West Tisbury, MA Homes

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  $2,995,000

  • 4 Beds
  • 3.5 Baths
  • 2,515 Sq Ft

  300 North Rd, Chilmark, MA 02535

  Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and two

  Rebecca V Conroy Conroy & Company R.E., Inc.

  300 North Rd, Chilmark, MA 02535
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  $19,000 total monthly price

  • 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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  $990,000 Sold Feb 19, 2025

  5 Rock Pond Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $612/SF
  • 145 Days On Market

  Current Estimated Value $1,045,307

  Last Listing Agent Kerry Quinlan-Potter Breakwater MV

  5 Rock Pond Rd, Vineyard Haven, MA 02568
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  Est $1,294,940 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  16 Rock Pond Rd, Vineyard Haven, MA 02568

  16 Rock Pond Rd, Vineyard Haven, MA 02568
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  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,583 Sq Ft

  25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

  Maranda Post Compass | The O'Hanlon Group

  25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  $32,000 total monthly price

  • 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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  /2

  $1,595,000 Sold Jul 01, 2025

  10 Red Pony Rd, West Tisbury, MA 02568

  • 2 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1998

  Last Sold Summary

  • $1,356/SF

  Current Estimated Value $1,633,982

  Last Listing Agent Lisa Da Silva Compass | Point B

  10 Red Pony Rd, West Tisbury, MA 02568
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  Not Listed For Sale

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

  670 State Rd, Vineyard Haven, MA 02568

  670 State Rd, Vineyard Haven, MA 02568
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  $1,575,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  47 Quenames Rd, Chilmark, MA 02535

  On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

  Dawn Bellante Sandpiper Realty, Inc.

  47 Quenames Rd, Chilmark, MA 02535
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  $50,700 total monthly price

  • 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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  $1,150,000 Sold Jun 13, 2025

  46 Old Coach Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1981

  Last Sold Summary

  • 10% Below List Price
  • $837/SF
  • 43 Days On Market

  Current Estimated Value $1,221,384

  Last Listing Agent Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
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  /31

  Est $2,205,316 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,386 Sq Ft

  7 the Aerie, Chilmark, MA 02535

  7 the Aerie, Chilmark, MA 02535
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  $1,495,000

  • 4 Beds
  • 2 Baths
  • 1,332 Sq Ft

  40 Scotchmans Ln, Vineyard Haven, MA 02568

  A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

  Jim Osmundsen Donnelly + Co.

  40 Scotchmans Ln, Vineyard Haven, MA 02568
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  $13,200 total monthly price

  • 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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  $900,000 Sold Sep 17, 2025

  45 Quenames Rd Unit 30-02, Chilmark, MA 02535

  • Land
  • 3.05 Acres
  • $295,082 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 83 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  45 Quenames Rd Unit 30-02, Chilmark, MA 02535
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  Est $1,627,852 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  84 Christiantown Rd, Vineyard Haven, MA 02568

  84 Christiantown Rd, Vineyard Haven, MA 02568
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  $12,500,000

  • 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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  $22,000 total monthly price

  • 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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  $1,300,000 Sold Mar 03, 2025

  22 Briarwood Ln, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Below List Price
  • $1,048/SF
  • 4 Days On Market

  Current Estimated Value $1,187,266

  Last Listing Agent Carol Shore Donnelly + Co

  22 Briarwood Ln, Vineyard Haven, MA 02568
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  Est $3,232,931 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,239 Sq Ft

  18 S Pond Rd, Vineyard Haven, MA 02568

  18 S Pond Rd, Vineyard Haven, MA 02568
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  $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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  /20

  $16,800 total monthly price

  • 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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  $60,000 Sold Jul 01, 2025

  0 North Rd Unit 40 43533, Aquinnah, MA 02535

  • Land
  • 0 Acre

  Last Sold Summary

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

  0 North Rd Unit 40 43533, Aquinnah, MA 02535
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  Est $2,309,579 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 2,705 Sq Ft

  9 Heather Trail, Vineyard Haven, MA 02568

  9 Heather Trail, Vineyard Haven, MA 02568
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  $1,200,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  34 Pine Ln, Vineyard Haven, MA 02568

  One level living! This ranch-style home has a great layout and some sweet, unexpected features. The living spaces are opened up to each other allowing the wall of sliders in the living room to flood the rooms with light - and these sliders give access out to the deck with serene views of the woodlands beyond; where Stoney Hill Path bounds the entire south side of the property. The primary suite

  Candy DaRosa Feiner Real Estate

  34 Pine Ln, Vineyard Haven, MA 02568
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  $40,000 total monthly price

  • 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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  $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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  Est $1,987,420 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft

  82 South Rd, Chilmark, MA 02535

  82 South Rd, Chilmark, MA 02535
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  $1,100,000

  • Land
  • 1 Acre
  • $1,100,000 per Acre

  25 Coffins Field Rd, Edgartown, MA 02539

  Per the BOH, this property can accommodate a 3 bedroom home and with appropriate permitting may allow for an additional/separate structure such as a garage or studioProperty 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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  $22,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,290 Sq Ft
  • House for Rent

  36 Henry Hough Lane Ch206, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

  Karen Overtoom Karen M. Overtoom R.E.

  36 Henry Hough Lane Ch206, Chilmark, MA 02535
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  $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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  Est $1,841,150 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,461 Sq Ft

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  29 Brook Hollow Rd, Vineyard Haven, MA 02568
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  $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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  /19

  $24,000 total monthly price

  • 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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  $1,607,000 Sold Jul 10, 2025

  10 N Abels Hill Rd, Chilmark, MA 02535

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft
  • Built 1978

  Last Sold Summary

  • 39% Below List Price
  • $564/SF
  • 354 Days On Market

  Current Estimated Value $1,980,288

  Last Listing Agent Elissa Lash Tea Lane Associates

  10 N Abels Hill Rd, Chilmark, MA 02535
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  Est $1,252,041 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  31 Music St, Vineyard Haven, MA 02568

  31 Music St, Vineyard Haven, MA 02568
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  $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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  $36,000 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  29 Cemetery Rd Ch216, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

  Karen Overtoom Karen M. Overtoom R.E.

  29 Cemetery Rd Ch216, Chilmark, MA 02535
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  $1,150,000 Sold Apr 11, 2025

  41 Old County Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft
  • Built 1983

  Last Sold Summary

  • 11% Below List Price
  • $910/SF
  • 216 Days On Market

  Current Estimated Value $1,188,011

  Last Listing Agent Jared Bicknell Compass | The O'Hanlon Group

  41 Old County Rd, Vineyard Haven, MA 02568
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  Est $1,100,157 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 934 Sq Ft

  10 Briarwood Ln, Vineyard Haven, MA 02568

  10 Briarwood Ln, Vineyard Haven, MA 02568

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