Dukes County, MA Homes

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  $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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  $20,000 total monthly price

  • 5 Beds
  • 3 Baths
  • 2,352 Sq Ft
  • House for Rent

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

  Karen Overtoom Karen M. Overtoom R.E.

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
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  $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
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  Est $1,565,237 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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  $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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  $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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  $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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  Est $1,268,189 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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  $1,999,000

  • 3 Beds
  • 3.5 Baths
  • 2,453 Sq Ft

  34 Davis St, Tisbury, MA 02568

  NEW CONSTRUCTION – Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island’s harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

  Andrew McElhinney Compass LLC

  34 Davis St, Tisbury, MA 02568
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  $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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  $4,200,000 Sold Jan 15, 2026

  1 Wilsons Ln, Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 3,715 Sq Ft
  • Built 2025

  Last Sold Summary

  • $1,131/SF
  • 68 Days On Market

  Last Listing Agent Michele Casavant Vineyard Village Realty

  1 Wilsons Ln, Edgartown, MA 02539
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  /13

  Est $1,241,679 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
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  $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

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  76 Washque Ave, Edgartown, MA 02539
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  $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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  $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 $1,570,516

  Last Listing Agent Josseph Barkett Compass

  37 Knoll Dr, Edgartown, MA 02539
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  Est $1,013,552 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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  $1,999,000

  • 4 Beds
  • 3 Baths
  • 2,730 Sq Ft

  5 Pine Tree Ln, Vineyard Haven, MA 02568

  Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  5 Pine Tree Ln, Vineyard Haven, MA 02568
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  $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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  $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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  Est $2,464,428 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
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  $2,250,000

  • 5 Beds
  • 3.5 Baths
  • 3,250 Sq Ft

  28 Pine Tree Ln, Vineyard Haven, MA 02568

  Enjoy beach-close living—just 0.2 miles to the shore—in sought-after West Chop. This welcoming 5BR/3.5BA colonial blends classic Vineyard character with modern comforts, including central air, an updated kitchen, and three fireplaces. Approximately 3,152± sq ft (expanded from 2,632± with a 520± sq ft finished space over the garage) offers flexible, easy flow to a large fenced backyard with a

  Lisa Da Silva Compass | Point B

  28 Pine Tree Ln, Vineyard Haven, MA 02568
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  $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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  $1,800,000 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

  Current Estimated Value $1,646,192

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  Est $2,548,131 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
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  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 2,690 Sq Ft

  151 Tashmoo Ave, Vineyard Haven, MA 02568

  The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to

  Brenda Galligan Karen M. Overtoom R.E.

  151 Tashmoo Ave, Vineyard Haven, MA 02568
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  $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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  $1,200,000 Sold Jan 22, 2026

  58 Marthas Rd, Edgartown, MA 02539

  • Land
  • 0.5 Acre
  • $2,400,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 182 Days On Market

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  58 Marthas Rd, Edgartown, MA 02539
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  Est $3,009,324 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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  $2,499,000 Pre-Foreclosure

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  47 Tiffany Dr, Oak Bluffs, MA 02557

  Your private oasis with a POOL awaits in this beautifully updated Lagoon Hills retreat on over 1.5 acres. Enjoy a carefree, single-level lifestyle featuring an open-concept kitchen and dining area, spacious living room, office and exercise room — all thoughtfully designed for comfort and flow. Step outside to a stunning backyard anchored by a sparkling pool, surrounded by decks, patios, and lush

  Jennifer DaSilva Compass | Point B

  47 Tiffany Dr, Oak Bluffs, MA 02557
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  $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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  $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
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  Est $2,473,034 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
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  $2,495,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  268 Tashmoo Ave, Vineyard Haven, MA 02568

  Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

  Michele Casavant Vineyard Village Realty

  268 Tashmoo Ave, Vineyard Haven, MA 02568
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  $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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  $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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  Est $2,104,866 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,636 Sq Ft

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  131 Shubael Weeks Path, Vineyard Haven, MA 02568
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  $3,990,000 Pending

  • 3 Beds
  • 6 Baths
  • 3,171 Sq Ft

  15 Old Farm Rd, Chilmark, MA 02535

  CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

  Tina Miller Donnelly + Co.

  15 Old Farm Rd, Chilmark, MA 02535
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  $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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  $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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  Est $1,809,681 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,102 Sq Ft

  26 Old Coach Rd, Vineyard Haven, MA 02568

  26 Old Coach Rd, Vineyard Haven, MA 02568

Showing Results 41 - 80, Page 2 of 18