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21 Flamingo Drive, Edgartown

Set on 4.9 acres surrounded by the natural beauty of Chappaquiddick, this residence offers approximately 2,900 square feet of living space, quality craftsmanship, and a private setting. The home features three bedrooms, including a first-floor primary suite with a private bath. Upstairs, two additional bedrooms each have ensuite baths. The living room features soaring cathedral ceilings finished in tongue-and-groove wood and a wood-burning fireplace. Custom interior doors and detailed woodwork are found throughout, while the kitchen is appointed with high-end appliances and custom Neff cabinetry.The enclosed, year-round porch features tongue-and-groove ceilings, slate flooring, and a wood-burning fireplace, providing additional living space in every season. A mahogany deck overlooks the surrounding property. Above the detached garage is an additional bedroom and full bath, offering flexibility for guests, a home office, or studio. A new Mitsubishi inverter-technology heating and cooling system, installed in 2026, features six independently controlled zones, with heating and cooling extending to the basement and enclosed porch. Owned solar panels provide a net $100.00 per month positive utility bill. There is an 8 bedroom septic system and so expansion opportunities are plenty. Approximately one acre of the property is located across Litchfield Road, offering potential for a future guest house or accessory dwelling unit (ADU), subject to applicable approvals. Located on Chappaquiddick, the property offers convenient access to beaches, conservation trails, and the natural surroundings that define Chappy, all just a short ferry ride from downtown Edgartown.

4 Beds ⋅ 5 Baths ⋅ 73594795 MLS

Set on 4.9 acres surrounded by the natural beauty of Chappaquiddick, this residence offers approximately 2,900 square feet of living space, quality craftsmanship, and a private setting. The home features three bedrooms, including a first-floor primary suite with a private bath. Upstairs, two additional bedrooms each have ensuite baths. The living room features soaring cathedral ceilings finished in tongue-and-groove wood and a wood-burning fireplace. Custom interior doors and detailed woodwork are found throughout, while the kitchen is appointed with high-end appliances and custom Neff cabinetry.The enclosed, year-round porch features tongue-and-groove ceilings, slate flooring, and a wood-burning fireplace, providing additional living space in every season. A mahogany deck overlooks the surrounding property. Above the detached garage is an additional bedroom and full bath, offering flexibility for guests, a home office, or studio. A new Mitsubishi inverter-technology heating and cooling system, installed in 2026, features six independently controlled zones, with heating and cooling extending to the basement and enclosed porch. Owned solar panels provide a net $100.00 per month positive utility bill. There is an 8 bedroom septic system and so expansion opportunities are plenty. Approximately one acre of the property is located across Litchfield Road, offering potential for a future guest house or accessory dwelling unit (ADU), subject to applicable approvals. Located on Chappaquiddick, the property offers convenient access to beaches, conservation trails, and the natural surroundings that define Chappy, all just a short ferry ride from downtown Edgartown.

91 Litchfield Rd, Edgartown

$3,950,000

Welcome home to this meticulously renovated Martha's Vineyard property, where coastal elegance meets effortless indoor-outdoor living. Offered fully furnished, "turn-key" ready and spanning over 4,100 square feet of beautiful living space, this property offers a total of 5 bedrooms and 4.5 baths between the main house and detached 1 bedroom guest suite. In the main house, the spacious great room boasts cathedral ceilings, wood-burning fireplace, and glass doors that seamlessly connect the interior to the outdoors. The custom kitchen is outfitted with an expansive granite center island, stainless steel appliances and a generous dining area. The private primary retreat includes a custom walk-in closet and en suite bath, featuring a double sink vanity and a walk-in shower with dual shower heads. 3 private guest rooms and 2 additional full baths, located on a separate floor, ensure plenty of privacy for everyone. The finished basement offers approximately 670 square feet of additional living space to the main house and is perfect for entertaining, complete with a custom bar, built-in cabinetry, and a half bath. The detached 1 bedroom and 1 bath guest suite is located above the oversize 2-bay garage and is ideal for extended family and friends. This beautifully appointed space features an open floor plan, high-end materials throughout and a large private deck. From the moment you arrive, the professionally landscaped grounds invite you to enjoy everything this property has to offer. With dedicated outdoor entertaining areas, multiple decks, outdoor tv, firepit and hot tub, the space is perfectly designed for both grand hosting and quiet relaxation. This exceptional property checks off all the boxes for the perfect Vineyard home.

5 Beds ⋅ 5 Baths ⋅ 73592553 MLS

Welcome home to this meticulously renovated Martha's Vineyard property, where coastal elegance meets effortless indoor-outdoor living. Offered fully furnished, "turn-key" ready and spanning over 4,100 square feet of beautiful living space, this property offers a total of 5 bedrooms and 4.5 baths between the main house and detached 1 bedroom guest suite. In the main house, the spacious great room boasts cathedral ceilings, wood-burning fireplace, and glass doors that seamlessly connect the interior to the outdoors. The custom kitchen is outfitted with an expansive granite center island, stainless steel appliances and a generous dining area. The private primary retreat includes a custom walk-in closet and en suite bath, featuring a double sink vanity and a walk-in shower with dual shower heads. 3 private guest rooms and 2 additional full baths, located on a separate floor, ensure plenty of privacy for everyone. The finished basement offers approximately 670 square feet of additional living space to the main house and is perfect for entertaining, complete with a custom bar, built-in cabinetry, and a half bath. The detached 1 bedroom and 1 bath guest suite is located above the oversize 2-bay garage and is ideal for extended family and friends. This beautifully appointed space features an open floor plan, high-end materials throughout and a large private deck. From the moment you arrive, the professionally landscaped grounds invite you to enjoy everything this property has to offer. With dedicated outdoor entertaining areas, multiple decks, outdoor tv, firepit and hot tub, the space is perfectly designed for both grand hosting and quiet relaxation. This exceptional property checks off all the boxes for the perfect Vineyard home.

6 Hollow Way, Edgartown

$3,295,000

Coastal Contemporary in Katama - Thoughtfully designed for relaxed Vineyard living and effortless entertaining, this custom-built home is set on beautifully landscaped grounds between Edgartown Village and South Beach. A dramatic two-story Great Room with gas fireplace anchors the light-filled living and dining spaces, which open to a spacious screened porch. The eat-in kitchen features custom cabinetry and all-new appliances. A private first-floor primary suite is complemented by an upstairs guest suite and open loft-style living and recreation area, enhanced by a recent 200+ sq. ft. expansion. Outdoors, a stone terrace with hot tub invites evenings under the stars, while the private grounds offer ample room for a future pool. Additional features include central air, a full unfinished basement with potential for added living space, and a two-car garage. An inviting Katama retreat combining architectural character, comfort, and an ideal island location.

3 Beds ⋅ 3 Baths ⋅ 73591230 MLS

Coastal Contemporary in Katama - Thoughtfully designed for relaxed Vineyard living and effortless entertaining, this custom-built home is set on beautifully landscaped grounds between Edgartown Village and South Beach. A dramatic two-story Great Room with gas fireplace anchors the light-filled living and dining spaces, which open to a spacious screened porch. The eat-in kitchen features custom cabinetry and all-new appliances. A private first-floor primary suite is complemented by an upstairs guest suite and open loft-style living and recreation area, enhanced by a recent 200+ sq. ft. expansion. Outdoors, a stone terrace with hot tub invites evenings under the stars, while the private grounds offer ample room for a future pool. Additional features include central air, a full unfinished basement with potential for added living space, and a two-car garage. An inviting Katama retreat combining architectural character, comfort, and an ideal island location.

