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Dukes County MA Homes for Sale

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  • 16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    /24

    $6,500,000

    • 6 Beds
    • 7 Baths
    • 4,753 Sq Ft

    16 Red Coat Hill Rd, Vineyard Haven, MA 02568

    Private West Tisbury Oasis – Modern Luxury on 4.85 Acres Built by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an additional unfinished

    Joe & Nicole Holland Vineyard Dream Realty LLC

    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
  • 14 Ridge Rd Unit 94, Aquinnah, MA 02535
    14 Ridge Rd Unit 94, Aquinnah, MA 02535
    14 Ridge Rd Unit 94, Aquinnah, MA 02535
    /15

    $1,195,000

    • Land
    • 5.7 Acres
    • $209,649 per Acre

    14 Ridge Rd Unit 94, Aquinnah, MA 02535

    Nearly 6 acres of land bordered by stonewalls on two sides. The property has been cleared, so you are able to see the level topography and mature trees. The location lends itself to a short walk to Lobsterville Beach or Red Beach on Menemsha Pond, where you can hop on your paddleboard or kayak or get to your mooring. There is fresh fish to catch off the beach or clams to gather from the Pond for

    Jill Napior Tea Lane Associates

    14 Ridge Rd Unit 94, Aquinnah, MA 02535
  • 4 Quail Run Unit 1, Oak Bluffs, MA 02557
    4 Quail Run Unit 1, Oak Bluffs, MA 02557
    4 Quail Run Unit 1, Oak Bluffs, MA 02557
    /23

    $869,000

    $30K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 1,182 Sq Ft

    4 Quail Run Unit 1, Oak Bluffs, MA 02557

    Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. This year-round home is filled with natural light and features a spacious deck —perfect for

    Jarrett Hurwitz Keller Williams Realty

    4 Quail Run Unit 1, Oak Bluffs, MA 02557
  • 114 Meetinghouse Way, Edgartown, MA 02539
    114 Meetinghouse Way, Edgartown, MA 02539
    114 Meetinghouse Way, Edgartown, MA 02539
    /22

    $3,100,000

    • 1 Bed
    • 1 Bath
    • 1,250 Sq Ft

    114 Meetinghouse Way, Edgartown, MA 02539

    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

    Rose Ryley Wallace & Co. Sotheby's International Realty

    114 Meetinghouse Way, Edgartown, MA 02539
  • Lot 1 Dolan Ave, Tisbury, MA 02568
    Lot 1 Dolan Ave, Tisbury, MA 02568
    Lot 1 Dolan Ave, Tisbury, MA 02568
    /3

    $525,000

    • Land
    • 10,454 Sq Ft
    • $2,187,500 per Acre

    Lot 1 Dolan Ave, Tisbury, MA 02568

    A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    Lot 1 Dolan Ave, Tisbury, MA 02568
  • 14 Thayer St, Edgartown, MA 02539
    14 Thayer St, Edgartown, MA 02539
    14 Thayer St, Edgartown, MA 02539
    /60

    $11,900,000

    $1M PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,466 Sq Ft

    14 Thayer St, Edgartown, MA 02539

    Set within the historic fabric of Edgartown Village, 14 Thayer Street is a property of uncommon scale and quiet distinction. Occupying a 0.62-acre parcel, rare for this in-town setting, the grounds offer a sense of space and privacy just moments from the harbor and village center.The residence is attributed to Frederick Baylies Jr., the builder of the Whaling Church, and reflects the enduring

    Paul Pertile The Agency

    14 Thayer St, Edgartown, MA 02539
  • 12 E Pasture Rd, Aquinnah, MA 02535
    12 E Pasture Rd, Aquinnah, MA 02535
    12 E Pasture Rd, Aquinnah, MA 02535
    /24

    $3,325,000

    $170K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    12 E Pasture Rd, Aquinnah, MA 02535

    This elegant architectural home is set within a lovely rolling meadow on four and a half generous acres, surrounded by stone walls, blue sky, and tranquility at all times of year. 12 East Pasture is a peaceful retreat on the westernmost side of Martha's Vineyard, known for the beautiful beaches and quiet privacy. The house features multiple large windows and sliding glass doors, which flood the

