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$5,700,000

Perched 59 feet above sea level for commanding views and peace of mind, this exceptional contemporary estate—designed by noted architect Kenton van Boer—rests on 9.4 private acres, of which 2.7 acres are buildable, and offers 561 feet of premier waterfront on Smiths Cove. Sweeping panoramic vistas of the Sound and the tranquil yacht anchorage set the scene for direct beachfront access and creek frontage along the serene Miss Annie’s Creek—plus the rare opportunity to create your own private dock and mooring. The 1,504-square-foot residence features 2 bedrooms, a study and 2 spa-inspired full baths. A chef’s kitchen anchors the open layout, flowing into a light-filled living room with a stone-accented fireplace and a custom built-in dining area. Thoughtful architectural details by Kenton van Boer. Quartzite flagstone masonry patios and walkways add an additional 1,120 square feet of outdoor living, seamlessly extending the home’s footprint and immersing you in the surrounding natural beauty. Nestled in a serene coastal setting of wood shingles, flagstone patios, and unspoiled shoreline, this property offers unmatched privacy while being just moments from the Shelter Island Ferry to Sag Harbor. A rare blend of seclusion, convenience, and timeless design.

2 Beds ⋅ 2 Baths ⋅ 906564 MLS

Perched 59 feet above sea level for commanding views and peace of mind, this exceptional contemporary estate—designed by noted architect Kenton van Boer—rests on 9.4 private acres, of which 2.7 acres are buildable, and offers 561 feet of premier waterfront on Smiths Cove. Sweeping panoramic vistas of the Sound and the tranquil yacht anchorage set the scene for direct beachfront access and creek frontage along the serene Miss Annie’s Creek—plus the rare opportunity to create your own private dock and mooring. The 1,504-square-foot residence features 2 bedrooms, a study and 2 spa-inspired full baths. A chef’s kitchen anchors the open layout, flowing into a light-filled living room with a stone-accented fireplace and a custom built-in dining area. Thoughtful architectural details by Kenton van Boer. Quartzite flagstone masonry patios and walkways add an additional 1,120 square feet of outdoor living, seamlessly extending the home’s footprint and immersing you in the surrounding natural beauty. Nestled in a serene coastal setting of wood shingles, flagstone patios, and unspoiled shoreline, this property offers unmatched privacy while being just moments from the Shelter Island Ferry to Sag Harbor. A rare blend of seclusion, convenience, and timeless design.

21 Thompson Road, Shelter Island

$2,799,000

Located in the desirable Harborview area of Shelter Island, this stunning modern farmhouse offers the perfect blend of luxury, comfort, and coastal living. As a member of a private waterfront association just one and a half blocks away, enjoy easy access to kayaking, boating, and beach front. Set on a beautifully landscaped half-acre, this meticulously maintained property is designed for indoor-outdoor living. The open-concept interior is flooded with natural light from oversized windows that frame views of the expansive backyard oasis. Outside, enjoy a heated Gunite pool, outdoor shower, firepit lounge area, spacious deck with a seating area with a retractable awning, and a covered dining area ideal for al fresco entertaining. With five generous bedrooms, this home easily accommodates everyone. Both the first and second floors feature primary bedroom suites, with the upstairs suite including a gas fireplace and opening to a private covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den/gym with direct access to the yard, and a spacious fifth bedroom with a large hall bath. This exceptional property is move-in ready—your Shelter Island lifestyle begins here.

5 Beds ⋅ 5 Baths ⋅ 882843 MLS

Located in the desirable Harborview area of Shelter Island, this stunning modern farmhouse offers the perfect blend of luxury, comfort, and coastal living. As a member of a private waterfront association just one and a half blocks away, enjoy easy access to kayaking, boating, and beach front. Set on a beautifully landscaped half-acre, this meticulously maintained property is designed for indoor-outdoor living. The open-concept interior is flooded with natural light from oversized windows that frame views of the expansive backyard oasis. Outside, enjoy a heated Gunite pool, outdoor shower, firepit lounge area, spacious deck with a seating area with a retractable awning, and a covered dining area ideal for al fresco entertaining. With five generous bedrooms, this home easily accommodates everyone. Both the first and second floors feature primary bedroom suites, with the upstairs suite including a gas fireplace and opening to a private covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den/gym with direct access to the yard, and a spacious fifth bedroom with a large hall bath. This exceptional property is move-in ready—your Shelter Island lifestyle begins here.

12 Terry Drive, Shelter Island

$2,679,000

Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom with balcony is as dreamy as the view, which is truly incredible. An oversized bath and additional upper-level bedroom complete this private owner's area. Two main level bedrooms serviced by a full bath will accommodate family and friends beautifully. A two-car garage and studio with a half bath is a great place to set up your game room or home office. A full basement with high ceilings can be finished to incorporate an exercise or workout room. Lush landscaping with charming stone walls on 1.90 acres completes this peaceful location. Finished Square Footage 3420 includes the Studio. Property could accommodate a pool.

