19,907

Dukes County, MA Homes

Section Image Section Image
  • /34

    $2,150,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,126 Sq Ft

    17 Oakdale Dr, Edgartown, MA 02539

    PRIVATE EDGARTOWN RETREAT WITH TIMELESS COTTAGE CHARM. Tucked away in a quiet and serene setting on the edge of Edgartown Village, this charming Vineyard retreat is ideally positioned halfway between town and State Beach, with the bicycle path nearby for easy access to both. Set along a private lane and bordered by classic Vineyard stonewalls, the property offers a rare sense of privacy with an

    Agent Photo

    Wendy Harman

    Compass | Point B

    (508) 590-9321

    17 Oakdale Dr, Edgartown, MA 02539
  • /20

    $16,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • /2

    $3,300,000

    Sold Dec 09, 2025

    1 Muskoday Way, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 2,194 Sq Ft
    • Built 1972

    Last Sold Summary

    • $1,504/SF
    • 0 Days On Market

    Current Estimated Value $2,964,363

    Last Listing Agent LINK Email Cache LINK

    1 Muskoday Way, Edgartown, MA 02539
    • /38

      Est $1,064,388

      Not Listed For Sale

      287 County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1998
      287 County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10 Days On Market

  • /6

    $1,125,000

    • Land
    • 10,097 Sq Ft
    • $4,853,322 per Acre

    15 Chapman Ln Unit 111.1, Edgartown, MA 02539

    OPPORTUNITY ABOUNDS: This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer (see notes below) creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the

    Agent Photo

    Wendy Harman

    Compass | Point B

    (508) 276-2117

    15 Chapman Ln Unit 111.1, Edgartown, MA 02539
  • /21

    $9,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,579 Sq Ft
    • House for Rent

    155 Skiff Ave, Vineyard Haven, MA 02568

    **SUMMER RENTAL ONLY** PRICE IS WEEKLY** Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    155 Skiff Ave, Vineyard Haven, MA 02568
  • /26

    $1,935,000

    Sold May 06, 2026

    34 Davis St, Tisbury, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 2,453 Sq Ft
    • Built 2025

    Last Sold Summary

    • 19% Below List Price
    • $789/SF
    • 160 Days On Market

    Last Listing Agent Andrew McElhinney Compass LLC

    34 Davis St, Tisbury, MA 02568
    • /26

      Est $1,575,714

      Not Listed For Sale

      19 Quantapog Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,822 Sq Ft
      • Built 1988
      19 Quantapog Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 177 Days On Market

  • /56

    $9,995,000

    • 6 Beds
    • 7.5 Baths
    • 7,205 Sq Ft

    25 Lelands Path, Edgartown, MA 02539

    YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent residence is privately sited at the end of a winding drive on 16.4 acres, offering more than 7,200

    Agent Photo

    Wendy Harman

    Compass | Point B

    (508) 403-9546

    25 Lelands Path, Edgartown, MA 02539
  • /42

    $19,000 Per Month

    • 6 Beds
    • 6.5 Baths
    • 6,950 Sq Ft
    • House for Rent

    40 Sweet William Way, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

    Karen Overtoom Karen M. Overtoom R.E.

    40 Sweet William Way, West Tisbury, MA 02575
  • /2

    $1,850,000

    Sold Mar 31, 2026

    7 S Meadow Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Above List Price
    • $589/SF
    • 74 Days On Market

    Current Estimated Value $1,948,992

    Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    7 S Meadow Ln, Oak Bluffs, MA 02557
    • /12

      Est $1,232,984

      Not Listed For Sale

      3 Carole Ave, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,997 Sq Ft
      • Built 1985
      3 Carole Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 209 Days On Market

  • /34

    $3,350,000

    • 3 Beds
    • 4.5 Baths
    • 2,912 Sq Ft

    40 Edgewood Dr, Edgartown, MA 02539

    This is an excellent opportunity to own a beautiful crafted custom home set on over half an acre in a peaceful neighborhood just minutes from downtown Edgartown. The property offers striking curb appeal with stone walls, granite steps, professional landscaping, and ample parking, and it borders protected association land that will remain undeveloped. Inside, the home features three spacious

    Carol McManus C McManus Realty Group

    40 Edgewood Dr, Edgartown, MA 02539
  • /25

    $24,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,257 Sq Ft
    • House for Rent

    5 Laurel Ave, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include

    Karen Overtoom Karen M. Overtoom R.E.

    5 Laurel Ave, Oak Bluffs, MA 02557
  • /27

    $1,560,000

    Sold Jan 15, 2026

    36 Ferro Way, Tisbury, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 4,032 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $387/SF
    • 37 Days On Market

    Current Estimated Value $1,600,938

    Last Listing Agent Hope O'Brien Compass LLC

    36 Ferro Way, Tisbury, MA 02568
    • /29

      Est $1,247,672

      Not Listed For Sale

      33 Menahan St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft
      • Built 1993
      33 Menahan St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 30 Days On Market

  • /32

    $510,000

    $50K PRICE DROP
    • 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
  • /21

    $7,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    27 Beach Plum Ln, Chilmark, MA 02535

    weekly rental rate negotiable, cost $400-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt . it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • /26

    $800,000

    Sold Jun 04, 2026

    17 Mariner Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1983

    Last Sold Summary

    • 11% Below List Price
    • $694/SF
    • 32 Days On Market

    Current Estimated Value $920,974

    Last Listing Agent Karl Olsen Carlson & Company, LLC

    17 Mariner Rd, Vineyard Haven, MA 02568
    • /14

      Est $1,011,919

      Not Listed For Sale

      51 Manchester Ave, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 1,024 Sq Ft
      • Built 1978
      51 Manchester Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 22 Days On Market