    Elissa Lash Tea Lane Associates

    12 E Pasture Rd, Aquinnah, MA 02535
  • 31 Lamberts Cove Rd, Vineyard Haven, MA 02568
    31 Lamberts Cove Rd, Vineyard Haven, MA 02568
    31 Lamberts Cove Rd, Vineyard Haven, MA 02568
    /38

    $5,800,000

    $450K PRICE DROP
    • 6 Beds
    • 9 Baths
    • 5,732 Sq Ft

    31 Lamberts Cove Rd, Vineyard Haven, MA 02568

    Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and burgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    31 Lamberts Cove Rd, Vineyard Haven, MA 02568
  • 70 Spring St, Vineyard Haven, MA 02568
    70 Spring St, Vineyard Haven, MA 02568
    70 Spring St, Vineyard Haven, MA 02568
    /68

    $2,300,000

    $900K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,274 Sq Ft

    70 Spring St, Vineyard Haven, MA 02568

    Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

    June Flake Viewpoints

    70 Spring St, Vineyard Haven, MA 02568
  • 24 Beetle Swamp Rd, Edgartown, MA 02539
    24 Beetle Swamp Rd, Edgartown, MA 02539
    24 Beetle Swamp Rd, Edgartown, MA 02539
    /40

    $2,895,000

    $305K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    24 Beetle Swamp Rd, Edgartown, MA 02539

    Set in a private community, Sweetened Water Farm offers the pastoral charm of Martha's Vineyard's rural up-island, just minutes from the energy of downtown Edgartown. Residents share access to the association's horse barn and common pastures, ideal for keeping horses or other livestock, adding to the farm's authentic agrarian character. This custom-built home is a true Vineyard gem, crafted over

    Kathleen Dawson Donnelly + Co.

    24 Beetle Swamp Rd, Edgartown, MA 02539
  • 23 Onkokemmy Rd, West Tisbury, MA 02557
    23 Onkokemmy Rd, West Tisbury, MA 02557
    23 Onkokemmy Rd, West Tisbury, MA 02557
    /9

    $1,200,000

    • Land
    • 3.42 Acres
    • $350,877 per Acre

    23 Onkokemmy Rd, West Tisbury, MA 02557

    Just beyond the Great White Oak and down scenic Rogers Path, this pastoral West Tisbury parcel offers nearly 3.5 acres of privacy and natural beauty. Moments from the village center yet tucked into a peaceful landscape, the property presents an opportunity to create a custom Vineyard compound. As you traverse your own grove of majestic oak trees, the landscape opens to an idyllic pasture dotted

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    23 Onkokemmy Rd, West Tisbury, MA 02557
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /37

    $3,795,000

    • 3 Beds
    • 4 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • 261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    /34

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 1,682 Sq Ft

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation and a more single-family feel—along with a one-car garage and additional storage for bikes and beach

    Jennifer O'hanlon Compass LLC

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
  • 21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
    /37

    $389,900

    • 1 Bed
    • 1.5 Baths
    • 584 Sq Ft

    21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568

    HERE'S YOUR CHANCE TO OWN A PIECE of the ISLAND!!! Live the beautiful Island Life with this gorgeous seasonal condo at the Island Inn Resort. AFFORDABLE & PRICED APPROX $100,000 less than an identical unit that Just Sold this summer!!Don't miss this delightful one and a half bedroom seasonal condo (sleeps 6) available for your families use. When you’re not here, the management team will rent

    Susan Austin Austin R.E. Properties of MV

    21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
  • 48 Plantingfield Way, Edgartown, MA 02539
    48 Plantingfield Way, Edgartown, MA 02539
    48 Plantingfield Way, Edgartown, MA 02539
    /5

    $3,495,000

    Open Tue 1PM - 2PM
    • 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
  • 41 & 0 Cook Rd, Vineyard Haven, MA 02568
    41 & 0 Cook Rd, Vineyard Haven, MA 02568
    41 & 0 Cook Rd, Vineyard Haven, MA 02568
    /33

