Dukes County MA Homes for Sale

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  /46

  $1,650,000

  $145K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,406 Sq Ft

  17 John Wesley Ave, Vineyard Haven, MA 02568

  Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features

  kyle Neyer Tea Lane Associates

  17 John Wesley Ave, Vineyard Haven, MA 02568
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  /42

  $7,500,000

  $1M PRICE DROP

  • 5 Beds
  • 7 Baths
  • 4,531 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  /25

  $5,995,000

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft

  43 Sengekontacket Rd, Oak Bluffs, MA 02557

  Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

  Peyton Wallace Studio Realty LLC

  43 Sengekontacket Rd, Oak Bluffs, MA 02557
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  /22

  $325,000

  $5K PRICE DROP

  • Land
  • 7,313 Sq Ft
  • $1,935,676 per Acre

  00 Moshup Trail Unit 6, Aquinnah, MA 02535

  Tucked along the south shore of Aquinnah on Martha’s Vineyard, this beach lot presents a chance to enjoy true oceanfront ownership. Accessed via Moshup Trail, this lot features a private gated entry with a pea stone parking area. A boardwalk, that winds through natural coastal vegetation, connects to a sandy trail that brings you over the bluff to the expansive shoreline. Secure your own stretch

  Diana Gilmore Island Real Estate

  00 Moshup Trail Unit 6, Aquinnah, MA 02535
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  /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
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  /7

  $549,000

  $50K PRICE DROP

  • Land
  • 3,049 Sq Ft
  • $7,842,857 per Acre

  112 Dukes County Ave, Oak Bluffs, MA 02557

  Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha’s Vineyard’s most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park.This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved

  Rose Ryley Wallace & Co. Sotheby's International Realty

  112 Dukes County Ave, Oak Bluffs, MA 02557
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  /4

  $429,000

  $66K PRICE DROP

  • Land
  • 9,997 Sq Ft
  • $1,869,281 per Acre

  0 California Ave Unit 76 42933, Oak Bluffs, MA 02568

  Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for a one bedroom home of any size. Water and electric are nearby.

  Jim Joyce Carroll & Vincent R.E.

  0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
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  /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
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  /44

  $4,450,000

  $350K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 2,960 Sq Ft

  104 Pond View Farm Rd, Vineyard Haven, MA 02568

  Two homes on over three acres of waterfront on the beautiful and coveted Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two existing homes and a private permitted dock.Both the main house and guest house boast unobstructed water views, creating a tranquil and picturesque setting perfect for birdwatching, relaxation, and

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /41

  $4,800,000

  Open House 8/10

  • 4 Beds
  • 3.5 Baths
  • 3,715 Sq Ft

  9 Martha's Way, Edgartown, MA 02539

  Welcome to this NEWLY CONSTRUCTED gorgeous gambrel home with a POOL that is close to SOUTH BEACH and EDGARTOWN VILLAGE! This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home presents an inviting covered porch with free standing columns, a granite entry step, mahogany decking and shiplapped ceiling. Attention to architectural detail presents at moment one.

  Michele Casavant Vineyard Village Realty

  9 Martha's Way, Edgartown, MA 02539
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  /55

  $5,450,000

  • 5 Beds
  • 4 Baths
  • 3,513 Sq Ft

  61 Stonewall Rd, Chilmark, MA 02535

  Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  61 Stonewall Rd, Chilmark, MA 02535
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  /10

  $1,425,000

  • Land
  • 3.01 Acres
  • $473,422 per Acre

  38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568

  The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

  Elissa Lash Tea Lane Associates

  38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
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  /7

  $1,150,000

  • Land
  • 1.09 Acres
  • $1,055,046 per Acre

  30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557

  Create an extraordinary Martha's Vineyard estate in the exclusive Lagoon Ridge community of Oak Bluffs. This mostly wooded estate parcel of over one acre features gently rolling topography, providing an exceptional canvas for a custom-designed luxury residence. Privately situated within an intimate enclave of just four estate parcels, the property is accessed by a welcoming paved approach. This

  Marilyn Moses Ocean Park Realty Inc

  30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557
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  /6

  $650,000

  • Land
  • 1.02 Acres
  • $637,255 per Acre

  23 Calebs Common Ln, Edgartown, MA 02539

  CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create your own island retreat. Per the Board of Health, the lot may support a three-bedroom home with an

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  23 Calebs Common Ln, Edgartown, MA 02539
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  /25

  $1,696,000

  $199K 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
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  /13

