Chilmark, MA Homes

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  /2

  $2,400,000 Sold Feb 04, 2025

  • 3,035 Sq Ft
  • $791/SF
  • 213 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 2007

  23 Oak Ln, Vineyard Haven, MA 02568

  Oasis in the woods of West Tisbury! This meticulously constructed, updated and well-maintained home is set on an expansive, yet private, 2.7 acre parcel. This 6-bedroom home has three levels of living space, 2,363 square feet on the spacious first floor, 672 over the garage and 1,877 in the bright, sunlight-filled lower level, for a total of 4,912 square feet. This home abounds in gathering

  Lynn Buder Sandpiper Realty Inc

  23 Oak Ln, Vineyard Haven, MA 02568
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  /7

  Est $1,466,962 Not Listed For Sale

  35 Plum Bush Point Rd, West Tisbury, MA 02568

  35 Plum Bush Point Rd, West Tisbury, MA 02568
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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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  $2,895,000 Sold Jan 08, 2025

  • 4,239 Sq Ft
  • $683/SF
  • 339 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1999

  18 S Pond Rd, Vineyard Haven, MA 02568

  DEEP BOTTOM POND: 5-bedroom custom home with heated Pebbletec pool and exclusive association access to Tisbury Great Pond. This spacious layout features two primary suites, two guest rooms, and a third private guest suite. Perfect for entertaining, the open floor plan centers around the kitchen, dining, and living areas. The dramatic living room has cathedral ceilings, floor-to-ceiling windows, a

  Rose Ryley Sandpiper Realty Inc

  18 S Pond Rd, Vineyard Haven, MA 02568
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  /42

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,928 Sq Ft

  23 Indian Hollow Rd, West Tisbury, MA 02575

  23 Indian Hollow Rd, West Tisbury, MA 02575
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  /22

  $3,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,703 Sq Ft
  • House for Rent

  41 Oak Lane Wt147, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

  Karen Overtoom Karen M. Overtoom R.E.

  41 Oak Lane Wt147, West Tisbury, MA 02575
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  /2

  $2,280,000 Sold Aug 05, 2024

  • 3,527 Sq Ft
  • $646/SF
  • 100 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1999

  230 Pond Rd, Vineyard Haven, MA 02568

  This distinguished four bedroom, four bathroom home in Deep Bottom Pond is meticulously maintained and ready for the 2024 season. Featuring a grand foyer, screened in porch, elegant living room with wood burning fireplace, oversized primary suite with private bathroom and private balcony, finished lower level, mahogany decking, attached two car garage and generator. Neighborhood amenities include

  Rose Ryley Sandpiper Realty Inc

  230 Pond Rd, Vineyard Haven, MA 02568
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  /22

  Est $1,035,280 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  57 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  57 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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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

  $5,300,000 Sold Jun 14, 2024

  • 6,565 Sq Ft
  • $807/SF
  • 173 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1714

  5 Stillpoint Meadows Rd, West Tisbury, MA 02575

  5 Stillpoint Meadows is where modern luxury and historic preservation seamlessly blend, creating the casual yet refined lifestyle so highly sought after in West Tisbury. The five-bedroom home, enriched by original details, offers several living areas and an expansive eat-in kitchen. Immaculately manicured grounds, elevated by serene plantings and mature trees, will be enjoyed from several outdoor

  Katherine Donahue Sandpiper Realty Inc

  5 Stillpoint Meadows Rd, West Tisbury, MA 02575
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  /27

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  8 Yellow Brick Rd, Vineyard Haven, MA 02568

  8 Yellow Brick Rd, Vineyard Haven, MA 02568
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  /10

  $17,600 per month

  • 4 Beds
  • 3.5 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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  /13

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,480 Sq Ft

  205 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  205 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  /34

  $12,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • House for Rent

  267 Great Plains Road Wt117, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

  Karen Overtoom Karen M. Overtoom R.E.

