19,872

Dukes County, MA Homes

Section Image
  • /42

    $2,325,000

    $25K 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
  • /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
  • /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
    • /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

      • $1,444/SF
      • 100 Days On Market
      • Last Sold Price $6,665,000
      • Sep 16, 2024

      Last Listing Agent Wendy Harman Compass

  • /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
  • /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
  • /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 $1,241,377

    Last Listing Agent David Dickinson Compass

    128 W Spring St, Vineyard Haven, MA 02568
    • /35

      Est $4,529,964

      Not Listed For Sale

      225 Bigelow Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 2,603 Sq Ft
      • Built 1976
      225 Bigelow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10% Above List Price
      • $1,575/SF
      • 70 Days On Market
      • Last Sold Price $4,100,000
      • Nov 03, 2014

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

  • /36

    $4,500,000

    • 4 Beds
    • 3 Baths
    • 2,715 Sq Ft

    94 Weaver Ln, Vineyard Haven, MA 02568

    Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

    Emma Kennedy Sandpiper Realty, Inc.

    94 Weaver Ln, Vineyard Haven, 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
  • /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 $2,091,936

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    26 Box Turtle Ln, Oak Bluffs, MA 02557
    • /7

      Est $4,969,592

      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

      • 13% Below List Price
      • $840/SF
      • 329 Days On Market
      • Last Sold Price $5,700,000
      • Aug 23, 2023

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /60

    $14,500,000

    $2M PRICE DROP
    • 5 Beds
    • 7.5 Baths
    • 6,781 Sq Ft

    3 Field Club Ln, Edgartown, MA 02539

    An exquisite offering, also known as Sand Castle, in the highly coveted Field Club. Nestled within the luxury Field Club enclave, this sophisticated 5-bedroom, 7.5-bath residence embodies modern luxury with pristine coastal charm. Step into an expansive open living plan where refined millwork, soaring ceilings, and elegant finishes define each space. A gourmet chef’s kitchen features top-tier

    Thomas Wallace Wallace & Co. Sotheby's

    3 Field Club Ln, Edgartown, MA 02539
  • /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
  • /18

    $995,000

    Sold Nov 06, 2025

    2 Flamingo Dr, Edgartown, MA 02539

    • 3 Beds
    • 1 Bath
    • 990 Sq Ft
    • Built 1983

    Last Sold Summary

    • 5% Below List Price
    • $1,005/SF
    • 5 Days On Market

    Current Estimated Value $1,051,210

    Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

    2 Flamingo Dr, Edgartown, MA 02539
    • /20

      Est $1,672,490

      Not Listed For Sale

      21 Bold Meadow Ln, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,971 Sq Ft
      • Built 1991
      21 Bold Meadow Ln, Edgartown, MA 02539

      Last Sold Summary

      • 22% Above List Price
      • $698/SF
      • 34 Days On Market
      • Last Sold Price $1,375,000
      • Jul 14, 2023

      Last Listing Agent Martha Smith C McManus Realty Group

  • /19

    $9,250,000

    $1M PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    33 Goethals Way, Vineyard Haven, MA 02568

    A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

    Buder Team Sandpiper Realty, Inc.

    33 Goethals Way, Vineyard Haven, MA 02568
  • /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
  • /44

    $1,890,000

    Sold Aug 29, 2025

    1 Thames Ct, Edgartown, MA 02539

    • 4 Beds
    • 3 Baths
    • 3,270 Sq Ft
    • Built 1981

    Last Sold Summary

    • $578/SF
    • 38 Days On Market

    Current Estimated Value $2,024,127

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

    1 Thames Ct, Edgartown, MA 02539
    • /27

      Est $1,277,631

      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

      • 7% Above List Price
      • $786/SF
      • 1,366 Days On Market
      • Last Sold Price $1,195,000
      • Jun 05, 2015

      Last Listing Agent Fran Agnoli The Agency

  • /2

    $6,250,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,624 Sq Ft

    68 Turkeyland Cove Rd, Edgartown, MA 02539

    Nestled in one of Edgartown's most sought-after waterfront neighborhoods, Turkeyland Cove offers the best of both worlds: a tranquil, nature-immersed sanctuary that feels miles from anywhere, yet remains moments from everything Martha's Vineyard has to offer. This exclusive enclave strikes a perfect balance between natural beauty, sophisticated living, and convenient access to Island

