4,094

Chilmark, MA Homes

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  • /13

    $1,575,000

    $70K PRICE DROP
    • Land
    • 3.32 Acres
    • $474,398 per Acre

    26 Flint Hill Rd, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no

    Dawn Bellante Sandpiper Realty, Inc.

    26 Flint Hill Rd, West Tisbury, MA 02575
  • /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
  • /44

    $8,178,500

    Sold Oct 27, 2025

    94 Menemsha Inn Rd, Chilmark, MA 02535

    • 6 Beds
    • 4.5 Baths
    • 4,104 Sq Ft
    • Built 2001

    Last Sold Summary

    • 3% Below List Price
    • $1,993/SF
    • 38 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    94 Menemsha Inn Rd, Chilmark, MA 02535
    • /23

      Not Listed For Sale

      51 Blueberry Ridge Ln, Chilmark, MA 02535

      • 6 Beds
      • 3.5 Baths
      • 2,229 Sq Ft
      • Built 1989
      51 Blueberry Ridge Ln, Chilmark, MA 02535

      Last Sold Summary

      • 11 Days On Market

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

  • /48

    $5,850,000

    Pending
    • 6 Beds
    • 6.5 Baths
    • 3,608 Sq Ft

    9 Ridge Hill Rd, Chilmark, MA 02535

    Set on three beautifully landscaped acres, this exceptional six-bedroom property offers a seamless blend of modern farmhouse design and timeless Vineyard appeal. The estate features a five-bedroom, five and a half bathroom main residence, along with a one-bedroom guest suite above a two-car barn and 16' x 40' swimming pool. This thoughtfully designed post and beam main home was featured in

    Alexis Holden Tea Lane Associates

    9 Ridge Hill Rd, Chilmark, MA 02535
  • /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
  • /34

    $2,475,000

    Sold Sep 05, 2025

    31 N Slope Ln, Chilmark, MA 02535

    • 4 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • Built 1983

    Last Sold Summary

    • 15% Below List Price
    • $1,076/SF
    • 117 Days On Market

    Current Estimated Value $2,936,209

    Last Listing Agent Bill Rossi Studio Realty

    31 N Slope Ln, Chilmark, MA 02535
    • /2

      Est $1,807,932

      Not Listed For Sale

      323 Lamberts Cove Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,144 Sq Ft
      • Built 1900
      323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • /53

    $1,700,000

    $145K PRICE DROP Under Contract
    • 5 Beds
    • 3 Baths
    • 2,552 Sq Ft

    10 Danls Way, West Tisbury, MA 02575

    Historic West Tisbury farmhouse with detached guest cottage on 1.27 acres in the heart of West Tisbury. Just moments from Alley's General Store, 7a Foods, North Tisbury Village, and a short drive to beaches and both up- and downd Island destinations. This property presents a rare opportunity for a family compound, multi-generational living, or investment with rental income potential.The

    Emma Bryant Studio Realty

    10 Danls Way, West Tisbury, MA 02575
  • /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
  • /36

    $3,700,000

    Sold May 28, 2026

    122 Old Farm Rd, Chilmark, MA 02535

    • 5 Beds
    • 4 Baths
    • 3,413 Sq Ft
    • Built 1790

    Last Sold Summary

    • 38% Below List Price
    • $1,084/SF
    • 261 Days On Market

    Current Estimated Value $1,631,500

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
    • /31

      Est $2,523,816

      Not Listed For Sale

      106 Panhandle Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 3,310 Sq Ft
      • Built 1991
      106 Panhandle Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 80 Days On Market

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

  • /39

    $2,400,000

    • 7 Beds
    • 4 Baths
    • 2,232 Sq Ft

    220 North Rd, Chilmark, MA 02535

    Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Line Woods Preserve, and then all the way to Tea Lane Farm. A two-thirds of an acre conservation

    David Lott Vineyard Open House Real Estate

    220 North Rd, Chilmark, MA 02535
  • /20

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    BOOKING SUMMER 2027 AND FALL/SPRING '26 SPRING '27 Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • /44

    $1,525,000

    Sold Feb 03, 2026

    105 Stoney Hill Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 2.5 Baths
    • 1,815 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $840/SF
    • 60 Days On Market

    Current Estimated Value $1,737,716

    Last Listing Agent Lisa Da Silva Signal House Group at Compass

    105 Stoney Hill Rd, Vineyard Haven, MA 02568
    • /20

      Est $1,308,948

      Not Listed For Sale

      46 Old Coach Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,374 Sq Ft
      • Built 1981
      46 Old Coach Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Lisa Gilberto C McManus Realty Group

  • /38

    $16,000,000

    • Land
    • 46 Acres
    • $347,826 per Acre

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535

    Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff’s Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom seasonal home sits on one lot with two detached studios alongside. Close to nature, this home

