Chilmark, MA Homes

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  $2,475,000

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

  16 South Rd, Chilmark, MA 02535

  Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly

  Michele Casavant Vineyard Village Realty

  16 South Rd, Chilmark, MA 02535
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  $10,000 Per Month

  • 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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  $1,595,000 Sold Jul 01, 2025

  10 Red Pony Rd, West Tisbury, MA 02568

  • 2 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1998

  Last Sold Summary

  • $1,356/SF

  Current Estimated Value $1,666,764

  Last Listing Agent Lisa Da Silva Signal House Group at Compass

  10 Red Pony Rd, West Tisbury, MA 02568
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  Est $2,433,079 Not Listed For Sale

  23 Oak Ln, Vineyard Haven, MA 02568

  • 6 Beds
  • 5 Baths
  • 3,035 Sq Ft
  • Built 2007

  23 Oak Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Below List Price
  • $791/SF

  • Last Sold Price $2,400,000

  Last Listing Agent Lynn Buder Sandpiper Realty
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  $2,950,000

  • 3 Beds
  • 3 Baths
  • 3,506 Sq Ft

  24 Cournoyer Rd, Vineyard Haven, MA 02568

  This mixed use building is zoned for residential and commercial use. It is extremely well built with an emphasis on non-toxic materials throughout. High ceilings on all three levels. There are radiant floors mixed with forced hot air/AC. The building offers a variety of uses for a new owner. The existing spaces are very versatile and would be ideal for any service oriented business given the

  Jill Napior Tea Lane Associates

  24 Cournoyer Rd, Vineyard Haven, MA 02568
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  /25

  $13,600 Per Month

  • 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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  $375,000 Sold Apr 06, 2026

  99 Cygnet Way Unit 103, Chilmark, MA 02535

  • Land
  • 8,712 Sq Ft
  • $1,875,000 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 120 Days On Market

  Last Listing Agent Russell Maloney Russell Maloney Real Estate

  99 Cygnet Way Unit 103, Chilmark, MA 02535
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  Est $1,556,989 Not Listed For Sale

  84 Christiantown Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 2018

  84 Christiantown Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 11% Above List Price
  • $964/SF
  • 59 Days On Market

  • Last Sold Price $1,400,000
  • May 20, 2024

  Last Listing Agent Candy DaRosa Feiner Real Estate
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  $950,000

  • 2 Beds
  • 2 Baths
  • 1,583 Sq Ft

  25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  NEW PRICE - Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

  Maranda Post Compass LLC

  25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  $8,250 Per Month

  • 7 Beds
  • 5 Baths
  • 3,528 Sq Ft
  • House for Rent

  227 S Gate Rd Wt120, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

  Karen Overtoom Karen M. Overtoom R.E.

  227 S Gate Rd Wt120, West Tisbury, MA 02575
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  $1,150,000 Sold Jun 13, 2025

  46 Old Coach Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1981

  Last Sold Summary

  • 10% Below List Price
  • $837/SF
  • 43 Days On Market

  Current Estimated Value $1,283,412

  Last Listing Agent Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
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  Est $3,309,782 Not Listed For Sale

  18 S Pond Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 4.5 Baths
  • 4,239 Sq Ft
  • Built 1999

  18 S Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 14% Above List Price
  • $683/SF
  • 341 Days On Market

  • Last Sold Price $2,895,000
  • Jan 10, 2025

  Last Listing Agent Rose Ryley Wallace & Co. Sotheby's
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  $2,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,522 Sq Ft

  29 Old Nursery Ln, Chilmark, MA 02535

  Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

  Julianna Flanders Flanders Real Estate

  29 Old Nursery Ln, Chilmark, MA 02535
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  $22,000 Per Month

  • 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
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  $900,000 Sold Sep 17, 2025

  00 Quenames Rd Unit 30-02, Chilmark, MA 02535

  • Land
  • 3.05 Acres
  • $295,082 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 83 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  00 Quenames Rd Unit 30-02, Chilmark, MA 02535
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  Est $1,935,899 Not Listed For Sale

  82 South Rd, Chilmark, MA 02535

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft
  • Built 1960

  82 South Rd, Chilmark, MA 02535

  Last Sold Summary

  • 6% Above List Price
  • $983/SF
  • 10 Days On Market

  • Last Sold Price $1,830,000
  • Dec 05, 2024

  Last Listing Agent Meg Bodnar Tea Lane Associates
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  $6,750,000

  • 5 Beds
  • 3.5 Baths
  • 4,050 Sq Ft

  78 Hammett Rd, Chilmark, MA 02535

  Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

  Robert Kenney Tea Lane Associates

  78 Hammett Rd, Chilmark, MA 02535
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  $17,600 Per Month

  • 4 Beds
  • 4 Baths
  • 2,676 Sq Ft
  • House for Rent

  40 Summer Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

  Karen Overtoom Karen M. Overtoom R.E.

