19,930

Martha's Vineyard, MA Homes

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  • 169 Clover Hill Dr, Vineyard Haven, MA 02568
    169 Clover Hill Dr, Vineyard Haven, MA 02568
    169 Clover Hill Dr, Vineyard Haven, MA 02568
    /42

    $1,350,000

    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft

    169 Clover Hill Dr, Vineyard Haven, MA 02568

    Located on a cul-de-sac in a serene neighborhood, this classic Cape-style home sits on a generous 0.86-acre lot less than 1.5 miles from Main Street, Vineyard Haven. The location is ideal—close to restaurants, shopping, and the ferry, yet with enough land to accommodate the existing detached two-car garage and the potential for an Accessory Dwelling Unit. The three-bedroom home offers a

    Stephanie Roache Donnelly + Co.

    169 Clover Hill Dr, Vineyard Haven, MA 02568
  • 223 Sandpiper Lane Vh405, Tisbury, MA 02568
    223 Sandpiper Lane Vh405, Tisbury, MA 02568
    223 Sandpiper Lane Vh405, Tisbury, MA 02568
    /17

    $12,000 total monthly price

    • 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
  • 26 Mill Hill Rd Unit 57.2, Edgartown, MA 02539
    26 Mill Hill Rd Unit 57.2, Edgartown, MA 02539
    26 Mill Hill Rd Unit 57.2, Edgartown, MA 02539
    /4

    $2,300,000 Sold Oct 29, 2025

    • Land
    • 1.52 Acres
    • $1,513,158 per Acre
    • 271 Days On Market

    26 Mill Hill Rd Unit 57.2, Edgartown, MA 02539

    PRIME 1.5 ACRE BUILDING LOT IN EDGARTOWN - Seize this opportunity to design and build your very own signature estate in Katama including the possibility of a Main House, Guest House, Garage, Pool, and more! This conforming, R-20 prime building parcel will support EIGHT BEDROOMS (8) with a standard Title 5 septic system. Nestled in an area of fine homes and ideally located on the edge of famed

    Leslie C. Floyd Portfolio Real Estate, Inc.

    26 Mill Hill Rd Unit 57.2, Edgartown, MA 02539
    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,241,450 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,386 Sq Ft

      7 the Aerie, Chilmark, MA 02535

      7 the Aerie, Chilmark, MA 02535
  • 20 Brook Hollow Rd, Vineyard Haven, MA 02568
    20 Brook Hollow Rd, Vineyard Haven, MA 02568
    20 Brook Hollow Rd, Vineyard Haven, MA 02568
    /50

    $1,900,000

    • 4 Beds
    • 3 Baths
    • 2,056 Sq Ft

    20 Brook Hollow Rd, Vineyard Haven, MA 02568

    This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

    Jim Feiner Feiner Real Estate

    20 Brook Hollow Rd, Vineyard Haven, MA 02568
  • 100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
    /40

    $32,500 total monthly price

    • 6 Beds
    • 4.5 Baths
    • 3,222 Sq Ft
    • House for Rent

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

    Karen Overtoom Karen M. Overtoom R.E.

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
  • 26 Mill Hill Rd, Edgartown, MA 02539
    26 Mill Hill Rd, Edgartown, MA 02539
    26 Mill Hill Rd, Edgartown, MA 02539
    /4

    $2,300,000 Sold Oct 29, 2025

    • Land
    • 1.52 Acres
    • $1,513,158 per Acre
    • 267 Days On Market

    26 Mill Hill Rd, Edgartown, MA 02539

    PRIME 1.5 ACRE BUILDING LOT IN EDGARTOWN - Seize this opportunity to design and build your very own signature estate in Katama including the possibility of a Main House, Guest House, Garage, Pool, and more! This conforming, R-20 prime building parcel will support EIGHT BEDROOMS (8) with a standard Title 5 septic system. Nestled in an area of fine homes and ideally located on the edge of famed

    Leslie Floyd Portfolio Properties

    26 Mill Hill Rd, Edgartown, MA 02539
    • 5 Bold Meadow Cir, Edgartown, MA 02539
      5 Bold Meadow Cir, Edgartown, MA 02539
      5 Bold Meadow Cir, Edgartown, MA 02539
      /23