26 Pulpit Ln, Edgartown

$6,125,000

Set within one of historic Edgartown Village’s most coveted neighborhoods, this gracious 4-bedroom, 5.5-bath home with guest suite is a rare opportunity to acquire a true heirloom property. Inside, a grand foyer, soaring ceilings and generously proportioned rooms create an atmosphere of understated elegance, while beautiful wood floors and custom millwork throughout, add character and a sense of history. Interior photos coming soon. The thoughtful floor plan flows seamlessly from one living space to the next, making the home as comfortable for quiet evenings as it is for entertaining family and friends. Two fireplaces anchor the principal gathering spaces, adding charm through every season. Adding a truly one-of-a-kind touch in the dining room, trompe l’oeil murals by Linda Carnegie bring scenes of Edgartown indoors as works of art. The first-floor primary suite is a private retreat, complete with custom closets and cabinetry. The spa-like full bath features a sunken tub, and the suite opens to its own private deck with an outdoor shower. The living extends outdoors through an impressive collection of spaces designed for relaxed island days and long summer evenings. Multiple decks provide room to dine and lounge, while the screened porch offers a shaded retreat from morning coffee to sunset cocktails. Surrounding it all, lush gardens designed by Donaroma’s bring color, texture, and privacy, with each season offering something new to admire. Above the garage, a separate guest suite offers its own kitchen, full bath, and private entrance – ideal for visiting family, extended-stay guests, a caregiver, or an independent retreat for older children. With its refined interiors, beautiful grounds, and prized location just moments from Edgartown’s shops, restaurants, harbor, and historic waterfront, this exceptional property is a unique opportunity.

4 Beds ⋅ 6 Baths ⋅ 73590664 MLS

Set within one of historic Edgartown Village’s most coveted neighborhoods, this gracious 4-bedroom, 5.5-bath home with guest suite is a rare opportunity to acquire a true heirloom property. Inside, a grand foyer, soaring ceilings and generously proportioned rooms create an atmosphere of understated elegance, while beautiful wood floors and custom millwork throughout, add character and a sense of history. Interior photos coming soon. The thoughtful floor plan flows seamlessly from one living space to the next, making the home as comfortable for quiet evenings as it is for entertaining family and friends. Two fireplaces anchor the principal gathering spaces, adding charm through every season. Adding a truly one-of-a-kind touch in the dining room, trompe l’oeil murals by Linda Carnegie bring scenes of Edgartown indoors as works of art. The first-floor primary suite is a private retreat, complete with custom closets and cabinetry. The spa-like full bath features a sunken tub, and the suite opens to its own private deck with an outdoor shower. The living extends outdoors through an impressive collection of spaces designed for relaxed island days and long summer evenings. Multiple decks provide room to dine and lounge, while the screened porch offers a shaded retreat from morning coffee to sunset cocktails. Surrounding it all, lush gardens designed by Donaroma’s bring color, texture, and privacy, with each season offering something new to admire. Above the garage, a separate guest suite offers its own kitchen, full bath, and private entrance – ideal for visiting family, extended-stay guests, a caregiver, or an independent retreat for older children. With its refined interiors, beautiful grounds, and prized location just moments from Edgartown’s shops, restaurants, harbor, and historic waterfront, this exceptional property is a unique opportunity.

78 Plantingfield Way, Edgartown

$3,200,000

The one you have been waiting for! Originally reimagined to be the owners forever home, this turnkey Katama gem is now ready for its next chapter. No expense or detail was spared in the magnificent, top-to-bottom transformation of this comfortable 3-bedroom, 4-full-bath Cape. From the thoughtful finishes to the seamless layout, every inch of this home has been lovingly updated to offer the ultimate blend of comfort and modern living. A spectacular custom built three season room --complete with a cozy fireplace--is the perfect place to entertain or just unwind and enjoy the incredible professionally landscaped grounds. The 37,000 ft, lot is surrounded by serene conservation land, ensuring privacy and beautiful, blooming views from every single window. Close to South Beach, this exceptional property is the perfect vacation home. Don't miss this chance to make it yours!

3 Beds ⋅ 4 Baths ⋅ 22605187 MLS

The one you have been waiting for! Originally reimagined to be the owners forever home, this turnkey Katama gem is now ready for its next chapter. No expense or detail was spared in the magnificent, top-to-bottom transformation of this comfortable 3-bedroom, 4-full-bath Cape. From the thoughtful finishes to the seamless layout, every inch of this home has been lovingly updated to offer the ultimate blend of comfort and modern living. A spectacular custom built three season room --complete with a cozy fireplace--is the perfect place to entertain or just unwind and enjoy the incredible professionally landscaped grounds. The 37,000 ft, lot is surrounded by serene conservation land, ensuring privacy and beautiful, blooming views from every single window. Close to South Beach, this exceptional property is the perfect vacation home. Don't miss this chance to make it yours!

16 Old Dunham's Corner Way, Edgartown

$5,820,000

A Private Edgartown Compound with Sweeping Farm Views. Set on over an acre bordering Land Bank conservation land, 29 Llewellyn Way offers privacy, refined living, and sweeping views of Morning Glory Farm's picturesque fields. Just moments from the bike path, Downtown Edgartown, and South Beach, this exceptional compound features over 4,000 square feet of living space across a renovated four-bedroom main house, a newly built two-bedroom guest house, and a detached garage with office and half bath above. The main residence offers vaulted ceilings, a gas fireplace, a modern renovated kitchen, a cozy den, and an expansive deck overlooking the heated infinity-edge pool, spa, and outdoor kitchen. The private second-floor primary suite features a renovated bath, while three additional bedrooms and two full baths occupy the lower level. The guest house boasts cathedral ceilings with exposed beams, a modern kitchen, spacious living room, full bath, and laundry, with direct pool access. Beautifully landscaped grounds and vibrant flower gardens complete this private Vineyard retreat, offering an ideal setting for entertaining, relaxing, and enjoying the best of Edgartown living.

4 Beds ⋅ 3 Baths ⋅ 22605188 MLS

A Private Edgartown Compound with Sweeping Farm Views. Set on over an acre bordering Land Bank conservation land, 29 Llewellyn Way offers privacy, refined living, and sweeping views of Morning Glory Farm's picturesque fields. Just moments from the bike path, Downtown Edgartown, and South Beach, this exceptional compound features over 4,000 square feet of living space across a renovated four-bedroom main house, a newly built two-bedroom guest house, and a detached garage with office and half bath above. The main residence offers vaulted ceilings, a gas fireplace, a modern renovated kitchen, a cozy den, and an expansive deck overlooking the heated infinity-edge pool, spa, and outdoor kitchen. The private second-floor primary suite features a renovated bath, while three additional bedrooms and two full baths occupy the lower level. The guest house boasts cathedral ceilings with exposed beams, a modern kitchen, spacious living room, full bath, and laundry, with direct pool access. Beautifully landscaped grounds and vibrant flower gardens complete this private Vineyard retreat, offering an ideal setting for entertaining, relaxing, and enjoying the best of Edgartown living.

