19,907

Dukes County, MA Homes

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  • /36

    $2,260,000

    $335K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,810 Sq Ft

    4 High Meadow Ln, Oak Bluffs, MA 02557

    Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by

    Kate Burnside Portfolio Properties

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • /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
  • /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 $1,249,039

    Last Listing Agent Stephanie Roache Donnelly + Co.

    1054 State Rd, Vineyard Haven, MA 02568
    • /34

      Est $1,587,563

      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

  • /37

    $2,950,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,845 Sq Ft

    33 Ocean Ave, Oak Bluffs, MA 02557

    A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, the 3-bedroom home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, a new kitchen, updated baths, and

    Katrina Lima Donnelly + Co

    33 Ocean Ave, Oak Bluffs, MA 02557
  • /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
  • /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 $3,719,201

    Last Listing Agent Michelle Kelly Tea Lane Associates

    29 Oxcart Rd, Aquinnah, MA 02535
    • /2

      Est $1,819,993

      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

  • /27

    $1,800,000

    • 3 Beds
    • 3 Baths
    • 2,293 Sq Ft

    10 Trotters Ln, West Tisbury, MA 02575

    Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

    Rebecca V Conroy Conroy & Company R.E., Inc.

    10 Trotters Ln, West Tisbury, MA 02575
  • /21

    $8,000 Per Month

    • 1 Bed
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    10 James Pond Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

    Karen Overtoom Karen M. Overtoom R.E.

    10 James Pond Way, West Tisbury, MA 02575
  • /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 $2,493,395

      Not Listed For Sale

      10 Gerts Way, Edgartown, MA 02539

      • 4 Beds
      • 3 Baths
      • 2,404 Sq Ft
      • Built 1987
      10 Gerts Way, Edgartown, MA 02539

  • /26

    $1,299,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,150 Sq Ft

    9 Galway Rd, Vineyard Haven, MA 02568

    Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

    Julianna Flanders Flanders Real Estate

    9 Galway Rd, Vineyard Haven, MA 02568
  • /20

    $12,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,068 Sq Ft
    • House for Rent

    76 Ben Chase Rd Wt136, West Tisbury, MA 02575

    Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

    Karen Overtoom Karen M. Overtoom R.E.

    76 Ben Chase Rd Wt136, West Tisbury, MA 02575
  • /20

    $929,000

    Sold Aug 18, 2025

    299 Franklin St, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,286 Sq Ft
    • Built 1950

    Last Sold Summary

    • $722/SF
    • 7 Days On Market

    Current Estimated Value $988,031

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    299 Franklin St, Vineyard Haven, MA 02568
    • /39

      Est $3,277,697

      Not Listed For Sale

      18 S Pond Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 4,239 Sq Ft
      • Built 1999
      18 S Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 341 Days On Market

  • /20

    $1,195,000

    $80K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,110 Sq Ft

    34 10th St S, Edgartown, MA 02539

    Welcome to easy Edgartown living in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout ideal for both everyday life and entertaining. The private primary suite includes its own bath, while two additional

    Michael McGuire Insight Realty Group, Inc

    34 10th St S, Edgartown, MA 02539
  • /8

    $16,000 Per Month

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

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

    Karen Overtoom Karen M. Overtoom R.E.

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
  • /30

    $1,525,000

    Sold Jun 18, 2025

    54 Lake St, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft
    • Built 1967

    Last Sold Summary

    • 12% Below List Price
    • $756/SF
    • 110 Days On Market

    Current Estimated Value $1,570,184

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

    54 Lake St, Vineyard Haven, MA 02568
    • /29

      Est $1,932,022

      Not Listed For Sale

      165 W Tisbury Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,750 Sq Ft
      • Built 2007
      165 W Tisbury Rd, Edgartown, MA 02539

      Last Sold Summary

      • 37 Days On Market

  • /8

    $330,000

    • Land
    • 1.26 Acres
    • $261,905 per Acre

    0 Moshup Trail Unit 73508205, Aquinnah, MA 02535

    Enjoy coveted access to one of Martha's Vineyard’s most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah’s iconic “Painted House,” the property includes use of a private gated parking area for 1 vehicle and a picturesque stretch of shoreline

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    0 Moshup Trail Unit 73508205, Aquinnah, MA 02535
  • /3

    $13,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    224 N Rd Ch248, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

    Karen Overtoom Karen M. Overtoom R.E.

    224 N Rd Ch248, Chilmark, MA 02535
  • /42

    $4,150,000

    Sold Feb 19, 2026

    97 Longview Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 5.5 Baths
    • 4,003 Sq Ft
    • Built 2008

    Last Sold Summary

    • 12% Below List Price
    • $1,037/SF
    • 74 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co.

