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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!!

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

$1,495,000

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.

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

$999,999

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 boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a beautifully landscaped yard with deck perfect for relaxing, entertaining, or summer gatherings. A wonderful opportunity to enjoy easy island living in a move-in-ready home.

3 Beds ⋅ 2 Baths ⋅ 1013318 MLS

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 boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a beautifully landscaped yard with deck perfect for relaxing, entertaining, or summer gatherings. A wonderful opportunity to enjoy easy island living in a move-in-ready home.

16 Bowditch Road, Shelter Island

$1,275,000

This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. A large, inviting living room with a wood-burning fireplace provides a comfortable gathering space year-round. Just off the kitchen, sliding French doors open to a covered three-season room/screened porch with a vaulted ceiling, creating a seamless indoor-outdoor flow and easy access to the backyard—ideal for barbecuing and relaxing. The home includes three generously sized bedrooms and two and a half baths, all set on a .46-acre lot. Additional highlights include an outdoor shower, a partial basement with finished space for added flexibility, an attached two-car garage, and a detached 1.5-car garage offering additional storage or workspace. A wonderful opportunity to enjoy the charm and tranquility of Shelter Island living.

3 Beds ⋅ 3 Baths ⋅ 1001893 MLS

This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. A large, inviting living room with a wood-burning fireplace provides a comfortable gathering space year-round. Just off the kitchen, sliding French doors open to a covered three-season room/screened porch with a vaulted ceiling, creating a seamless indoor-outdoor flow and easy access to the backyard—ideal for barbecuing and relaxing. The home includes three generously sized bedrooms and two and a half baths, all set on a .46-acre lot. Additional highlights include an outdoor shower, a partial basement with finished space for added flexibility, an attached two-car garage, and a detached 1.5-car garage offering additional storage or workspace. A wonderful opportunity to enjoy the charm and tranquility of Shelter Island living.

11 Mimosa Place, Shelter Island