Chilmark, MA Homes

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  $1,575,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  20 Brook Hollow Rd, Vineyard Haven, MA 02568

  This spacious custom designed home 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 is designed to have an intimate relationship with the

  Jim Feiner Feiner Real Estate

  20 Brook Hollow Rd, Vineyard Haven, MA 02568
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  $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
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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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  /35

  Est $1,785,181 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

  • 3% Below List Price
  • $1,111/SF
  • 182 Days On Market

  • Last Sold Price $1,837,500
  • Apr 18, 2025

  Last Listing Agent Wendy Harman Compass | Point B
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  /5

  $1,025,000

  • Land
  • 43,472 Sq Ft
  • $1,027,054 per Acre

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539

  Per Board of Health approval, this one-acre parcel can support a six-bedroom home. Ideally situated in a centrally located neighborhood, the property offers a rare combination of privacy and convenience. Abutting conservation land, it features a peaceful, natural setting perfect for your future home. Enjoy close proximity to town, beautiful beaches, scenic bike paths, a public gym, veterinary

  Casandra Hyland Sandpiper Realty

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539
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  $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
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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 $1,222,338

  Last Listing Agent Jennifer O'hanlon Compass LLC

  110 Otis Bassett Rd, Vineyard Haven, MA 02568
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  /2

  Est $1,360,718 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

  Last Sold Summary

  • 27% Below List Price
  • $1,253/SF

  • Last Sold Price $1,072,500

  Last Listing Agent Russell Maloney Russell Maloney Real Estate
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  /4

  $1,449,000 Pending

  • Land
  • 3.9 Acres
  • $371,538 per Acre

  34 Ebens Ln, Chilmark, MA 02535

  Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

  Thomas Wallace Wallace & Co. Sotheby's

  34 Ebens Ln, Chilmark, MA 02535
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  $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
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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 $1,192,428

  Last Listing Agent Kathleen Kendrick Kathleen Kendrick

  52 Old Coach Rd, Vineyard Haven, MA 02568
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  /26

  Est $1,100,050 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

  • 16% Above List Price
  • $804/SF
  • 10 Days On Market

  • Last Sold Price $950,000
  • Oct 25, 2024

  Last Listing Agent Stephanie Roache Donnelly + Co
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  /2

  $799,000

  • Land
  • 39,996 Sq Ft
  • $870,181 per Acre

  22 Bramble Path Unit 214, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path Unit 214, West Tisbury, MA 02568
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  $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
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  $435,000 Sold Aug 26, 2025

  0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

  • Land
  • 4,356 Sq Ft
  • $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 $1,315,042 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

  • 17% Above List Price
  • $732/SF
  • 19 Days On Market

  • Last Sold Price $1,125,000
  • Nov 15, 2023

  Last Listing Agent Joanna Fairchild eXp Realty
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  $35,000,000

  • 8 Beds
  • 8 Baths
  • 6,841 Sq Ft

  146 Quenames Rd, Chilmark, MA 02535

  Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

  Grace Hagerty Grace Hagerty Real Estate Inc

  146 Quenames Rd, Chilmark, MA 02535
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  /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
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  /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 $1,481,257

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

  19 S Vine Ln, Vineyard Haven, MA 02568
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  Est $1,245,475 Not Listed For Sale

  43 Skiffs Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1991

  43 Skiffs Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 12% Above List Price
  • $847/SF
  • 32 Days On Market

  • Last Sold Price $1,115,000
  • Nov 07, 2024

  Last Listing Agent Chelsea Brennan Lamacchia Realty, Inc.
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  /20

  $1,650,000

  • 2 Beds
  • 1 Bath
  • 716 Sq Ft

  46 Tiercel Ln, Chilmark, MA 02535

  Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting. Recent updates include a new roof, siding, and HVAC system, ensuring comfort and

  Stacy Ickes Donnelly + Co

  46 Tiercel Ln, Chilmark, MA 02535
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  /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
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  $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
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  Est $1,893,502 Not Listed For Sale

  75 Skiffs Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft
  • Built 1984

  75 Skiffs Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 8% Above List Price
  • $687/SF
  • 186 Days On Market

  • Last Sold Price $1,750,000
  • Jan 31, 2025

  Last Listing Agent Kelly Mercier The Agency
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  $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 features a beautifully renovated farmhouse blending modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property also includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  $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
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  $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 $3,947,969

  Last Listing Agent Tina Miller Donnelly + Co.

  15 Old Farm Rd, Chilmark, MA 02535
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  /22

  Est $1,216,965 Not Listed For Sale

  496 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 1,286 Sq Ft
  • Built 1955

  496 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 9% Above List Price
  • $867/SF
  • 212 Days On Market

  • Last Sold Price $1,115,000
  • Mar 14, 2025

  Last Listing Agent Stephanie Roache Donnelly + Co
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  $1,495,000

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

  651 State Rd, Vineyard Haven, MA 02568

  Fabulous four-building farmhouse compound offered in the heart of West Tisbury. This cherished property features a well-maintained classic 1880 main house with 4 bedrooms and 3 baths, plus a fully separate guest cottage with 1 bedroom and 1 bath — offering immediate income potential through seasonal or year-round rental. A bunkhouse/office building provides flexible space ideal for a home office

  Jim Feiner Feiner Real Estate

  651 State Rd, Vineyard Haven, MA 02568
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  $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
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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 Properties

  25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
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  Est $1,539,676 Not Listed For Sale

  33 Hidden Village Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 2.5 Baths
  • 1,968 Sq Ft
  • Built 1980

  33 Hidden Village Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 16% Above List Price
  • $673/SF
  • 73 Days On Market

  • Last Sold Price $1,325,000
  • Oct 31, 2023

  Last Listing Agent Elissa Lash Tea Lane Associates
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  $1,295,000

  • Land
  • 4.4 Acres
  • $294,318 per Acre

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535

  This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation, NHESP has been completed and there are no restrictions on the lot, there's a septic design and the

  Elissa Lash Tea Lane Associates

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
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  $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
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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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  Est $2,447,019 Not Listed For Sale

  41 Hidden Village Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 2,540 Sq Ft
  • Built 1981

  41 Hidden Village Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 2% Above List Price
  • $945/SF
  • 335 Days On Market

  • Last Sold Price $2,400,000
  • Apr 30, 2024

  Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.
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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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  /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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  Est $1,215,159 Not Listed For Sale

  5 Rock Pond Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft
  • Built 1999

  5 Rock Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 23% Above List Price
  • $612/SF
  • 145 Days On Market

  • Last Sold Price $990,000
  • Feb 19, 2025

  Last Listing Agent Kerry Quinlan-Potter Breakwater MV
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  $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

Showing Results 121 - 160, Page 4 of 18