29 Llewellyn Way, Edgartown

$5,820,000

Set on over an acre of beautifully landscaped grounds, this estate offers a rare combination of privacy, refined living, and exceptional proximity to all that makes Martha’s Vineyard special. Bordering Land Bank conservation land and overlooking the picturesque fields of Morning Glory Farm, the property enjoys a peaceful pastoral setting with vibrant flower gardens and expansive outdoor living spaces. Just moments from the bike path, Downtown Edgartown, and South Beach, this exceptional compound offers the best of both worlds. With more than 4,000 square feet of living space across the main house, guest house, and detached garage with office above, there is ample room for both gathering and privacy. The recently renovated four-bedroom main residence is thoughtfully designed for comfortable living and entertaining. A dramatic living room with vaulted ceilings and a gas fireplace opens through sliding doors to an expansive deck overlooking the pool and outdoor kitchen. The dining room features soaring cathedral ceilings and direct deck access, while the beautifully renovated modern kitchen offers generous space for entertaining. A cozy den just off the kitchen provides a quiet retreat. The second floor is dedicated to the private primary suite with a renovated bath, while the lower level offers three additional bedrooms and two full bathrooms. The newly built two-bedroom guest house delivers an equally inviting experience, with cathedral ceilings accented by exposed beams, a modern kitchen, a spacious living room, a full bathroom, and laundry. Outdoor living is at the heart of this remarkable property. A heated infinity-edge pool and spa create a resort-like atmosphere, surrounded by beautifully manicured grounds and gardens with views across the working fields of Morning Glory Farm. A detached garage with an office and half bath above provides a versatile space for work or quiet retreat, complemented by an additional garage attached to the main house. Combining exceptional privacy, multiple living spaces and stunning farm views, 29 Llewellyn Way is a distinctive Vineyard compound designed for effortless year-round living and unforgettable summer gatherings.

6 Beds ⋅ 6 Baths ⋅ 73589183 MLS

Set on over an acre of beautifully landscaped grounds, this estate offers a rare combination of privacy, refined living, and exceptional proximity to all that makes Martha’s Vineyard special. Bordering Land Bank conservation land and overlooking the picturesque fields of Morning Glory Farm, the property enjoys a peaceful pastoral setting with vibrant flower gardens and expansive outdoor living spaces. Just moments from the bike path, Downtown Edgartown, and South Beach, this exceptional compound offers the best of both worlds. With more than 4,000 square feet of living space across the main house, guest house, and detached garage with office above, there is ample room for both gathering and privacy. The recently renovated four-bedroom main residence is thoughtfully designed for comfortable living and entertaining. A dramatic living room with vaulted ceilings and a gas fireplace opens through sliding doors to an expansive deck overlooking the pool and outdoor kitchen. The dining room features soaring cathedral ceilings and direct deck access, while the beautifully renovated modern kitchen offers generous space for entertaining. A cozy den just off the kitchen provides a quiet retreat. The second floor is dedicated to the private primary suite with a renovated bath, while the lower level offers three additional bedrooms and two full bathrooms. The newly built two-bedroom guest house delivers an equally inviting experience, with cathedral ceilings accented by exposed beams, a modern kitchen, a spacious living room, a full bathroom, and laundry. Outdoor living is at the heart of this remarkable property. A heated infinity-edge pool and spa create a resort-like atmosphere, surrounded by beautifully manicured grounds and gardens with views across the working fields of Morning Glory Farm. A detached garage with an office and half bath above provides a versatile space for work or quiet retreat, complemented by an additional garage attached to the main house. Combining exceptional privacy, multiple living spaces and stunning farm views, 29 Llewellyn Way is a distinctive Vineyard compound designed for effortless year-round living and unforgettable summer gatherings.

29 Llewellyn Way, Edgartown

$3,995,000

Tucked into a quiet corner of Chappaquiddick, with protected views of Nantucket Sound and abutting the Pocha Pond Reservation and miles of endless hiking trails, this beautifully crafted custom home offers a rare combination of privacy, natural beauty, and effortless island living. The home is defined by a sense of casual elegance, with dramatic soaring ceilings and a striking prism skylight that fills the interior with warmth and natural light. An expansive, open living area is anchored by a floor-to-ceiling, double-sided fieldstone fireplace, creating a welcoming gathering space with a strong connection to the surrounding landscape. A remarkable two-story screened porch captures the water views and extends the living space outdoors, with a comfortable gathering area on the first level and a charming sleeping porch above. Four generously sized bedrooms, each with its own ensuite bath, offer privacy and comfort, with two enjoying water views. A finished lower level and oversized attached garage provide ample space for beach, boating, and fishing gear. Close to the ocean beaches of Wasque, yet within easy reach of downtown Edgartown, the property offers the best of Chappaquiddick, quiet, natural, and wonderfully removed, while still connected to everything the island has to offer. A cherished home in a truly special setting, ready for its next chapter.

4 Beds ⋅ 6 Baths ⋅ 73588921 MLS

Tucked into a quiet corner of Chappaquiddick, with protected views of Nantucket Sound and abutting the Pocha Pond Reservation and miles of endless hiking trails, this beautifully crafted custom home offers a rare combination of privacy, natural beauty, and effortless island living. The home is defined by a sense of casual elegance, with dramatic soaring ceilings and a striking prism skylight that fills the interior with warmth and natural light. An expansive, open living area is anchored by a floor-to-ceiling, double-sided fieldstone fireplace, creating a welcoming gathering space with a strong connection to the surrounding landscape. A remarkable two-story screened porch captures the water views and extends the living space outdoors, with a comfortable gathering area on the first level and a charming sleeping porch above. Four generously sized bedrooms, each with its own ensuite bath, offer privacy and comfort, with two enjoying water views. A finished lower level and oversized attached garage provide ample space for beach, boating, and fishing gear. Close to the ocean beaches of Wasque, yet within easy reach of downtown Edgartown, the property offers the best of Chappaquiddick, quiet, natural, and wonderfully removed, while still connected to everything the island has to offer. A cherished home in a truly special setting, ready for its next chapter.