  267 Great Plains Road Wt117, West Tisbury, MA 02575
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  /40

  Est $1,475,492 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,812 Sq Ft

  28 Rustling Oaks Rd, West Tisbury, MA 02575

  28 Rustling Oaks Rd, West Tisbury, MA 02575
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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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  /23

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,512 Sq Ft

  259 State Rd, West Tisbury, MA 02575

  259 State Rd, West Tisbury, MA 02575
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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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  /10

  Not Listed For Sale

  139 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  139 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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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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  /26

  Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 4,805 Sq Ft

  48 Forest Rd, West Tisbury, MA 02575

  48 Forest Rd, West Tisbury, MA 02575
• 

  

  /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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  /11

  Est $2,199,106 Not Listed For Sale

  21 Tea Ln, Chilmark, MA 02535

  21 Tea Ln, Chilmark, MA 02535
• 

  

  /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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  /4

  Not Listed For Sale

  209 Oak Ln, West Tisbury, MA 02575

  209 Oak Ln, West Tisbury, MA 02575
• 

  

  /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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  /25

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,670 Sq Ft

  32 S Pond Rd, West Tisbury, MA 02575

  32 S Pond Rd, West Tisbury, MA 02575
• 

  

  /25

  $13,600 per month

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft
  • House for Rent

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

  Karen Overtoom Karen M. Overtoom R.E.

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
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  /41

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,962 Sq Ft

  6 Bea Ln, West Tisbury, MA 02575

  6 Bea Ln, West Tisbury, MA 02575
• 

  

  /41

  $14,500 per month

  • 5 Beds
  • 5.5 Baths
  • 3,392 Sq Ft
  • House for Rent

  76 School House Lane Wt101, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced

  Karen Overtoom Karen M. Overtoom R.E.

  76 School House Lane Wt101, West Tisbury, MA 02575
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  /7

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft

  105 Charles Neck Way, West Tisbury, MA 02575

  105 Charles Neck Way, West Tisbury, MA 02575
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  /9

  $10,800 per month

  • 4 Beds
  • 2 Baths
  • 702 Sq Ft
  • House for Rent

  141 N Rd Ch202, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

  Karen Overtoom Karen M. Overtoom R.E.

  141 N Rd Ch202, Chilmark, MA 02535
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  /33

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,075 Sq Ft

  63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  /21

  $11,000 per month

  • 2 Beds
  • 1.5 Baths
  • 800 Sq Ft
  • House for Rent

  55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. Nestled on a quiet country lane, this charming two BR guest house will enchant you with its inviting character and custom features throughout. From the cathedral living area and newly furnished interior to the covered front porch and expansive deck, this lovely cottage has it all. Privately situated , yet convenient to the village, bike path and local

  Karen Overtoom Karen M. Overtoom R.E.

  55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
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  /22

  Est $2,140,237 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,047 Sq Ft

  510 Lamberts Cove Rd, West Tisbury, MA 02568

  510 Lamberts Cove Rd, West Tisbury, MA 02568
• 

  

  /22

  $10,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • House for Rent

  21 Leona Lane Wt115, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This very charming post & beam home is the perfect getaway for those who appreciate West Tisbury's rural character. The home is very nicely furnished and equipped, has a lovely, big yard, and the location, adjacent to the bike path, is central to up-Island shopping and the fantastic sandy beaches of Lambert's Cove and Long Point Reservation. There is no land line

  Karen Overtoom Karen M. Overtoom R.E.

  21 Leona Lane Wt115, West Tisbury, MA 02575
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  /6

  Est $2,498,500 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 1,135 Sq Ft

  31 Tower Ln, Chilmark, MA 02535

  31 Tower Ln, Chilmark, MA 02535
• 

  

  /16

  $30,000 per month

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • House for Rent

  45A Buttonwood Farm Wt121, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This stunning sanctuary offers a unique balance of simplicity and sophistication. There is a lot of room for family and friends to enjoy both indoors and out. Nestled about midway between Tisbury and West Tisbury, here you will find yourself close to two of Martha's Vineyard's town centers. Enjoy ping pong in the retro style game room or a fire in the fire pit. This

  Karen Overtoom Karen M. Overtoom R.E.

  45A Buttonwood Farm Wt121, West Tisbury, MA 02575
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  /33

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft

  72 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  72 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
• 

  

  /11

  $25,000 per month

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • House for Rent

  61 Roadto Greatneck, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This lovely new build house features 3 bedrooms, and 3 bathrooms. There is a full gourmet kitchen, open to the dining, living and patio area. French doors off the living area open up to a beautiful blue stone patio complete with breath taking water views. All three bedrooms are located on the upstairs level including the master suite. Lambert's Cove Beach Access.

  Karen Overtoom Karen M. Overtoom R.E.

  61 Roadto Greatneck, West Tisbury, MA 02575

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