19,751

Martha's Vineyard, MA Homes

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  • /66

    $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
  • /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
    • /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

  • /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
  • /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
  • /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
    • /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

  • /17

    $1,500,000

    $200K PRICE DROP
    • Land
    • 37,026 Sq Ft
    • $1,764,706 per Acre

    4 Wilson's Landing Unit 49.2, Edgartown, MA 02539

    Build your dream home in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of vibrant Edgartown village. This wooded parcel of vacant land is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool and Accessory Dwelling Unit are allowed "by right" (certain restrictions apply to ADUs; an unrestricted 900 sq ft

    Mark Jenkins Wallace & Co. Sotheby's

    4 Wilson's Landing Unit 49.2, Edgartown, MA 02539
  • /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

    $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
    • /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

  • /16

    $565,000

    $90K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

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

    MOVE RIGHT IN! Just in time to ENJOY FOR THE SUMMER! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island.

    Rene Jackson Island Real Estate

    124 Skiff Ave Unit C-12, 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
  • /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
    • /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

  • /40

    $4,300,000

    $395K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,606 Sq Ft

    95 Hines Point Rd, Vineyard Haven, MA 02568

    A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor

    Elissa Lash Tea Lane Associates

    95 Hines Point Rd, Vineyard Haven, MA 02568
  • /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
  • /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
    • /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

  • /46

    $6,250,000

    • 5 Beds
    • 2.5 Baths
    • 2,269 Sq Ft

    34 Edys Island Way, Chilmark, MA 02535

    Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. The property is only a

    Jill Napior Tea Lane Associates

    34 Edys Island Way, Chilmark, 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
  • /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
    • /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

  • /41

    $1,975,000

    $175K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /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
  • /2

    $1,100,000

    Sold Oct 29, 2025

    11 Quammox Rd, Edgartown, MA 02539

    • 2 Beds
    • 1 Bath
    • 685 Sq Ft
    • Built 1940

    Last Sold Summary

    • $1,606/SF
    • 0 Days On Market

    Current Estimated Value $1,221,184

    Last Listing Agent LINK Email Cache LINK

    11 Quammox Rd, Edgartown, MA 02539
    • /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

  • /48

    $839,000

    $60K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 804 Sq Ft

    26 Winthrop Ave, Oak Bluffs, MA 02557

    This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with tons of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    26 Winthrop Ave, Oak Bluffs, MA 02557
  • /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

    $1,390,000

    Sold Jul 22, 2025

    57 Colonial Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,299 Sq Ft
    • Built 1984

    Last Sold Summary

    • $1,070/SF
    • 0 Days On Market

    Current Estimated Value $1,145,136

    Last Listing Agent LINK Email Cache LINK

    57 Colonial Dr, Vineyard Haven, MA 02568
    • /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

  • /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
  • /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
  • /30

    $1,050,000

    Sold Oct 06, 2025

    4 Quail Run Unit 2, Oak Bluffs, MA 02557

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • 11% Below List Price
    • $794/SF
    • 62 Days On Market

    Current Estimated Value $1,052,291

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    4 Quail Run Unit 2, Oak Bluffs, MA 02557
    • /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

  • /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
  • /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
  • /36

    $2,900,000

    Sold Mar 30, 2026

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft
    • Built 1988

    Last Sold Summary

    • $561/SF
    • 35 Days On Market

    Current Estimated Value $2,879,613

    Last Listing Agent Casandra Hyland Sandpiper Realty, Inc.

    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    • /10

      Est $944,009

      Not Listed For Sale

      345 Franklin St, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,012 Sq Ft
      • Built 1986
      345 Franklin St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 29 Days On Market

Showing Results 201 - 240, Page 6 of 18

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