Aquinnah, MA Homes

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  /31

  $1,699,999

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  43 N Slope Ln, Chilmark, MA 02535

  Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

  

  Barbara O'Hara

  North Star Real Estate, LLC

  (508) 850-0854

  43 N Slope Ln, Chilmark, MA 02535
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  /33

  $22,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • House for Rent

  2 Strikers Way Ch211, Chilmark, MA 02535

  SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the

  Karen Overtoom Karen M. Overtoom R.E.

  2 Strikers Way Ch211, Chilmark, MA 02535
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  $3,120,000 Sold Sep 16, 2025

  140 Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 3,669 Sq Ft
  • Built 1993

  Last Sold Summary

  • 10% Below List Price
  • $850/SF
  • 84 Days On Market

  Current Estimated Value $3,690,599

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  140 Pond Rd, Vineyard Haven, MA 02568
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  /2

  Est $2,636,263 Not Listed For Sale

  230 Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 3,527 Sq Ft
  • Built 2002

  230 Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 16% Below List Price
  • $646/SF

  • Last Sold Price $2,280,000

  Last Listing Agent Rose Ryley Wallace & Co. Sotheby's
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  $3,950,000

  • 3 Beds
  • 4.5 Baths
  • 3,314 Sq Ft

  20 Edson Forrest Rd, West Tisbury, MA 02575

  Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. A full restoration of this this three-bedroom house (with six-bedroom septic) in 2022 created a luxury home with a thoughtful layout, 2 story expansion, and exceptional

  Meg Bodnar Tea Lane Associates

  20 Edson Forrest Rd, West Tisbury, MA 02575
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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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  /30

  $1,550,000 Sold Oct 16, 2025

  251 State Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,986 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $780/SF
  • 114 Days On Market

  Current Estimated Value $1,614,002

  Last Listing Agent Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
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  /4

  Est $3,039,348 Not Listed For Sale

  188 Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,789 Sq Ft
  • Built 1996

  188 Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 3% Below List Price
  • $1,124/SF

  • Last Sold Price $3,135,000
  • May 16, 2023

  Last Listing Agent Rose Ryley Wallace & Co. Sotheby's
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  /13

  $2,500,000

  • 1 Bed
  • 1 Bath
  • 726 Sq Ft

  18 Allen Farm Rd, Chilmark, MA 02535

  Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered full furnished with exception of some art and a few

  Patty Kendall Kendall & Kendall

  18 Allen Farm Rd, Chilmark, MA 02535
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  /20

  $16,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft
  • House for Rent

  31 S Ridge Rd Ch218, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

  Karen Overtoom Karen M. Overtoom R.E.

  31 S Ridge Rd Ch218, Chilmark, MA 02535
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  /2

  $1,700,000 Sold Oct 20, 2025

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  • 5 Beds
  • 3 Baths
  • 1,803 Sq Ft
  • Built 1982

  Last Sold Summary

  • $943/SF
  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  /2

  Est $2,386,335 Not Listed For Sale

  248 Pond Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 4 Baths
  • 3,208 Sq Ft
  • Built 1998

  248 Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Below List Price
  • $717/SF

  • Last Sold Price $2,300,000

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.
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  /36

  $3,950,000 Under Contract

  • 5 Beds
  • 4 Baths
  • 3,413 Sq Ft

  122 Old Farm Rd, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

  Mark Jenkins Wallace & Co. Sotheby's

  122 Old Farm Rd, Chilmark, MA 02535
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  $19,000 Per Month

  • 6 Beds
  • 6.5 Baths
  • 6,950 Sq Ft
  • House for Rent

  40 Sweet William Way, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

  Karen Overtoom Karen M. Overtoom R.E.

  40 Sweet William Way, West Tisbury, MA 02575
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  /7

  $650,000 Sold Aug 14, 2025

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

  • Land
  • 8,712 Sq Ft
  • $3,250,000 per Acre

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Deb Hancock Hancock Real Estate

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
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  /25

  Est $2,088,418 Not Listed For Sale

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 3,636 Sq Ft
  • Built 1985

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Above List Price
  • $550/SF
  • 0 Days On Market

  • Last Sold Price $2,000,000
  • May 31, 2024

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's
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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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  $7,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  27 Beach Plum Ln, Chilmark, MA 02535

  weekly rental rate negotiable, cost $400-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt . it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a

  Bryan Hummel Commonwealth Realty Group

  27 Beach Plum Ln, Chilmark, MA 02535
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  /25

  $1,125,000 Sold Oct 28, 2025

  140 Longview Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,432 Sq Ft
  • Built 1964

  Last Sold Summary

  • 13% Below List Price
  • $786/SF
  • 97 Days On Market

  Current Estimated Value $1,145,289

  Last Listing Agent Candy DaRosa Feiner Real Estate

  140 Longview Rd, Vineyard Haven, MA 02568
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  /2

  Est $1,705,893 Not Listed For Sale

  26 Old Coach Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,923 Sq Ft
  • Built 1998

  26 Old Coach Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 2% Above List Price
  • $869/SF
  • 0 Days On Market

  • Last Sold Price $1,671,100
  • Feb 22, 2012

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty
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  /65

  $2,690,000

  • 6 Beds
  • 4 Baths
  • 2,618 Sq Ft

  55 Old House Way, West Tisbury, MA 02575

  Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with stainless

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
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  /28

  $32,000 Per Month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  37 Mempremagog Ave Vh410, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  37 Mempremagog Ave Vh410, Tisbury, MA 02568
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  /37

