Oak Bluffs, MA Homes

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  /10

  $1,575,000

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  45 Quenames Rd, Chilmark, MA 02535

  Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with

  Dawn Bellante Sandpiper Realty, Inc.

  45 Quenames 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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  $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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  /2

  Est $2,200,128 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

  Last Sold Summary

  • $673/SF
  • 76 Days On Market

  Last Sold Price $2,200,000

  Last Listing Agent Emma Kennedy Sandpiper Realty Inc
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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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  /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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  /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

  Last Listing Agent Lisa Da Silva Compass | Point B

  105 Stoney Hill Rd, Vineyard Haven, MA 02568
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  /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

  • $1,581/SF
  • 38 Days On Market

  Last Sold Price $6,100,000

  Last Listing Agent Jill Napior Tea Lane Associates
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  /40

  $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
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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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  /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 $1,297,665

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

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  /43

  Not Listed For Sale

  39 Sarita Walker Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3.5 Baths
  • 2,674 Sq Ft
  • Built 1830

  39 Sarita Walker Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • $1,370/SF
  • 306 Days On Market

  Last Sold Price $3,662,500

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty
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  $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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  /39

  $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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  /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
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  /13

  Est $4,056,406 Not Listed For Sale

  144 Pond View Farm Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1996

  144 Pond View Farm Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 8% Below List Price
  • $3,385/SF
  • 104 Days On Market

  Last Sold Price $4,400,000

  Last Listing Agent Brenda Codding Up Island Realty
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  /42

  $7,950,000

  • 5 Beds
  • 7 Baths
  • 4,531 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's

  85 Reservoir Rd, 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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  /24

  $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 $1,157,704

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

  110 Otis Bassett Rd, Vineyard Haven, MA 02568
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  /42

  Est $1,868,960 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

  • 2% Below List Price
  • $875/SF
  • 66 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Jill Napior Tea Lane Associates
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  /55

  $4,450,000

  • 6 Beds
  • 4.5 Baths
  • 2,960 Sq Ft

  104 Pond View Farm Rd, Vineyard Haven, MA 02568

  An exceptional Waterfront Compound on Tisbury Great Pond. Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, this remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond. Both the main house

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, MA 02568
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  $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 proportions

  Karen Overtoom Karen M. Overtoom R.E.

  76 School House Lane Wt101, West Tisbury, MA 02575
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  $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 $1,240,511

  Last Listing Agent Kathleen Kendrick Kathleen Kendrick

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

  Est $1,944,877 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

  • 3% Below List Price
  • $1,460/SF
  • 16 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Julianna Flanders Flanders Real Estate
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  $1,195,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and sunlight

  Kerry Quinlan-Potter Breakwater MV

  4 Rock Pond Rd, Vineyard Haven, MA 02568
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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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  /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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  /6

  Est $2,994,550 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

  • 9% Below List Price
  • $1,703/SF
  • 0 Days On Market

  Last Sold Price $3,295,000

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty
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  /59

  $2,250,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,983 Sq Ft

  157 Ben Chase Rd, West Tisbury, MA 02575

  You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

  Madelyn Silvia Wallace & Co. Sotheby's

  157 Ben Chase Rd, West Tisbury, MA 02575
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  $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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  /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
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  Est $1,608,578 Not Listed For Sale

  111 Charles Neck Way, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft
  • Built 1999

  111 Charles Neck Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 11% Above List Price
  • $928/SF
  • 11 Days On Market

  Last Sold Price $1,450,000

  Last Listing Agent Lynn Buder Sandpiper Realty Inc
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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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  $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
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  /31

  Est $1,196,294 Not Listed For Sale

  16 Elias Ln, Vineyard Haven, MA 02568

  • 1 Bed
  • 1.5 Baths
  • 855 Sq Ft
  • Built 1993

  16 Elias Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 12% Above List Price
  • $1,254/SF
  • 0 Days On Market

  Last Sold Price $1,072,500

  Last Listing Agent Russell Maloney Russel Maloney Real Estate
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  /43

  $2,100,000 Sold Nov 25, 2025

  6 Tabor Hills, Chilmark, MA 02535

  • 4 Beds
  • 3 Baths
  • 1,968 Sq Ft
  • Built 1993

  Last Sold Summary

  • 11% Below List Price
  • $1,067/SF
  • 50 Days On Market

  Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  6 Tabor Hills, Chilmark, MA 02535
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  /26

  Est $1,034,913 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

  • 9% Above List Price
  • $804/SF
  • 10 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Stephanie Roache Donnelly + Co
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  /20

  $821,000 Sold Jun 17, 2025

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

  • Land
  • 1.4 Acres
  • $586,429 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 0 Days On Market

  Last Listing Agent Janna O'Loughlin Portfolio Properties

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
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  /28

  Est $1,272,772 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

  • 13% Above List Price
  • $732/SF
  • 19 Days On Market

  Last Sold Price $1,125,000

  Last Listing Agent Joanna Fairchild eXp Realty
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  /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 $1,816,541

  Last Listing Agent Jill Napior Tea Lane Associates

  3 Fulling Mill Rd, Chilmark, MA 02535

Showing Results 121 - 160, Page 4 of 18