4 Garrett Way, Edgartown

$4,195,000

Nestled within Edgartown’s coveted Katama/Island Grove enclave, 32 Martha’s Road is a masterfully crafted 2023 modern farmhouse where elevated design meets the effortless elegance of Vineyard living. Built by renowned island builder Shawn Chapps, this five-bedroom residence is a study in sophistication—rich with architectural intention, bathed in natural light, and thoughtfully composed for both intimate daily living and memorable entertaining. Set on .5 acres, the home unfolds across approximately 3,594 square feet, with an additional 2,300+ square feet of high-ceilinged, unfinished basement space offering extraordinary future potential. Cathedral ceilings, refined millwork, and expansive windows throughout create an atmosphere of lightness and luxury. A soaring, cathedral-height entryway immediately captivates, framed by striking two-story windows that draw the eye through the home to the serene, professionally landscaped backyard beyond. The foyer’s scale and natural light set the tone for the residence’s modern, airy aesthetic. The open-concept kitchen, dining, and living areas form an inviting central gathering space anchored by a warm gas fireplace and illuminated by windows on both sides. The gourmet kitchen is a true showpiece, featuring Thermador appliances, an expansive center island, and exceptional craftsmanship. It opens to a deep, walk-in pantry and a beautifully designed entertaining area complete with a sink, Zephyr beverage refrigerator, generous shelving, and abundant storage—functioning perfectly as a wet bar when hosting family and friends. Just beyond, a stunning screened porch extends the living space outdoors, offering a wood-burning fireplace and direct access to the stone patio and level backyard. With ample room for recreation and the potential for a future pool, the property invites endless enjoyment. With commanding curb appeal, flexible expansion opportunities, and abundant outdoor space, 32 Martha’s Road stands as an exceptional offering in one of Edgartown’s most desirable neighborhoods. Beautifully conceived, crafted with care, and designed with intention, this modern farmhouse is ready to be made uniquely your own—a rare opportunity to enjoy Vineyard living at its most refined.

5 Beds ⋅ 4 Baths ⋅ 73586815 MLS

Nestled within Edgartown’s coveted Katama/Island Grove enclave, 32 Martha’s Road is a masterfully crafted 2023 modern farmhouse where elevated design meets the effortless elegance of Vineyard living. Built by renowned island builder Shawn Chapps, this five-bedroom residence is a study in sophistication—rich with architectural intention, bathed in natural light, and thoughtfully composed for both intimate daily living and memorable entertaining. Set on .5 acres, the home unfolds across approximately 3,594 square feet, with an additional 2,300+ square feet of high-ceilinged, unfinished basement space offering extraordinary future potential. Cathedral ceilings, refined millwork, and expansive windows throughout create an atmosphere of lightness and luxury. A soaring, cathedral-height entryway immediately captivates, framed by striking two-story windows that draw the eye through the home to the serene, professionally landscaped backyard beyond. The foyer’s scale and natural light set the tone for the residence’s modern, airy aesthetic. The open-concept kitchen, dining, and living areas form an inviting central gathering space anchored by a warm gas fireplace and illuminated by windows on both sides. The gourmet kitchen is a true showpiece, featuring Thermador appliances, an expansive center island, and exceptional craftsmanship. It opens to a deep, walk-in pantry and a beautifully designed entertaining area complete with a sink, Zephyr beverage refrigerator, generous shelving, and abundant storage—functioning perfectly as a wet bar when hosting family and friends. Just beyond, a stunning screened porch extends the living space outdoors, offering a wood-burning fireplace and direct access to the stone patio and level backyard. With ample room for recreation and the potential for a future pool, the property invites endless enjoyment. With commanding curb appeal, flexible expansion opportunities, and abundant outdoor space, 32 Martha’s Road stands as an exceptional offering in one of Edgartown’s most desirable neighborhoods. Beautifully conceived, crafted with care, and designed with intention, this modern farmhouse is ready to be made uniquely your own—a rare opportunity to enjoy Vineyard living at its most refined.

32 Marthas Road, Edgartown

$3,200,000

The one you have been waiting for! Originally reimagined to be the owners forever home, this turnkey Katama gem is now ready for its next chapter. No expense or detail was spared in the magnificent, top-to-bottom transformation of this comfortable 3-bedroom, 4-full-bath Cape. From the thoughtful finishes to the seamless layout, every inch of this home has been lovingly updated to offer the ultimate blend of comfort and modern living. A spectacular custom built three season room --complete with a cozy fireplace--is the perfect place to entertain or just unwind and enjoy the incredible professionally landscaped grounds. The 37,000 ft, lot is surrounded by serene conservation land, ensuring privacy and beautiful, blooming views from every single window. Close to South Beach, this exceptional property is the perfect vacation home. Don't miss this chance to make it yours!

3 Beds ⋅ 4 Baths ⋅ 73586583 MLS

The one you have been waiting for! Originally reimagined to be the owners forever home, this turnkey Katama gem is now ready for its next chapter. No expense or detail was spared in the magnificent, top-to-bottom transformation of this comfortable 3-bedroom, 4-full-bath Cape. From the thoughtful finishes to the seamless layout, every inch of this home has been lovingly updated to offer the ultimate blend of comfort and modern living. A spectacular custom built three season room --complete with a cozy fireplace--is the perfect place to entertain or just unwind and enjoy the incredible professionally landscaped grounds. The 37,000 ft, lot is surrounded by serene conservation land, ensuring privacy and beautiful, blooming views from every single window. Close to South Beach, this exceptional property is the perfect vacation home. Don't miss this chance to make it yours!

16 Old Dunhams Corner Way, Edgartown

$6,900,000

4 Beds ⋅ 5 Baths ⋅ 73586485 MLS

8 Beach Plum Mdws, Edgartown

$2,950,000

Perched atop the highest point on Chappaquiddick, this private compound truly has it all, while still being a short distance from Chappy favorites including the Community Center, Beach Club, Ferry, and Slip Away Farm. Designed for both relaxation and recreation, the property offers endless ways to enjoy time with family and friends. Spend the afternoon on the sports courts, cool off at the pool, or relax on one of the expansive porches or patios. The guest house provides additional space and privacy. The pool house, complete with a half bath and kitchenette, makes entertaining effortless, with everything you need close at hand. A separate gym and game room offer even more ways to stay active or unwind, whatever the weather. With a strong rental history, the property also presents an excellent investment opportunity, while its generous amenities and multiple living spaces make it an ideal generational home to be enjoyed for years to come.

8 Beds ⋅ 7 Baths ⋅ 73586117 MLS

Perched atop the highest point on Chappaquiddick, this private compound truly has it all, while still being a short distance from Chappy favorites including the Community Center, Beach Club, Ferry, and Slip Away Farm. Designed for both relaxation and recreation, the property offers endless ways to enjoy time with family and friends. Spend the afternoon on the sports courts, cool off at the pool, or relax on one of the expansive porches or patios. The guest house provides additional space and privacy. The pool house, complete with a half bath and kitchenette, makes entertaining effortless, with everything you need close at hand. A separate gym and game room offer even more ways to stay active or unwind, whatever the weather. With a strong rental history, the property also presents an excellent investment opportunity, while its generous amenities and multiple living spaces make it an ideal generational home to be enjoyed for years to come.