    Abby Rabinovitz Tea Lane Associates

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
  • /23

    $24,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,637 Sq Ft
    • House for Rent

    56 Chilmark Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • /19

    $1,330,000

    Sold Oct 17, 2025

    32 MacHipscat Trail, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,404 Sq Ft
    • Built 1983

    Last Sold Summary

    • 11% Below List Price
    • $947/SF
    • 112 Days On Market

    Current Estimated Value $1,417,863

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

    32 MacHipscat Trail, Vineyard Haven, MA 02568
    • /35

      Est $2,161,383

      Not Listed For Sale

      159 Charles Neck Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,995 Sq Ft
      • Built 2003
      159 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Wendy Harman Compass

  • /30

    $3,995,000

    • 6 Beds
    • 3.5 Baths
    • 3,070 Sq Ft

    30 & 40 Elias Ln, West Tisbury, MA 02575

    A beautiful pastoral, private family compound in West Tisbury, on 7.5 glorious acres of meadow comprised of two parcels, offers a rare opportunity. Elias Lane is a quiet country road tucked behind Misty Meadows and just minutes from West Tisbury village. The property features a lovingly maintained 4 BDR main house with a well appointed kitchen, recent sun porch addition an elegant Lew French

    Elissa Lash Tea Lane Associates

    30 & 40 Elias Ln, West Tisbury, MA 02575
  • /18

    $10,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,439 Sq Ft
    • House for Rent

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

    Karen Overtoom Karen M. Overtoom R.E.

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
  • /12

    $1,250,000

    Sold Oct 23, 2025

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

    • Land
    • 4.12 Acres
    • $303,398 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 127 Days On Market

    Last Listing Agent Abby Rabinovitz Tea Lane Associates

    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    • /2

      Est $1,988,353

      Not Listed For Sale

      163 Charles Neck Way, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 2,508 Sq Ft
      • Built 1987
      163 Charles Neck Way, Vineyard Haven, MA 02568

  • /32

    $1,140,000

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,059 Sq Ft

    4 Rock Pond, West Tisbury, MA 02575

    4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the

    Trish Lyman Compass | Point B

    4 Rock Pond, West Tisbury, MA 02575
  • /10

    $8,500 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

    Karen Overtoom Karen M. Overtoom R.E.

    29 Bea Lane Wt160 Unit 1, 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 $1,285,685

    Last Listing Agent Kathleen Kendrick Kathleen Kendrick

    52 Old Coach Rd, Vineyard Haven, MA 02568
    • /30

      Est $2,937,173

      Not Listed For Sale

      23 Alex Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 5 Baths
      • 2,926 Sq Ft
      • Built 2004
      23 Alex Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /39

    $3,495,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    64 Christiantown Rd, Vineyard Haven, MA 02568

    This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home

    Karen Overtoom Karen M. Overtoom R.E.

    64 Christiantown Rd, Vineyard Haven, MA 02568
  • /19

    $30,000 Per Month

    • 5 Beds
    • 4 Baths
    • 3,600 Sq Ft
    • House for Rent

    37 Sachem Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

    Karen Overtoom Karen M. Overtoom R.E.

    37 Sachem Cir, 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 $1,574,920

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

    19 S Vine Ln, Vineyard Haven, MA 02568
    • /20

      Est $1,354,941

      Not Listed For Sale

      225 Longview Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,730 Sq Ft
      • Built 1977
      225 Longview Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /31

    $1,140,000

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,059 Sq Ft

    4 Rock Pond Rd, Vineyard Haven, MA 02568

    4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the home

    Patricia Lyman Compass

    4 Rock Pond Rd, Vineyard Haven, MA 02568
  • /19

    $24,000 Per Month

    • 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
  • /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
    • /2

      Est $2,295,585

      Not Listed For Sale

      59 Field View Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 3,269 Sq Ft
      • Built 1975
      59 Field View Ln, Vineyard Haven, MA 02568

  • /25

    $6,950,000

    $350K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 3,539 Sq Ft

    65 Carl's Way, West Tisbury, MA 02568

    Stylized Private Waterfront Retreat close to townperched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes

    Jill Napior Tea Lane Associates

    65 Carl's Way, West Tisbury, MA 02568
  • /39

    $46,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    99 Pond Road Wt104, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

    Karen Overtoom Karen M. Overtoom R.E.

    99 Pond Road Wt104, 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 $4,107,387

    Last Listing Agent Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
    • /47

      Est $1,717,370

      Not Listed For Sale

      21 Coffins Field Rd, Edgartown, MA 02539

      • 5 Beds
      • 3 Baths
      • 1,822 Sq Ft
      • Built 2003
      21 Coffins Field Rd, Edgartown, MA 02539

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Helena Kirschenbaum Studio Realty

Showing Results 81 - 120, Page 3 of 18

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