4,264

Aquinnah, MA Homes

Section Image
  • /20

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,749 Sq Ft

    10 Abels Neck Rd, Chilmark, MA 02535

    Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway

    Julianna Flanders Flanders Real Estate

    10 Abels Neck Rd, Chilmark, MA 02535
  • /12

    $6,180 Per Month

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • House for Rent

    44 Music St Wt153, West Tisbury, MA 02575

    PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

    Karen Overtoom Karen M. Overtoom R.E.

    44 Music St Wt153, West Tisbury, MA 02575
  • /29

    $1,150,000

    Sold Dec 16, 2025

    52 Old Coach Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Below List Price
    • $887/SF
    • 18 Days On Market

    Current Estimated Value $1,197,612

    Last Listing Agent Kathleen Kendrick Kathleen Kendrick

    52 Old Coach Rd, Vineyard Haven, MA 02568
    • /23

      Est $1,998,751

      Not Listed For Sale

      50 Campbell Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,370 Sq Ft
      • Built 1994
      50 Campbell Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 16 Days On Market

  • /39

    $7,350,000

    • 4 Beds
    • 4.5 Baths
    • 3,490 Sq Ft

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, Chilmark, MA 02535
  • /29

    $10,900 Per Month

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    58 Forest Rd Wt140, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

    Karen Overtoom Karen M. Overtoom R.E.

    58 Forest Rd Wt140, West Tisbury, MA 02575
  • /21

    $435,000

    Sold Aug 26, 2025

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

    • Land
    • 4,356 Sq Ft
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 20 Days On Market

    Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    • /6

      Est $2,952,719

      Not Listed For Sale

      71 Runner Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,935 Sq Ft
      • Built 1982
      71 Runner Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /33

    $1,575,000

    $325K PRICE DROP
    • 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
  • /34

    $12,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft
    • House for Rent

    267 Great Plains Road Wt117, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

    Karen Overtoom Karen M. Overtoom R.E.

    267 Great Plains Road Wt117, West Tisbury, MA 02575
  • /22

    $1,325,000

    Sold Aug 29, 2025

    19 S Vine Ln, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,982 Sq Ft
    • Built 1992

    Last Sold Summary

    • 17% Below List Price
    • $669/SF
    • 89 Days On Market

    Current Estimated Value $1,461,153

    Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's

    19 S Vine Ln, Vineyard Haven, MA 02568
    • /18

      Est $1,316,181

      Not Listed For Sale

      108 Charles Neck Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,512 Sq Ft
      • Built 1986
      108 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 99 Days On Market

  • /6

    $995,000

    $105K PRICE DROP
    • Land
    • 43,472 Sq Ft
    • $996,994 per Acre

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539

    Per Board of Health approval, this 1.0-acre parcel is approved for the construction of a six-bedroom dwelling. Seller is offering a $40,000 credit at closing to assist the buyer with costs associated with the design, permitting, and installation of the septic system. The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently

    Casandra Hyland Sandpiper Realty

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
  • /28

    $38,000 Per Month

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

    17 Otis Bassett Rd, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

    Karen Overtoom Karen M. Overtoom R.E.

    17 Otis Bassett Rd, West Tisbury, MA 02575
  • /49

    $6,100,000

    Sold Mar 24, 2026

    60 Meetinghouse Rd, Chilmark, MA 02535

    • 6 Beds
    • 8 Baths
    • 5,660 Sq Ft
    • Built 2021

    Last Sold Summary

    • 6% Below List Price
    • $1,078/SF
    • 111 Days On Market

    Last Listing Agent Jim Feiner Feiner Real Estate

    60 Meetinghouse Rd, Chilmark, MA 02535
    • /26

      Not Listed For Sale

      137 Charles Neck Way, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 2,610 Sq Ft
      • Built 1986
      137 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 8 Days On Market

  • /13

    $2,250,000

    $250K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 726 Sq Ft

    18 Allen Farm Rd, Chilmark, MA 02535

    Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered full furnished with exception of some art and a few

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd, Chilmark, MA 02535
  • /22

    $20,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • House for Rent

    709 Old County Rd Wt134, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

    Karen Overtoom Karen M. Overtoom R.E.

    709 Old County Rd Wt134, West Tisbury, MA 02575
  • /42

    $3,710,000

    Sold Mar 12, 2026

    15 Old Farm Rd, Chilmark, MA 02535

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft
    • Built 2002

    Last Sold Summary

    • 13% Below List Price
    • $1,170/SF
    • 136 Days On Market

    Current Estimated Value $3,907,832

    Last Listing Agent Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
    • /35

      Est $1,768,114

      Not Listed For Sale

      55 Charles Neck Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,654 Sq Ft
      • Built 1984
      55 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 182 Days On Market

  • /4

    $1,449,000

    $251K PRICE DROP Pending
    • Land
    • 3.9 Acres
    • $371,538 per Acre

    34 Ebens Ln, Chilmark, MA 02535

    Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

    Thomas Wallace Wallace & Co. Sotheby's

    34 Ebens Ln, Chilmark, MA 02535
  • /8

    $11,800 Per Month

    • 4 Beds
    • 4 Baths
    • 2,612 Sq Ft
    • House for Rent

    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

    Karen Overtoom Karen M. Overtoom R.E.