72 Chappaquiddick, Edgartown

$9,500,000

A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

8 Beds ⋅ 11 Baths ⋅ 73584420 MLS

A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

12 Boldwater Road, Edgartown

$2,995,000

In a beautiful coastal setting, this 4-bedroom, 4.5-bath wood-sided contemporary is perched on 1.8 private waterfront acres in Major’s Cove, with frontage on Sengekontacket Pond, and offers a functional floor plan with exceptional views. Expanded over time, the home now includes a primary suite and laundry on the main living level, with comfortable living spaces opening to expansive wraparound decks. The home offers approximately 3,148 square feet of finished space, including approximately 800 square feet on the finished lower level, with substantial above-grade exposure at the rear. An upper-level ensuite bedroom and two additional bedrooms with two full baths on the lower level provide flexibility for family and guests. Improvements include newer windows and doors, new mini-split systems, new hot water heaters, and work to several bathrooms. The September 2026 Title V inspection passed and supports a five-bedroom septic capacity. With town water, only one existing structure on the 1.8-acre parcel, and substantial acreage, the property may offer long-term potential for expansion or future improvements, subject to applicable approvals. Life at Major’s Cove includes access to tennis and pickleball courts, a community boat launch, and kayak storage. HOA services include private-road maintenance, snow removal, and common-area landscaping. Whether enjoyed as a peaceful waterfront retreat or a home with room to evolve over time, this property offers exceptional privacy, versatility, and a distinctive island setting.

4 Beds ⋅ 5 Baths ⋅ 73583186 MLS

In a beautiful coastal setting, this 4-bedroom, 4.5-bath wood-sided contemporary is perched on 1.8 private waterfront acres in Major’s Cove, with frontage on Sengekontacket Pond, and offers a functional floor plan with exceptional views. Expanded over time, the home now includes a primary suite and laundry on the main living level, with comfortable living spaces opening to expansive wraparound decks. The home offers approximately 3,148 square feet of finished space, including approximately 800 square feet on the finished lower level, with substantial above-grade exposure at the rear. An upper-level ensuite bedroom and two additional bedrooms with two full baths on the lower level provide flexibility for family and guests. Improvements include newer windows and doors, new mini-split systems, new hot water heaters, and work to several bathrooms. The September 2026 Title V inspection passed and supports a five-bedroom septic capacity. With town water, only one existing structure on the 1.8-acre parcel, and substantial acreage, the property may offer long-term potential for expansion or future improvements, subject to applicable approvals. Life at Major’s Cove includes access to tennis and pickleball courts, a community boat launch, and kayak storage. HOA services include private-road maintenance, snow removal, and common-area landscaping. Whether enjoyed as a peaceful waterfront retreat or a home with room to evolve over time, this property offers exceptional privacy, versatility, and a distinctive island setting.

24 Myober Ln, Edgartown

$1,850,000

Discover this turnkey Edgartown home in a prime location near downtown dining and shopping, Edgartown Golf Club, and popular beaches. The refreshed interior features modern flooring, modern LED lighting, bathroom, and a bright kitchen with dark green granite countertops, tall windows, and a vaulted ceiling. All bedrooms have private en suite full baths, with two bedrooms on each floor. A sunroom opens to the deck and spacious backyard, offering room to relax or entertain. The home has town water and sewer and is being sold turnkey, excluding books and select personal items. Easy to show. This property is part of a First Look program. It allows owner occupant buyers to have their offers negotiated on day 8 of being listed. Owner occupants are those buyers that will occupy the property as their principal residence within 60 days of closing and will maintain their occupancy for at least 1 year. These buyers are required to sign an Owner Occupant Certification as part of the contract. An investor, trust, vacation or part-time residence, or purchasing for another person will be considered an Investor and are not eligible for First Look. Investors are welcomed to make offers the initial 30 DOM, but will not be countered until day 31. Some images in this listing have been virtually staged. Highest and Best due by 9am, EST on 10/27/2026.

4 Beds ⋅ 6 Baths ⋅ 73582365 MLS

Discover this turnkey Edgartown home in a prime location near downtown dining and shopping, Edgartown Golf Club, and popular beaches. The refreshed interior features modern flooring, modern LED lighting, bathroom, and a bright kitchen with dark green granite countertops, tall windows, and a vaulted ceiling. All bedrooms have private en suite full baths, with two bedrooms on each floor. A sunroom opens to the deck and spacious backyard, offering room to relax or entertain. The home has town water and sewer and is being sold turnkey, excluding books and select personal items. Easy to show. This property is part of a First Look program. It allows owner occupant buyers to have their offers negotiated on day 8 of being listed. Owner occupants are those buyers that will occupy the property as their principal residence within 60 days of closing and will maintain their occupancy for at least 1 year. These buyers are required to sign an Owner Occupant Certification as part of the contract. An investor, trust, vacation or part-time residence, or purchasing for another person will be considered an Investor and are not eligible for First Look. Investors are welcomed to make offers the initial 30 DOM, but will not be countered until day 31. Some images in this listing have been virtually staged. Highest and Best due by 9am, EST on 10/27/2026.

32 Norton Orchard Rd, Edgartown

$4,995,000

COASTAL LUXURY IN KATAMA — EXCEPTIONAL LIVING NEAR SOUTH BEACH. Set in one of Katama’s most coveted locations, where the sound of the ocean drifts in and South Beach is within easy reach, this distinctive coastal contemporary was thoughtfully designed to maximize natural light, energy efficiency, and long-term flexibility.The reverse-style floor plan places the main gathering spaces on the upper level, where abundant windows fill the interiors with sunlight and frame distant views across the lower reaches of Katama Bay. The open-concept Living, Dining, and Kitchen areas flow seamlessly together, creating an inviting setting for relaxed Vineyard living and effortless entertaining. At the heart of the home, the oversized Chef’s Kitchen opens directly onto a spacious porch for outdoor dining, gathering, and lounging, while two additional porches further extend the living space. The upper porch also enjoys seasonal views of the Edgartown fireworks, and nearby Fisherman’s Wharf and the public boat landing offer convenient access to Katama Bay and Edgartown Harbor.The home features four light-filled en suite bedrooms, each with a private bath and spacious shower. The generous Primary Suite includes dual oversized closets, a walk-in shower, and a private water closet. A bright first-floor bonus room offers flexible use as a Den, In-Home Gym, yoga studio, or additional guest space, with sliding glass doors for privacy, its own porch, and an adjacent half bath.Future accessibility was incorporated into the original design through a fully framed, wired, and mechanically prepared elevator shaft, allowing for the potential installation of an elevator with minimal disruption.Offered turnkey with indoor and outdoor furnishings and an established rental history, 98 Edgartown Bay Road is equally compelling as a personal Vineyard retreat, an income-producing investment, or a combination of both. The property also offers room for a future swimming pool and detached garage, subject to local approvals. Thoughtfully conceived for entertaining, sustainability, accessibility, and lasting enjoyment, this exceptional Katama residence presents a rare opportunity just moments from South Beach.

