4,094

Chilmark, MA Homes

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  • /7

    $2,000,000

    • Land
    • 21,801 Sq Ft
    • $3,996,004 per Acre

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568

    1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

    Peter Cronig Cronigs Real Estate

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
  • /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
  • /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
    • /34

      Not Listed For Sale

      391 Middle Rd, Chilmark, MA 02535

      • 6 Beds
      • 4.5 Baths
      • 3,859 Sq Ft
      • Built 1941
      391 Middle Rd, Chilmark, MA 02535

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /4

    $995,000

    $105K PRICE DROP
    • Land
    • 1 Acre
    • $995,000 per Acre

    25 Coffins Field Rd, Edgartown, MA 02539

    This 1.0-acre parcel is approved by the West Tisbury Board of Health for the construction of a six-bedroom dwelling. Seller is offering a $40,000 credit at closing to assist 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, Inc.

    25 Coffins Field Rd, Edgartown, MA 02539
  • /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
  • /42

    $2,013,500

    Sold Aug 05, 2026

    35 Nat's Farm Ln, West Tisbury, MA 02568

    • 4 Beds
    • 3.5 Baths
    • 2,428 Sq Ft
    • Built 1986

    Last Sold Summary

    • 12% Below List Price
    • $829/SF
    • 79 Days On Market

    Current Estimated Value $2,565,136

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

    35 Nat's Farm Ln, West Tisbury, MA 02568
    • /42

      Est $1,942,284

      Not Listed For Sale

      44 Music St, Vineyard Haven, MA 02568

      • 4 Beds
      • 5 Baths
      • 2,172 Sq Ft
      • Built 1984
      44 Music St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /17

    $2,695,000

    $505K PRICE DROP
    • Land
    • 19.3 Acres
    • $139,637 per Acre

    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

    A Rare Offering in West Tisbury — Over 19 Acres of Opportunity with approvals in place for a six lot subdivision.An exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island

    Jill Napior Tea Lane Associates

    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
  • /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
  • /48

    $1,375,000

    Sold Jul 20, 2026

    651 State Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 4 Baths
    • 2,516 Sq Ft
    • Built 1880

    Last Sold Summary

    • 8% Below List Price
    • $547/SF
    • 41 Days On Market

    Current Estimated Value $1,537,170

    Last Listing Agent Jim Feiner Feiner Real Estate

    651 State Rd, Vineyard Haven, MA 02568
    • /23

      Est $2,047,455

      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

      Last Listing Agent Julianna Flanders Flanders Real Estate

  • /25

    $1,450,000

    $100K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 2,266 Sq Ft

    345 North Rd, Chilmark, MA 02535

    This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected

    Jessica Campbell Flanders Real Estate

    345 North Rd, Chilmark, MA 02535
  • /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
  • /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 $2,046,848

    Last Listing Agent Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535
    • /6

      Est $2,839,914

      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

      Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  • /42

    $4,995,000

    $405K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,710 Sq Ft

    35 S Bowl Rd, Chilmark, MA 02535

    Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking

    Tina Miller Donnelly + Co.

    35 S Bowl 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
  • /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 $4,722,902

    Last Listing Agent Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
    • /18

      Est $1,378,339

      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

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

  • /14

    $2,725,000

    • Land
    • 7.6 Acres
    • $358,553 per Acre

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

    This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

    Peyton Wallace Studio Realty

    34 Ebens Ln Unit 20 and 22, 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
  • /37

    $4,350,000

    Sold Jan 07, 2026

    146 Quansoo Rd, Chilmark, MA 02535

    • 5 Beds
    • 3 Baths
    • 3,440 Sq Ft
    • Built 1988

    Last Sold Summary

    • 21% Below List Price
    • $1,265/SF
    • 155 Days On Market

    Current Estimated Value $4,659,512

    Last Listing Agent Meg Bodnar Tea Lane Associates

    146 Quansoo 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

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

  • /20

    $1,450,000

    Under Contract
    • 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

    Julianna Flanders Flanders Real Estate

    10 Abels Neck Rd, Chilmark, MA 02535
  • /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
  • /17

    $1,790,000

    Sold Sep 23, 2025

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

    • Land
    • 3.3 Acres
    • $542,424 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 77 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    • /35

      Est $1,845,655

      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

      Last Listing Agent Wendy Harman Compass | Point B

  • /33

    $1,325,000

    $575K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,056 Sq Ft

    20 Brook Hollow Rd, Vineyard Haven, MA 02568

    Fantastic opportunity for a great locationb and a spacious custom designed home! This house 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

    Jim Feiner Feiner Real Estate

    20 Brook Hollow Rd, Vineyard Haven, MA 02568
  • /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
  • /28

    $2,550,000

    Sold Oct 02, 2025

    10 Mollys Way, Chilmark, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft
    • Built 1926

    Last Sold Summary

    • 14% Below List Price
    • $1,673/SF
    • 130 Days On Market

    Current Estimated Value $2,591,106

    Last Listing Agent Peyton Wallace Studio Realty

    10 Mollys Way, Chilmark, MA 02535
    • /2

      Est $1,397,297

      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

  • /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
  • /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
  • /37

    $1,925,000

    Sold Aug 28, 2025

    50 Bradley Martin Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $1,109/SF
    • 0 Days On Market

    Current Estimated Value $1,869,855

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

    50 Bradley Martin Rd, Vineyard Haven, MA 02568
    • /26

      Est $1,093,848

      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

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /56

    $16,250,000

    • 6 Beds
    • 8 Baths
    • 8,648 Sq Ft

    25 Brickyard Rd, Chilmark, MA 02535

    Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets.

    Peyton Wallace Studio Realty LLC

    25 Brickyard Rd, Chilmark, MA 02535
  • /38

    $1,850,000

    Sold Sep 09, 2025

    234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 1,918 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Below List Price
    • $965/SF
    • 41 Days On Market

    Current Estimated Value $1,709,339

    Last Listing Agent Stephanie Roache Donnelly + Co.

    234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    • /28

      Est $1,318,233

      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

      Last Listing Agent Joanna Fairchild eXp Realty

  • /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

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