Chilmark, MA Homes

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  $4,850,000 Pending

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

  146 Quansoo Rd, Chilmark, MA 02535

  Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

  Meg Bodnar Tea Lane Associates

  146 Quansoo Rd, Chilmark, MA 02535
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  /2

  $10,000 total monthly price

  • 6 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  15 Crowell Lane Wt119, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

  Karen Overtoom Karen M. Overtoom R.E.

  15 Crowell Lane Wt119, West Tisbury, MA 02575
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  /21

  $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 $1,402,208

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

  19 S Vine Ln, Vineyard Haven, MA 02568
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  /43

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,674 Sq Ft

  39 Sarita Walker Rd, Vineyard Haven, MA 02568

  39 Sarita Walker Rd, Vineyard Haven, MA 02568
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  $22,950,000

  • 7 Beds
  • 8.5 Baths
  • 8,200 Sq Ft

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568

  This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design,

  Gerrett Conover Landvest MV

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568
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  /25

  $13,600 total monthly price

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft
  • House for Rent

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

  Karen Overtoom Karen M. Overtoom R.E.

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
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  /23

  $1,500,000 Sold Sep 25, 2025

  190 Longview Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1995

  Last Sold Summary

  • 15% Below List Price
  • $1,071/SF
  • 43 Days On Market

  Last Listing Agent Kathleen Kendrick Kendrick Real Estate

  190 Longview Rd, Vineyard Haven, MA 02568
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  /41

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  566 Scrubby Neck Rd, Vineyard Haven, MA 02568

  566 Scrubby Neck Rd, Vineyard Haven, MA 02568
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  /36

  $2,500,000

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft

  16 South Rd, Chilmark, MA 02535

  Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been updated

  Michele Casavant Vineyard Village Realty

  16 South Rd, Chilmark, MA 02535
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  /18

  $10,000 total monthly price

  • 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
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  /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
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  /15

  Est $2,614,745 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 512 Sq Ft

  119 Old Thumb Point Rd, Vineyard Haven, MA 02568

  119 Old Thumb Point Rd, Vineyard Haven, MA 02568
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  /7

  $2,500,000

  • Land
  • 1.4 Acres
  • $1,785,714 per Acre

  2 Other House Rd Unit 173, Chilmark, MA 02535

  Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

  Russell Maloney Russell Maloney Real Estate

  2 Other House Rd Unit 173, Chilmark, MA 02535
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  $46,000 total monthly price

  • 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
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  /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 $2,543,751

  Last Listing Agent Bill Rossi Studio Realty

  31 N Slope Ln, Chilmark, MA 02535
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  /13

  Est $4,498,963 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  144 Pond View Farm Rd, Vineyard Haven, MA 02568

  144 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /63

  $5,000,000

  • 6 Beds
  • 3.5 Baths
  • 3,312 Sq Ft

  31 Josiah Sachem Way, Vineyard Haven, MA 02568

  An inspirational Oasis - come unwind and behold what this secluded multi-home compound has to offer. With two driveways and an open wildflower field bordered with plantings, the main house, studio barn, guesthouse and in-ground pool area at this private retreat are beautifully positioned and landscaped. Each structure is available for year-round use with abundant parking and unique charms.

  Helena Kirschenbaum Studio Realty

  31 Josiah Sachem Way, Vineyard Haven, MA 02568
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  $12,000 total monthly price

  • 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
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  /51

  $4,850,000 Sold Dec 05, 2025

  49 Gosnold's Way, Chilmark, MA 02535

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $1,199/SF
  • 115 Days On Market

  Last Listing Agent Meg Bodnar Tea Lane Associates

  49 Gosnold's Way, Chilmark, MA 02535
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  /42

  Est $1,939,115 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,172 Sq Ft

  44 Music St, Vineyard Haven, MA 02568

  44 Music St, Vineyard Haven, MA 02568
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  /26

  $1,345,000

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  9 Galway Rd, Vineyard Haven, MA 02568

  Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

  Julianna Flanders Flanders Real Estate

  9 Galway Rd, Vineyard Haven, MA 02568
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  /41

  $14,500 total monthly price

  • 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

  Karen Overtoom Karen M. Overtoom R.E.