      Est $2,664,048 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,252 Sq Ft

      5 Bold Meadow Cir, Edgartown, MA 02539

      5 Bold Meadow Cir, Edgartown, MA 02539
  • 35 Mariners Way, Edgartown, MA 02539
    35 Mariners Way, Edgartown, MA 02539
    35 Mariners Way, Edgartown, MA 02539
    /32

    $2,095,000

    • 4 Beds
    • 2.5 Baths
    • 2,706 Sq Ft

    35 Mariners Way, Edgartown, MA 02539

    35 Mariner’s Way is sited on nearly a half acre lot and lies within walking distance to Edgartown Village shops, restaurants, galleries, and inns and Sheriff’s Meadow conservation land. This 4 bedroom, 2 1⁄2 bath home features a large living room and formal dining room, chef’s kitchen with two ovens and wine room/pantry, and a spacious family room with a gas fireplace. There are two ensuite

    Russell Maloney Russell Maloney Real Estate

    35 Mariners Way, Edgartown, MA 02539
  • 2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    /33

    $22,000 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, 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. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • 140 Longview Rd, Vineyard Haven, MA 02568
    140 Longview Rd, Vineyard Haven, MA 02568
    140 Longview Rd, Vineyard Haven, MA 02568
    /25

    $1,125,000 Sold Oct 28, 2025

    • 1,432 Sq Ft
    • $786/SF
    • 97 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1964

    140 Longview Rd, Vineyard Haven, MA 02568

    Nestled in the hills of Longview, less than 1 mile from beautiful Lambert's Cove Beach, this 3-bedroom retreat is a cozy year-round home or an airy summer getaway - whatever your needs might be. The vaulted ceilings throughout the home allow it to live much larger than its square footage - and the expansive front deck stretches the living space all through the spring, summer and even fall

    Candy DaRosa Feiner Real Estate

    140 Longview Rd, Vineyard Haven, MA 02568
    • 11 Cummings Way, Edgartown, MA 02539
      11 Cummings Way, Edgartown, MA 02539
      11 Cummings Way, Edgartown, MA 02539
      /42

      Not Listed For Sale

      • 6 Beds
      • 8 Baths
      • 4,617 Sq Ft

      11 Cummings Way, Edgartown, MA 02539

      11 Cummings Way, Edgartown, MA 02539
  • 36 Boylston Dr, Edgartown, MA 02539
    36 Boylston Dr, Edgartown, MA 02539
    36 Boylston Dr, Edgartown, MA 02539
    /7

    $475,000

    • Land
    • 0.52 Acre
    • $913,462 per Acre

    36 Boylston Dr, Edgartown, MA 02539

    Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    36 Boylston Dr, Edgartown, MA 02539
  • 31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    /20

    $16,800 total monthly price

    • 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
  • 211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    /17

    $1,200,000 Sold Oct 28, 2025

    • 1,680 Sq Ft
    • $714/SF
    • 209 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1987

    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

    MULTIFAMILY OPPORTUNITYA wonderful compound on the outskirts of town. Set nicely back off the Edgartown Road, the existing home has 4/5 comfortable bedrooms and 2 baths on a nice 1-acre parcel with a good sense of privacy. Behind the home is a fire pit, a shed and another septic system already installed that will serve an additional 5 bedrooms! This property is on a trail to the Bare Hill

    Jim Feiner Feiner Real Estate

    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    • 225 Bigelow Rd, Vineyard Haven, MA 02568
      225 Bigelow Rd, Vineyard Haven, MA 02568
      225 Bigelow Rd, Vineyard Haven, MA 02568
      /32

      Est $4,566,360 Not Listed For Sale

      • 5 Beds
      • 8 Baths
      • 5,305 Sq Ft

      225 Bigelow Rd, Vineyard Haven, MA 02568

      225 Bigelow Rd, Vineyard Haven, MA 02568
  • 36 Boylston Dr Unit 1.329, Edgartown, MA 02539
    36 Boylston Dr Unit 1.329, Edgartown, MA 02539
    36 Boylston Dr Unit 1.329, Edgartown, MA 02539
    /8

    $475,000

    • Land
    • 0.52 Acre
    • $913,462 per Acre

    36 Boylston Dr Unit 1.329, Edgartown, MA 02539

    Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

    Mark Jenkins Wallace & Co. Sotheby's

    36 Boylston Dr Unit 1.329, Edgartown, MA 02539
  • 384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    /31

    $40,000 total monthly price

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • 94 Menemsha Inn Rd, Chilmark, MA 02535
    94 Menemsha Inn Rd, Chilmark, MA 02535
    94 Menemsha Inn Rd, Chilmark, MA 02535
    /44

