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21 Flamingo Drive, Edgartown

Listing courtesy of Listing Agent: Jared Bicknell from Listing Office: Compass.

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

Listing courtesy of Listing Agent: Theresa Geary from Listing Office: Donnelly + Co..

$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

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$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

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

$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

Listing courtesy of Listing Agent: Patricia Lyman from Listing Office: Compass.

$6,900,000

4 Beds ⋅ 5 Baths ⋅ 73586485 MLS

8 Beach Plum Mdws, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$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

Listing courtesy of Listing Agent: Jeffrey Pierce from Listing Office: Compass.

$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

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$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

Listing courtesy of Listing Agent: Michele Casavant from Listing Office: Vineyard Village Realty.

$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

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.

$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

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

$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

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

$1,395,000

Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining area, efficient kitchen and welcoming living room with wood-burning fireplace. Outdoor living includes a sunny south-facing front deck, newer rear deck for grilling and dining, and a second-floor balcony perfect for morning coffee. Natural landscaping keeps upkeep simple, while a detached Party/Game Shed with French doors opens to the backyard and firepit area, offering flexible bonus space for entertaining, remote work or relaxing after a day at the beach or in town.

3 Beds ⋅ 2 Baths ⋅ 73549401 MLS

Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining area, efficient kitchen and welcoming living room with wood-burning fireplace. Outdoor living includes a sunny south-facing front deck, newer rear deck for grilling and dining, and a second-floor balcony perfect for morning coffee. Natural landscaping keeps upkeep simple, while a detached Party/Game Shed with French doors opens to the backyard and firepit area, offering flexible bonus space for entertaining, remote work or relaxing after a day at the beach or in town.

44 Prices Way, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$1,775,000

Set at the end of a cul-de-sac, this property offers a peaceful setting on .71 acres, with easy access to more than 25 acres of Land Bank conservation land. Morning Glory Farm is just a short distance away, offering a wonderful connection to the seasonal beauty and character of the Island. The bike path, Edgartown Village, and South Beach are also nearby, providing an easy balance of privacy and convenience. Filled with natural light, the post-and-beam home features a spacious kitchen with a large center island, walk-in pantry, and garden access. The dining area opens to a generous deck, while the sunken living room features cathedral ceilings, a floor-to-ceiling brick fireplace, and views of the surrounding landscape. A first-floor bedroom and full bath offer flexibility for guests. Upstairs, the primary suite includes a half bath, along with two additional bedrooms and a full bath. Established gardens, an outdoor shower, and expansive decking extend the living space outdoors. A basement provides additional storage and overflow space. Town sewer allows for expansion to as many as seven bedrooms, offering meaningful future potential in a private and well-connected Edgartown setting.

4 Beds ⋅ 3 Baths ⋅ 73531632 MLS

Set at the end of a cul-de-sac, this property offers a peaceful setting on .71 acres, with easy access to more than 25 acres of Land Bank conservation land. Morning Glory Farm is just a short distance away, offering a wonderful connection to the seasonal beauty and character of the Island. The bike path, Edgartown Village, and South Beach are also nearby, providing an easy balance of privacy and convenience. Filled with natural light, the post-and-beam home features a spacious kitchen with a large center island, walk-in pantry, and garden access. The dining area opens to a generous deck, while the sunken living room features cathedral ceilings, a floor-to-ceiling brick fireplace, and views of the surrounding landscape. A first-floor bedroom and full bath offer flexibility for guests. Upstairs, the primary suite includes a half bath, along with two additional bedrooms and a full bath. Established gardens, an outdoor shower, and expansive decking extend the living space outdoors. A basement provides additional storage and overflow space. Town sewer allows for expansion to as many as seven bedrooms, offering meaningful future potential in a private and well-connected Edgartown setting.

99 Old Purchase Road, Edgartown

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

$2,950,000

This classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a blend of comfort and Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a sitting area. Sliders lead to a spacious mahogany deck. This level also includes an additional family room, a generously sized bedroom with access to a private terrace and a full bath. Upstairs, the 3rd floor is dedicated to the primary suite, with vaulted, beamed ceilings and walls of glass that flood the space with natural light. The bath features a glass shower, completing the quiet atmosphere. On the first floor, you’ll find a third bedroom, large bath with laundry, and an additional living area with direct access to a covered porch. Set on a generous 0.7-acre lot, the property includes an outdoor shower. The property also boasts a strong rental history. Please inquire

4 Beds ⋅ 3 Baths ⋅ 73522670 MLS

This classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a blend of comfort and Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a sitting area. Sliders lead to a spacious mahogany deck. This level also includes an additional family room, a generously sized bedroom with access to a private terrace and a full bath. Upstairs, the 3rd floor is dedicated to the primary suite, with vaulted, beamed ceilings and walls of glass that flood the space with natural light. The bath features a glass shower, completing the quiet atmosphere. On the first floor, you’ll find a third bedroom, large bath with laundry, and an additional living area with direct access to a covered porch. Set on a generous 0.7-acre lot, the property includes an outdoor shower. The property also boasts a strong rental history. Please inquire

13 Young Street, Edgartown

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..

$1,395,000

Opportunity Knocks - Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat, while building value in a sought-after location. A fantastic opportunity to customize, restore, and make it your own. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

3 Beds ⋅ 1 Baths ⋅ 73490019 MLS

Opportunity Knocks - Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat, while building value in a sought-after location. A fantastic opportunity to customize, restore, and make it your own. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

17 Chapman La, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$2,299,000

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres. of pristine conservation land, with scenic trails, abundant wildlife, and direct ocean access. Whether you're seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque has it all. With

4 Beds ⋅ 3 Baths ⋅ 73472929 MLS

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres. of pristine conservation land, with scenic trails, abundant wildlife, and direct ocean access. Whether you're seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque has it all. With

76 Washque Ave, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

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