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

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

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  /23

  Est $2,085,280 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,370 Sq Ft

  50 Campbell Rd, Vineyard Haven, MA 02568

  50 Campbell Rd, Vineyard Haven, MA 02568
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  $3,500,000

  • 3 Beds
  • 4 Baths
  • 2,500 Sq Ft

  27 Clambelly Rd, Chilmark, MA 02535

  A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

  Julianna Flanders Flanders Real Estate

  27 Clambelly Rd, Chilmark, MA 02535
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  /22

  $3,000 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,703 Sq Ft
  • House for Rent

  41 Oak Lane Wt147, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

  Karen Overtoom Karen M. Overtoom R.E.

  41 Oak Lane Wt147, West Tisbury, MA 02575
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  $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
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  /6

  Est $2,980,493 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,935 Sq Ft

  71 Runner Rd, Vineyard Haven, MA 02568

  71 Runner Rd, Vineyard Haven, MA 02568
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  /2

  $799,000

  • Land
  • 0.91 Acre
  • $878,022 per Acre

  22 Bramble Path, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been done that supports a four bedroom title five system. It is the buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path, West Tisbury, MA 02568
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  /9

  $10,800 total monthly price

  • 4 Beds
  • 2 Baths
  • 702 Sq Ft
  • House for Rent

  141 N Rd Ch202, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

  Karen Overtoom Karen M. Overtoom R.E.

  141 N Rd Ch202, Chilmark, MA 02535
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  $1,200,180 Sold Aug 12, 2025

  110 Otis Bassett Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1972

  Last Sold Summary

  • $1,049/SF
  • 13 Days On Market

  Current Estimated Value $1,084,267

  Last Listing Agent Jen O'Hanlon Compass | The O'Hanlon Group

  110 Otis Bassett Rd, Vineyard Haven, MA 02568
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  /31

  Est $1,312,470 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 855 Sq Ft

  16 Elias Ln, Vineyard Haven, MA 02568

  16 Elias Ln, Vineyard Haven, MA 02568
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  /60

  $14,000,000

  • 6 Beds
  • 7 Baths
  • 6,967 Sq Ft

  8 Snail Rd, Chilmark, MA 02535

  This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

  Alyssa Halisky Wallace & Co. Sotheby's

  8 Snail Rd, Chilmark, MA 02535
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  /8

  $7,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • House for Rent

  2 Paddock Cir, Chilmark, MA 02535

  Karen Overtoom Karen M. Overtoom R.E.

  2 Paddock Cir, Chilmark, MA 02535
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  /21

  $435,000 Sold Aug 26, 2025

  0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

  • Land
  • 0.1 Acre
  • $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
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  Est $1,051,339 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,182 Sq Ft

  4 Elias Ln, Vineyard Haven, MA 02568

  4 Elias Ln, Vineyard Haven, MA 02568
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  /19

  $2,675,000

  • 3 Beds
  • 1.5 Baths
  • 1,540 Sq Ft

  5 Ocean View Farm Rd, Chilmark, MA 02535

  Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

  Natalie Conroy Conroy & Company R.E., Inc.

  5 Ocean View Farm Rd, Chilmark, MA 02535
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  $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 Real Estate, Inc.

  25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
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  Est $1,299,006 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  175 Oak Ln, Vineyard Haven, MA 02568

  175 Oak Ln, Vineyard Haven, MA 02568
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  $1,495,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft

  42 Hidden Village Rd, Vineyard Haven, MA 02568

  Nestled off Hidden Village Road on 2.1 private wooded acres, this spacious 4-bedroom, 2-bath home offers the perfect blend of peace and convenience--just 1.5 miles from Lambert's Cove Beach and a short distance to Ice House Pond. Inside, enjoy an open-concept layout with cathedral ceilings, skylights, and an abundance of natural light. Sliding doors lead to a sunny, south-facing deck with

  Sheila Morse Island Real Estate

  42 Hidden Village Rd, Vineyard Haven, MA 02568

Showing Results 121 - 160, Page 4 of 18