    $8,178,500 Sold Oct 27, 2025

    • 4,104 Sq Ft
    • $1,993/SF
    • 38 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2001

    94 Menemsha Inn Rd, Chilmark, MA 02535

    Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large

    Julianna Flanders Flanders Real Estate

    94 Menemsha Inn Rd, Chilmark, MA 02535
    • 3 Duarte Cir, Edgartown, MA 02539
      3 Duarte Cir, Edgartown, MA 02539
      3 Duarte Cir, Edgartown, MA 02539
      /7

      Est $4,982,107 Not Listed For Sale

      • 6 Beds
      • 7 Baths
      • 6,783 Sq Ft

      3 Duarte Cir, Edgartown, MA 02539

      3 Duarte Cir, Edgartown, MA 02539
  • 21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    /32

    $560,000

    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

    Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

    Diana Gilmore Island Real Estate

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
  • 19 Lake Rd, Chilmark, MA 02535
    19 Lake Rd, Chilmark, MA 02535
    19 Lake Rd, Chilmark, MA 02535
    /32

    $42,000 total monthly price

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • 26 Winne Ave, Vineyard Haven, MA 02568
    26 Winne Ave, Vineyard Haven, MA 02568
    26 Winne Ave, Vineyard Haven, MA 02568
    /39

    $1,470,000 Sold Oct 27, 2025

    • 1,620 Sq Ft
    • $907/SF
    • 23 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2007

    26 Winne Ave, Vineyard Haven, MA 02568

    Welcome to your dream home just a short walk to the lagoon. This home offers easy access for dropping a kayak or taking a refreshing afternoon dip from a public access point. Discover this charming home nestled on a corner lot within a serene neighborhood. This beach home has an updated kitchen and bathrooms. The kitchen is equipped with new appliances and gorgeous quartz countertops, making it a

    Joe & Nicole Holland Vineyard Dream Realty LLC

    26 Winne Ave, Vineyard Haven, MA 02568
    • 21 Bold Meadow Ln, Edgartown, MA 02539
      21 Bold Meadow Ln, Edgartown, MA 02539
      21 Bold Meadow Ln, Edgartown, MA 02539
      /20

      Est $1,723,617 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,971 Sq Ft

      21 Bold Meadow Ln, Edgartown, MA 02539

      21 Bold Meadow Ln, Edgartown, MA 02539
  • 31 Butlers Cove Rd, Edgartown, MA 02539
    31 Butlers Cove Rd, Edgartown, MA 02539
    31 Butlers Cove Rd, Edgartown, MA 02539
    /47

    $5,500,000

    • 4 Beds
    • 2 Baths
    • 2,808 Sq Ft

    31 Butlers Cove Rd, Edgartown, MA 02539

    This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 1910 as one of the first houses on the storied 200-acre farm with over 2,000 ft of private Atlantic

    Gerrett Conover Landvest MV

    31 Butlers Cove Rd, Edgartown, MA 02539
  • 36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    /35

    $22,000 total monthly price

    • 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
  • 79 E Cape Pogue Ave, Edgartown, MA 02539
    79 E Cape Pogue Ave, Edgartown, MA 02539
    79 E Cape Pogue Ave, Edgartown, MA 02539
    /19

    $975,000 Sold Oct 24, 2025

    • 1,092 Sq Ft
    • $893/SF
    • 6 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 2000

    79 E Cape Pogue Ave, Edgartown, MA 02539

    CHAPPY CAPE — TWO BEDROOM HIDEAWAY Step into your own slice of Chappy serenity with this sweet and stylish 2-bedroom Cape-style home—an affectionate wink to classic New England charm, with clean lines, a comfortable footprint, and room to play. Perched on Chappaquiddick Island, a slender peninsula (or island, depending on the tides) just off the eastern flank of Martha’s Vineyard. Connected by

    Leslie C. Floyd Portfolio Real Estate, Inc.