  $7,289,000 Sold Oct 15, 2025

  25 Osprey Ln, Chilmark, MA 02535

  • 4 Beds
  • 5 Baths
  • 3,777 Sq Ft
  • Built 1988

  Last Sold Summary

  • 9% Below List Price
  • $1,930/SF
  • 77 Days On Market

  Current Estimated Value $6,853,287

  Last Listing Agent Deb Hancock Hancock Real Estate

  25 Osprey Ln, Chilmark, MA 02535
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  /79

  Not Listed For Sale

  260 South Rd, Chilmark, MA 02535

  • 6 Beds
  • 2.5 Baths
  • 2,604 Sq Ft
  • Built 1688

  260 South Rd, Chilmark, MA 02535

  Last Sold Summary

  • $1,671/SF
  • 109 Days On Market

  • Last Sold Price $4,350,000
  • Oct 19, 2023

  Last Listing Agent Jill Napior Tea Lane Associates
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  $3,199,000

  • 3 Beds
  • 3.5 Baths
  • 3,082 Sq Ft

  53 Stoney Hill Rd, Vineyard Haven, MA 02568

  This custom-built residence is nestled in one of Martha’s Vineyard’s most coveted up-island towns. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, Wolf stove and wall oven, Sub-Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, and Rohl satin nickel gooseneck faucet. A custom bar is appointed with

  Jennifer B. DaSilva Compass

  53 Stoney Hill Rd, Vineyard Haven, MA 02568
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  /8

  $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
• 

  

  /22

  $435,000 Sold Aug 26, 2025

  0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

  • Land
  • 4,356 Sq Ft
  • $4,350,000 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 18 Days On Market

  Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate

  0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
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  Est $2,893,860 Not Listed For Sale

  34 S Pond Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 3,311 Sq Ft
  • Built 2000

  34 S Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Below List Price
  • $906/SF

  • Last Sold Price $3,000,000
  • Apr 29, 2025

  Last Listing Agent Stephanie Roache Donnelly + Co
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  $4,650,000

  • 4 Beds
  • 3.5 Baths
  • 3,702 Sq Ft

  7 Black Point Rd, Chilmark, MA 02535

  Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the house via breezy walkway, leading to a bedroom wing including a separate family room, off the

  Meg Bodnar Tea Lane Associates

  7 Black Point Rd, Chilmark, MA 02535
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  /31

  $40,000 Per Month

  • 6 Beds
  • 6 Baths
  • 3,960 Sq Ft
  • House for Rent

  384 Middle Rd Ch222, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

  Karen Overtoom Karen M. Overtoom R.E.

  384 Middle Rd Ch222, Chilmark, MA 02535
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  $1,250,000 Sold Nov 12, 2025

  1054 State Rd, Vineyard Haven, MA 02568

  • 6 Beds
  • 2 Baths
  • 1,845 Sq Ft
  • Built 1881

  Last Sold Summary

  • 16% Below List Price
  • $678/SF
  • 60 Days On Market

  Current Estimated Value $1,274,063

  Last Listing Agent Stephanie Roache Donnelly + Co.

  1054 State Rd, Vineyard Haven, MA 02568
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  Est $2,288,109 Not Listed For Sale

  377 State Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 1970

  377 State Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Above List Price
  • $902/SF
  • 518 Days On Market

  • Last Sold Price $2,197,000
  • Oct 12, 2023

  Last Listing Agent Jill Napior Tea Lane Associates
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  /35

  $2,650,000

  • 4 Beds
  • 3 Baths
  • 2,967 Sq Ft

  11 By the Woods, Chilmark, MA 02535

  Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main

  Julianna Flanders Flanders Real Estate

  11 By the Woods, Chilmark, MA 02535
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  $50,700 Per Month

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft
  • House for Rent

  6 Trails End Ch241, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

  Karen Overtoom Karen M. Overtoom R.E.

  6 Trails End Ch241, Chilmark, MA 02535
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  $4,150,000 Sold Feb 19, 2026

  97 Longview Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 5.5 Baths
  • 4,003 Sq Ft
  • Built 2008

  Last Sold Summary

  • 12% Below List Price
  • $1,037/SF
  • 74 Days On Market

  Last Listing Agent Stephanie Roache Donnelly + Co.

  97 Longview Rd, Vineyard Haven, MA 02568
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  /14

  Est $2,580,689 Not Listed For Sale

  30 Pond Ln, Vineyard Haven, MA 02568

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

  30 Pond Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 17% Above List Price
  • $754/SF
  • 5 Days On Market

  • Last Sold Price $2,207,500
  • Jan 03, 2024

  Last Listing Agent Elissa Lash Tea Lane Associates
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  /39

  $3,395,000

  • 3 Beds
  • 4 Baths
  • 2,500 Sq Ft

  27 Clambelly Rd, Chilmark, MA 02535

  A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood

  Julianna Flanders Flanders Real Estate

  27 Clambelly 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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  $2,100,000 Sold Nov 25, 2025

  6 Tabor Hills, Chilmark, MA 02535

  • 4 Beds
  • 3 Baths
  • 2,544 Sq Ft
  • Built 1993

  Last Sold Summary

  • 11% Below List Price
  • $825/SF
  • 48 Days On Market

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  6 Tabor Hills, Chilmark, MA 02535
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  Not Listed For Sale

  670 State Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3.5 Baths
  • 2,092 Sq Ft
  • Built 1920

  670 State Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • $550/SF
  • 68 Days On Market

  • Last Sold Price $1,150,000
  • Jul 09, 2024

  Last Listing Agent Nya Clarke Martha's Vineyard Island-Wide Realty

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