Shelter Island Homes with Pool

Shelter Island Homes with Pool

Welcome to Shelter Island, NY – a hidden gem nestled in the heart of Suffolk County, where the charm of coastal living meets a vibrant community spirit. Known for its picturesque landscapes and serene atmosphere, Shelter Island is not just a beautiful place to live; it’s also home to an exceptional school district that prioritizes the education and well-being of its students.

The Shelter Island School District is dedicated to fostering a nurturing and stimulating environment for children from preschool through high school. With small class sizes and a dedicated staff, students receive personalized attention that encourages academic excellence and character development. The district boasts a comprehensive curriculum enriched with arts, athletics, and extracurricular activities, ensuring that every child has the opportunity to explore their passions and talents. Parents can rest easy knowing that their children are receiving a quality education in a supportive community.

In addition to its educational offerings, Shelter Island is renowned for its stunning homes, many of which feature luxurious pools that provide the perfect oasis for relaxation and entertainment. Imagine spending warm summer days lounging by your private pool, hosting barbecues with friends, or simply enjoying the tranquil surroundings. Homes with pools in Shelter Island not only enhance your lifestyle but also add value to your investment in this idyllic location.

Whether you’re seeking a family-friendly environment, a picturesque retreat, or a vibrant community, Shelter Island offers the perfect blend of all these elements. Come discover your dream home in this enchanting corner of New York, where exceptional education and leisure await!

Newest Shelter Island Homes with Pool

$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
$3,625,000
5 Beds ⋅ 5 Baths ⋅ 1012419 MLS
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 lens of effortless living. Set on a sprawling 0.92-acre parcel with captivating winter water views of Gardiners Bay, this masterfully designed home offers a seamless daily rhythm, beginning in the light-filled foyer where exquisite millwork meets glass doors that open to the expansive grounds. Designed for both high-end entertaining and absolute ease, the flowing main level connects a stately firelit living room to a magnificent chef's kitchen—complete with a professional cooktop, a walk-in pantry, and dual dishwashers for effortless cleanup—before transitioning outside to a resort-style pool featuring an electric safety cover and direct cabana-bath access. A sanctuary of personal wellness, the second floor boasts a marble-clad primary suite with a private water-view office overlooking the bay, alongside three generous guest rooms and two laundry rooms configured for ultimate convenience. Below, the fully finished lower level serves as a private wellness and entertainment pavilion, featuring a home gym, media room, and a temperature-controlled wine cellar, balanced by an abundant bulk-provisioning storage room and an attached garage for your water toys. Situated just steps from the pristine sands of Menhaden Lane Beach and moments from the island’s premier marinas, boutiques, and acclaimed dining, this estate offers a turnkey, worry-free island lifestyle where every modern luxury is already perfectly in place.

43 Gardiners Bay Drive, Shelter Island
$1,850,000
4 Beds ⋅ 3 Baths ⋅ 1003398 MLS
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 coffee or hosting unforgettable gatherings, this waterfront oasis provides the perfect backdrop for every occasion. Don't miss this opportunity to own a piece of paradise in Mashomack Preserve.

4 Irene Lane, Shelter Island
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 991700 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 July 2026. Still time to pick your colors and more

5 Marc Street, Shelter Island
$5,500,000
4 Beds ⋅ 6 Baths ⋅ 990118 MLS
An architecturally significant modern retreat set on two private acres within coveted Shelter Island Heights owners association. Floor-to-ceiling glass dissolves the boundary between indoors and out, framing the surrounding natural environment from nearly every room. Conceived by developer Angelo Varischetti in collaboration with the award-winning team at WE+ Architecture & Design, the home is a study in light, landscape, and contemporary form. Newly constructed and spanning approximately 4,000 square feet, the residence offers four bedrooms and five-and-a-half bathrooms, thoughtfully designed for both privacy and connection. The open-concept living spaces are anchored by soaring window walls and refined materiality, creating a seamless flow between living, dining, and kitchen areas. The chef's kitchen is both functional and sculptural, featuring premium appliances, custom millwork, and an oversized island designed for gathering. Throughout the home, curated finishes including stone surfaces, bespoke cabinetry, and carefully considered architectural details reinforce the home's modern design language. Each bedroom suite is privately positioned with its own ensuite bath and direct access to the surrounding landscape, offering a retreat-like experience for both owners and guests. The lower level provides flexibility for a wellness area, gym, or media space. Outdoor living is equally compelling. A 50x14 heated knife-edge pool is set within lush, natural surroundings, complemented by expansive decking, an outdoor shower, full bath, and multiple areas for dining and entertaining. The setting is intentionally private, with mature greenery and open sky enhancing the sense of escape. Located within the Shelter Island Heights community, the property offers access to private beaches, tennis, and the island's most sought-after destinations, all while maintaining a sense of seclusion that is increasingly rare. This is Shelter Island at its best. Where architecture, landscape, and lifestyle converge to create a home that feels both elevated and effortless.

