Gosnold, MA Homes

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  /31

  $12,500,000 Pending

  • 6 Beds
  • 4 Baths
  • 4,876 Sq Ft

  44 Forest Rd, Vineyard Haven, MA 02568

  Quintessential Seven Gates waterfront compound offering outstanding views and immediate beachfront access. This exceptional Martha’s Vineyard retreat includes a main residence and barn, thoughtfully designed and built by South Mountain Company. Immaculately maintained, both structures are virtually turn-key.The interiors showcase rich detail, the highest level of craftsmanship, and elegant

  Bill Rossi Studio Realty

  44 Forest Rd, Vineyard Haven, MA 02568
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  /29

  $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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  /2

  $3,772,500 Sold May 29, 2025

  3 Tennis Ln, Chilmark, MA 02535

  • 4 Beds
  • 4.5 Baths
  • 3,234 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $1,167/SF
  • 0 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  3 Tennis Ln, Chilmark, MA 02535
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  /42

  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

  Last Listing Agent Jill Napior Tea Lane Associates
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  /13

  $1,645,000

  • Land
  • 3.32 Acres
  • $495,482 per Acre

  26 Flint Hill Rd, West Tisbury, MA 02575

  Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no

  Dawn Bellante Sandpiper Realty, Inc.

  26 Flint Hill Rd, West Tisbury, MA 02575
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  /8

  $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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  /9

  $1,500,000 Sold Oct 20, 2025

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

  • Land
  • 3.9 Acres
  • $384,615 per Acre

  Last Sold Summary

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

  49 Cobbs Hill Rd Unit 24.3, 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

  Last Listing Agent Julianna Flanders Flanders Real Estate
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  /40

  $1,895,000

  • 4 Beds
  • 3.5 Baths
  • 2,061 Sq Ft

  174 Middle Rd, Chilmark, MA 02535

  Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

  Sheila Morse Island Real Estate

  174 Middle Rd, Chilmark, MA 02535
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  /26

  $50,000 per month

  • 4 Beds
  • 3 Baths
  • 3,237 Sq Ft
  • House for Rent

  29 Naushon Rd Wt142, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

  Karen Overtoom Karen M. Overtoom R.E.

  29 Naushon Rd Wt142, West Tisbury, MA 02575
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  /13

  $2,237,500 Sold Nov 19, 2025

  26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

  • 4 Beds
  • 3 Baths
  • 2,299 Sq Ft
  • Built 1974

  Last Sold Summary

  • 16% Below List Price
  • $973/SF
  • 120 Days On Market

  Last Listing Agent Jill Napior Tea Lane Associates

  26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
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  /6

  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

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty
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  /7

  $400,000 Pending

  • Land
  • 0.2 Acre
  • $2,000,000 per Acre

  99 Cygnet Way Unit 103, Chilmark, MA 02535

  Escape the crowds at Lucy Vincent and Squibnocket and take advantage of this very rare opportunity to own a private, 17 member, Atlantic Ocean beach lot at Thumb Cove (abuts Hancock Beach). Included in the sale of this property is a deeded .2 acres of sandy beach, a deeded parking spot at Chilmark Pond and the right to launch boats from a dock in the pond. Sail, kayak, row, swim(!) or motor

  Russell Maloney Russell Maloney Real Estate

  99 Cygnet Way Unit 103, 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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  /3

  $1,695,000 Sold May 30, 2025

  5 Vincent Rd, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1960

  Last Sold Summary

  • $1,308/SF

  Current Estimated Value $1,480,902

  Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

  5 Vincent Rd, 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

  Last Listing Agent Russell Maloney Russel Maloney Real Estate
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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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  /17

  $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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  $1,442,000 Sold Dec 29, 2025

  24 White Alder Way, South Dartmouth, MA 02748

  • 4 Beds
  • 3.5 Baths
  • 5,384 Sq Ft
  • Built 2001

  Last Sold Summary

  • 10% Below List Price
  • $268/SF
  • 109 Days On Market

  Current Estimated Value $1,483,062

  Last Listing Agent Team MCM Gibson Sotheby's International Realty

  24 White Alder Way, South Dartmouth, MA 02748
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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

  Last Listing Agent Stephanie Roache Donnelly + Co
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  /15

  $1,495,000

  • Land
  • 3.01 Acres
  • $496,678 per Acre

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568

  Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a

  Cassie Courtney Wallace & Co. Sotheby's

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568
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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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  /42

  $1,600,000 Sold Mar 26, 2026

  54 Whitman Rd, Woods Hole, MA 02543

  • 3 Beds
  • 2.5 Baths
  • 2,029 Sq Ft
  • Built 1924

  Last Sold Summary

  • 5% Above List Price
  • $789/SF
  • 16 Days On Market

  Current Estimated Value $1,542,548

  Last Listing Agent Irene O'Connell Sotheby's International Realty

  54 Whitman Rd, Woods Hole, MA 02543
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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

  Last Listing Agent Stephanie Roache Donnelly + Co
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  /33

  $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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  /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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  /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 $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

  Last Listing Agent Elissa Lash Tea Lane Associates
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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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  /29

  $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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  $790,525 Sold Oct 14, 2025

  9 James St, Woods Hole, MA 02543

  • 4 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Above List Price
  • $465/SF
  • 18 Days On Market

  Current Estimated Value $841,591

  Last Listing Agent Dennis Murphy Weichert, Realtors-Donahue Partners

  9 James St, Woods Hole, MA 02543
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  /30

  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

  Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.
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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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  /13

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  19 Lighthouse Road Aq605, Aquinnah, MA 02535

  This family-friendly, three-bedroom retreat on Lighthouse Road in Aquinnah offers all the comforts of home with stunning water views of the Vineyard Sound and the Elizabeth Islands. It is beautifully decorated and nicely furnished. The home features stylish post-and-beam architecture. The main level features cathedral ceilings, wrap-around picture windows and skylights. The main level opens out

  Karen Overtoom Karen M. Overtoom R.E.

  19 Lighthouse Road Aq605, Aquinnah, MA 02535
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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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  /25

  Est $5,531,270 Not Listed For Sale

  135 Capawock Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3.5 Baths
  • 2,921 Sq Ft
  • Built 2001

  135 Capawock Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Below List Price
  • $1,969/SF
  • 7 Days On Market

  Last Sold Price $5,750,000

  Last Listing Agent Jill Napior Tea Lane Associates
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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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  /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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  $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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  /2

  Est $2,328,402 Not Listed For Sale

  84 Cuttyhunk Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 2,396 Sq Ft
  • Built 2001

  84 Cuttyhunk Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $960/SF
  • 40 Days On Market

  Last Sold Price $2,300,000

  Last Listing Agent Rose Ryley Sandpiper Realty Inc

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