19,357

Dukes County, MA Homes

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  • /33

    $3,600,000

    • 5 Beds
    • 3 Baths
    • 2,701 Sq Ft

    20 James Pond Way, Vineyard Haven, MA 02568

    Tucked away on 4.5 acres off Lambert's Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert's Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a

    Sheila Morse Island Real Estate

    20 James Pond Way, Vineyard Haven, MA 02568
  • /30

    $28,500 Per Month

    • 9 Beds
    • 6.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    9 Tuckernuck Ave, Oak Bluffs, MA 02557

    **SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    9 Tuckernuck Ave, Oak Bluffs, MA 02557
  • /22

    $435,000

    Sold Aug 26, 2025

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

    • Land
    • 4,356 Sq Ft
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 18 Days On Market

    Last Listing Agent Emma Bryant Studio Realty

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    • /2

      Est $2,368,218

      Not Listed For Sale

      23 Oak Ln, Vineyard Haven, MA 02568

      • 6 Beds
      • 5 Baths
      • 3,035 Sq Ft
      • Built 2007
      23 Oak Ln, Vineyard Haven, MA 02568

  • /53

    $6,750,000

    • 5 Beds
    • 3.5 Baths
    • 4,050 Sq Ft

    78 Hammett Rd, Chilmark, MA 02535

    This magnificent Spring Point waterfront property, perched 50 ft above sea level and 425 ft back from the North Shore bluff, boasts beautiful views of the Vineyard Sound, Aquinnah coastline and the Elizabeth Islands -- and year dramatic year round sunsets. The property at the end of a well maintained wide dirt road 1 mile from North Rd is SECLUDED and TRANQUIL. It's a SHORT WALK TO THE BEACH,

    Robert Kenney Tea Lane Associates

    78 Hammett Rd, Chilmark, MA 02535
  • /22

    $3,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,703 Sq Ft
    • House for Rent

    41 Oak Lane Wt147, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

    Karen Overtoom Karen M. Overtoom R.E.

    41 Oak Lane Wt147, West Tisbury, MA 02575
  • /37

    $2,775,000

    Sold Jun 29, 2026

    33 Ocean Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 2.5 Baths
    • 1,845 Sq Ft
    • Built 1875

    Last Sold Summary

    • 6% Below List Price
    • $1,504/SF
    • 140 Days On Market

    Current Estimated Value $2,969,044

    Last Listing Agent Katrina Lima Donnelly + Co

    33 Ocean Ave, Oak Bluffs, MA 02557
    • /23

      Est $2,105,560

      Not Listed For Sale

      79 Watcha Path, Edgartown, MA 02539

      • 4 Beds
      • 6 Baths
      • 4,306 Sq Ft
      • Built 1980
      79 Watcha Path, Edgartown, MA 02539

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Robin Perschel Feiner Real Estate

  • /4

    $625,000

    • Land
    • 14,997 Sq Ft
    • $1,815,277 per Acre

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • /8

    $13,600 Per Month

    • 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
  • /20

    $15,000,000

    Sold Mar 31, 2026

    30 Oyster Watcha Rd, Edgartown, MA 02539

    • 4 Beds
    • 5.5 Baths
    • 4,153 Sq Ft
    • Built 1986

    Last Sold Summary

    • $3,612/SF
    • 0 Days On Market

    Current Estimated Value $8,975,322

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    30 Oyster Watcha Rd, Edgartown, MA 02539
    • /42

      Not Listed For Sale

      11 Cummings Way, Edgartown, MA 02539

      • 6 Beds
      • 8 Baths
      • 4,617 Sq Ft
      • Built 2007
      11 Cummings Way, Edgartown, MA 02539

      Last Sold Summary

      • 100 Days On Market

      Last Listing Agent Wendy Harman Compass

  • /40

    $1,795,000

    • 3 Beds
    • 3 Baths
    • 3,702 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • /10

    $20,000 Per Month

    • 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
  • /21

    $435,000

    Sold Aug 26, 2025

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

    • Land
    • 4,356 Sq Ft
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 20 Days On Market

    Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    • /7

      Est $5,774,589

      Not Listed For Sale

      3 Duarte Cir, Edgartown, MA 02539

      • 6 Beds
      • 7 Baths
      • 6,783 Sq Ft
      • Built 2023
      3 Duarte Cir, Edgartown, MA 02539

      Last Sold Summary

      • 329 Days On Market

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /25

    $3,100,000

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

    114 Meeting House Way Unit 73478796, 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 Meeting House Way Unit 73478796, Edgartown, MA 02539
  • /9

    $10,800 Per Month

    • 4 Beds
    • 2 Baths
    • 702 Sq Ft
    • House for Rent

    141 N Rd Ch202, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

    Karen Overtoom Karen M. Overtoom R.E.

    141 N Rd Ch202, Chilmark, MA 02535
  • /2

    $5,375,000

    Sold Nov 14, 2025

    37 Morse St, Edgartown, MA 02539

    • 4 Beds
    • 5.5 Baths
    • 2,911 Sq Ft
    • Built 1820

    Last Sold Summary

    • $1,846/SF
    • 0 Days On Market

    Current Estimated Value $5,660,774

    Last Listing Agent LINK Email Cache LINK

    37 Morse St, Edgartown, MA 02539
    • /27

      Est $1,297,728

      Not Listed For Sale

      46 Windsor Dr, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft
      • Built 1987
      46 Windsor Dr, Edgartown, MA 02539

      Last Sold Summary

      • 1,366 Days On Market

      Last Listing Agent Martha Smith C McManus Realty Group

  • /6

    $975,000

    • Land
    • 1.07 Acres
    • $912,921 per Acre

    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557

    Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process.The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development.Subject to the Town of

    Casandra Hyland Sandpiper Realty

    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557
  • /18

    $10,000 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft
    • House for Rent

    100 Franklin Terrace Vh411, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

    Karen Overtoom Karen M. Overtoom R.E.

