Oak Bluffs, MA Homes

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  $2,000,000

  • Land
  • 21,801 Sq Ft
  • $3,996,004 per Acre

  0 State Rd Unit 29.3, Vineyard Haven, MA 02568

  1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

  Peter Cronig Cronigs Real Estate

  0 State Rd Unit 29.3, Vineyard Haven, MA 02568
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  $34,000 per month

  • 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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  $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 $1,754,727

  Last Listing Agent Stephanie Roache Donnelly + Co.

  234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  /33

  Est $1,903,295 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
  • Jul 10, 2024

  Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty
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  $1,025,000

  • Land
  • 1 Acre
  • $1,025,000 per Acre

  25 Coffins Field Rd, Edgartown, MA 02539

  Per the BOH, this property can accommodate a 6-bedroom home and with appropriate permitting may allow for an additional/separate structure such as a garage or studio. Property is not serviced by a well or septic system. Buyer is responsible for obtaining permits and installation. Association Dues $650.00

  Casandra Hyland Sandpiper Realty, Inc.

  25 Coffins Field Rd, Edgartown, MA 02539
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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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  /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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  Est $2,884,524 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

  • 4% Above List Price
  • $945/SF
  • 109 Days On Market

  • Last Sold Price $2,765,000
  • Sep 30, 2024

  Last Listing Agent Elissa Lash Tea Lane Associates
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  /25

  $3,200,000

  • Land
  • 19.3 Acres
  • $165,803 per Acre

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

  A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

  Jill Napior Tea Lane Associates

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
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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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  $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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  /20

  Est $1,358,504 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

  • 1% Above List Price
  • $780/SF
  • 18 Days On Market

  • Last Sold Price $1,350,000
  • Nov 20, 2023

  Last Listing Agent Michele Casavant Vineyard Village Realty
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  /23

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 2,266 Sq Ft

  345 North Rd, Chilmark, MA 02535

  This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected

  Jessica Campbell Flanders Real Estate

  345 North Rd, Chilmark, MA 02535
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  /19

  $17,600 per month

  • 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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  /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 $1,455,768

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

  5 Scottys Ln, Vineyard Haven, MA 02568
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  Est $2,225,668 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

  • 1% Above List Price
  • $673/SF
  • 76 Days On Market

  • Last Sold Price $2,200,000
  • Apr 11, 2024

  Last Listing Agent Emma Kennedy Sandpiper Realty Inc
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  /22

  $1,200,000

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft

  31 North Rd, Chilmark, MA 02535

  Surrounded by three-season perennial gardens, this sun-filled two bedroom cottage offers an airy open floor plan with high ceilings that create an impressive sense of space. Natural light pours in through four skylights and classic 8 over 8 windows, while a deck off the side and rear of the home provides seamless indoor outdoor living.This home underwent a major renovation in Spring of 2024

  Russell Maloney Russell Maloney Real Estate

  31 North 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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  /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 $1,481,257

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

  19 S Vine Ln, Vineyard Haven, MA 02568
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  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
  • Oct 16, 2024

  Last Listing Agent Jill Napior Tea Lane Associates
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  /21

  $2,725,000

  • Land
  • 7.6 Acres
  • $358,553 per Acre

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

  This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

  Peyton Wallace Studio Realty

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
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  /21

  $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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  /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 $1,520,498

  Last Listing Agent Kathleen Kendrick Kendrick Real Estate

  190 Longview Rd, Vineyard Haven, MA 02568
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  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
  • Jul 24, 2023

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty
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  $1,650,000

  • 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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  /20

  $12,000 per month

  • 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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  $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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  Est $1,919,292 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

  • 1% Above List Price
  • $875/SF
  • 66 Days On Market

  • Last Sold Price $1,900,000
  • Oct 24, 2024

  Last Listing Agent Jill Napior Tea Lane Associates
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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

  This one-acre lot is nestled in a peaceful, centrally located neighborhood, offering the perfect balance of privacy and convenience. Abutting conservation land, the property provides a serene natural setting while supporting a spacious six-bedroom home. Enjoy easy access to town, nearby beaches, bike paths, a public gym, veterinarian services, shopping, the airport, and a variety of dining

  Casandra Hyland Sandpiper Realty

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539
• 

  

  /19

  $30,000 per month

  • 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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  /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 $2,668,145

  Last Listing Agent Bill Rossi Studio Realty

  31 N Slope Ln, Chilmark, MA 02535
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  /23

  Est $2,052,201 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% Above List Price
  • $1,460/SF
  • 16 Days On Market

  • Last Sold Price $2,000,000
  • Aug 15, 2024

  Last Listing Agent Julianna Flanders Flanders 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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  $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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  /51

  $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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  Est $3,054,777 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

  • 7% Below List Price
  • $1,703/SF
  • 0 Days On Market

  • Last Sold Price $3,295,000
  • Aug 24, 2023

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty
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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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  /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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  /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

  Current Estimated Value $1,597,517

  Last Listing Agent Lisa Da Silva Signal House Group

  105 Stoney Hill Rd, Vineyard Haven, 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

Showing Results 81 - 120, Page 3 of 18