Aquinnah, 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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  /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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  /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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  /2

  Est $1,406,986 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% Below List Price
  • $908/SF

  • Last Sold Price $1,330,000

  Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate
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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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  $16,000 Per Month

  • 7 Beds
  • 3.5 Baths
  • 4,000 Sq Ft
  • House for Rent

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

  Karen Overtoom Karen M. Overtoom R.E.

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
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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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  /2

  Est $1,944,974 Not Listed For Sale

  163 Charles Neck Way, Vineyard Haven, MA 02568

  • 5 Beds
  • 4 Baths
  • 2,508 Sq Ft
  • Built 1987

  163 Charles Neck Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 19% Below List Price
  • $652/SF

  • Last Sold Price $1,635,000

  Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's
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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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  /3

  $13,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • House for Rent

  224 N Rd Ch248, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

  Karen Overtoom Karen M. Overtoom R.E.

  224 N Rd Ch248, Chilmark, 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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  /30

  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

  $7,300,000

  • 5 Beds
  • 5.5 Baths
  • 3,539 Sq Ft

  65 Carl's Way, West Tisbury, MA 02568

  Stylized Private Waterfront Retreat close to townperched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes

  Jill Napior Tea Lane Associates

  65 Carl's Way, West Tisbury, MA 02568
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  /20

  $6,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • House for Rent

  11 Hammett Ln, Chilmark, MA 02535

  ** WEEKLY SUMMER RATE** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  11 Hammett Ln, Chilmark, MA 02535
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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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  /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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  $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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  /23

  $24,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,637 Sq Ft
  • House for Rent

  56 Chilmark Rd, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation

  Karen Overtoom Karen M. Overtoom R.E.

  56 Chilmark Rd, Chilmark, MA 02535
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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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  /2

  Est $2,260,316 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

  • 3% Below List Price
  • $673/SF

  • Last Sold Price $2,200,000

  Last Listing Agent Emma Kennedy Sandpiper Realty
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  /4

  $1,025,000

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

  25 Coffins Field Rd, 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, Inc.

  25 Coffins Field Rd, Edgartown, MA 02539
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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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  $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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  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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  /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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  $8,500 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

  Karen Overtoom Karen M. Overtoom R.E.

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
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  $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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  Not Listed For Sale

  39 Sarita Walker Rd, Vineyard Haven, MA 02568

  • 6 Beds
  • 5 Baths
  • 3,540 Sq Ft
  • Built 1830

  39 Sarita Walker Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • $1,035/SF

  • Last Sold Price $3,662,500

  Last Listing Agent Thomas Wallace Wallace & Co. Sotheby's
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  /25

  $1,550,000 Open House 5/23

  • 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

  $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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  $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 $1,894,555 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

  • $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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  /22

  $1,200,000 Under Contract

  • 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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  /19

  $24,000 Per Month

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

  44 Flanders Ln, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

  Karen Overtoom Karen M. Overtoom R.E.

  44 Flanders Ln, Chilmark, MA 02535
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  $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 $1,622,178

  Last Listing Agent Lisa Da Silva Signal House Group at Compass

  105 Stoney Hill Rd, Vineyard Haven, MA 02568
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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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  /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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  /39

  $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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  /19

  $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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  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

Showing Results 81 - 120, Page 3 of 18