    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
  • /9

    $900,000

    Sold Oct 10, 2025

    25 N Vine Ln Unit 70.3, West Tisbury, MA 02568

    • Land
    • 3.73 Acres
    • $241,287 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 462 Days On Market

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
    • /2

      Est $1,335,049

      Not Listed For Sale

      16 Elias Ln, Vineyard Haven, MA 02568

      • 1 Bed
      • 2 Baths
      • 856 Sq Ft
      • Built 1993
      16 Elias Ln, Vineyard Haven, MA 02568

  • /2

    $799,000

    • Land
    • 39,996 Sq Ft
    • $870,181 per Acre

    22 Bramble Path Unit 214, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path Unit 214, West Tisbury, MA 02568
  • /8

    $4,800 Per Month

    • 3 Beds
    • 3 Baths
    • 3,279 Sq Ft
    • House for Rent

    165 Christiantown Rd, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

    Karen Overtoom Karen M. Overtoom R.E.

    165 Christiantown Rd, West Tisbury, MA 02575
  • /44

    $37,000,000

    Sold Jul 10, 2025

    41 Cobbs Hill Rd, Chilmark, MA 02535

    • 8 Beds
    • 5.5 Baths
    • 7,846 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $4,716/SF
    • 39 Days On Market

    Last Listing Agent Brian Dougherty Corcoran Property Advisors

    41 Cobbs Hill Rd, Chilmark, MA 02535
    • /26

      Est $1,080,588

      Not Listed For Sale

      4 Elias Ln, Vineyard Haven, MA 02568

      • 1 Bed
      • 1 Bath
      • 1,182 Sq Ft
      • Built 1977
      4 Elias Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10 Days On Market

  • /30

    $2,995,000

    • 4 Beds
    • 3.5 Baths
    • 2,515 Sq Ft

    300 N Rd 18 Belhaven Way, Chilmark, MA 02535

    Tucked away on 4.4 spectacular acres just off North Road, this one-of-a-kind Chilmark retreat blends timeless Vineyard charm with exceptional privacy. A shaded driveway leads to classic stone walls and cedar gates opening into a beautifully landscaped courtyard. The inviting porch overlooks lush gardens, creating a peaceful outdoor sanctuary. Inside, warm, light-filled living spaces and the

    Bonnie Pierce Wallace & Co. Sotheby's International Realty

    300 N Rd 18 Belhaven Way, Chilmark, MA 02535
  • /32

    $36,000 Per Month

    • 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
  • /48

    $1,775,000

    Sold Nov 07, 2025

    3 Fulling Mill Rd, Chilmark, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $1,027/SF
    • 170 Days On Market

    Current Estimated Value $1,884,275

    Last Listing Agent Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535
    • /28

      Est $1,304,469

      Not Listed For Sale

      175 Oak Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1986
      175 Oak Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19 Days On Market

  • /78

    $35,000,000

    • 8 Beds
    • 8 Baths
    • 6,841 Sq Ft

    146 Quenames Rd, Chilmark, MA 02535

    Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

    Grace Hagerty Grace Hagerty Real Estate Inc

    146 Quenames Rd, Chilmark, MA 02535
  • /41

    $14,500 Per Month

    • 5 Beds
    • 5.5 Baths
    • 3,392 Sq Ft
    • House for Rent

    76 School House Lane Wt101, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions

    Karen Overtoom Karen M. Overtoom R.E.

    76 School House Lane Wt101, West Tisbury, MA 02575
  • /36

    $1,950,000

    Sold Jul 02, 2025

    51 Black Brook Crossing Rd, West Tisbury, MA 02568

    • 4 Beds
    • 2.5 Baths
    • 2,691 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $725/SF
    • 30 Days On Market

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

    51 Black Brook Crossing Rd, West Tisbury, MA 02568
    • /37

      Est $1,220,941

      Not Listed For Sale

      43 Skiffs Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1991
      43 Skiffs Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 32 Days On Market

  • /12

    $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-Holand Sandpiper Realty

    47 Quenames Rd, Chilmark, MA 02535
  • /24

    $4,325,000

    Sold Dec 05, 2025

    18 Homeward Way, Chilmark, MA 02535

    • 5 Beds
    • 2.5 Baths
    • 3,885 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $1,113/SF
    • 8 Days On Market

    Current Estimated Value $4,570,969

    Last Listing Agent Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
    • /49

      Est $1,848,207

      Not Listed For Sale

      75 Skiffs Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,548 Sq Ft
      • Built 1984
      75 Skiffs Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 186 Days On Market

  • /36

    $1,399,000

    Open Sat 10AM - 12PM
    • 4 Beds
    • 2 Baths
    • 1,436 Sq Ft

    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    This coastal contemporary residence is located on a private 1.60-acre lot in West Tisbury, with convenient access to Long Point Wildlife Refuge and access to "Coveted" Lambert's Cove Beach. The home features four bedrooms and two full bathrooms. On the first floor, you'll find two bright bedrooms, a modernized bathroom, and sliders from the living area that lead to a new AZEK deck and enclosed

    Marilyn Moses Ocean Park Realty Inc

    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Showing Results 121 - 160, Page 4 of 18

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