4 Beds ⋅ 4 Baths ⋅ L3577201 MLS

Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom with balcony is as dreamy as the view, which is truly incredible. An oversized bath and additional upper-level bedroom complete this private owner's area. Two main level bedrooms serviced by a full bath will accommodate family and friends beautifully. A two-car garage and studio with a half bath is a great place to set up your game room or home office. A full basement with high ceilings can be finished to incorporate an exercise or workout room. Lush landscaping with charming stone walls on 1.90 acres completes this peaceful location. Finished Square Footage 3420 includes the Studio. Property could accommodate a pool.

156 Ram Island Drive, Shelter Island

$1,725,000

Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant custom home was lovingly crafted by a local artist in 2011 and spans 3,170 square feet. Designed to maximize natural light, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. The home features 21' vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm and inviting ambiance. The gourmet kitchen is equipped with high-end appliances, and a granite island seating 10, a spacious breakfast/bar with ample counter space, perfect for cooking and entertaining. A large adjacent sunroom, with double doors opening to beautifully landscaped gardens and a patio, provides an ideal setting for gatherings or quiet relaxation. The first floor boasts a luxurious primary suite with custom-built storage, two walk-in closets, and a spacious en-suite bath with a dedicated vanity area. A second bedroom, a full bath, and a versatile art studio with skylights—also with double doors leading to the patio—complete the main level. Upstairs, you’ll find an additional large bedroom, and a 12'x30' framed out space for a theater, office, gym, game room, or whatever you desire. The home also includes a generous two-car garage, ensuring ample space for vehicles and equipment, a whole house generator, 1000 gallon propane tank, and radiant heat flooring. With its thoughtful design, high-quality finishes, and prime location near sought-after beaches and golf courses, this exceptional home is a must-see.

3 Beds ⋅ 2 Baths ⋅ 842082 MLS

Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant custom home was lovingly crafted by a local artist in 2011 and spans 3,170 square feet. Designed to maximize natural light, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. The home features 21' vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm and inviting ambiance. The gourmet kitchen is equipped with high-end appliances, and a granite island seating 10, a spacious breakfast/bar with ample counter space, perfect for cooking and entertaining. A large adjacent sunroom, with double doors opening to beautifully landscaped gardens and a patio, provides an ideal setting for gatherings or quiet relaxation. The first floor boasts a luxurious primary suite with custom-built storage, two walk-in closets, and a spacious en-suite bath with a dedicated vanity area. A second bedroom, a full bath, and a versatile art studio with skylights—also with double doors leading to the patio—complete the main level. Upstairs, you’ll find an additional large bedroom, and a 12'x30' framed out space for a theater, office, gym, game room, or whatever you desire. The home also includes a generous two-car garage, ensuring ample space for vehicles and equipment, a whole house generator, 1000 gallon propane tank, and radiant heat flooring. With its thoughtful design, high-quality finishes, and prime location near sought-after beaches and golf courses, this exceptional home is a must-see.

27 Country Club Drive, Shelter Island

$1,600,000

A thoughtfully designed retreat offering peace, privacy, and understated luxury. Tucked away on a private drive in the island's center, you're close enough to bike to all of the island’s beaches or restaurants. The approach sets the tone: a winding drive reveals the house gradually. The home emerges across an expansive lawn, its clean black lines and Anderson windows throughout creating a striking silhouette against the natural canopy. That hammock strung between two trees? Exactly where you'll spend Sunday mornings with coffee and a good read. Inside, the design philosophy is clear: let the outside take the stage. White walls, black accents, and a massive window wall make the front yard feel like your living room's best feature. The newly installed Ortal 110 TS fireplace anchors the open space, a sculptural centerpiece that warms the kitchen, dining, and living areas. Ascoli smart lighting throughout means you can set the color temperature to exactly your liking and automate it to match the rhythms of your day. The kitchen features Robern cabinets, a Thermador gas range, a double oven, and a refrigerator, plus a generous island for preparing all that local fish and farmstand produce. Upstairs, three bedrooms include a primary with an ensuite walk-in shower, a second bedroom with queen-sized built-in bunk beds and clever storage nooks, and a third with expansive windows overlooking the rolling front lawn. A second full bathroom with a tub serves the floor. Downstairs, heated floors make winter mornings civilized. The spacious bathroom features Robern cabinets and heated towel rack, while walk-in closets are generous enough that you and your partner won't need to negotiate territory treaties. Every detail considered, nothing overdone. The fully fenced backyard is its own retreat. Your dog thinks it's paradise. Your green thumb agrees. The newly built backyard office/art studio/yoga sanctuary, properly insulated with new windows and doors, offers a legitimate reason to "work from home" that doesn't involve your kitchen table. Whether it becomes your creative sanctuary, your focus zone, or just where you hide from houseguests, it's ready. The house comes with complete pool plans designed by Glenn Lawton at Spatial Arts. Modern amenities where they matter: EV charger, bike and board storage, without sacrificing the serenity that brought you to Shelter Island in the first place. Even the entrance makes a statement with its sculptural fountain and thoughtfully designed wood and bluestone steps.