    100 Franklin Terrace Vh411, Tisbury, MA 02568
  • /18

    $1,450,000

    Sold Aug 26, 2025

    61 Dodgers Hole Rd, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 2,311 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Below List Price
    • $627/SF
    • 78 Days On Market

    Current Estimated Value $1,466,853

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    61 Dodgers Hole Rd, Edgartown, MA 02539
    • /22

      Est $4,605,865

      Not Listed For Sale

      1 Skippers View Ln, Aquinnah, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,905 Sq Ft
      • Built 2001
      1 Skippers View Ln, Aquinnah, MA 02535

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.

  • /41

    $2,225,000

    $125K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,630 Sq Ft

    81 Whalers Walk, Edgartown, MA 02539

    Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home with four levels of lifestyle. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters, and a custom

    Dawn Bellante Sandpiper Realty, Inc.

    81 Whalers Walk, Edgartown, MA 02539
  • /25

    $10,800 Per Month

    • 2 Beds
    • 4 Baths
    • 1,800 Sq Ft
    • House for Rent

    256 Sandpiper Lane Vh417, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

    Karen Overtoom Karen M. Overtoom R.E.

    256 Sandpiper Lane Vh417, Tisbury, MA 02568
  • /2

    $505,000

    Sold Sep 26, 2025

    02 John Hoft Rd Unit 2, Tisbury, MA 02568

    • Land
    • 1.3 Acres
    • $388,462 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 120 Days On Market

    Last Listing Agent Tony Tobia Tobia Real Estate, LTD

    02 John Hoft Rd Unit 2, Tisbury, MA 02568
    • /2

      Est $1,745,801

      Not Listed For Sale

      11 Deacon Vincent Way, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,250 Sq Ft
      • Built 1986
      11 Deacon Vincent Way, Edgartown, MA 02539

  • /24

    $1,599,000

    • 2 Beds
    • 1 Bath
    • 981 Sq Ft

    13 Beach Rd, Oak Bluffs, MA 02557

    OAK BLUFFS Beach Road: VINEYARD HAVEN OUTER HARBOR WATERFRONT WITH DOCK... 1860’s Beach House with substantial 60’ dock built in 2004, is situated on OUTER HARBOR in private waterfront setting. Enjoy all variety of watersports, dramatic sunsets every evening, refreshing swims, or just relax on your back porch and watch the colorful boating activity unfold. Property features 2 bedrooms, 1 full

    Alan Schweikert Ocean Park Realty Inc

    13 Beach Rd, Oak Bluffs, MA 02557
  • /15

    $7,500 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    83 Ashtons Way, Vineyard Haven, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

    Karen Overtoom Karen M. Overtoom R.E.

    83 Ashtons Way, Vineyard Haven, MA 02568
  • /38

    $1,500,000

    Sold Jan 23, 2026

    128 W Spring St, Vineyard Haven, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 2,436 Sq Ft
    • Built 2013

    Last Sold Summary

    • 14% Below List Price
    • $616/SF
    • 145 Days On Market

    Current Estimated Value $1,180,390

    Last Listing Agent David Dickinson Compass

    128 W Spring St, Vineyard Haven, MA 02568
    • /2

      Est $6,838,254

      Not Listed For Sale

      103 Main St, Vineyard Haven, MA 02568

      • 5 Beds
      • 6 Baths
      • 6,546 Sq Ft
      • Built 2008
      103 Main St, Vineyard Haven, MA 02568

  • /15

    $2,490,000

    Pending
    • Land
    • 7.2 Acres
    • $345,833 per Acre

    3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539

    Build your dream home on the special 7.2 acre North lot 1 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

    Robert Kenney Tea Lane Associates

    3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539
  • /4

    $6,000 Per Month

    • 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
  • /6

    $160,000

    Sold Aug 03, 2026

    60 Beach Rd Unit 240 - Building 2 -, Vineyard Haven, MA 02568

    • 1 Bed
    • 1 Bath
    • 381 Sq Ft
    • Built 1958

    Last Sold Summary

    • 11% Below List Price
    • $420/SF
    • 0 Days On Market

    Last Listing Agent Rene Jackson Island Real Estate

    60 Beach Rd Unit 240 - Building 2 -, Vineyard Haven, MA 02568
    • /34

      Est $1,543,873

      Not Listed For Sale

      84 Christiantown Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 2018
      84 Christiantown Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /35

    $1,225,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    52 Oak Knoll Rd, Vineyard Haven, MA 02568

    Year-round living in the desirable Island Farms Road neighborhood of West Tisbury. This well-built three-bedroom, two-bath home offers a comfortable layout with a first-floor primary bedroom. While ready for your personal updates, it provides a solid foundation to create your forever home. The open kitchen and living area offer a welcoming space for everyday living while the screened porch

    Tina Miller Donnelly + Co.

    52 Oak Knoll Rd, Vineyard Haven, MA 02568
  • /8

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

    THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
  • /30

    $1,995,000

    Sold Aug 29, 2025

    26 Box Turtle Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 3.5 Baths
    • 2,891 Sq Ft
    • Built 1980

    Last Sold Summary

    • $690/SF
    • 5 Days On Market

    Current Estimated Value $2,267,563

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    26 Box Turtle Ln, Oak Bluffs, MA 02557
    • /2

      Est $1,863,644

      Not Listed For Sale

      8 Harpoon Hollow, Aquinnah, MA 02535

      • 3 Beds
      • 3 Baths
      • 2,046 Sq Ft
      • Built 1940
      8 Harpoon Hollow, Aquinnah, MA 02535

Showing Results 161 - 200, Page 5 of 18

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