    $1,790,000

    • 3 Beds
    • 2.5 Baths
    • 2,347 Sq Ft

    41 & 0 Cook Rd, Vineyard Haven, MA 02568

    Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready for your plans or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or future investment. An easement is being established along the existing driveway to

    Jennifer O'hanlon Compass LLC

    41 & 0 Cook Rd, Vineyard Haven, MA 02568
  • 00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535
    00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535
    00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535
    /7

    $349,000

    • Land
    • 1.26 Acres
    • $276,984 per Acre

    00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535

    Lovely beach lot off Moshup Trail in Aquinnah. Enjoy the sandy beach, Atlantic Ocean water and beauty of the South shore. This private beach lot is shared with only seven other members. Parking is located a short walk across the road from the beach access.Private parking limited to one car per member. This is not a buildable lot.

    Julianna Flanders Flanders Real Estate

    00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535
  • 7 Overview Ln Unit 47, Oak Bluffs, MA 02557
    7 Overview Ln Unit 47, Oak Bluffs, MA 02557
    7 Overview Ln Unit 47, Oak Bluffs, MA 02557
    /14

    $5,100,000

    • Land
    • 2.34 Acres
    • $2,182,285 per Acre

    7 Overview Ln Unit 47, Oak Bluffs, MA 02557

    A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

    Alyssa Halisky Wallace & Co. Sotheby's

    7 Overview Ln Unit 47, Oak Bluffs, MA 02557
  • 31 Josiah Sachem Way, Vineyard Haven, MA 02568
    31 Josiah Sachem Way, Vineyard Haven, MA 02568
    31 Josiah Sachem Way, Vineyard Haven, MA 02568
    /73

    $4,125,000

    $525K PRICE DROP
    • 7 Beds
    • 4.5 Baths
    • 3,312 Sq Ft

    31 Josiah Sachem Way, Vineyard Haven, MA 02568

    An Inspirational Oasis - Come unwind and experience a secluded multi-dwelling compound nestled along the gentle slopes of Indian Hill, where rural tranquility meets effortless island living on more than three acres of uncommon beauty. Centered around a heated saltwater pool reminiscent of a private resort, the main house, studio barn, and guesthouse with a total of 4,464 square feet of living

    Helena Kirschenbaum Studio Realty

    31 Josiah Sachem Way, Vineyard Haven, MA 02568
  • 42 Field View Ln Unit 79, West Tisbury, MA 02575
    42 Field View Ln Unit 79, West Tisbury, MA 02575
    42 Field View Ln Unit 79, West Tisbury, MA 02575
    /19

    $799,000

    • Land
    • 2.1 Acres
    • $380,476 per Acre

    42 Field View Ln Unit 79, West Tisbury, MA 02575

    Nestled among the open fields of West Tisbury, this beautiful building parcel offers apeaceful, bucolic setting with endless potential. An eclectic artists' camp graces theproperty, creating a unique sense of character and inspiration. Meandering walking trailswind through a diverse landscape of pine, oak, and beech trees, inviting you to exploreand enjoy the natural surroundings.

    kyle Neyer Tea Lane Associates

    42 Field View Ln Unit 79, West Tisbury, MA 02575
  • 131 State Rd, Chilmark, MA 02535
    131 State Rd, Chilmark, MA 02535
    131 State Rd, Chilmark, MA 02535
    /29

    $3,950,000

    $400K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    131 State Rd, Chilmark, MA 02535

    Magical waterfront Quitsa pond cottage with private dock will change your life living on the water. Every day is special when you have an intimate relationship with Quitsa Pond. Calm, safe and breathtaking, adventure is out the doorstep and the sunsets.... Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller

    Jim Feiner Feiner Real Estate

    131 State Rd, Chilmark, MA 02535
  • 35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
    /8

    $695,000

    $55K PRICE DROP
    • Land
    • 11,417 Sq Ft
    • $2,651,660 per Acre

    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

    GOING, GOING... GONE!This is the LAST 3-bedroom lot available in Cluster C.12 lots SOLD 9 homes already built.Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes.The lot is ready

