Dukes County, MA Homes

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  $1,200,000

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  70 Carol Ln, Oak Bluffs, MA 02557

  Charming Renovated Ranch in the Heart of Oak Bluffs Discover the perfect blend of comfort, convenience, and coastal charm in this beautifully renovated ranch home, ideally located in a central Oak Bluffs neighborhood close to everything down-Island. Set on a spacious 1/3-acre lot, this property offers both privacy and proximity — just minutes from the Oak Bluffs School, town center, and all the

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 456-5742

  70 Carol Ln, Oak Bluffs, MA 02557
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  /12

  $5,500 total monthly price

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • House for Rent

  2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY VACATION RENTAL PROPERTY. The home’s timeless interior offers a sitting room with a wood-burning fireplace, a hallway opening to a large, bright, modern kitchen featuring a Viking range and large dining table. Ample counter space and a wall of built-ins are the perfect complement to family and friends that enjoy cooking together. A gas grill and outdoor seating are only

  Karen Overtoom Karen M. Overtoom R.E.

  2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539
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  $2,860,000 Sold Mar 10, 2025

  49 William St, Vineyard Haven, MA 02568

  • 5 Beds
  • 4.5 Baths
  • 3,752 Sq Ft
  • Built 1836

  Last Sold Summary

  • 12% Below List Price
  • $762/SF
  • 290 Days On Market

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

  49 William St, Vineyard Haven, MA 02568
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  /58

  Est $6,561,929 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,945 Sq Ft

  394 Lighthouse Rd, Aquinnah, MA 02535

  394 Lighthouse Rd, Aquinnah, MA 02535
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  /9

  $2,000,000

  • Land
  • 1.28 Acres
  • $1,562,500 per Acre

  5 Louis Field Rd, Edgartown, MA 02539

  CREATE YOUR LEGACY ISLAND RETREAT IN THIS IDYLLIC LOCATION. Nestled within the entrance to Sweetened Water Farm, this 1.28-acre parcel represents a rare opportunity to create your own vision within one of Edgartown’s most sought-after settings. Located just one mile from the heart of historic Edgartown Village, this beautifully sited lot offers the ideal balance of privacy and proximity,

  

  Wendy Harman

  Compass

  (508) 694-9959

  5 Louis Field Rd, Edgartown, MA 02539
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  /8

  $17,500 total monthly price

  • 8 Beds
  • 4.5 Baths
  • 3,876 Sq Ft
  • House for Rent

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and relaxing

  Karen Overtoom Karen M. Overtoom R.E.

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
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  /42

  $9,725,000 Sold Apr 24, 2025

  2 Squibnocket Rd, Chilmark, MA 02535

  • 6 Beds
  • 5.5 Baths
  • 5,808 Sq Ft
  • Built 2008

  Last Sold Summary

  • 22% Below List Price
  • $1,674/SF
  • 295 Days On Market

  Last Listing Agent Tina Miller Donnelly + Co.

  2 Squibnocket Rd, Chilmark, MA 02535
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  /38

  Est $1,047,737 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  287 County Rd, Vineyard Haven, MA 02568

  287 County Rd, Vineyard Haven, MA 02568
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  /6

  $700,000

  • Land
  • 0.1 Acre
  • $7,000,000 per Acre

  0 Massasoit Ave, Oak Bluffs, MA 02557

  Commercial Land Downtown Oak Bluffs on Circuit Avenue. Explore the many potentials this commercial land has to offer in the desirable location in the heart of Oak Bluffs.

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 978-2876

  0 Massasoit Ave, Oak Bluffs, MA 02557
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  /10

  $8,500 total monthly price

  • 3 Beds
  • 2 Baths
  • House for Rent

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

  Karen Overtoom Karen M. Overtoom R.E.

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
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  /24

  $3,300,000 Sold Sep 18, 2025

  28 Crocker Dr, Edgartown, MA 02539

  • 4 Beds
  • 6 Baths
  • 3,793 Sq Ft
  • Built 1960

  Last Sold Summary

  • 11% Below List Price
  • $870/SF
  • 139 Days On Market

  Current Estimated Value $3,358,691

  Last Listing Agent Jennifer O'hanlon Compass

  28 Crocker Dr, Edgartown, MA 02539
• 

  

  /17

  Est $1,573,311 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,298 Sq Ft

  19 Quantapog Rd, Vineyard Haven, MA 02568

  19 Quantapog Rd, Vineyard Haven, MA 02568
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  /34

  $3,250,000

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

  6 Brewster Ave, Oak Bluffs, MA 02557

  Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

  Katherine Donahue Sandpiper Realty Inc

  6 Brewster Ave, Oak Bluffs, MA 02557
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  /8

  $11,800 total monthly price

  • 4 Beds
  • 4 Baths
  • 2,612 Sq Ft
  • House for Rent

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

  Karen Overtoom Karen M. Overtoom R.E.

