105

Homes for Sale in 02539

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  • /38

    $17,500,000

    • 5 Beds
    • 4.5 Baths
    • 6,061 Sq Ft

    12 Calebs Pond Ln, Edgartown, MA 02539

    This stunning custom-built waterfront estate offers sweeping views of Edgartown Harbor and exceptional craftsmanship throughout. Set on a private Chappaquiddick compound, the property features a beautifully designed main house, a separate one-bedroom guest house, a pool and spa, and expansive outdoor living spaces perfect for entertaining. Inside, warm wood finishes complement the home's

    Gerrett Conover Landvest MV

    12 Calebs Pond Ln, Edgartown, MA 02539
  • /4

    $995,000

    • Land
    • 7,840 Sq Ft
    • $5,527,778 per Acre

    34 Curtis Ln Unit 94, Edgartown, MA 02539

    COMING SOON — EXCITING IN-TOWN EDGARTOWN OPPORTUNITY. Tucked away on a quiet lane at the edge of Edgartown Village, this Curtis Lane property presents a rare opportunity to create a distinctive in-town residence close to village shops, restaurants, galleries, the harbor, and more. Curtis Lane is undergoing a notable transformation, with significant new construction and property improvements

    Agent Photo

    Wendy Harman

    Compass | Point B

    34 Curtis Ln Unit 94, Edgartown, MA 02539
  • /24

    $4,850,000

    $650K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,808 Sq Ft

    31 Butlers Cove Rd, Edgartown, MA 02539

    This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 1910 as one of the first houses on the storied 200-acre farm with over 2,000 ft of private Atlantic

    Gerrett Conover Landvest MV

    31 Butlers Cove Rd, Edgartown, MA 02539
  • /27

    $6,250,000

    • 5 Beds
    • 4 Baths
    • 3,443 Sq Ft

    118 S Water St, Edgartown, MA 02539

    Built in 1900, this beautiful South Water Street home is ideally located where the road begins its gentle rise up the hill. The original street-facing portion of the residence showcases classic Victorian architecture, complete with a charming covered front porch that reflects its timeless character. Thoughtfully expanded over the years, the home now offers five bedrooms and three bathrooms,

    Gerrett Conover Landvest MV

    118 S Water St, Edgartown, MA 02539
  • /19

    $3,100,000

    • Land
    • 1 Acre
    • $3,100,000 per Acre

    6 Kent Harbor Rd Unit 312, Edgartown, MA 02539

    DOWN HARBOR OPPORTUNITY! Introducing 6 Kent Harbor, a full acre of land in an ideal location for your next build or renovation project. Equidistant between South Beach and Edgartown Village, Down Harbor offers residents a walking path to a private sandy shoreline on Katama Bay. The existing 1972 ranch-style home has 1,525 sq ft with 3 bedrooms, 2 baths, living room and galley kitchen. Sliding

    Cheri Mason Landvest MV

    6 Kent Harbor Rd Unit 312, Edgartown, MA 02539
  • /20

    $9,495,000

    • 4 Beds
    • 6 Baths
    • 4,605 Sq Ft

    29 Slough Cove Rd, Edgartown, MA 02539

    Timeless architect-designed Katama retreat made for summer living. Privately set at the end of a long drive on 1.53 acres near South Beach, this Patrick Ahearn-designed estate offers 4,605 square feet of refined Vineyard living. Built in 2022, the home blends award-winning coastal architecture with vaulted ceilings, custom shiplap, millwork, antique rough-hewn beams, Rubio Monocoat floors,

    Agent Photo

    Wendy Harman

    Compass

    29 Slough Cove Rd, Edgartown, MA 02539
  • /69

    $3,650,000

    • 4 Beds
    • 4.5 Baths
    • 3,729 Sq Ft

    128 W Tisbury Rd, Edgartown, MA 02539

    Set against roughly ten acres of undeveloped meadow, this beautifully renovated Colonial delivers a coveted Vineyard experience: countryside privacy just minutes from the heart of Edgartown. Bike to Main Street or coast down to Morning Glory Farm, then return to the calm of a home wrapped in open field and mature plantings, as inviting in the quiet of winter as it is at the height of summer. A