    Marilyn Moses Ocean Park Realty Inc

    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
  • 22 Bramble Path, West Tisbury, MA 02568
    22 Bramble Path, West Tisbury, MA 02568
    /2

    $799,000

    • Land
    • 39,639 Sq Ft
    • $878,022 per Acre

    22 Bramble Path, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. A perc test has been done that supports a four bedroom title five system. It is the buyers responsibility to install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path, West Tisbury, MA 02568
  • 11 Boylston Dr, Edgartown, MA 02539
    11 Boylston Dr, Edgartown, MA 02539
    11 Boylston Dr, Edgartown, MA 02539
    /4

    $445,000

    • Land
    • 23,958 Sq Ft
    • $809,091 per Acre

    11 Boylston Dr, Edgartown, MA 02539

    A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island’s top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    11 Boylston Dr, Edgartown, MA 02539
  • 299 Daggett Ave, Vineyard Haven, MA 02568
    299 Daggett Ave, Vineyard Haven, MA 02568
    299 Daggett Ave, Vineyard Haven, MA 02568
    /21

    $1,175,000

    $74K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 998 Sq Ft

    299 Daggett Ave, Vineyard Haven, MA 02568

    This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

    Alyson Parker Karen M. Overtoom R.E.

    299 Daggett Ave, Vineyard Haven, MA 02568
  • 6 Brewster Ave, Oak Bluffs, MA 02557
    6 Brewster Ave, Oak Bluffs, MA 02557
    6 Brewster Ave, Oak Bluffs, MA 02557
    /34

    $3,250,000

    • 4 Beds
    • 3 Baths
    • 1,728 Sq Ft

    6 Brewster Ave, Oak Bluffs, MA 02557

    Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home’s original charm. Tucked privately at the rear of the property, the guest cottage

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    6 Brewster Ave, Oak Bluffs, MA 02557
  • 15 Goah Way, Vineyard Haven, MA 02568
    15 Goah Way, Vineyard Haven, MA 02568
    15 Goah Way, Vineyard Haven, MA 02568
    /10

    $975,000

    $225K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,581 Sq Ft

    15 Goah Way, Vineyard Haven, MA 02568

    2 bedroom 2 bath cottage with 1 bedroom 1 bath ADU. Large 15,950 square foot lot, short distance to school and town. Second floor bedroom space is large and possibly convertable to 2 bedrooms. New windows and 2 mini split systems, ADU also has a mini split unit. ADU is beleived to have been built in 2017. Property is loacted in Tashmoo watershed district and will require an upgrade to an nitrogen

    Roy Cutrer Jr Laer Realty Partners

    15 Goah Way, Vineyard Haven, MA 02568
  • 4 Wilsons Ln, Edgartown, MA 02539
    4 Wilsons Ln, Edgartown, MA 02539
    4 Wilsons Ln, Edgartown, MA 02539
    /18

    $1,500,000

    $200K PRICE DROP
    • Land
    • 37,026 Sq Ft
    • $1,764,706 per Acre

    4 Wilsons Ln, Edgartown, MA 02539

    Build your dream home in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of vibrant Edgartown village. This wooded parcel of vacant land is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool and Accessory Dwelling Unit are allowed ''by right'' (certain restrictions apply to ADUs; an unrestricted 900 sq ft

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    4 Wilsons Ln, Edgartown, MA 02539
  • 19 Perkins Ave, Oak Bluffs, MA 02557
    19 Perkins Ave, Oak Bluffs, MA 02557
    19 Perkins Ave, Oak Bluffs, MA 02557
    /14

    $825,000

    • 2 Beds
    • 1 Bath
    • 985 Sq Ft

    19 Perkins Ave, Oak Bluffs, MA 02557

    Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

    Katherine Donahue Sandpiper Realty

    19 Perkins Ave, Oak Bluffs, MA 02557
  • 308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    /36

    $7,350,000

    • 4 Beds
    • 4.5 Baths
    • 3,490 Sq Ft

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, Chilmark, MA 02535
  • 48 Plaintingfield Way Unit 10, Edgartown, MA 02539
    48 Plaintingfield Way Unit 10, Edgartown, MA 02539
    48 Plaintingfield Way Unit 10, 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
  • 16 Frog Hollow, Vineyard Haven, MA 02568
    16 Frog Hollow, Vineyard Haven, MA 02568
    16 Frog Hollow, Vineyard Haven, MA 02568
    /25