    Emma Kennedy Sandpiper Realty

    68 Turkeyland Cove Rd, Edgartown, MA 02539
  • /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
  • /32

    $899,000

    Sold Jul 11, 2025

    8 Rock Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1.5 Baths
    • 955 Sq Ft
    • Built 1871

    Last Sold Summary

    • $941/SF
    • 6 Days On Market

    Current Estimated Value $943,726

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    8 Rock Ave, Oak Bluffs, MA 02557
    • /22

      Est $4,377,281

      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

      • 4% Below List Price
      • $1,575/SF
      • 0 Days On Market
      • Last Sold Price $4,575,000
      • Nov 19, 2024

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

  • /54

    $2,000,000

    • 5 Beds
    • 3.5 Baths
    • 2,075 Sq Ft

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island’s most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

    Valene Pires The Agency

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • /41

    $8,750 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,811 Sq Ft
    • House for Rent

    11 High Meadow Ln, Vineyard Haven, MA 02568

    **SUMMER WEEKLY RATE ** INQUIRE FOR LONG TERM OFFSEASON RATE**Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 High Meadow Ln, Vineyard Haven, MA 02568
  • /23

    $1,067,000

    Sold Sep 26, 2025

    112 W Spring St, Vineyard Haven, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 1,503 Sq Ft
    • Built 2000

    Last Sold Summary

    • 7% Below List Price
    • $710/SF
    • 9 Days On Market

    Current Estimated Value $1,081,951

    Last Listing Agent Katherine Donahue Sandpiper Realty

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

      Est $1,713,037

      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

      Last Sold Summary

      • 2% Below List Price
      • $1,340/SF
      • Last Sold Price $1,675,000

      Last Listing Agent Courtney Marek Sandpiper Realty

  • /6

    $1,495,000

    $80K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    47 Quenames Rd, Chilmark, MA 02535

    On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

    Dawn Bellante Sandpiper Realty, Inc.

    47 Quenames Rd, Chilmark, MA 02535
  • /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
  • /32

    $1,250,000

    Sold Nov 12, 2025

    1054 State Rd, Vineyard Haven, MA 02568

    • 6 Beds
    • 2 Baths
    • 1,845 Sq Ft
    • Built 1881

    Last Sold Summary

    • 16% Below List Price
    • $678/SF
    • 60 Days On Market

    Current Estimated Value $1,232,202

    Last Listing Agent Stephanie Roache Donnelly + Co.

    1054 State Rd, Vineyard Haven, MA 02568
    • /2

      Est $5,940,988

      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

      Last Sold Summary

      • 50% Below List Price
      • $1,833/SF
      • Last Sold Price $12,000,000

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

  • /47

    $3,690,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,108 Sq Ft

    13 Plantingfield Way, Edgartown, MA 02539

    Set in the heart of Edgartown Village, this pristine Cape offers an exceptional combination of charm, comfort, and in-town convenience. Just moments from boutique shopping, acclaimed galleries, fine dining, and the scenic harbor, this four-bedroom, three-bath home captures the quintessential Vineyard lifestyle. Two entrances enhance the home’s functionality: a formal front entry leads directly to

    Stephanie Roache Donnelly + Co

    13 Plantingfield Way, Edgartown, MA 02539
  • /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
  • /31

    $3,750,000

    Sold Oct 31, 2025

    29 Oxcart Rd, Aquinnah, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 2009

    Last Sold Summary

    • 11% Below List Price
    • $2,943/SF
    • 380 Days On Market

    Current Estimated Value $3,596,804

    Last Listing Agent Michelle Kelly Tea Lane Associates

    29 Oxcart Rd, Aquinnah, MA 02535
    • /34

      Est $1,555,523

      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

      • 11% Above List Price
      • $964/SF
      • 59 Days On Market
      • Last Sold Price $1,400,000
      • May 20, 2024

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /42

    $9,499,000

    • 4 Beds
    • 7 Baths
    • 5,902 Sq Ft

    43 Peases Point Way S, Edgartown, MA 02539

    Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown's most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    43 Peases Point Way S, 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
  • /42

    $15,725,000

    Sold Oct 22, 2025

    111 N Water St, Edgartown, MA 02539

    • 6 Beds
    • 4.5 Baths
    • 3,606 Sq Ft
    • Built 1850

    Last Sold Summary

    • 5% Below List Price
    • $4,361/SF
    • 41 Days On Market

    Last Listing Agent Wendy Harman Compass

    111 N Water St, Edgartown, MA 02539
    • /2

      Est $1,790,216

      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

      Last Sold Summary

      • 12% Below List Price
      • $782/SF
      • Last Sold Price $1,600,000

      Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

Showing Results 161 - 200, Page 5 of 18

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