    Patrick McCarthy Grace Hagerty Real Estate Inc

    128 W Tisbury Rd, Edgartown, MA 02539
  • /30

    $3,100,000

    • 3 Beds
    • 2 Baths
    • 1,525 Sq Ft

    6 Kent Harbor Rd, Edgartown, MA 02539

    DOWN HARBOR OPPORTUNITY! Introducing 6 Kent Harbor, a full acre of land in an ideal location for your next build or renovation project. Equidistant between South Beach and Edgartown Village, Down Harbor offers residents a walking path to a private sandy shoreline on Katama Bay. The existing 1972 ranch-style home has 1,525 sq ft with 3 bedrooms, 2 baths, living room and galley kitchen. Sliding

    Cheri Mason Landvest MV

    6 Kent Harbor Rd, Edgartown, MA 02539
  • /42

    $3,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,056 Sq Ft

    9 Thaxter Ln, Edgartown, MA 02539

    A contemporary Katama retreat, newly refreshed and ready for summer. Set in one of Edgartown’s most coveted coastal enclaves, moments from South Beach, this tri-level home offers sun-filled interiors, generous gathering spaces, strong rental appeal, and a private backyard oasis with an 18x40-foot saltwater pool. The dramatic open-concept living level features vaulted ceilings, a wood-burning

    Agent Photo

    Wendy Harman

    Compass

    9 Thaxter Ln, Edgartown, MA 02539
  • /2

    $525,000

    • Land
    • 7.7 Acres
    • $68,182 per Acre

    240 Chappaquiddick Rd Unit 35.1, Edgartown, MA 02539

    A rare opportunity to own 7.7 acres on the beautiful and sought-after island of Chappaquiddick. This wooded parcel offers exceptional privacy, natural contours, and the quiet, untouched landscape that defines Chappy living. Preliminary information suggests there is potential upland area to support the creation of a custom island retreat, with possible capacity for 4–6 bedrooms subject to final

    Leslie C. Floyd Portfolio Properties

    240 Chappaquiddick Rd Unit 35.1, Edgartown, MA 02539
  • /5

    $3,495,000

    • 2 Beds
    • 1.5 Baths
    • 1,388 Sq Ft

    48 Plantingfield Way, Edgartown, MA 02539

    Set on an exceptional .65 -acre parcel, this rare offering combines privacy, space, and an unbeatable location just moments from town and the water. The expansive lot offers a unique opportunity to expand and create a custom estate tailored to your vision. Surrounded by mature landscaping and generous outdoor space, the property offers a peaceful retreat while remaining conveniently close to

    Julia Smith Donnelly + Co

    48 Plantingfield Way, Edgartown, MA 02539
  • /4

    $3,495,000

    • Land
    • 28,314 Sq Ft
    • $5,376,923 per Acre

    48 Plaintingfield Way Unit 10, Edgartown, MA 02539

    Set on an exceptional .65 -acre parcel, this rare offering combines privacy, space, and an unbeatable location just moments from town and the water. The expansive lot offers a unique opportunity to expand and create a custom estate tailored to your vision. Surrounded by mature landscaping and generous outdoor space, the property offers a peaceful retreat while remaining conveniently close to

    Julia Smith Donnelly + Co

    48 Plaintingfield Way Unit 10, Edgartown, MA 02539
  • /10

    $896,000

    • 2 Beds
    • 1 Bath
    • 834 Sq Ft

    21 Clay Pit Rd, Edgartown, MA 02539

    This home is walk in ready to enjoy while you let your imagination go to work for this ideal property. Located a short walk along the bike path to Post Office square you will find this quiet location is perfect. You feel the old Vineyard charm along this peaceful lane. This represents the best entry way into Edgartown Real Estate today so do not let this opportunity pass you by. A 3rd bedroom

    Jim Joyce Carroll & Vincent R.E.

    21 Clay Pit Rd, Edgartown, MA 02539
  • /30

    $2,295,000

    • 5 Beds
    • 4 Baths
    • 3,119 Sq Ft

    2 Old Pocha Rd, Edgartown, MA 02539

    Tucked away down a quiet country road, this one-of-a-kind Chappaquiddick retreat invites you to exhale the moment you arrive. With no visible neighbors and the sounds of nature all around, the property offers a rare sense of privacy, peace, and timeless island charm. Built in an era when homes were crafted with artistry and intention, this distinctive post-and-beam residence blends warmth,