4 Beds ⋅ 3 Baths ⋅ 929830 MLS

A thoughtfully designed retreat offering peace, privacy, and understated luxury. Tucked away on a private drive in the island's center, you're close enough to bike to all of the island’s beaches or restaurants. The approach sets the tone: a winding drive reveals the house gradually. The home emerges across an expansive lawn, its clean black lines and Anderson windows throughout creating a striking silhouette against the natural canopy. That hammock strung between two trees? Exactly where you'll spend Sunday mornings with coffee and a good read. Inside, the design philosophy is clear: let the outside take the stage. White walls, black accents, and a massive window wall make the front yard feel like your living room's best feature. The newly installed Ortal 110 TS fireplace anchors the open space, a sculptural centerpiece that warms the kitchen, dining, and living areas. Ascoli smart lighting throughout means you can set the color temperature to exactly your liking and automate it to match the rhythms of your day. The kitchen features Robern cabinets, a Thermador gas range, a double oven, and a refrigerator, plus a generous island for preparing all that local fish and farmstand produce. Upstairs, three bedrooms include a primary with an ensuite walk-in shower, a second bedroom with queen-sized built-in bunk beds and clever storage nooks, and a third with expansive windows overlooking the rolling front lawn. A second full bathroom with a tub serves the floor. Downstairs, heated floors make winter mornings civilized. The spacious bathroom features Robern cabinets and heated towel rack, while walk-in closets are generous enough that you and your partner won't need to negotiate territory treaties. Every detail considered, nothing overdone. The fully fenced backyard is its own retreat. Your dog thinks it's paradise. Your green thumb agrees. The newly built backyard office/art studio/yoga sanctuary, properly insulated with new windows and doors, offers a legitimate reason to "work from home" that doesn't involve your kitchen table. Whether it becomes your creative sanctuary, your focus zone, or just where you hide from houseguests, it's ready. The house comes with complete pool plans designed by Glenn Lawton at Spatial Arts. Modern amenities where they matter: EV charger, bike and board storage, without sacrificing the serenity that brought you to Shelter Island in the first place. Even the entrance makes a statement with its sculptural fountain and thoughtfully designed wood and bluestone steps.

73 N Midway Road, Shelter Island

$1,460,000

Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the kitchen-perfect for relaxing or entertaining. There's plenty of potential here to update or expand with your own design vision. The property also includes a separate, renovated 1-bedroom cottage, complete with a legal kitchen, spacious bathroom, and inviting living area-ideal for guests, extended family, or as a rental income opportunity. A detached 2-car garage and ample outdoor space, including room for a pool, complete this rare offering in one of the area's most desirable locations. Owned solar panels provide significant energy savings with little to no ongoing cost. Don't miss your chance to enjoy the peaceful living just minutes from local favorites and the charm of the surrounding community. The sauna, lap pool in the basement are not being represented. This home is being sold "As Is"

4 Beds ⋅ 4 Baths ⋅ 905186 MLS

Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the kitchen-perfect for relaxing or entertaining. There's plenty of potential here to update or expand with your own design vision. The property also includes a separate, renovated 1-bedroom cottage, complete with a legal kitchen, spacious bathroom, and inviting living area-ideal for guests, extended family, or as a rental income opportunity. A detached 2-car garage and ample outdoor space, including room for a pool, complete this rare offering in one of the area's most desirable locations. Owned solar panels provide significant energy savings with little to no ongoing cost. Don't miss your chance to enjoy the peaceful living just minutes from local favorites and the charm of the surrounding community. The sauna, lap pool in the basement are not being represented. This home is being sold "As Is"

26 S Menantic Road, Shelter Island

$1,180,000

This enchanting Shelter Island home feels like a true getaway. Tucked into a peaceful setting, it offers a sense of calm and ease the moment you arrive. The house has a warm and welcoming atmosphere, with open, airy spaces that invite you to slow down and unwind. A large living room and kitchen create the heart of the home, centered by a wood-burning fireplace - perfect for gathering with friends or family. Cozy bedrooms provide comfort and privacy, while the flow of the house makes it easy to host and enjoy time together. With a separate entrance to the upstairs, this additional living space offers rental opportunity or dual living accommodation. With its retreat-like atmosphere and charming character, this home is a place to relax, recharge, and enjoy all that Shelter Island has to offer. Some highlights include new appliances, a new water filtration system, beautiful landscaping, and room for a pool!