  $1,645,000

  • Land
  • 3.32 Acres
  • $495,482 per Acre

  26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575

  Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides - a setting unlike

  Dawn Bellante-Holand Sandpiper Realty

  26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
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  /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
• 

  

  /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
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  /20

  $2,495,000

  • 1 Bed
  • 1.5 Baths
  • 1,236 Sq Ft

  218 Upper Main St, Edgartown, MA 02539

  Located on Upper Main Street in Edgartown’s BII zoning district, this versatile property is currently home to Lucky Hank’s restaurant. Set on a desirable lot with a large private parking area, and in a coveted high-visibility location. The building offers a turnkey restaurant space and thriving business complete with a fully equipped commercial kitchen on the first floor. Upstairs, you’ll find

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  218 Upper Main St, Edgartown, MA 02539
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  /48

  $4,695,000

  • 7 Beds
  • 4.5 Baths
  • 5,320 Sq Ft

  8 Fresh Pond Rd, Oak Bluffs, MA 02557

  The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

  Jarrett Hurwitz Keller Williams Realty

  8 Fresh Pond Rd, Oak Bluffs, MA 02557
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  /46

  $3,400,000

  • 4 Beds
  • 2.5 Baths
  • 2,383 Sq Ft

  100 Gosnolds Way, Chilmark, MA 02535

  Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you

  Julianna Flanders Flanders Real Estate

  100 Gosnolds Way, Chilmark, MA 02535
• 

  

  /23

  $2,900,000

  $300K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft

  6 Trails End, Chilmark, MA 02535

  Enjoy the carefree ease of Mid Century Modern architecture in this pristine classic, filled with sunshine and treetop views. Located on a quiet hilltop in Chilmark and offered turn-key furnished, this simple but elegant summer home features four bedrooms, three baths, with original details and design. Its open all-on-one-floor layout with large glass panel doors and windows throughout lead to a

  Russell Maloney Russell Maloney Real Estate

  6 Trails End, Chilmark, MA 02535
• 

  

  /20

  $1,600,000

  • 4 Beds
  • 3 Baths
  • 2,334 Sq Ft

  150 Field View Ln, Vineyard Haven, MA 02568

  A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you

  Sheila Morse Island Real Estate

  150 Field View Ln, Vineyard Haven, MA 02568
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  /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
• 

  

  /6

  $2,300,000

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  60 Crocker Dr, Edgartown, MA 02539

  Close to South Beach! Close to Katama Airpark and nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a

  Sheila Morse Island Real Estate

  60 Crocker Dr, Edgartown, MA 02539
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  /19

  $2,950,000

  • 3 Beds
  • 3 Baths
  • 3,506 Sq Ft

  24 Cournoyer Rd, Vineyard Haven, MA 02568

  This mixed use building is zoned for residential and commercial use. It is extremely well built with an emphasis on non-toxic materials throughout. High ceilings on all three levels. There are radiant floors mixed with forced hot air/AC. The building offers a variety of uses for a new owner. The existing spaces are very versatile and would be ideal for any service oriented business given the

  Jill Napior Tea Lane Associates

  24 Cournoyer Rd, Vineyard Haven, MA 02568
• 

  

  /26

  $1,349,000

  • 3 Beds
  • 2 Baths
  • 1,863 Sq Ft

  3 Troy St, Oak Bluffs, MA 02557

  Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  3 Troy St, Oak Bluffs, MA 02557
• 

  

  /39

  $1,488,000

  • 5 Beds
  • 4 Baths
  • 2,884 Sq Ft

  39 Ferro Way, Vineyard Haven, MA 02568

  Tucked away on a quiet cul-de-sac, this beautifully maintained multi-family property offers the perfect blend of privacy, flexibility, and convenience. Built in 2020, the home encompasses 2,884 square feet of thoughtfully designed living space, featuring a total of 5 bedrooms and 4 full bathrooms. The walkout lower level is a fully permitted Accessory Dwelling Unit (ADU), creating an ideal

  Emily Flake Viewpoints

  39 Ferro Way, Vineyard Haven, MA 02568
• 

  

  /9

  $4,800,000

  • 4 Beds
  • 4.5 Baths
  • 3,816 Sq Ft

  7 Martha's Way, Edgartown, MA 02539

  Welcome to this coastal chic farmhouse set in the heart of Katama, a few blocks from the Field Club, close to SOUTH BEACH and close to Edgartown Village. To be built is a four bedroom en-suite home with a heated saltwater POOL. This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home offers an inviting covered porch with free standing columns, a granite entry

  Michele Casavant Vineyard Village Realty

  7 Martha's Way, 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

Showing Results 321 - 350, Page 9 of 9