19,346

Dukes County, MA Homes

Section Image
  • /32

    $2,150,000

    $100K PRICE DROP
    • 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
  • /12

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • House for Rent

    43 Edgartown Rd, Vineyard Haven, MA 02568

    Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an open floor plan with wood floors on the first level, wall to wall carpet in the upstairs bedrooms and an in-ground pool in the backyard. Available

    Karen Overtoom Karen M. Overtoom R.E.

    43 Edgartown Rd, Vineyard Haven, MA 02568
  • /21

    $982,000

    Sold Dec 19, 2025

    25 Windy Hill Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Below List Price
    • $1,002/SF
    • 10 Days On Market

    Current Estimated Value $1,061,116

    Last Listing Agent Rene Jackson Island Real Estate

    25 Windy Hill Rd, Oak Bluffs, MA 02557
    • /5

      Est $2,552,473

      Not Listed For Sale

      21 Old Oklahoma Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 1,657 Sq Ft
      • Built 1948
      21 Old Oklahoma Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /23

    $1,800,000

    • 4 Beds
    • 3 Baths
    • 2,864 Sq Ft

    18 Wood Duck Way, Edgartown, MA 02539

    Welcome to your coastal retreat in sought-after Sengekontacket, offered fully turnkey and ready to enjoy from day one. This light-filled contemporary home blends comfort, style, and exceptional community amenities in one of Martha's Vineyard's most desirable central Island locations.Designed with soaring vaulted ceilings and oversized windows, the home is flooded with natural sunlight

    Janna O'Loughlin Portfolio Properties

    18 Wood Duck Way, Edgartown, MA 02539
  • /25

    $13,600 Per Month

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft
    • House for Rent

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

    Karen Overtoom Karen M. Overtoom R.E.

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
  • /33

    $830,000

    Sold Mar 24, 2026

    12 Beach Plum Path, East Falmouth, MA 02536

    • 3 Beds
    • 2.5 Baths
    • 2,679 Sq Ft
    • Built 2021

    Last Sold Summary

    • 1% Below List Price
    • $310/SF
    • 90 Days On Market

    Last Listing Agent Pamela Heylin Berkshire Hathaway HomeServices Robert Paul Properties

    12 Beach Plum Path, East Falmouth, MA 02536
    • /20

      Not Listed For Sale

      467 Katama Rd Unit B2, Edgartown, MA 02539

      • 3 Beds
      • 2.5 Baths
      • 1,411 Sq Ft
      • Built 1973
      467 Katama Rd Unit B2, Edgartown, MA 02539

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Cheri Mason Landvest MV

  • /28

    $1,850,000

    Under Contract
    • 3 Beds
    • 6 Baths
    • 2,641 Sq Ft

    33 Tia Anna Ln, Oak Bluffs, MA 02557

    33 Tia Anna Lane has so much to offer; a charming, bright, renovated main and guest house on a half-acre in Oak Bluffs with proximity to town and walking distance to Lagoon Pond for swimming, fishing, boating and sunset enjoyment. The property is ready to enjoy, offering a turn-key home on a quiet side street as well as a detached guest house with its own yard and deck. The inviting main house

    Elissa Lash Tea Lane Associates

    33 Tia Anna Ln, Oak Bluffs, MA 02557
  • /8

    $18,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 1,714 Sq Ft
    • House for Rent

    4 Windy Way Wt143, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

    Karen Overtoom Karen M. Overtoom R.E.

    4 Windy Way Wt143, West Tisbury, MA 02575
  • /31

    $1,350,000

    Sold Aug 15, 2025

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Below List Price
    • $724/SF
    • 9 Days On Market

    Last Listing Agent Lesley Heidt Sandpiper Realty

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
    • /2

      Est $1,567,571

      Not Listed For Sale

      39 Prices Way, Edgartown, MA 02539

      • 4 Beds
      • 2 Baths
      • 1,532 Sq Ft
      • Built 1986
      39 Prices Way, Edgartown, MA 02539

  • /12

    $750,000

    Under Contract
    • 1 Bed
    • 1 Bath
    • 400 Sq Ft

    52 Summer St, Vineyard Haven, MA 02568

    "Sandcastle" has been lovingly enjoyed by the current owner for the past 20 years. This charming one-bedroom, one-bath cottage (NOT in the Nitrogen Management Overlay District) features, an open living room, kitchen area and a cozy office nook—ideal for working remotely. A deck just off the kitchen provides the perfect spot for outdoor dining, morning coffee, or relaxing in the fresh Vineyard

    Susie Wallo Compass LLC

    52 Summer St, Vineyard Haven, MA 02568
  • /8

    $8,250 Per Month

    • 7 Beds
    • 5 Baths
    • 3,528 Sq Ft
    • House for Rent

    227 S Gate Rd Wt120, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • /16

    $530,000

    Sold Aug 07, 2026

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft
    • Built 1953

    Last Sold Summary

    • 19% Below List Price
    • $753/SF
    • 270 Days On Market

    Current Estimated Value $612,029

    Last Listing Agent Rene Jackson Island Real Estate

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
    • /14

      Est $2,668,873

      Not Listed For Sale

      30 Pond Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,926 Sq Ft
      • Built 2004
      30 Pond Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /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
  • /8

    $17,500 Per Month

    • 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
  • /25

    $1,125,000

    Sold Oct 28, 2025

    140 Longview Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,432 Sq Ft
    • Built 1964

    Last Sold Summary

    • 13% Below List Price
    • $786/SF
    • 97 Days On Market

    Current Estimated Value $1,217,677

    Last Listing Agent Candy DaRosa Feiner Real Estate

    140 Longview Rd, Vineyard Haven, MA 02568
    • /23

      Est $2,067,211

      Not Listed For Sale

      31 Pulpit Ln, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,704 Sq Ft
      • Built 2001
      31 Pulpit Ln, Edgartown, MA 02539