4 Beds ⋅ 3 Baths ⋅ 901615 MLS

This enchanting Shelter Island home feels like a true getaway. Tucked into a peaceful setting, it offers a sense of calm and ease the moment you arrive. The house has a warm and welcoming atmosphere, with open, airy spaces that invite you to slow down and unwind. A large living room and kitchen create the heart of the home, centered by a wood-burning fireplace - perfect for gathering with friends or family. Cozy bedrooms provide comfort and privacy, while the flow of the house makes it easy to host and enjoy time together. With a separate entrance to the upstairs, this additional living space offers rental opportunity or dual living accommodation. With its retreat-like atmosphere and charming character, this home is a place to relax, recharge, and enjoy all that Shelter Island has to offer. Some highlights include new appliances, a new water filtration system, beautiful landscaping, and room for a pool!

1 Gazon Road, Shelter Island

$1,140,000

This island classic is truly a home for all seasons. The bright and open floor plan is beautifully complemented by the natural surroundings of Shelter Island, creating an inviting atmosphere throughout the year. The spacious living room and dining room feature sliding doors that open onto surrounding decks, making summer relaxation a breeze. A cozy fireplace offers comfort on the chilliest autumn evenings, providing a warm and inviting space to unwind. The kitchen and den become the heart of the home during winter weekends with friends. Located on a quiet street and close to the hiking trails of Mashomack Preserve, making it ideal for spring adventures. The sandy shores of the nearby Wades Beach will bring you right back to summer fun and gatherings. With 3 bedrooms ,3 baths and 1950 sqft., creates ample space for visiting guests, ensuring comfort and convenience all year long. This Shelter Island retreat is truly a home for all.

3 Beds ⋅ 3 Baths ⋅ 981688 MLS

This island classic is truly a home for all seasons. The bright and open floor plan is beautifully complemented by the natural surroundings of Shelter Island, creating an inviting atmosphere throughout the year. The spacious living room and dining room feature sliding doors that open onto surrounding decks, making summer relaxation a breeze. A cozy fireplace offers comfort on the chilliest autumn evenings, providing a warm and inviting space to unwind. The kitchen and den become the heart of the home during winter weekends with friends. Located on a quiet street and close to the hiking trails of Mashomack Preserve, making it ideal for spring adventures. The sandy shores of the nearby Wades Beach will bring you right back to summer fun and gatherings. With 3 bedrooms ,3 baths and 1950 sqft., creates ample space for visiting guests, ensuring comfort and convenience all year long. This Shelter Island retreat is truly a home for all.

16 Shelterlands Path, Shelter Island

$999,000

Nestled on a serene .58-acre parcel just minutes from Wades Beach and Fresh Pond, this well-maintained ranch-style home offers the perfect blend of classic Shelter Island charm and modern convenience. Built in 1967 and lovingly cared for, the home features 1,340 square feet of single-level living with 3 bedrooms and 2 full baths, including a primary en-suite for added comfort and privacy. The light-filled interior boasts a thoughtful layout, complemented by a hall bath tastefully renovated in 2021. The property also includes a full basement, partially finished, offering flexible space for storage, recreation, or hobbies. Energy-conscious buyers will appreciate the leased solar panels, reducing utility costs and enhancing sustainability. In the expansive backyard, you'll find a versatile barn built in 2006, complete with a wood shop on the first floor and a spacious second-floor storage area. While the barn is equipped with propane heat, there is no running water. Whether you're looking for a full-time home, a weekend getaway, or a place with space to create, this Shelter Island spot has it all-great location, charm, and room to make it your own, just minutes from the beach and peaceful island surroundings.

3 Beds ⋅ 2 Baths ⋅ 901821 MLS

Nestled on a serene .58-acre parcel just minutes from Wades Beach and Fresh Pond, this well-maintained ranch-style home offers the perfect blend of classic Shelter Island charm and modern convenience. Built in 1967 and lovingly cared for, the home features 1,340 square feet of single-level living with 3 bedrooms and 2 full baths, including a primary en-suite for added comfort and privacy. The light-filled interior boasts a thoughtful layout, complemented by a hall bath tastefully renovated in 2021. The property also includes a full basement, partially finished, offering flexible space for storage, recreation, or hobbies. Energy-conscious buyers will appreciate the leased solar panels, reducing utility costs and enhancing sustainability. In the expansive backyard, you'll find a versatile barn built in 2006, complete with a wood shop on the first floor and a spacious second-floor storage area. While the barn is equipped with propane heat, there is no running water. Whether you're looking for a full-time home, a weekend getaway, or a place with space to create, this Shelter Island spot has it all-great location, charm, and room to make it your own, just minutes from the beach and peaceful island surroundings.

10 Strawberry Lane, Shelter Island