    Jim Feiner Feiner Real Estate

    2 Old Pocha Rd, Edgartown, MA 02539
  • /17

    $3,995,000

    • 5 Beds
    • 3 Baths
    • 2,733 Sq Ft

    49 High St, Edgartown, MA 02539

    A rare opportunity to create a premier in-town compound in one of Edgartown's most desirable locations. Set on High Street, just moments from downtown Edgartown, this exceptional 16,000+ square foot lot offers tremendous potential to create a substantial five-bedroom residence while enjoying the convenience and charm of village living. The property currently features a 4 bedroom main house,

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    49 High St, Edgartown, MA 02539
  • /12

    $3,850,000

    • Land
    • 1.14 Acres
    • $3,377,193 per Acre

    10 Pease Point Rd Unit 57, Edgartown, MA 02539

    PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned at the end of a private drive, on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Ideally situated just minutes from Edgartown

    Emma Bryant Studio Realty

    10 Pease Point Rd Unit 57, Edgartown, MA 02539
  • /26

    $32,500,000

    • 9 Beds
    • 12 Baths
    • 7,190 Sq Ft

    61 Butlers Cove, Edgartown, MA 02539

    Beach Farm is an extraordinary 18.6-acre waterfront estate offering exceptional privacy, 1,700 feet of water frontage, sweeping Atlantic views, two private beaches, and a rare walking path to the pristine South Shore. Set within the storied 200-acre Herring Creek Farm, a coastal enclave surrounding a working farm with barns, horses, sheep, and open meadows, Beach Farm is just a short bike ride to

    Brian Dougherty Corcoran Property Advisors

    61 Butlers Cove, Edgartown, MA 02539
  • /26

    $32,500,000

    • 9 Beds
    • 11 Baths
    • 7,190 Sq Ft

    61 Butlers Cove Rd, Edgartown, MA 02539

    Beach Farm is an extraordinary 18.6-acre waterfront estate offering exceptional privacy, 1,700 feet of water frontage, sweeping Atlantic views, private beaches, a rare walking path to the pristine South Shore, and a short bike ride to Edgartown Village. The estate is set within the storied 200-acre Herring Creek Farm, a coastal enclave surrounding a working farm with barns, horses, sheep, and

    Maggie Gold Seelig MGS Group Real Estate LTD

    61 Butlers Cove Rd, Edgartown, MA 02539
  • /12

    $18,500,000

    • Land
    • 12.77 Acres
    • $1,448,708 per Acre

    57 Butlers Cove Rd, Edgartown, MA 02539

    Set within the exclusive 200 acre coastal enclave of Herring Creek Farm, just minutes from Edgartown Village, Sunset Farm is a sprawling 12-acre waterfront property with an unprecedented 3 contiguous parcels. The three large building envelopes provide a rare opportunity to create multiple, substantial residences and amenities tailored to your vision. Sunset Farm has 700 feet of shoreline on the

    Maggie Gold Seelig MGS Group Real Estate LTD

    57 Butlers Cove Rd, Edgartown, MA 02539
  • /12

    $18,500,000

    • Land
    • 12.77 Acres
    • $1,448,708 per Acre

    57 Butlers Cove Unit 44, Edgartown, MA 02539

    Set within the exclusive 200 acre coastal enclave of Herring Creek Farm, just minutes from Edgartown Village, Sunset Farm is a sprawling 12-acre waterfront property with an unprecedented 3 contiguous parcels. The three large building envelopes provide a rare opportunity to create multiple, substantial residences and amenities tailored to your vision. Sunset Farm has 700 feet of shoreline on the

    Brian Dougherty Corcoran Property Advisors

    57 Butlers Cove Unit 44, Edgartown, MA 02539
  • /12

    $18,500,000

    • Land
    • 12.77 Acres
    • $1,448,708 per Acre

    Unlisted Address

    Set within the exclusive 200 acre coastal enclave of Herring Creek Farm, just minutes from Edgartown Village, Sunset Farm is a sprawling 12-acre waterfront property with an unprecedented 3 contiguous parcels. The three large building envelopes provide a rare opportunity to create multiple, substantial residences and amenities tailored to your vision. Sunset Farm has 700 feet of shoreline on the

