Oak Bluffs, MA Homes

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  /5

  $1,100,000

  • Land
  • 1 Acre
  • $1,102,204 per Acre

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539

  One acre lot situated in a peaceful, centrally located neighborhood. The parcel will support 3-bedrooms and offers privacy by abutting conservation land, convenience to town and beaches and access to bike paths, public gym, veterinarian, shopping, airport and restaurants.

  Casandra Hyland Sandpiper Realty

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539
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  /29

  $34,000 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  15 Loon Lane Ch203, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

  Karen Overtoom Karen M. Overtoom R.E.

  15 Loon Lane Ch203, Chilmark, MA 02535
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  /30

  $1,175,000 Sold Mar 20, 2025

  12 W Farm Rd, West Tisbury, MA 02575

  • 3 Beds
  • 2 Baths
  • 1,389 Sq Ft
  • Built 1988

  Last Sold Summary

  • 9% Below List Price
  • $846/SF
  • 173 Days On Market

  Last Listing Agent Carson Crissman Compass | Point B

  12 W Farm Rd, West Tisbury, MA 02575
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  /16

  Est $1,205,314 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

  • 7% Above List Price
  • $978/SF
  • 0 Days On Market

  Last Sold Price $1,125,000

  Last Listing Agent LINK Email Cache LINK
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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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  /8

  $18,000 total monthly price

  • 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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  /38

  $1,850,000 Sold Sep 09, 2025

  234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,918 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Below List Price
  • $965/SF
  • 60 Days On Market

  Current Estimated Value $1,692,114

  Last Listing Agent Stephanie Roache Donnelly + Co.

  234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  /17

  Est $1,093,447 Not Listed For Sale

  10 Briarwood Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 934 Sq Ft
  • Built 1984

  10 Briarwood Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 14% Above List Price
  • $1,022/SF
  • 78 Days On Market

  Last Sold Price $955,000

  Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate
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  /2

  $799,000

  • Land
  • 0.92 Acre
  • $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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  /28

  $38,000 total monthly price

  • 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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  /2

  $1,500,000 Sold Aug 13, 2025

  82 Christiantown Rd Unit R, West Tisbury, MA 02575

  • Land
  • 7.42 Acres
  • $202,156 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  82 Christiantown Rd Unit R, West Tisbury, MA 02575
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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

  Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.
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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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  /19

  $17,600 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • House for Rent

  50 Carls Way, 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. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

  Karen Overtoom Karen M. Overtoom R.E.

  50 Carls Way, West Tisbury, MA 02575
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  /42

  $2,900,000 Sold Jul 03, 2025

  67 Hidden Village Rd, Vineyard Haven, MA 02568

  • 7 Beds
  • 5.5 Baths
  • 4,476 Sq Ft
  • Built 1997

  Last Sold Summary

  • 24% Below List Price
  • $648/SF
  • 347 Days On Market

  Last Listing Agent Stephanie Roache Donnelly + Co.

  67 Hidden Village Rd, Vineyard Haven, MA 02568
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  /36

  Est $1,655,277 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

  • 2% Below List Price
  • $1,473/SF
  • 331 Days On Market

  Last Sold Price $1,685,000

  Last Listing Agent Diana Gilmore Island Real Estate
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  /49

  $6,490,000 Pending

  • 6 Beds
  • 8 Baths
  • 5,660 Sq Ft

  60 Meetinghouse Rd, Chilmark, MA 02535

  This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

  Jim Feiner Feiner Real Estate

  60 Meetinghouse Rd, Chilmark, MA 02535
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  /17

  $17,600 total monthly price

  • 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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  /28

  $1,400,000 Sold Nov 26, 2025

  5 Scottys Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft
  • Built 1968

  Last Sold Summary

  • 22% Below List Price
  • $879/SF
  • 126 Days On Market

  Current Estimated Value $1,448,099

  Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  5 Scottys Ln, Vineyard Haven, MA 02568
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  /31

  Est $2,746,679 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

  • 9% Above List Price
  • $763/SF
  • 80 Days On Market

  Last Sold Price $2,525,000

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

  Stacy Ickes Donnelly + Co

  46 Tiercel Ln, Chilmark, MA 02535
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  /21

  $8,000 total monthly price

  • 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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  /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 $1,495,267

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

  19 S Vine Ln, Vineyard Haven, MA 02568
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  /35

  Est $1,987,199 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

  • $1,000/SF
  • 47 Days On Market

  Last Sold Price $1,995,000

  Last Listing Agent Wendy Harman Compass
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  /39

  $2,500,000

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

  229 Oak Ln, West Tisbury, MA 02575

  A hidden gem in West Tisbury! Beautifully manicured, fenced in 2.2 - acre parcel with 100% privacy, and 84 evergreen trees. This modern, contemporary well maintained home is 3-bedroom, 3 bath with two levels of living and a partially finished basement. The first floor is a sunlight filled, open kitchen and dinning room, with hardwood floors throughout. There are multiple decks leading out to a

  Doug Burke Cronigs Real Estate

  229 Oak Ln, West Tisbury, MA 02575
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  /20

  $12,000 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,068 Sq Ft
  • House for Rent

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575

  Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

  Karen Overtoom Karen M. Overtoom R.E.

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575
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  /55

  $15,000,000 Sold Apr 09, 2025

  8 Snail Rd, Chilmark, MA 02535

  • 6 Beds
  • 7 Baths
  • 6,967 Sq Ft
  • Built 2006

  Last Sold Summary

  • 7% Above List Price
  • $2,153/SF
  • 25 Days On Market

  Current Estimated Value $3,678,000

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

  8 Snail Rd, Chilmark, MA 02535
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  /30

  Est $1,403,928 Not Listed For Sale

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • Built 1992

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6% Above List Price
  • $908/SF
  • 80 Days On Market

  Last Sold Price $1,330,000

  Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate
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  /16

  $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. There are so many outstanding possibilities for a future Buyer to build their dream home on this

  Elissa Lash Tea Lane Associates

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
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  /19

  $30,000 total monthly price

  • 5 Beds
  • 4 Baths
  • 3,600 Sq Ft
  • House for Rent

  37 Sachem Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

  Karen Overtoom Karen M. Overtoom R.E.

  37 Sachem Cir, 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

  Current Estimated Value $1,543,077

  Last Listing Agent Kathleen Kendrick Kendrick Real Estate

  190 Longview Rd, Vineyard Haven, MA 02568
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  /33

  Est $1,890,916 Not Listed For Sale

  163 Charles Neck Way, Vineyard Haven, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 2,508 Sq Ft
  • Built 1986

  163 Charles Neck Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 16% Above List Price
  • $652/SF
  • 90 Days On Market

  Last Sold Price $1,635,000

  Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty
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  /32

  $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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  /29

  $10,900 total monthly price

  • 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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  /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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  /30

  Est $2,804,561 Not Listed For Sale

  23 Alex Way, Vineyard Haven, MA 02568

  • 3 Beds
  • 5 Baths
  • 2,926 Sq Ft
  • Built 2004

  23 Alex Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $945/SF
  • 109 Days On Market

  Last Sold Price $2,765,000

  Last Listing Agent Elissa Lash Tea Lane Associates
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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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  /22

  $20,000 total monthly price

  • 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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  /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 $2,727,329

  Last Listing Agent Bill Rossi Studio Realty

  31 N Slope Ln, Chilmark, MA 02535
• 

  

  /20

  Est $1,315,457 Not Listed For Sale

  225 Longview Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft
  • Built 1977

  225 Longview Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 3% Below List Price
  • $780/SF
  • 18 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Michele Casavant Vineyard Village Realty

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