that serves the garage features custom board-formed retaining walls, exquisite plantings and warm landscape lighting that add to the property's striking visual impression. 2 Bayview Ave. is more than just a home; it's a lifestyle. It's a place where modern luxury meets the tranquility of nature.

2 Bayview Avenue, Shelter Island Heights

$2,690,000

4 Beds ⋅ 3 Baths ⋅ 1048489 MLS

Shelter Island Waterfront with Dock. A rare opportunity to own waterfront in Silver Beach, one of Shelter Island’s most beautiful and sought-after enclaves. Set directly on the tranquil Silver Beach lagoon, this four-bedroom, 2.5-bath home offers approximately 2,289 square feet on a private .76-acre property with approximately 102 feet of waterfront frontage—all just a five-minute walk to beautiful Silver Beach. The home has a distinctive character, combining comfortable interiors, hardwood floors and an abundance of natural light with wonderful water and landscape views from both levels. The kitchen and baths are fully functional and well maintained, while the home’s more traditional finishes offer an opportunity for a new owner to update and personalize the style over time. The waterfront setting is the true centerpiece. An expansive lawn framed by mature trees leads to the canal and an approximately 20-foot grandfathered dock with water and electric, creating direct access for boating, kayaking, paddleboarding, clamming and enjoying life on the water. 3 spacious decks provide an inviting setting for outdoor dining and entertaining, and an outdoor shower is perfect after a day at the beach. Additional features include a detached garage, newer roof and windows, generous outdoor space and a peaceful location tucked away on a tranquil block of beautiful homes. Enjoy morning coffee overlooking the canal, launch a kayak from your own backyard, walk to Silver Beach, or gather on the deck at the end of the day, so many memories to be made. 7 Wheeler Road offers the increasingly rare combination of true waterfront, privacy, water access and the relaxed lifestyle that makes Shelter Island so special—with the opportunity to make the home distinctly your own.

7 Wheeler Road, Shelter Island

$1,250,000

2 Beds ⋅ 2 Baths ⋅ 1049777 MLS

Welcome to your private Shelter Island retreat, where comfort, character, privacy, and exceptional outdoor living come together. This inviting 2-bedroom, 2-bath home offers thoughtfully designed spaces, beautiful hardwood flooring throughout, and an impressive collection of amenities for year-round living or the perfect island escape. The well-appointed kitchen features a refrigerator, dishwasher, built-in microwave, garbage compactor, kitchen-sink water filtration, and plenty of space for everyday cooking and entertaining. The adjoining living room is warm and welcoming with a gas fireplace, while an impressive 12-foot sliding glass door opens onto the expansive deck, creating a wonderful flow between indoor and outdoor living. The deck features a complete grilling station with its own sink and refrigerator, perfect for entertaining family and friends. The showpiece of the home is the extraordinary 17' x 24' primary suite. High ceilings and skylights create a bright, airy atmosphere, while authentic refurbished barn wood flooring adds warmth, character, and a distinctive touch. Sliding glass doors open directly onto the private primary bedroom deck overlooking the beautiful backyard, creating a peaceful retreat of its own. The spacious primary en-suite bath continues the feeling of comfort and luxury with radiant-heated flooring, a spacious open-concept shower with custom glass detailing, double-sink vanity, and dedicated vanity area. The home's extensive amenities include central air conditioning, a whole-house generator, whole-house water-filtration system, washer and dryer, boiler and water heater, two dehumidifiers, and a brand-new septic system. A full basement with a private walkout to a full patio provides additional space and convenient access to the spectacular grounds. Step outside and discover a backyard designed for relaxation, recreation, privacy, and entertaining. Enjoy the heated semi-inground pool with both propane and electric heating systems, surrounded by extensive wraparound decking. The fully fenced property also features a beautiful wood pergola with patio, full bocce court, putting green, fully enclosed vegetable garden, beautiful woodshed, and a large fishpond surrounded by lush greenery. A full line of arborvitae creates a wonderful sense of privacy, transforming the grounds into a peaceful island oasis. A wraparound front driveway adds convenience and completes this special property. Whether you're seeking a year-round residence, summer getaway, or private Shelter Island retreat, this home offers so much more than a place to live—it's an opportunity to embrace the relaxed indoor-outdoor lifestyle that makes Shelter Island so special. Come experience the privacy, comfort, character, and exceptional outdoor living this unique property has to offer, plus you can definitely add more Bedrooms and Bathrooms. This is A Must-See Property!!