    79 E Cape Pogue Ave, Edgartown, MA 02539
    • 10 Codman Spring Rd, Edgartown, MA 02539
      10 Codman Spring Rd, Edgartown, MA 02539
      10 Codman Spring Rd, Edgartown, MA 02539
      /32

      Est $2,694,607 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,101 Sq Ft

      10 Codman Spring Rd, Edgartown, MA 02539

      10 Codman Spring Rd, Edgartown, MA 02539
  • 344 Greenwood Ave, Vineyard Haven, MA 02568
    344 Greenwood Ave, Vineyard Haven, MA 02568
    344 Greenwood Ave, Vineyard Haven, MA 02568
    /20

    $1,300,000

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft

    344 Greenwood Ave, Vineyard Haven, MA 02568

    This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles

    Katie Donahue Sandpiper Realty

    344 Greenwood Ave, Vineyard Haven, MA 02568
  • 17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    /39

    $110,000 total monthly price

    • 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
  • 9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    /39

    $2,225,000 Sold Oct 24, 2025

    • 2,968 Sq Ft
    • $750/SF
    • 98 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1994

    9 Beetlebung Grove Way, Chilmark, MA 02535

    Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

    Stephanie Roache Donnelly + Co.

    9 Beetlebung Grove Way, Chilmark, MA 02535
    • 46 Windsor Dr, Edgartown, MA 02539
      46 Windsor Dr, Edgartown, MA 02539
      46 Windsor Dr, Edgartown, MA 02539
      /19

      Est $1,286,014 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft

      46 Windsor Dr, Edgartown, MA 02539

      46 Windsor Dr, Edgartown, MA 02539
  • 22 Clark Ave, Vineyard Haven, MA 02568
    22 Clark Ave, Vineyard Haven, MA 02568
    22 Clark Ave, Vineyard Haven, MA 02568
    /30

    $985,000

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    22 Clark Ave, Vineyard Haven, MA 02568

    A Sweet Spot to call Home. West Chop charms are many in this delightful setting. Acres upon acres of nearby conservation trails make walks, hikes and bike rides an easy daily appeal. Equal distance to Owen Little Way town beach and Vineyard Haven Main Street shops and amenities as well as harbor and ferry port. This move-in ready Clark Avenue abode offers the magic formula of single level living

    Helena Kirschenbaum Studio Realty

    22 Clark Ave, Vineyard Haven, MA 02568
  • 44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    /19

    $24,000 total monthly price

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • 25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    /12

    $1,250,000 Sold Oct 23, 2025

    • Land
    • 4.12 Acres
    • $303,398 per Acre
    • 127 Days On Market

    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

    This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property is

    Abby Rabinovitz Tea Lane Associates

    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    • 1 Skippers View Ln, Aquinnah, MA 02535
      1 Skippers View Ln, Aquinnah, MA 02535
      1 Skippers View Ln, Aquinnah, MA 02535
      /22

      Est $4,493,868 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,905 Sq Ft

      1 Skippers View Ln, Aquinnah, MA 02535

      1 Skippers View Ln, Aquinnah, MA 02535
  • 24 School St, Oak Bluffs, MA 02557
    24 School St, Oak Bluffs, MA 02557
    24 School St, Oak Bluffs, MA 02557
    /26

    $875,000

    • 2 Beds
    • 1 Bath
    • 861 Sq Ft

    24 School St, Oak Bluffs, MA 02557

    An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining

    Stephanie Roache Donnelly + Co.

    24 School St, Oak Bluffs, MA 02557
  • 29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    /32

    $36,000 total monthly price

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • 111 N Water St, Edgartown, MA 02539
    111 N Water St, Edgartown, MA 02539
    111 N Water St, Edgartown, MA 02539
    /42

    $15,725,000 Sold Oct 22, 2025

    • 3,606 Sq Ft
    • $4,361/SF
    • 41 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 1850

    111 N Water St, Edgartown, MA 02539

    Historic captain’s home circa 1850, brilliantly renovated by architect Patrick Ahearn in 2002, on coveted North Water Street. Enjoy sweeping 180 Edgartown Harbor views from bright, sunlit living spaces with heart pine floors and custom millwork. An open-concept first floor flows to an 18x29' mahogany deck, perfect for al fresco dining and entertaining. The rare double-wide lot offers a lawn

    Wendy Harman Compass

    111 N Water St, Edgartown, MA 02539
    • 11 Deacon Vincent Way, Edgartown, MA 02539
      11 Deacon Vincent Way, Edgartown, MA 02539
      /2

      Est $1,747,791 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,250 Sq Ft

      11 Deacon Vincent Way, Edgartown, MA 02539

      11 Deacon Vincent Way, Edgartown, MA 02539

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