      Last Sold Summary

      • 169 Days On Market

      Last Listing Agent Courtney Marek Sandpiper Realty

  • /48

    $3,950,000

    Pending
    • 3 Beds
    • 4.5 Baths
    • 3,314 Sq Ft

    20 Edson Forrest Rd, West Tisbury, MA 02575

    Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. A full restoration of this this three-bedroom house (with six-bedroom septic) in 2022 created a luxury home with a thoughtful layout, 2 story expansion, and exceptional

    Meg Bodnar Tea Lane Associates

    20 Edson Forrest Rd, West Tisbury, MA 02575
  • /29

    $18,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,027 Sq Ft
    • House for Rent

    12 Cottle Lane Ed341, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Walk to Fulton Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.

    Karen Overtoom Karen M. Overtoom R.E.

    12 Cottle Lane Ed341, Edgartown, MA 02539
  • /28

    $2,075,000

    Sold Sep 29, 2025

    24 Dark Woods Rd, Edgartown, MA 02539

    • 3 Beds
    • 3.5 Baths
    • 2,638 Sq Ft
    • Built 1998

    Last Sold Summary

    • 23% Below List Price
    • $787/SF
    • 372 Days On Market

    Current Estimated Value $2,266,731

    Last Listing Agent Stephanie Burke Portfolio Properties

    24 Dark Woods Rd, Edgartown, MA 02539
    • /49

      Not Listed For Sale

      670 State Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 2,092 Sq Ft
      • Built 1920
      670 State Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Nya Clarke Martha's Vineyard Island-Wide Realty

  • /30

    $1,850,000

    • 4 Beds
    • 2.5 Baths
    • 2,064 Sq Ft

    99 Old Purchase Rd, Edgartown, MA 02539

    Enjoying a private setting at the end of a quiet Edgartown cul-de-sac, this post-and-beam home is set on .71 acres with easy access to more than 25 acres of Land Bank conservation land. Conveniently located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, the property offers both privacy and accessibility. Filled with natural light, the home features a well-designed

    Stephanie Roache Donnelly + Co

    99 Old Purchase Rd, Edgartown, MA 02539
  • /35

    $22,000 Per Month

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • /37

    $1,175,000

    Sold Apr 22, 2026

    112 3rd St N, Edgartown, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $982/SF
    • 139 Days On Market

    Last Listing Agent Kristin Buck Donnelly + Co.

    112 3rd St N, Edgartown, MA 02568
    • /35

      Est $1,243,750

      Not Listed For Sale

      29 Dunham Ave, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1965
      29 Dunham Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /7

    $3,100,000

    • Land
    • 3.04 Acres
    • $1,019,737 per Acre

    114 Meeting House Way, 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

    Rose Ryley Wallace & Co. Sotheby's

    114 Meeting House Way, Edgartown, MA 02539
  • /17

    $17,600 Per Month

    • 4 Beds
    • 4 Baths
    • 2,676 Sq Ft
    • House for Rent

    40 Summer Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

    Karen Overtoom Karen M. Overtoom R.E.

    40 Summer Cir, West Tisbury, MA 02575
  • /9

    $7,289,000

    Sold Oct 15, 2025

    25 Osprey Ln, Chilmark, MA 02535

    • 4 Beds
    • 5 Baths
    • 3,777 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $1,930/SF
    • 77 Days On Market

    Last Listing Agent Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
    • /3

      Est $1,483,156

      Not Listed For Sale

      5 Vincent Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1960
      5 Vincent Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

  • /35

    $5,200,000

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    49 Gosnold's Way, Chilmark, MA 02535

    Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network.The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper

    Bonnie Pierce Wallace & Co. Sotheby's

    49 Gosnold's Way, Chilmark, MA 02535
  • /8

    $18,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

    Karen Overtoom Karen M. Overtoom R.E.

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
  • /36

    $1,029,000

    Sold Jul 17, 2026

    40 Scotchmans Ln, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1830

    Last Sold Summary

    • 31% Below List Price
    • $773/SF
    • 349 Days On Market

    Last Listing Agent Jim Osmundsen Donnelly + Co.

    40 Scotchmans Ln, Vineyard Haven, MA 02568
    • /13

      Est $803,570

      Not Listed For Sale

      32 Clark Ave, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1968
      32 Clark Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Diana Gilmore Island Real Estate

  • /23

    $3,988,000

    $300K PRICE DROP Pending
    • 7 Beds
    • 3.5 Baths
    • 2,461 Sq Ft

    69 School St, Edgartown, MA 02539

    Located in the heart of Edgartown Village, this circa 1840 Greek Revival residence offers a rare opportunity to own a piece of island history on a coveted block. The property features a total of seven bedrooms across the main house and carriage house, making it a superb destination for family and guests. The main house features wide plank hardwood flooring and bright and sunny spaces with five

    Peyton Wallace Studio Realty

    69 School St, Edgartown, MA 02539
  • /40

    $16,400 Per Month

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

    20 Katama Bay Rd Ed350, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,100. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.

    Karen Overtoom Karen M. Overtoom R.E.

    20 Katama Bay Rd Ed350, Edgartown, MA 02539
  • /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
    • /18

      Est $683,950

      Not Listed For Sale

      5 Village Ct Unit 3, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 658 Sq Ft
      • Built 1972
      5 Village Ct Unit 3, Vineyard Haven, MA 02568

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Martha Smith C McManus Realty Group

Showing Results 121 - 160, Page 4 of 18

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