19,352

Dukes County, MA Homes

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  • /41

    $1,450,000

    $45K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    44 Prices Way, Edgartown, MA 02539

    Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining area, efficient

    Agent Photo

    Wendy Harman

    Compass

    44 Prices Way, 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 $2,866,602

    Last Listing Agent LINK Email Cache LINK

    1 Muskoday Way, Edgartown, MA 02539
    • /38

      Est $1,056,884

      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

      Last Listing Agent Jill Napior Tea Lane Associates

  • /42

    $3,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,056 Sq Ft

    9 Thaxter Ln, Edgartown, MA 02539

    A contemporary Katama retreat, newly refreshed and ready for summer. Set in one of Edgartown’s most coveted coastal enclaves, moments from South Beach, this tri-level home offers sun-filled interiors, generous gathering spaces, strong rental appeal, and a private backyard oasis with an 18x40-foot saltwater pool. The dramatic open-concept living level features vaulted ceilings, a wood-burning

    Agent Photo

    Wendy Harman

    Compass

    9 Thaxter Ln, 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
  • /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 $1,558,733

      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

      Last Listing Agent Frank Markwica Sandpiper Realty

  • /38

    $5,795,000

    • 3 Beds
    • 3.5 Baths
    • 3,116 Sq Ft

    7 Katama Dr, Edgartown, MA 02539

    Stylish South Beach Retreat With Resort-Style Pool - Ideally located in the heart of Katama near South Beach, this stylish contemporary home offers the perfect blend of beach living and luxury amenities. Vaulted ceilings, a sleek linear fireplace, and a wall of 12-foot glass doors open the main living area to an expansive mahogany deck, creating seamless indoor-outdoor living. The gourmet

    Agent Photo

    Wendy Harman

    Compass

    7 Katama 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
  • /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 $2,047,658

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

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

      Est $1,204,550

      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

      Last Listing Agent Bob Sparks American Real Estate LLC

  • /4

    $995,000

    Pending
    • 1 Bed
    • 1 Bath
    • 448 Sq Ft

    34 Curtis Ln, Edgartown, MA 02539

    Exciting Edgartown In-Town Opportunity - Tucked away on a quiet lane at the edge of Edgartown Village, 34 Curtis Lane offers a rare opportunity to create a distinctive in-town residence close to shops, restaurants, galleries, the harbor, and more. Curtis Lane is undergoing a notable transformation, with significant new construction and property improvements adding to the neighborhood’s appeal.

    Agent Photo

    Wendy Harman

    Compass

    34 Curtis Ln, Edgartown, MA 02539
  • /21

    $6,800 Per Month

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

    27 Beach Plum Ln, Chilmark, MA 02535

    September Availability weekly rental rate negotiable, cost $600-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road .The house 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 chefs Kitchen, living room

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • /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 $1,690,530

    Last Listing Agent Hope O'Brien Compass LLC

    36 Ferro Way, Tisbury, MA 02568
    • /29

      Est $1,258,064

      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

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /28

    $1,195,000

    Open Tue 10AM - 11AM
    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    2 Winemack St, Oak Bluffs, MA 02557

    Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you’ll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping,

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    2 Winemack St, Oak Bluffs, MA 02557
  • /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
  • /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 $867,058

    Last Listing Agent Karl Olsen Carlson & Company, LLC

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

      Est $998,385

      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

      Last Listing Agent Roy Cutrer LAER Realty Partners

  • /42

    $6,595,000

    Pending
    • 4 Beds
    • 7 Baths
    • 3,717 Sq Ft

    17 Katama Point Rd, Edgartown, MA 02539

    Coastal chic living with pool and pool house near Katama Bay. Perfectly positioned in the coveted Edgartown Bay Road area, moments from the Town Landing, this custom-built residence offers effortless Vineyard living with exceptional craftsmanship and turnkey convenience. Designed as a builder’s own home, the property features shiplap paneling, a custom fieldstone wall with wood-burning fireplace,

    Agent Photo

    Wendy Harman

    Compass

    17 Katama Point Rd, Edgartown, MA 02539
  • /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
  • /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 $3,612,527

    Last Listing Agent Jennifer O'hanlon Compass

    28 Crocker Dr, Edgartown, MA 02539
    • /2

      Est $2,653,156

      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

  • /36

    $2,325,000

    $270K PRICE DROP Pending
    • 4 Beds
    • 4 Baths
    • 2,288 Sq Ft

    54 Amelia's Crossing, Tisbury, MA 02568

    COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living

    Agent Photo

    Wendy Harman

    Compass

    54 Amelia's Crossing, Tisbury, MA 02568
  • /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 $3,751,478

    Last Listing Agent Michele Casavant Vineyard Village Realty

    1 Wilsons Ln, Edgartown, MA 02539
    • /2

      Est $2,459,843

      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

  • /20

    $9,495,000

    • 4 Beds
    • 6 Baths
    • 4,605 Sq Ft

    29 Slough Cove Rd, Edgartown, MA 02539

    Timeless architect-designed Katama retreat made for summer living. Privately set at the end of a long drive on 1.53 acres near South Beach, this Patrick Ahearn-designed estate offers 4,605 square feet of refined Vineyard living. Built in 2022, the home blends award-winning coastal architecture with vaulted ceilings, custom shiplap, millwork, antique rough-hewn beams, Rubio Monocoat floors,

    Agent Photo

    Wendy Harman

    Compass

    29 Slough Cove Rd, 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 $2,012,782

    Last Listing Agent Heidi Vanderhoop Tea Lane Associates

    654 Lighthouse Rd, Aquinnah, MA 02535
    • /25

      Est $2,089,409

      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

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

  • /42

    $4,995,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,095 Sq Ft

    63 Putnam Rd, Chilmark, MA 02535

    Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a

    Agent Photo

    Wendy Harman

    Compass

    63 Putnam Rd, Chilmark, MA 02535
  • /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 $1,717,747

    Last Listing Agent Josseph Barkett Compass

    37 Knoll Dr, Edgartown, MA 02539
    • /2

      Est $1,793,582

      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

      Last Listing Agent LINK Email Cache LINK

  • /71

    $6,595,000

    Pending
    • 4 Beds
    • 7 Baths
    • 3,717 Sq Ft

    17 Town Lot Rd, Edgartown, MA 02539

    COASTAL CHIC LIVING WITH POOL AND POOL HOUSE NEAR KATAMA BAY. Perfectly positioned in the highly coveted Edgartown Bay Road area, just moments from the Town Landing on Katama Bay, this custom-built coastal residence offers the very best of the Vineyard lifestyle—effortless, elegant, and ready for immediate enjoyment. Designed and built as a builder’s own home, every detail reflects exceptional

    Agent Photo

    Wendy Harman

    Compass | Point B

    17 Town Lot Rd, Edgartown, MA 02539
  • /27

    $18,840 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    21 William St Vh430, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

    Karen Overtoom Karen M. Overtoom R.E.

    21 William St Vh430, Tisbury, MA 02568
  • /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
    • /45

      Est $1,786,952

      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

      Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

Showing Results 41 - 80, Page 2 of 18

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