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
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  /3

  $435,000 Sold Jul 23, 2025

  0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535

  • Land
  • 0.3 Acre
  • $1,457,775 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 96 Days On Market

  Last Listing Agent Jill Napior Tea Lane Associates

  0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535
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  /12

  Est $1,277,876 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,997 Sq Ft

  3 Carole Ave, Vineyard Haven, MA 02568

  3 Carole Ave, Vineyard Haven, MA 02568
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  $560,000

  • 1 Bed
  • 1.5 Baths
  • 590 Sq Ft

  21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

  Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

  Diana Gilmore Island Real Estate

  21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
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  /8

  $6,000 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  33 Kennebago Ave Vh414, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Kennebago Ave Vh414, Tisbury, MA 02568
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  $1,500,000 Sold Sep 03, 2025

  37 Knoll Dr, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1972

  Last Sold Summary

  • 15% Below List Price
  • $1,218/SF
  • 158 Days On Market

  Current Estimated Value $1,560,661

  Last Listing Agent Josseph Barkett Compass

  37 Knoll Dr, Edgartown, MA 02539
• 

  

  /13

  Est $1,272,457 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  33 Menahan St, Vineyard Haven, MA 02568

  33 Menahan St, Vineyard Haven, MA 02568
• 

  

  /16

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557

  East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living

  Perry Patterson MV Luxury Homes, LLC

  47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
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  /8

  $13,600 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Condo for Rent

  1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering spaces to enjoy your company over meals, snacks and games

  Karen Overtoom Karen M. Overtoom R.E.

  1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539
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  /2

  $1,700,000 Sold Oct 20, 2025

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  • 5 Beds
  • 3 Baths
  • 1,803 Sq Ft
  • Built 1982

  Last Sold Summary

  • $943/SF
  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  /14

  Est $1,014,872 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  51 Manchester Ave, Vineyard Haven, MA 02568

  51 Manchester Ave, Vineyard Haven, MA 02568
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  /3

  $1,650,000

  • Land
  • 1.57 Acres
  • $1,050,955 per Acre

  63 Division Rd Unit 46, Edgartown, MA 02539

  LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own

  Cheri Mason Landvest MV

  63 Division Rd Unit 46, Edgartown, MA 02539
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  /4

  $6,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • House for Rent

  836 State Rd, Aquinnah, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the

  Karen Overtoom Karen M. Overtoom R.E.

  836 State Rd, Aquinnah, MA 02535
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  $1,800,000 Sold Oct 15, 2025

  82 Skiff Ave, Tisbury, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 1,913 Sq Ft
  • Built 2020

  Last Sold Summary

  • 10% Below List Price
  • $941/SF
  • 128 Days On Market

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  /30

  Est $2,380,390 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  10 Crow Hollow Rd, Vineyard Haven, MA 02568

  10 Crow Hollow Rd, Vineyard Haven, MA 02568
• 

  

  /18

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,583 Sq Ft

  25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

  Maranda Post Compass | The O'Hanlon Group

  25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  /8

  $16,000 total monthly price

  • 7 Beds
  • 3.5 Baths
  • 4,000 Sq Ft
  • House for Rent

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

  Karen Overtoom Karen M. Overtoom R.E.

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
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  /24

  $2,700,000 Sold Dec 19, 2025

  43 Cottage St, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 1,112 Sq Ft
  • Built 1945

  Last Sold Summary

  • 16% Below List Price
  • $2,428/SF
  • 7 Days On Market

  Last Listing Agent Michele Casavant Vineyard Village Realty

  43 Cottage St, Edgartown, MA 02539
• 

  /2

  Est $2,599,314 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,527 Sq Ft

  230 Pond Rd, Vineyard Haven, MA 02568

  230 Pond Rd, Vineyard Haven, MA 02568
• 

  

  /24

  $3,250,000

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

  10 Peases 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 Landmarks at TODAY Real Estate

  10 Peases Point Rd, Edgartown, MA 02539
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  /8

  $3,300 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • House for Rent

  849 State Rd Unit 1, Aquinnah, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

  Karen Overtoom Karen M. Overtoom R.E.

  849 State Rd Unit 1, Aquinnah, MA 02535
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  /7

  $650,000 Sold Aug 14, 2025

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

  • Land
  • 0.2 Acre
  • $3,250,000 per Acre

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Deb Hancock Hancock Real Estate

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
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  /4

  Est $2,852,393 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,789 Sq Ft

  188 Pond Rd, Vineyard Haven, MA 02568

  188 Pond Rd, Vineyard Haven, MA 02568
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  /52

  $2,575,000

  • 4 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  76 Washque Ave, Edgartown, MA 02539

  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

  Katherine Donahue Sandpiper Realty Inc

  76 Washque Ave, Edgartown, MA 02539
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  /26

  $7,000 total monthly price

  • 7 Beds
  • 1.5 Baths
  • 2,900 Sq Ft
  • House for Rent

  39 N Neck Rd, Edgartown, MA 02539

  Historic Quaint Waterfront Cottage with spectacular 180 degree views of Edgartown Harbor, Oak Bluffs, Cape Cod and Cape Poge, Over 200 feet of secluded, completely private beach, The back yard abuts the fairways and club house of the ''Royal Ancient Chappaquiddick Links'' Private Golf Course. (You must pay dues to play golf), Great outdoor shower. You can see the fireworks (in 5 locations at

  Charles Petitti Coldwell Banker Realty - Newton

  39 N Neck Rd, Edgartown, MA 02539
• 

  

  /19

  $750,000 Sold Nov 07, 2025

  41 Trinity Park, Oak Bluffs, MA 02557

  • 4 Beds
  • 1 Bath
  • 1,154 Sq Ft
  • Built 1867

  Last Sold Summary

  • 6% Below List Price
  • $650/SF
  • 14 Days On Market

  Last Listing Agent Stacy Ickes Donnelly + Co.

  41 Trinity Park, Oak Bluffs, MA 02557
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  /34

  Est $2,462,956 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 1 Sq Ft

  248 Pond Rd, Vineyard Haven, MA 02568

  248 Pond Rd, Vineyard Haven, MA 02568

Showing Results 41 - 80, Page 2 of 18