4 Beds ⋅ 5 Baths ⋅ 73581090 MLS

COASTAL LUXURY IN KATAMA — EXCEPTIONAL LIVING NEAR SOUTH BEACH. Set in one of Katama’s most coveted locations, where the sound of the ocean drifts in and South Beach is within easy reach, this distinctive coastal contemporary was thoughtfully designed to maximize natural light, energy efficiency, and long-term flexibility.The reverse-style floor plan places the main gathering spaces on the upper level, where abundant windows fill the interiors with sunlight and frame distant views across the lower reaches of Katama Bay. The open-concept Living, Dining, and Kitchen areas flow seamlessly together, creating an inviting setting for relaxed Vineyard living and effortless entertaining. At the heart of the home, the oversized Chef’s Kitchen opens directly onto a spacious porch for outdoor dining, gathering, and lounging, while two additional porches further extend the living space. The upper porch also enjoys seasonal views of the Edgartown fireworks, and nearby Fisherman’s Wharf and the public boat landing offer convenient access to Katama Bay and Edgartown Harbor.The home features four light-filled en suite bedrooms, each with a private bath and spacious shower. The generous Primary Suite includes dual oversized closets, a walk-in shower, and a private water closet. A bright first-floor bonus room offers flexible use as a Den, In-Home Gym, yoga studio, or additional guest space, with sliding glass doors for privacy, its own porch, and an adjacent half bath.Future accessibility was incorporated into the original design through a fully framed, wired, and mechanically prepared elevator shaft, allowing for the potential installation of an elevator with minimal disruption.Offered turnkey with indoor and outdoor furnishings and an established rental history, 98 Edgartown Bay Road is equally compelling as a personal Vineyard retreat, an income-producing investment, or a combination of both. The property also offers room for a future swimming pool and detached garage, subject to local approvals. Thoughtfully conceived for entertaining, sustainability, accessibility, and lasting enjoyment, this exceptional Katama residence presents a rare opportunity just moments from South Beach.

98 Edgartown Bay Rd, Edgartown

$3,400,000

Ideally situated between South Beach and Edgartown Village, this newly renovated Katama compound offers exceptional flexibility for personal use and rental income.The four-bedroom contemporary main house features a newly constructed, expansive great room with a cathedral ceiling and an abundance of windows that fill the space with natural light. The open floor plan flows from the updated kitchen into a living room centered around a classic brick fireplace. Skylights bring in additional sunlight, while sliding doors open to expansive new south-facing decks—perfect for outdoor dining, entertaining, and relaxing after a day at the beach. The third floor provides a second living area, bedroom, and private half bath. A full basement offers ample storage and potential for additional finished living space. The detached two-car garage includes a private one-bedroom apartment above with its own wraparound deck. A bonus room with a half bath on the garage’s main level is ideal for an office. A custom-built cedar shed provides convenient storage for bicycles and beach gear. Set on a half-acre lot with easy access to the nearby bike path leading to Edgartown Village and South Beach, this turnkey property combines an outstanding location with a strong rental history. With multiple living spaces and excellent income-producing potential, this versatile Katama compound is a must-see. Photo's have been enhanced

5 Beds ⋅ 5 Baths ⋅ 73577862 MLS

Ideally situated between South Beach and Edgartown Village, this newly renovated Katama compound offers exceptional flexibility for personal use and rental income.The four-bedroom contemporary main house features a newly constructed, expansive great room with a cathedral ceiling and an abundance of windows that fill the space with natural light. The open floor plan flows from the updated kitchen into a living room centered around a classic brick fireplace. Skylights bring in additional sunlight, while sliding doors open to expansive new south-facing decks—perfect for outdoor dining, entertaining, and relaxing after a day at the beach. The third floor provides a second living area, bedroom, and private half bath. A full basement offers ample storage and potential for additional finished living space. The detached two-car garage includes a private one-bedroom apartment above with its own wraparound deck. A bonus room with a half bath on the garage’s main level is ideal for an office. A custom-built cedar shed provides convenient storage for bicycles and beach gear. Set on a half-acre lot with easy access to the nearby bike path leading to Edgartown Village and South Beach, this turnkey property combines an outstanding location with a strong rental history. With multiple living spaces and excellent income-producing potential, this versatile Katama compound is a must-see. Photo's have been enhanced

62 Schoolhouse Rd, Edgartown

$2,455,000

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddle boarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with a strong rental history!

4 Beds ⋅ 5 Baths ⋅ 73577541 MLS

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddle boarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with a strong rental history!

99 The Boulevard, Edgartown

$2,500,000

Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equally suited to quiet Island weekends, a house full of summer guests or comfortable year-round living. At the heart of the home is a beautifully remodeled kitchen, completed in 2023 and designed to be part of daily life rather than separate from it. From here, the home unfolds into a spacious living room warmed by a propane fireplace, a formal dining room and a separate sitting room—giving family and guests the increasingly rare luxury of having both places to come together and places to retreat. Three large bedrooms provide comfortable private quarters, while an open loft creates another flexible destination for working, reading, watching a movie or simply escaping the activity downstairs. Below, a substantial unfinished basement with high ceilings and both interior and exterior access provides exceptional storage and flexibility for the future. Summer living extends naturally outdoors. A generous back deck overlooks the wooded acre-plus setting, offering a private place for morning coffee, long dinners and evenings under the Vineyard sky. And after a day spent at the beach, there is perhaps no more quintessentially Island pleasure than coming home to an outdoor shower. Beyond the property, Woodhaven offers something increasingly difficult to find: a neighborhood setting surrounded by nature with access to trails connecting the Manuel F. Correllus State Forest - opening miles of the Island for walking, running and biking. Private without being isolated, spacious without feeling overwhelming, and thoughtfully updated where it matters most, 10 Woodhaven Drive offers a relaxed approach to Edgartown living—and a home designed to be enjoyed well beyond the summer season.

3 Beds ⋅ 3 Baths ⋅ 22604449 MLS

Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equally suited to quiet Island weekends, a house full of summer guests or comfortable year-round living. At the heart of the home is a beautifully remodeled kitchen, completed in 2023 and designed to be part of daily life rather than separate from it. From here, the home unfolds into a spacious living room warmed by a propane fireplace, a formal dining room and a separate sitting room—giving family and guests the increasingly rare luxury of having both places to come together and places to retreat. Three large bedrooms provide comfortable private quarters, while an open loft creates another flexible destination for working, reading, watching a movie or simply escaping the activity downstairs. Below, a substantial unfinished basement with high ceilings and both interior and exterior access provides exceptional storage and flexibility for the future. Summer living extends naturally outdoors. A generous back deck overlooks the wooded acre-plus setting, offering a private place for morning coffee, long dinners and evenings under the Vineyard sky. And after a day spent at the beach, there is perhaps no more quintessentially Island pleasure than coming home to an outdoor shower. Beyond the property, Woodhaven offers something increasingly difficult to find: a neighborhood setting surrounded by nature with access to trails connecting the Manuel F. Correllus State Forest - opening miles of the Island for walking, running and biking. Private without being isolated, spacious without feeling overwhelming, and thoughtfully updated where it matters most, 10 Woodhaven Drive offers a relaxed approach to Edgartown living—and a home designed to be enjoyed well beyond the summer season.

10 Woodhaven Drive, Edgartown

$3,075,000

Katama at its best ~ WITH A POOL! Set in one of Martha’s Vineyard’s most coveted locations, 21 Vickers Street is a classic beach home with an effortless connection to everything that makes Katama so special. Just one mile from South Beach, with the bike path, Katama General Store, and Edgartown Village close by, this updated, move-in-ready home puts the best of the Island within easy reach. A newly installed pool and expansive yard create a private setting for summer days and long afternoons outdoors. Inside, the kitchen features an inviting banquet dining area and opens to a spacious cathedral-ceilinged family room with sliders to the back deck, outdoor shower, pool, and yard. A separate living room provides another gathering space, while a first-floor bedroom and full bath offer flexibility for family and guests. Upstairs, two generous bedrooms share a full bath. The full basement provides ample storage for bicycles, beach chairs, paddleboards, and all the essentials of Vineyard life. With the ability to tie into town sewer for up to six bedrooms, the property also offers exciting possibilities for the future. The very best of Katama comes together here with a coveted location, a classic Vineyard home, and an easy way to enjoy everything that makes summer on Martha’s Vineyard so special. Sale is contingent on seller finding another home.