11 Jaspa Road, Shelter Island

13 Spring Garden Avenue, Shelter Island Heights

$2,995,000

3 Beds ⋅ 3 Baths ⋅ 1047801 MLS

Own a distinctive piece of Shelter Island Heights history in this beautifully restored circa-1875 residence, thoughtfully updated for today’s lifestyle while retaining the character and architectural details that make a historic home so special. Set on approximately 0.40 acres, the property offers second-level water views, inviting private gardens, and a classic wraparound porch ideal for enjoying the island setting. The home features three bedrooms, 2.5 baths, a chef’s kitchen, formal dining room, living room, parlor, office, full basement, and detached one-car garage—providing flexible space for everyday living, entertaining, work, or guests. Landscaped outdoor areas create a peaceful backdrop for dining, gardening, recreation, or quiet relaxation. Conveniently located near Bridge Street, local shops, restaurants, Shelter Island Yacht Club, and other Heights destinations, the home also includes access to Heights Association parks and the Beach Club, with nearby clay tennis courts. A rare opportunity to enjoy historic character, modern comfort, water views, and the sought-after Shelter Island Heights lifestyle.

13 Spring Garden Avenue, Shelter Island Heights

$1,595,000

1046396 MLS

Rare opportunity to own .62 Acres of waterfront buildable land along West Neck creek, offering a beautiful setting with water views and direct access to the shoreline. Nestled within the peaceful Silver Beach community, this private and tranquil property is surrounded by nature and offers an exceptional opportunity to create a waterfront retreat. Across the water, protected preserved land ensures that the natural setting and peaceful views will remain undisturbed, adding to the property's sense of privacy and tranquility. Buyers should conduct their own due diligence regarding zoning, permits, wetlands, building potential, waterfront regulations, and all other applicable requirements.

9 Bay Shore Drive, Shelter Island

$4,250,000

4 Beds ⋅ 6 Baths ⋅ 1036842 MLS

There are new homes, and then there is this - a turnkey Bartilucci Construction design-build masterpiece, styled by Heiberg Cummings tucked just outside the heart of Shelter Island Heights. No detail left to chance and no corner cut. What sets this location apart is the rare balance it strikes - total privacy paired with true convenience. The Heights business district, morning coffee, boutique shopping and art galleries are all just a short stroll away, and the North Ferry is a mere 3 minute drive from your door. Inside, soaring cathedral ceilings that draw the eye straight through to the heated gunite pool beyond. The kitchen is a showpiece - custom white oak cabinetry, dramatic Taj Mahal countertops, a butler's pantry with its own sink and refrigerator. The primary suite is a true retreat, with spa inspired finishes in the same white oak and Carrara marble found throughout, anchored by a showstopping Carrara marble vessel sink. Outside, the 20x40 heated gunite pool with bluestone coping sets the stage for long summer days across 1.36 private acres with views toward Chase Creek. This is a home built without compromise, the kind of opportunity that simply doesn't come along often. Easy to view, and not to be missed.

169 N Ferry Road, Shelter Island

$2,199,000

5 Beds ⋅ 4 Baths ⋅ 1029569 MLS

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 opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property offers remarkable versatility to fit your lifestyle. The welcoming ranch-style main home offers a comfortable living space with 3 bedrooms and two full bathrooms. A spacious kitchen with abundant cabinetry flows seamlessly into the dining area, creating an inviting setting for everyday living and entertaining. The living room, anchored by a wood-burning fireplace, provides a warm and cozy gathering place throughout the seasons. Step outside to the expansive rear deck, complete with a hot tub overlooking a large, private backyard with room for a pool, an ideal setting for entertaining, relaxing, or enjoying peaceful evenings. A welcoming front porch, an attached one-car garage, and a carport. Privately positioned toward the rear of the property, the stunning barn-style home feels like a secluded retreat. Overlooking a tranquil pond, this approx. The residence is filled with warmth, character, and natural light. The dramatic main room features soaring vaulted ceilings with exposed beams, a gas fireplace, and an impressive wall of windows that captures beautiful views while flooding the home with sunshine. French doors that open onto an expansive 500 square foot mahogany deck with built-in storage, creating the perfect place to enjoy morning coffee, outdoor dining, or simply unwind. The barn home also features two spacious bedrooms, two full bathrooms, a large loft, and a well-appointed kitchen. The oversized lower-level garage offers exceptional storage for vehicles, recreational equipment, bicycles, tools, and more, while additional facilities and energy-efficient solar panels further enhance the home’s appeal. The beautifully landscaped .95 acre property provides an uncommon sense of privacy while remaining just minutes from the Shelter Island beaches, marinas, restaurants, shops, farm stands, and nature preserve. 64A North Midway Road offers possibilities that are rarely available on Shelter Island.

64A N Midway Road, Shelter Island

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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.