11 Sunnyside Avenue, Shelter Island
$2,485,000
6 Beds ⋅ 4 Baths ⋅ 978923 MLS
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 natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

14 Freds Lane, Shelter Island
$2,950,000
5 Beds ⋅ 5 Baths ⋅ 977439 MLS
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 association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

12 Terry Dr., Shelter Island
$3,850,000
4 Beds ⋅ 6 Baths ⋅ 962070 MLS
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, featuring an open floor plan with elegant white oak and porcelain tile flooring, stone countertops, and premium Thermador appliances throughout. Expansive living spaces are designed to embrace the surrounding views, while the second level covered deck offers the perfect setting for unwinding against a picturesque bay backdrop. Additional amenities include a heated gunite pool, radiant heat, wet bar, fireplace, pantry, and other thoughtful features that enhance everyday living. Ideally situated in Shelter Island, the property provides a peaceful retreat with convenient access to local amenities, beaches, and the area's natural beauty. Whether envisioned as a year-round residence or a serene getaway, this exceptional new construction presents a rare opportunity to enjoy modern luxury in a tranquil waterfront setting. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

8 Hilo Drive, Shelter Island
$3,999,000
4 Beds ⋅ 7 Baths ⋅ 930022 MLS
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 driveway, the main house boasts 3 bedrooms and 3.5 bathrooms. The 1st floor main suite features include double doors that open to a private deck, a WIC and an expansive master bathroom equipped with a spa style rain shower. To add to the resort feel, the house is equipped with radiant flooring in all rooms and levels, a two story great room with an indoor/outdoor stone fireplace and a Chef's kitchen with custom-built cabinetry and granite counters. Large sliding doors lead you onto a wrap-around, mahogany deck with views of greenery and a stunning gunite pool. Upon leaving the main house, you will find every car lover's dream. A large barn style 4-car garage with ample height for additional car lifts. The 2nd floor features a 1 BR, 1 Bath apartment, full kitchen and an open floor plan living room/dining room.

141A N Ferry Road, Shelter Island
$4,295,000
6 Beds ⋅ 8 Baths ⋅ 864101 MLS
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 and function. The open floor plan is an entertainer's dream, seamlessly connecting the living, dining, and kitchen areas. The expansive living room showcases large vaulted ceilings with a floor to ceiling doors with transoms, inviting an abundance of natural light into the space, creating a warm and welcoming atmosphere with an indoor outdoor flow. The kitchen is a culinary delight featuring high-end stainless steel appliances, modern shaker style cabinetry, a wet bar, and pantry. The design is thoughtful and efficient, making it the perfect place to prepare meals and entertain guests. The primary suite, located for optimal privacy, is a sanctuary of peace and relaxation. It features a double shower with steam, creating a spa-like experience within your own home. The second-floor hosts three additional en-suite bedrooms, one of which has its own private deck, offering a tranquil space for morning coffee or evening reflection. The lower level presents a TV room and two more en-suite bedrooms, offering flexibility for various lifestyle needs. The property also includes a heated gunite pool, a large tiled patio, and a pickle ball/sport court, promising endless outdoor entertainment. The entire home is unified by stunning white oak flooring and complemented by well-thought-out outdoor landscape lighting, emphasizing the property's architectural beauty. The community environment is as inviting as the home itself. With easy access to local amenities and the South Ferry, residents can enjoy the best of Shelter Island living but also having the convenience to the “Sag Harbor Village” and “The Hamptons”. Experience the perfect blend of modern luxury and comfort in this well-designed home. No expense was spared in creating this oasis.

100 S Ferry Road, Shelter Island
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