    Brian Dougherty Corcoran Property Advisors

    Unlisted Address
  • /56

    $3,695,900

    • 3 Beds
    • 4.5 Baths
    • 3,056 Sq Ft

    9 Thaxter Ln, Edgartown, MA 02539

    A CONTEMPORARY KATAMA RETREAT, NEWLY REFRESHED AND READY FOR SUMMER. Set in one of Edgartown’s most coveted coastal enclaves, this contemporary retreat captures the effortless rhythm of Katama living: sun-filled interiors, generous gathering spaces, ocean breezes, and a private backyard oasis designed for long summer days by the pool. Moments from South Beach, this tri-level contemporary offers

    Agent Photo

    Wendy Harman

    Compass | Point B

    9 Thaxter Ln, Edgartown, MA 02539
  • /45

    $1,395,000

    • 2 Beds
    • 1.5 Baths
    • 1,126 Sq Ft

    29 Jernegan Ave, Edgartown, MA 02539

    Set on a generous .72-acre parcel just two miles from Edgartown Village and near the bike path, this thoughtfully renovated cottage offers comfortable living today with expansion potential. The property is move-in ready and provides easy access to beaches, boating, dining, and nearby conservation trails. The bright interior features an open floor plan with a spacious kitchen that flows into the

    Stephanie Roache Donnelly + Co

    29 Jernegan Ave, Edgartown, MA 02539
  • /19

    $1,150,000

    $45K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft

    34 10th St S, Edgartown, MA 02539

    Easy Edgartown living awaits in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout that works beautifully for everyday life, entertaining, or relaxed seasonal stays. The private primary suite includes its own

    Chrissie Teague Insight Realty Group, Inc.

    34 10th St S, Edgartown, MA 02539
  • /30

    $1,850,000

    • 4 Beds
    • 2.5 Baths
    • 2,064 Sq Ft

    99 Old Purchase Rd, Edgartown, MA 02539

    Enjoying a private setting at the end of a quiet Edgartown cul-de-sac, this post-and-beam home is set on .71 acres with easy access to more than 25 acres of Land Bank conservation land. Conveniently located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, the property offers both privacy and accessibility. Filled with natural light, the home features a well-designed

    Stephanie Roache Donnelly + Co

    99 Old Purchase Rd, Edgartown, MA 02539
  • /29

    $49,000,000

    • 12 Beds
    • 14 Baths
    • 8,994 Sq Ft

    15 Forever Wild Way, Edgartown, MA 02539

    Great Point is an unprecedented coastal estate encompassing a total of ~32 acres and 5 individual parcels within the coveted 200-acre Herring Creek Farm, just minutes from Edgartown Village and Harbor. This extraordinary property offers location, scale, privacy, and natural beauty, with architecturally significant residences and the rare opportunity to create three additional homes. More than

    Maggie Gold Seelig MGS Group Real Estate LTD

    15 Forever Wild Way, Edgartown, MA 02539
  • /11

    $650,000

    • 1 Bed
    • 1 Bath
    • 478 Sq Ft

    20 Peases Point Way N Unit 4, Edgartown, MA 02539

    Perfectly situated in the heart of downtown Edgartown, this recently renovated first-floor 1-bedroom, 1-bathroom retreat offers effortless access to the village’s acclaimed shops, galleries, restaurants, Fuller Street Beach, and Edgartown Harbor. The bright, open-concept living space seamlessly connects the kitchen, dining, and living areas, creating an inviting setting for relaxing or

    Jarrett Hurwitz Keller Williams Realty

    20 Peases Point Way N Unit 4, Edgartown, MA 02539
  • /65

    $7,999,000

    • 7 Beds
    • 6.5 Baths
    • 7,133 Sq Ft

    9 Sutton's Way, Edgartown, MA 02539

    Nestled in an enviable Katama setting, this masterfully designed shingle-style farmhouse compound epitomizes the peak of casual Vineyard luxury across a manicured coastal landscape. From the sprawling covered entry porch, the front door opens into an impeccably choreographed layout where a grand entry hall flows seamlessly into an expansive great room, an elegant formal dining space and a

    Jennifer DaSilva Compass | Point B

    9 Sutton's Way, Edgartown, MA 02539
  • /33

    $1,249,900

    • 3 Beds
    • 2 Baths
    • 1,338 Sq Ft

    37 Dodgers Hole Rd, Edgartown, MA 02539

    This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designed for comfortable island living. A hallway leads to the primary bedroom with private bath, along with