    97 Longview Rd, Vineyard Haven, MA 02568
    • /19

      Not Listed For Sale

      43 Look St, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 1,714 Sq Ft
      • Built 1900
      43 Look St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19 Days On Market

  • /52

    $5,295,000

    • 4 Beds
    • 3 Baths
    • 3,432 Sq Ft

    44 Cencelle St, Chilmark, MA 02535

    This private 17-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

    Meg Bodnar Tea Lane Associates

    44 Cencelle St, Chilmark, MA 02535
  • /23

    $36,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,556 Sq Ft
    • House for Rent

    74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

    Karen Overtoom Karen M. Overtoom R.E.

    74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
  • /3

    $665,000

    Sold Mar 06, 2026

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557

    • Land
    • 11,133 Sq Ft
    • $2,601,721 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 37 Days On Market

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557
    • /26

      Est $2,011,420

      Not Listed For Sale

      82 South Rd, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,862 Sq Ft
      • Built 1960
      82 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 10 Days On Market

  • /31

    $12,500,000

    Pending
    • 6 Beds
    • 4 Baths
    • 4,876 Sq Ft

    44 Forest Rd, Vineyard Haven, MA 02568

    Quintessential Seven Gates waterfront compound offering outstanding views and immediate beachfront access. This exceptional Martha’s Vineyard retreat includes a main residence and barn, thoughtfully designed and built by South Mountain Company. Immaculately maintained, both structures are virtually turn-key.The interiors showcase rich detail, the highest level of craftsmanship, and elegant

    Bill Rossi Studio Realty

    44 Forest Rd, Vineyard Haven, MA 02568
  • /17

    $12,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    223 Sandpiper Lane Vh405, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

    Karen Overtoom Karen M. Overtoom R.E.

    223 Sandpiper Lane Vh405, Tisbury, MA 02568
  • /2

    $880,000

    Sold Oct 17, 2025

    5 Johns Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Built 1987

    Last Sold Summary

    • $645/SF
    • 0 Days On Market

    Current Estimated Value $1,003,652

    Last Listing Agent LINK Email Cache LINK

    5 Johns Way, Oak Bluffs, MA 02557
    • /18

      Est $1,803,588

      Not Listed For Sale

      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,461 Sq Ft
      • Built 1994
      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 52 Days On Market

  • /7

    $2,850,000

    • Land
    • 1.52 Acres
    • $1,881,064 per Acre

    39 Slough Cove Rd Unit 12.2 (part of), Edgartown, MA 02539

    SPECTACULAR LOCATION! Build Your Katama Dream. Set in one of Martha’s Vineyard’s most sought-after locations, this newly created 1.5-acre parcel offers a rare opportunity to build your custom island retreat in the heart of Katama. Perfectly sited near the pristine shores of South Beach, the level and conforming R60 lot provides endless potential for a main residence and an outdoor oasis designed

    Fran Agnoli The Agency

    39 Slough Cove Rd Unit 12.2 (part of), Edgartown, MA 02539
  • /39

    $110,000 Per Month

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • House for Rent

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • /45

    $2,100,000

    Sold Nov 25, 2025

    6 Tabor Hills, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,544 Sq Ft
    • Built 1993

    Last Sold Summary

    • 11% Below List Price
    • $825/SF
    • 48 Days On Market

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    6 Tabor Hills, Chilmark, MA 02535
    • /25

      Est $1,452,777

      Not Listed For Sale

      101 Dunham Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 3 Baths
      • 2,287 Sq Ft
      • Built 1982
      101 Dunham Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /4

    $1,875,000

    $175K PRICE DROP
    • Land
    • 24,393 Sq Ft
    • $3,348,214 per Acre

    11A Duarte Cir, Edgartown, MA 02539

    Nestled in the HEART OF KATAMA, this ready-to-build unique deep lot offers the opportunity to create your DREAM COMPOUND just minutes to Edgartown Center & South Beach. Set back on a pristine cul-de-sac this property provides unparalleled privacy for a home in Katama with a country vibe. The SIX BEDROOM COMPOUND allows a MAIN HOUSE, GUEST HOUSE, GARAGE and has amble space for outdoor entertaining

    David White OwnerEntry.com

    11A Duarte Cir, Edgartown, MA 02539
  • /28

    $29,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,871 Sq Ft
    • House for Rent

    76 Mattakesett Way Ed313, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

    Karen Overtoom Karen M. Overtoom R.E.

    76 Mattakesett Way Ed313, Edgartown, MA 02539
  • /2

    $1,100,000

    Sold Jun 17, 2025

    17 Front St, Oak Bluffs, MA 02557

    • 2 Beds
    • 2 Baths
    • 2,912 Sq Ft
    • Built 1989

    Last Sold Summary

    • $378/SF
    • 0 Days On Market

    Current Estimated Value $1,293,146

    Last Listing Agent LINK Email Cache LINK

    17 Front St, Oak Bluffs, MA 02557
    • /38

      Est $2,020,751

      Not Listed For Sale

      83 Dolan Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 3,841 Sq Ft
      • Built 1994
      83 Dolan Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24 Days On Market

Showing Results 201 - 240, Page 6 of 18

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