    $4,695,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    16 Frog Hollow, Vineyard Haven, MA 02568

    Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage.Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water

    Rose Ryley Wallace & Co. Sotheby's International Realty

    16 Frog Hollow, Vineyard Haven, MA 02568
  • 10 & 12 Boldwater Rd, Edgartown, MA 02539
    10 & 12 Boldwater Rd, Edgartown, MA 02539
    10 & 12 Boldwater Rd, Edgartown, MA 02539
    /41

    $14,500,000

    • 11 Beds
    • 13 Baths
    • 9,500 Sq Ft

    10 & 12 Boldwater Rd, Edgartown, MA 02539

    A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for

    Michael Carucci Serhant

    10 & 12 Boldwater Rd, Edgartown, MA 02539
  • 33 Vineyard Ave, Oak Bluffs, MA 02557
    33 Vineyard Ave, Oak Bluffs, MA 02557
    33 Vineyard Ave, Oak Bluffs, MA 02557
    /29

    $1,995,000

    Open Sat 10:30AM - 12PM
    • 3 Beds
    • 2.5 Baths
    • 1,439 Sq Ft

    33 Vineyard Ave, Oak Bluffs, MA 02557

    Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property 3B/2Ba in total features a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined

    Allison Cameron Parry Douglas Elliman of MA, LLC

    33 Vineyard Ave, Oak Bluffs, MA 02557
  • 312 E Chop Dr, Oak Bluffs, MA 02557
    312 E Chop Dr, Oak Bluffs, MA 02557
    312 E Chop Dr, Oak Bluffs, MA 02557
    /36

    $2,295,000

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    312 E Chop Dr, Oak Bluffs, MA 02557

    “The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts

    Alyssa Halisky Wallace & Co. Sotheby's

    312 E Chop Dr, Oak Bluffs, MA 02557
  • 29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /57

    $3,295,000

    • 5 Beds
    • 4 Baths
    • 2,330 Sq Ft

    29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking.

    Madelyn Silvia Wallace & Co. Sotheby's

    29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
    Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
    Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
    /3

    $525,000

    • Land
    • 10,240 Sq Ft
    • $2,233,092 per Acre

    Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568

    A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

    Katherine Donahue Sandpiper Realty

    Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
  • 0 Jeffers Way Unit 165, Aquinnah, MA 02535
    0 Jeffers Way Unit 165, Aquinnah, MA 02535
    0 Jeffers Way Unit 165, Aquinnah, MA 02535
    /3

    $785,000

    • Land
    • 3.8 Acres
    • $206,579 per Acre

    0 Jeffers Way Unit 165, Aquinnah, MA 02535

    Nestled within the serene landscape of Aquinnah, this 3.8-acre parcel offers a unique blend of natural beauty and historical significance. Bordered by ancient stone walls and mature vegetation, the elevated terrain provides a bucolic setting for a private residence. Already in place is a private well, 3-bedroom septic, and full engineering.

    Michele Casavant Vineyard Village Realty

    0 Jeffers Way Unit 165, Aquinnah, MA 02535
  • 0 North Way, Chilmark, MA 02535
    0 North Way, Chilmark, MA 02535
    0 North Way, Chilmark, MA 02535
    /3

    $1,325,000

    • Land
    • 4.28 Acres
    • $309,579 per Acre

    0 North Way, Chilmark, MA 02535

    Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of

    Stacy Ickes Donnelly + Co.

    0 North Way, Chilmark, MA 02535
  • 53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    /51

    $3,199,000

    $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    Nestled in one of Martha’s Vineyard’s most coveted locations, this custom-built residence blends timeless elegance with contemporary luxury. Complete with exclusive access to the serene shores of Lambert’s Cove Beach. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, a handmade subway tile backsplash, Wolf stove

    Jennifer DaSilva Compass | Point B

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

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