  40 Summer Cir, West Tisbury, MA 02575
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  $4,250,000 Sold Sep 09, 2025

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 7 Beds
  • 6 Baths
  • 4,125 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $1,030/SF
  • 21 Days On Market

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

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  Est $1,774,865 Not Listed For Sale

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,461 Sq Ft
  • Built 1994

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6% Above List Price
  • $683/SF
  • 52 Days On Market

  • Last Sold Price $1,680,000
  • Oct 26, 2023

  Last Listing Agent Peyton Wallace Studio Realty
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  $2,000,000

  • 5 Beds
  • 3.5 Baths
  • 2,075 Sq Ft

  63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island’s most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

  Valene Pires The Agency

  63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  $18,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

  Karen Overtoom Karen M. Overtoom R.E.

  71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
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  $60,000 Sold Jul 01, 2025

  0 North Rd Unit 40 43533, Aquinnah, MA 02535

  • Land
  • 0 Sq Ft

  Last Sold Summary

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

  0 North Rd Unit 40 43533, Aquinnah, MA 02535
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  Est $1,242,402 Not Listed For Sale

  31 Music St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1817

  31 Music St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 10% Above List Price
  • $978/SF
  • 0 Days On Market

  • Last Sold Price $1,125,000
  • Feb 29, 2024

  Last Listing Agent LINK Email Cache LINK
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  $1,575,000

  • 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 Sandpiper Realty, Inc.

  47 Quenames Rd, Chilmark, MA 02535
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  $3,000 Per Month

  • 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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  $3,772,500 Sold May 29, 2025

  3 Tennis Ln, Chilmark, MA 02535

  • 4 Beds
  • 4.5 Baths
  • 3,234 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $1,167/SF
  • 0 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  3 Tennis Ln, Chilmark, MA 02535
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  /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

  • $1,032/SF
  • 11 Days On Market

  • Last Sold Price $2,300,000
  • Nov 08, 2024

  Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.
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  $1,390,000

  • 4 Beds
  • 2 Baths
  • 1,332 Sq Ft

  40 Scotchmans Ln, Vineyard Haven, MA 02568

  A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

  Jim Osmundsen Donnelly + Co.

  40 Scotchmans Ln, Vineyard Haven, MA 02568
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  $10,800 Per Month

  • 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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  $1,500,000 Sold Oct 20, 2025

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

  • Land
  • 3.9 Acres
  • $384,615 per Acre

  Last Sold Summary

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

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
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  Est $1,663,812 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

  Last Sold Summary

  • 1% Below List Price
  • $1,473/SF

  • Last Sold Price $1,685,000

  Last Listing Agent Diana Gilmore Island Real Estate
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  $1,800,000

  • 3 Beds
  • 3 Baths
  • 2,293 Sq Ft

  10 Trotters Ln, West Tisbury, MA 02575

  Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

  Rebecca V Conroy Conroy & Company R.E., Inc.

  10 Trotters Ln, West Tisbury, MA 02575
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  $4,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • House for Rent

  33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

  THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
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  $1,075,000 Sold Feb 26, 2026

  34 Pine Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1984

  Last Sold Summary

  • 14% Below List Price
  • $960/SF
  • 93 Days On Market

  Current Estimated Value $1,240,755

  Last Listing Agent Candy DaRosa Feiner Real Estate

  34 Pine Ln, Vineyard Haven, MA 02568
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  Est $2,610,171 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

  • 3% Above List Price
  • $763/SF
  • 80 Days On Market

  • Last Sold Price $2,525,000
  • Jan 17, 2025

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.
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  $1,299,000 Under Contract

  • 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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  $8,000 Per Month

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  10 James Pond Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

  Karen Overtoom Karen M. Overtoom R.E.

  10 James Pond Way, West Tisbury, MA 02575
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  $1,607,000 Sold Jul 10, 2025

  10 N Abels Hill Rd, Chilmark, MA 02535

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft
  • Built 1978

  Last Sold Summary

  • 39% Below List Price
  • $564/SF
  • 354 Days On Market

  Current Estimated Value $1,993,418

  Last Listing Agent Elissa Lash Tea Lane Associates

  10 N Abels Hill Rd, Chilmark, MA 02535
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  Est $2,066,306 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

  • 4% Above List Price
  • $1,000/SF
  • 47 Days On Market

  • Last Sold Price $1,995,000
  • Nov 15, 2024

  Last Listing Agent Wendy Harman Compass

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