3 Beds ⋅ 2 Baths ⋅ 73567342 MLS

Katama at its best ~ WITH A POOL! Set in one of Martha’s Vineyard’s most coveted locations, 21 Vickers Street is a classic beach home with an effortless connection to everything that makes Katama so special. Just one mile from South Beach, with the bike path, Katama General Store, and Edgartown Village close by, this updated, move-in-ready home puts the best of the Island within easy reach. A newly installed pool and expansive yard create a private setting for summer days and long afternoons outdoors. Inside, the kitchen features an inviting banquet dining area and opens to a spacious cathedral-ceilinged family room with sliders to the back deck, outdoor shower, pool, and yard. A separate living room provides another gathering space, while a first-floor bedroom and full bath offer flexibility for family and guests. Upstairs, two generous bedrooms share a full bath. The full basement provides ample storage for bicycles, beach chairs, paddleboards, and all the essentials of Vineyard life. With the ability to tie into town sewer for up to six bedrooms, the property also offers exciting possibilities for the future. The very best of Katama comes together here with a coveted location, a classic Vineyard home, and an easy way to enjoy everything that makes summer on Martha’s Vineyard so special. Sale is contingent on seller finding another home.

21 Vickers Street, Edgartown

$2,500,000

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

4 Beds ⋅ 3 Baths ⋅ 22604104 MLS

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

9 Codman Spring Road, Edgartown

$2,850,000

Two side by side cottages built in 1945 Directly Pondfront on Sengekontacket with 180 degree views over the pond out to the Causeway, State Beach, Nantucket Sound and beyond. A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond. Set along the Boulevard, behind a traditional white picket fence, this .66 acre property features two side-by-side cottages dating back to the 1940s and captures the relaxed character of an earlier Vineyard. The larger cottage is a quintessential Vineyard retreat with beautiful direct waterviews from the Main living areas, dining area and porch. Upstairs, a sitting area and small upper deck provide exceptional views across Sengekontacket Pond to State Beach extending out towards Cape Cod. The porch and the spacious lush side yard with lawn and lovely plantings, offer an inviting setting for morning coffee, summer dinners, entertaining, or simply enjoying the changing light and activity on the water. The larger cottage has an established rental history. An attractive option for seasonal rental income. The second smaller cottage offer the opportunity for a new owner to renovate and make the space their own as additional living space, a guest cottage or studio, subject to applicable approvals. Another compelling option is to explore removing the cottages and combining the existing square footage together with a percentage of additional square footage as allowed, to create one larger residence to take full advantage of this extraordinary waterfront setting. Any renovations, expansion or redevelopment would be subject to all applicable approvals and zoning regulations. Additionally, just a stone's throw away, the nearby boat landing provides convenient access to the pond, with openings into the Nantucket Sound, for launching kayaks, paddleboards and trailered boats. putting one of the Vineyard's most beautiful waterways practically at your doorstep. With two cottages, acreage, established rental history, convenient boating access and remarkable views.#49 The Boulevard offers a special opportunity to enjoy a classic Vineyard property today while imagining and planning its possibilities for the future.

6 Beds ⋅ 2 Baths ⋅ 22604053 MLS

Two side by side cottages built in 1945 Directly Pondfront on Sengekontacket with 180 degree views over the pond out to the Causeway, State Beach, Nantucket Sound and beyond. A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond. Set along the Boulevard, behind a traditional white picket fence, this .66 acre property features two side-by-side cottages dating back to the 1940s and captures the relaxed character of an earlier Vineyard. The larger cottage is a quintessential Vineyard retreat with beautiful direct waterviews from the Main living areas, dining area and porch. Upstairs, a sitting area and small upper deck provide exceptional views across Sengekontacket Pond to State Beach extending out towards Cape Cod. The porch and the spacious lush side yard with lawn and lovely plantings, offer an inviting setting for morning coffee, summer dinners, entertaining, or simply enjoying the changing light and activity on the water. The larger cottage has an established rental history. An attractive option for seasonal rental income. The second smaller cottage offer the opportunity for a new owner to renovate and make the space their own as additional living space, a guest cottage or studio, subject to applicable approvals. Another compelling option is to explore removing the cottages and combining the existing square footage together with a percentage of additional square footage as allowed, to create one larger residence to take full advantage of this extraordinary waterfront setting. Any renovations, expansion or redevelopment would be subject to all applicable approvals and zoning regulations. Additionally, just a stone's throw away, the nearby boat landing provides convenient access to the pond, with openings into the Nantucket Sound, for launching kayaks, paddleboards and trailered boats. putting one of the Vineyard's most beautiful waterways practically at your doorstep. With two cottages, acreage, established rental history, convenient boating access and remarkable views.#49 The Boulevard offers a special opportunity to enjoy a classic Vineyard property today while imagining and planning its possibilities for the future.

49 The Boulevard, Edgartown

$2,500,000

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

4 Beds ⋅ 3 Baths ⋅ 73564299 MLS

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

9 Codman Spring Road, Edgartown

$10,750,000

Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and truly exceptional family compound, the property offers an extraordinary combination of scale, privacy, waterfront, and amenities. Expansive grounds unfold toward sweeping water views, with a gentle slope leading to a protected stretch of sandy beach and access to a 190-foot private dock with mooring. The stately main residence offers beautifully proportioned spaces updated with today’s comforts, with a thoughtful layout well suited to both intimate family living and multigenerational gatherings. The estate extends beyond the main residence to include 75 Landing Place, an additional waterfront parcel that seamlessly expands the property, offering beautiful vistas, greater privacy, and a sense of scale rarely found on Chappaquiddick. An additional three-acre parcel is also available, creating a singular opportunity to assemble a one-of-a-kind family compound of exceptional size and privacy, with the flexibility to shape the property for generations to come. Cherished by the same family for generations, this remarkable waterfront estate represents a rare opportunity to create something truly enduring—a private family retreat with the space, setting, and flexibility to become a legacy for generations to come.

7 Beds ⋅ 4 Baths ⋅ 73563263 MLS

Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and truly exceptional family compound, the property offers an extraordinary combination of scale, privacy, waterfront, and amenities. Expansive grounds unfold toward sweeping water views, with a gentle slope leading to a protected stretch of sandy beach and access to a 190-foot private dock with mooring. The stately main residence offers beautifully proportioned spaces updated with today’s comforts, with a thoughtful layout well suited to both intimate family living and multigenerational gatherings. The estate extends beyond the main residence to include 75 Landing Place, an additional waterfront parcel that seamlessly expands the property, offering beautiful vistas, greater privacy, and a sense of scale rarely found on Chappaquiddick. An additional three-acre parcel is also available, creating a singular opportunity to assemble a one-of-a-kind family compound of exceptional size and privacy, with the flexibility to shape the property for generations to come. Cherished by the same family for generations, this remarkable waterfront estate represents a rare opportunity to create something truly enduring—a private family retreat with the space, setting, and flexibility to become a legacy for generations to come.