    Beth Welch Viewpoints

    37 Dodgers Hole Rd, Edgartown, MA 02539
  • /34

    $2,999,000

    $196K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,881 Sq Ft

    10 N Bog Rd, Edgartown, MA 02539

    Set on 2.2 acres in Edgartown, this five-bedroom home with a heated saltwater pool is just moments from Morning Glory Farm, South Beach, the bike path, and Edgartown Village. It features three finished levels designed for coastal living, with gathering spaces and indoor-outdoor flow. At the center of the home is the kitchen and dining area that opens onto an expansive deck overlooking the 16’ x

    Michele Casavant Vineyard Village Realty

    10 N Bog Rd, Edgartown, MA 02539
  • /33

    $1,495,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    44 Prices Way, Edgartown, MA 02539

    CONTEMPORARY ISLAND RETREAT. As a smart opportunity for Vineyard buyers seeking a low-maintenance Island home close to Edgartown Village, this contemporary home offers easy access to shopping, services, and the bicycle path connecting the three down-Island towns. Whether used as a year-round residence, seasonal getaway or potential vacation rental, the setting and layout make it easy to enjoy the

    Agent Photo

    Wendy Harman

    Compass | Point B

    44 Prices Way, Edgartown, MA 02539
  • /25

    $1,749,000

    $146K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,638 Sq Ft

    21 Schoolhouse Rd, Edgartown, MA 02539

    Located in the heart of Katama between South beach and Edgartown Village. Biking or walking distance along the the shared use path to beach or town. With 2 first floor bedrooms along with a full bath for one floor living. Second floor has 2 more bedrooms, bath along with a loft area for extra bed space. The full basement could be finished off for additional living areas. Plenty of room to grow on

    Jim Joyce Carroll & Vincent R.E.

    21 Schoolhouse Rd, Edgartown, MA 02539
  • /66

    $2,675,000

    Open House 7/28 $275K PRICE DROP
    • 4 Beds
    • 8 Baths
    • 3,740 Sq Ft

    15 21st St N, Edgartown, MA 02539

    Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main

    Jennifer O'hanlon Compass LLC

    15 21st St N, Edgartown, MA 02539
  • /52

    $2,195,000

    • 5 Beds
    • 3.5 Baths
    • 2,628 Sq Ft

    7 Pip'N Rd, Edgartown, MA 02539

    A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everything in between.Gather around the custom firepit under a canopy of stars, soak in the sauna and

    Dawn Bellante-Holand Sandpiper Realty

    7 Pip'N Rd, Edgartown, MA 02539
  • /29

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,208 Sq Ft

    13 Young St, Edgartown, MA 02539

    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

    Stacy Ickes Donnelly + Co.

    13 Young St, Edgartown, MA 02539
  • /56

    $9,995,000

    • 6 Beds
    • 7.5 Baths
    • 7,205 Sq Ft

    25 Lelands Path, Edgartown, MA 02539

    YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent residence is privately sited at the end of a winding drive on 16.4 acres, offering more than 7,200

    Agent Photo

    Wendy Harman

    Compass | Point B

    25 Lelands Path, Edgartown, MA 02539
  • /41

    $2,195,000

    • 5 Beds
    • 3.5 Baths
    • 2,628 Sq Ft

    7 Pipn Cir, Edgartown, MA 02539

    Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own

    Dawn Bellante Sandpiper Realty, Inc.

    7 Pipn Cir, Edgartown, MA 02539
  • /30

    $6,995,000

    • 4 Beds
    • 3 Baths
    • 2,624 Sq Ft

    103 Edgartown Bay Rd, Edgartown, MA 02539

    Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an

    Bonnie Pierce Wallace & Co. Sotheby's

    103 Edgartown Bay Rd, Edgartown, MA 02539
  • /4

    $890,000

    $105K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    51 Chase Rd, Edgartown, MA 02539

    Edgartown opportunity! Bring your vision to this two-bedroom, one-bath ranch situated close to the heart of downtown Edgartown. This property presents a rare chance to create value in a highly sought-after location. Just minutes to downtown, with off-street parking for three vehicles, the home features functional single-level living, including a living area, kitchen, two bedrooms, and a

    Lisa Gilberto C McManus Realty Group

    51 Chase Rd, Edgartown, MA 02539
  • /21

    $3,850,000

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    10 Pease Point Rd, Edgartown, MA 02539

    NEWLY LISTED l PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Ideally situated just minutes from Edgartown Village, with

    Emma Bryant Studio Realty

    10 Pease Point Rd, Edgartown, MA 02539

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