Oak Bluffs, MA Homes

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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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  $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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  $1,330,000 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 $1,320,925

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

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  /31

  Est $1,396,814 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

  • 30% Above List Price
  • $1,254/SF
  • 0 Days On Market

  • Last Sold Price $1,072,500
  • Sep 25, 2023

  Last Listing Agent Russell Maloney Russel Maloney Real Estate
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  /31

  $2,395,000

  • 4 Beds
  • 3 Baths
  • 1,918 Sq Ft

  25 Fulling Mill Rd, Chilmark, MA 02535

  Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

  Thomas Wallace Wallace & Co. Sotheby's

  25 Fulling Mill Rd, Chilmark, MA 02535
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  $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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  $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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  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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  /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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  /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
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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 $1,222,338

  Last Listing Agent Jennifer O'hanlon Compass LLC

  110 Otis Bassett Rd, Vineyard Haven, MA 02568
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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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  $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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  $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
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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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  /23

  Est $1,957,778 Not Listed For Sale

  171 Otis Bassett Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 2.5 Baths
  • 3,026 Sq Ft
  • Built 1999

  171 Otis Bassett Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 9% Above List Price
  • $593/SF
  • 11 Days On Market

  • Last Sold Price $1,795,000
  • Apr 28, 2023

  Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.
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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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  $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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  $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 $1,245,475 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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  $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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  $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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  $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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  $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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  /22

  $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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  $3,710,000 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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  $1,575,000

  • 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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  $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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  $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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  $5,650,000

  • 4 Beds
  • 4.5 Baths
  • 5,402 Sq Ft

  205 South Rd, Chilmark, MA 02535

  CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a

  Tina Miller Donnelly + Co.

  205 South Rd, Chilmark, MA 02535
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  $7,900 per month

  • 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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  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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  $1,600,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  1 Red Arrow Rd, Vineyard Haven, MA 02568

  South Mountain designed and built, energy efficient home that takes excellent advantage of the 3-acre parcel's southerly orientation with both passive solar gain and solar panels. The sun-lit great room combines living room, dining and kitchen and opens out onto the lovely screened porch and patio beyond. The original 3-bedroom home was thoughtfully expanded by buiding out finished space in the

  Candy DaRosa Feiner Real Estate

  1 Red Arrow Rd, Vineyard Haven, MA 02568
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  $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

  Current Estimated Value $2,084,531

  Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  6 Tabor Hills, Chilmark, MA 02535
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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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  $1,800,000

  • 4 Beds
  • 3 Baths
  • 3,158 Sq Ft

  188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  Long Point Beach - House plus ADU! The crashing surf of the south shore, the tranquil waters of Long Cove Pond, the walking trails of the Wildlife Refuge - all minutes from this charming West Tisbury property, appropriately referred to as "Pinch Me" by the current owners. Here, the connection to nature is seamless. The main house sits high atop the trees and overlooks a sprawling lawn from two

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

Showing Results 121 - 160, Page 4 of 18