139 Chappaquiddick Road, Edgartown

$1,500,000

CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Chappaquiddick Community Center, the Ferry, Wasque Beach, and Quammox Preserve with its public access to Katama Bay, this property is perfectly positioned to enjoy the best of Chappy. Abutting conservation land, with the Cross Chappy Trail and Pocha Pond Reservation just outside your door, it offers direct access to some of the island's most treasured natural landscapes. The home's efficient floor plan features a first-floor bedroom, open living spaces, and a cozy sunroom, creating the perfect retreat to enjoy all that Chappaquiddick has to offer today, while providing outstanding opportunities for future expansion.

3 Beds ⋅ 2 Baths ⋅ 73559452 MLS

CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Chappaquiddick Community Center, the Ferry, Wasque Beach, and Quammox Preserve with its public access to Katama Bay, this property is perfectly positioned to enjoy the best of Chappy. Abutting conservation land, with the Cross Chappy Trail and Pocha Pond Reservation just outside your door, it offers direct access to some of the island's most treasured natural landscapes. The home's efficient floor plan features a first-floor bedroom, open living spaces, and a cozy sunroom, creating the perfect retreat to enjoy all that Chappaquiddick has to offer today, while providing outstanding opportunities for future expansion.

8 Pip'n Circle, Edgartown

$2,300,000

South Beach! Katama Airfield! Look no further if you are hoping to find a great lot within close proximity to all Katama has to offer. Nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a garage underneath. The guest house is an A-frame home. Conveniently located just off the bike path, a mile from the desirable South Beach, two miles from downtown, and close to Katama Airfield, the location doesn't get much better than this. Property is being sold ''as is''. Buyer is responsible for the research on how to make this pre-existing, non-conforming property conform to today's building and zoning requirements.

3 Beds ⋅ 3 Baths ⋅ 22601571 MLS

South Beach! Katama Airfield! Look no further if you are hoping to find a great lot within close proximity to all Katama has to offer. Nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a garage underneath. The guest house is an A-frame home. Conveniently located just off the bike path, a mile from the desirable South Beach, two miles from downtown, and close to Katama Airfield, the location doesn't get much better than this. Property is being sold ''as is''. Buyer is responsible for the research on how to make this pre-existing, non-conforming property conform to today's building and zoning requirements.

60 Crocker Drive, Edgartown

$3,100,000

3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach and Edgartown Village. Featuring a custom guesthouse built in 2018, with solid rental history and is outfitted with modern amenities. With a 6-bedroom septic system in place, there's ample opportunity to build a main house or additional structures, pending necessary town approvals. Expansion to 8 bedrooms possible with septic upgrade. This unique opportunity allows the developer to enjoy Edgartown now while envisioning the full potential.

1 Beds ⋅ 1 Baths ⋅ 22602741 MLS

3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach and Edgartown Village. Featuring a custom guesthouse built in 2018, with solid rental history and is outfitted with modern amenities. With a 6-bedroom septic system in place, there's ample opportunity to build a main house or additional structures, pending necessary town approvals. Expansion to 8 bedrooms possible with septic upgrade. This unique opportunity allows the developer to enjoy Edgartown now while envisioning the full potential.

114 Meetinghouse Way, Edgartown

$7,695,000

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors the home and connects seamlessly to the cathedral-ceiling great room with a wood-burning fireplace and a 20' x 40' heated gunite pool. The chef's kitchen features a Patagonia Tiffany stone island, breakfast nook, and butler's pantry. Private bedroom suites occupy separate wings, including a spa-inspired primary suite with a circular skylit shower and wall-to-wall travertine. A bright lower level with 10-foot ceilings provides generous recreation and entertaining space. A custom furniture package is available upon request for a truly turnkey offering. Conveniently located near Crocker Drive with easy access to South Beach, bike paths, Katama, and downtown Edgartown. A refined interpretation of the Vineyard summer house, thoughtfully designed for relaxed coastal living.

4 Beds ⋅ 5 Baths ⋅ 22603541 MLS

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors the home and connects seamlessly to the cathedral-ceiling great room with a wood-burning fireplace and a 20' x 40' heated gunite pool. The chef's kitchen features a Patagonia Tiffany stone island, breakfast nook, and butler's pantry. Private bedroom suites occupy separate wings, including a spa-inspired primary suite with a circular skylit shower and wall-to-wall travertine. A bright lower level with 10-foot ceilings provides generous recreation and entertaining space. A custom furniture package is available upon request for a truly turnkey offering. Conveniently located near Crocker Drive with easy access to South Beach, bike paths, Katama, and downtown Edgartown. A refined interpretation of the Vineyard summer house, thoughtfully designed for relaxed coastal living.

2 Lexington Avenue, Edgartown

$3,200,000

Perfectly situated just moments from the bike path, Edgartown Village, and South Beach, this exceptional Edgartown compound offers the best of Vineyard living. The main house is filled with warmth and character, featuring soaring ceilings, exposed beams, and an inviting open living area centered around a custom stone fireplace. Thoughtfully designed and perfectly sited for privacy, the Casita offers a comfortable and welcoming retreat for family and guests. Beautifully manicured grounds and gardens overlook the picturesque fields of Morning Glory Farm, creating a serene backdrop and a true sense of tranquility. With town sewer available, the property offers the potential for additional bedrooms, providing even greater flexibility for future expansion. A rare opportunity to own a distinctive island compound in one of Edgartown's most convenient and desirable locations!Built in 2018, the guest house features exposed beams and cathedral ceilings in the open-concept kitchen and living area. The first floor also includes a den with porch access, a half bath with laundry, and interior access to an approximately 4-foot cement crawl space. Upstairs, the bedroom offers an ensuite bath and a private deck. Thoughtfully separated from the main house, the guest house also includes its own outdoor shower and dedicated parking area.

4 Beds ⋅ 6 Baths ⋅ 73554803 MLS

Perfectly situated just moments from the bike path, Edgartown Village, and South Beach, this exceptional Edgartown compound offers the best of Vineyard living. The main house is filled with warmth and character, featuring soaring ceilings, exposed beams, and an inviting open living area centered around a custom stone fireplace. Thoughtfully designed and perfectly sited for privacy, the Casita offers a comfortable and welcoming retreat for family and guests. Beautifully manicured grounds and gardens overlook the picturesque fields of Morning Glory Farm, creating a serene backdrop and a true sense of tranquility. With town sewer available, the property offers the potential for additional bedrooms, providing even greater flexibility for future expansion. A rare opportunity to own a distinctive island compound in one of Edgartown's most convenient and desirable locations!Built in 2018, the guest house features exposed beams and cathedral ceilings in the open-concept kitchen and living area. The first floor also includes a den with porch access, a half bath with laundry, and interior access to an approximately 4-foot cement crawl space. Upstairs, the bedroom offers an ensuite bath and a private deck. Thoughtfully separated from the main house, the guest house also includes its own outdoor shower and dedicated parking area.

19 Llewellyn Way, Edgartown

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