  • /5

    $585,000

    $615K PRICE DROP Under Contract
    • Land
    • 39,204 Sq Ft
    • $650,000 per Acre

    87 Whalers Walk Unit 113, Edgartown, MA 02539

    Beautiful .9 acre lot in a tranquil residential neighborhood, ideally located near Morning Glory Farm, Vineyard Golf Club, the bike paths to Edgartown Village, South Beach, and up-island. A unique chance to build your Martha’s Vineyard home in a private yet convenient Edgartown location. This property is subject to M.G.L. Chapter 40A Section 6 of the Affordable Homes Act: a single-family

    Dawn Bellante-Holand Sandpiper Realty

    87 Whalers Walk Unit 113, Edgartown, MA 02539
  • /8

    $6,000 Per Month

    • 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
  • /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 $3,441,102

    Last Listing Agent Jennifer O'hanlon Compass

    28 Crocker Dr, Edgartown, MA 02539
    • /2

      Est $2,425,647

      Not Listed For Sale

      230 Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 3,527 Sq Ft
      • Built 2002
      230 Pond Rd, Vineyard Haven, MA 02568

  • /30

    $950,000

    $150K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,583 Sq Ft

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    NEW PRICE - 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 LLC

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • /27

    $21,700 Per Month

    • 5 Beds
    • 3 Baths
    • 2,168 Sq Ft
    • House for Rent

    97 3rd St N, Edgartown, MA 02539

    YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

    Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

    97 3rd St N, Edgartown, MA 02539
  • /3

    $435,000

    Sold Jul 23, 2025

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

    • Land
    • 12,998 Sq Ft
    • $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
    • /2

      Est $2,434,073

      Not Listed For Sale

      248 Pond Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 3,208 Sq Ft
      • Built 1998
      248 Pond Rd, Vineyard Haven, MA 02568

  • /32

    $2,250,000

    • 4 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    29 Old Nursery Ln, Chilmark, MA 02535

    Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

    Julianna Flanders Flanders Real Estate

    29 Old Nursery Ln, Chilmark, MA 02535
  • /28

    $32,000 Per Month

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

    37 Mempremagog Ave Vh410, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    37 Mempremagog Ave Vh410, Tisbury, MA 02568
  • /18

    $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

    Current Estimated Value $3,711,224

    Last Listing Agent Michele Casavant Vineyard Village Realty

    1 Wilsons Ln, Edgartown, MA 02539
    • /25

      Est $2,103,856

      Not Listed For Sale

      131 Shubael Weeks Path, Vineyard Haven, MA 02568

      • 5 Beds
      • 3 Baths
      • 3,636 Sq Ft
      • Built 1985
      131 Shubael Weeks Path, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /33

    $3,150,000

    • 4 Beds
    • 3.5 Baths
    • 2,791 Sq Ft

    8 Atwood Cir, Edgartown, MA 02539

    This charming and historic home is ideally situated at the head of Atwood Circle, a private neighborhood just off Dunham Road, and only a short stroll to town. Recently renovated, the residence blends classic character with modern comfort. The main level features a spacious living room, a cozy den with fireplace, a dining area, and an updated kitchen—perfect for both everyday living and

    Gerrett Conover Landvest MV

    8 Atwood Cir, Edgartown, MA 02539
  • /17

    $48,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,675 Sq Ft
    • House for Rent

    9 Thaxter Lane Ed310, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Enjoy the pool with this Stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high end neighborhood within

    Karen Overtoom Karen M. Overtoom R.E.

    9 Thaxter Lane Ed310, Edgartown, MA 02539
  • /29

    $1,470,000

    Sold Mar 24, 2026

    654 Lighthouse Rd, Aquinnah, MA 02535

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1972

    Last Sold Summary

    • 22% Below List Price
    • $919/SF
    • 195 Days On Market

    Current Estimated Value $1,775,370

    Last Listing Agent Heidi Vanderhoop Tea Lane Associates

    654 Lighthouse Rd, Aquinnah, MA 02535
    • /2

      Est $1,751,647

      Not Listed For Sale

      26 Old Coach Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 1,923 Sq Ft
      • Built 1998
      26 Old Coach Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /51

    $1,800,000

    • 4 Beds
    • 3 Baths
    • 3,158 Sq Ft

    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    House & Guesthouse near Longpoint Beach! The crashing surf is minutes from this charming West Tisbury property, appropriately referred to as ''Pinch Me'' by the owners. Here, the connection to nature is seamless. The main house sits atop the trees and overlooks a sprawling lawn from two decks. Inside is an open floor plan with natural light from windows and skylights. The kitchen flows to the

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
  • /8

    $7,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,107 Sq Ft
    • House for Rent

    2 Paddock Cir, Chilmark, MA 02535

    Karen Overtoom Karen M. Overtoom R.E.

    2 Paddock Cir, Chilmark, MA 02535
  • /26

    $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 $1,588,026

    Last Listing Agent Josseph Barkett Compass

    37 Knoll Dr, Edgartown, MA 02539
    • /45

      Est $1,777,078

      Not Listed For Sale

      38 Edgewood Dr, Edgartown, MA 02539

      • 3 Beds
      • 2.5 Baths
      • 2,576 Sq Ft
      • Built 1987
      38 Edgewood Dr, Edgartown, MA 02539

      Last Sold Summary

      • 48 Days On Market

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home