Shelter Island Homes with Shelter Island School Elementary school

Welcome to Shelter Island, a hidden gem nestled in the heart of Suffolk County, New York. This enchanting island, surrounded by the pristine waters of Peconic Bay and the Atlantic Ocean, offers a unique blend of tranquility and vibrant community life. Known for its stunning natural beauty, Shelter Island is a haven for outdoor enthusiasts, with miles of hiking trails, serene beaches, and picturesque parks that invite exploration and relaxation.

One of the standout features of Shelter Island is its commitment to education, exemplified by the presence of the Shelter Island School. This well-respected institution serves as the cornerstone of the community, providing a nurturing environment for young learners. Families looking to settle in this idyllic locale will find that the proximity to the Shelter Island School enhances the appeal of local homes, making it an ideal choice for those prioritizing education.

Real estate on Shelter Island is as diverse as its landscape, ranging from charming cottages to luxurious waterfront estates. Each property boasts its own unique character, often featuring stunning views and easy access to the island’s many recreational offerings. Whether you’re seeking a seasonal retreat or a year-round residence, Shelter Island provides a welcoming atmosphere where neighbors become friends, and every day feels like a vacation.

With its rich history, vibrant community spirit, and commitment to education, Shelter Island is more than just a place to live—it's a lifestyle. Discover your dream home on this captivating island and experience the magic of Shelter Island for yourself!

Newest Shelter Island Homes with Shelter Island School Elementary school

$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

$2,690,000

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

$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

$4,995,000

5 Beds ⋅ 7 Baths ⋅ 1027086 MLS

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 blend of luxury, location, and design. Defined by soaring proportions, sleek attention to detail and bathed in natural light, the home features 5 ensuite bedrooms, 6 full baths and one half bathroom across two levels. Upon entry, a dramatic gallery corridor blurs the boundary between indoors and out, where floor-to-ceiling glass frames curated views of the surrounding landscape. Warm white oak flooring and an abundance of natural light create a quiet sense of sophistication, transforming a simple passage into an architectural experience. Anchored by dramatic wood-clad cathedral ceilings and expansive walls of glass, the main level's open-concept living spaces unfold with effortless flow. A sculptural chef's kitchen takes center stage, featuring a dramatic oversized island, custom cabinetry, and seamlessly integrated appliances. Just beyond, a thoughtfully designed entertaining bar creates a refined transition into the expansive living room, where a striking wood burning fireplace serves as the architectural focal point and oversized glass doors open directly to the poolside patio, creating a seamless flow between gathering, dining, and indoor-outdoor entertaining. Privately positioned off the main living spaces, the first-floor primary suite includes a spacious ensuite featuring a freestanding soaking tub, oversized glass-enclosed shower, custom oak dual vanity, and premium fixtures throughout, and premium fixtures throughout, where natural materials and clean lines create a calm, understated aesthetic. A separate wing features three additional ensuite bedrooms, a spacious great room and bath, with every room opening directly to the outdoors. Its thoughtful placement creates a sense of separation while complementing the home's open-concept design. The lower level offers a media room, wine cellar, guest ensuite bedroom and laundry. Set on .94± acres, outdoor amenities include a 32'x16'' heated gunite pool and integrated spa, a barrel sauna, cold plunge, outdoor shower, outdoor dining, an attached two-car garage, and professionally designed landscaping that enhances the property's sense of retreat. Just moments from Gardiner's Bay Country Club, Shelter Island's village, and renowned dining, 6 Great Circle presents a rare opportunity to own a custom-built new construction residence where thoughtful design, exceptional craftsmanship, and modern luxury come together.

6 Great Circle Drive, Shelter Island

$1,495,000

4 Beds ⋅ 2 Baths ⋅ 1017824 MLS

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 for entertaining and a welcoming wraparound porch ideal for relaxing summer evenings. Inside, the home boasts a spacious living room with a wood-burning fireplace, a gracious parlor, formal dining room, and a first-floor bedroom with a full bath. Upstairs are two additional bedrooms and another full bath. A full basement provides ample storage and utility space. Just a stone’s throw from downtown shopping, restaurants, and all that the Heights has to offer, this is a rare find in one of Shelter Island’s most sought-after neighborhoods.

6 Oxford Avenue, 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.