Chilmark, MA Homes

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  /53

  $4,800,000

  • 6 Beds
  • 5 Baths
  • 2,960 Sq Ft

  104 Pond View Farm Rd, Vineyard Haven, MA 02568

  An exceptional Waterfront Compound on Tisbury Great Pond. Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, this remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.Both the main house and

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, 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
• 

  

  

  /22

  $1,500,000 Sold Nov 05, 2024

  • 1,008 Sq Ft
  • $1488/SF
  • 361 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2010

  5 Meetinghouse Rd, Chilmark, MA 02535

  CHARMING CHILMARK- This sweet, sunny home comes with deeded access to Chilmark Pond and South Shore Beach. Kayak, paddleboard, sail, or motor across the pond to one of Chilmark's most pristine private beaches. The location is also convenient, being centrally located and close to West Tisbury Center, Grey Barn, the Yoga Barn, Chilmark Center, Beetlebung Farm, Chilmark Store, and Chilmark Tavern.

  Tina Miller Compass

  5 Meetinghouse Rd, Chilmark, MA 02535
• 

  

  

  /13

  Est $4,432,489 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  144 Pond View Farm Rd, Vineyard Haven, MA 02568

  144 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /52

  $6,750,000

  • 5 Beds
  • 4 Baths
  • 4,050 Sq Ft

  78 Hammett Rd, Chilmark, MA 02535

  Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

  Robert Kenney Tea Lane Associates

  78 Hammett Rd, Chilmark, MA 02535
• 

  

  /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
• 

  

  /16

  $3,950,000 Sold Nov 01, 2024

  • 1,024 Sq Ft
  • $3857/SF
  • 16 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1973

  201 Thumb Point Rd, Vineyard Haven, MA 02568

  Private and tranquil waterfront retreat with sweeping water views and sandy beaches on Tisbury Great Pond. This charming, five-bedroom camp, perched in the dunes above the water, was designed in a summer-camp architectural style with common gathering space in the main cottage surrounded by decks connecting to bedroom cottages. The simple and classic set up with the Great Pond bordering two sides

  Meg Bodnar Tea Lane Associates

  201 Thumb Point Rd, Vineyard Haven, MA 02568
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  /6

  Est $3,012,122 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,935 Sq Ft

  71 Runner Rd, Vineyard Haven, MA 02568

  71 Runner Rd, Vineyard Haven, MA 02568
• 

  

  /45

  $19,500,000

  • 7 Beds
  • 6 Baths
  • 3,344 Sq Ft

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

  This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

  Thomas Leclair Landvest MV

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535
• 

  

  /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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  /26

  $950,000 Sold Oct 25, 2024

  • 1,182 Sq Ft
  • $804/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1977

  4 Elias Ln, Vineyard Haven, MA 02568

  This iconic West Tisbury property features a rustic post and beam farmhouse with endless charm. The inviting home highlights original wide-planked wood floors, cathedral ceiling, wood-burning stove and fireplace, and exposed brick. Enjoy the cozy kitchen, dining, and living area on the first floor, including a full bath and mudroom. The bedroom occupies the second floor with room for an

  Stephanie Roache Donnelly + Co

  4 Elias Ln, Vineyard Haven, MA 02568
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  /32

  Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,150 Sq Ft

  6 N Vine Ln, Vineyard Haven, MA 02568

  6 N Vine Ln, Vineyard Haven, MA 02568
• 

  

  /23

  $6,000,000

  • 3 Beds
  • 2 Baths
  • 2,710 Sq Ft

  35 S Bowl Rd, Chilmark, MA 02535

  This exceptionally elegant and tranquil home in Seven Gates Farm combines contemporary architectural design with timeless high-end features for Vineyard casual, nature-inspired living. Extraordinary and rare, this move-in ready three-bedroom home with six-bedroom septic system sits on an oversized 5.3-acre parcel in Chilmark. This thoughtful layout has an easy flow, soothing tones with cypress

  Meg Bodnar Tea Lane Associates

  35 S Bowl Rd, 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
• 

  

  /19

  $2,200,000 Sold Oct 25, 2024

  • 2,450 Sq Ft
  • $898/SF
  • 182 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1964

  27 Ocean View Farm Rd, Chilmark, MA 02535

  27 Ocean View Farm Road is a unique house with the main living spaces designed by architect Elizabeth Carlhian in 1964 along with a connected, yet private bed and bath suite designed by architects Modigliani/Noyes in 1987. A covered breezeway between the two spaces frames the ocean views while providing cover from the weather. Taken together the house consists of 4 bedrooms and 3 baths sited high

  Russell Maloney Russel Maloney Real Estate

  27 Ocean View Farm Rd, Chilmark, MA 02535
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  /24

  Est $3,908,516 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,415 Sq Ft

  175 Pond Rd, Vineyard Haven, MA 02568

  175 Pond Rd, Vineyard Haven, MA 02568
• 

  

  /13

  $2,950,000

  • 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, brick patio and outside shower. 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 fully furnished,

  Patty Kendall Kendall & Kendall

  18 Allen Farm 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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  /42

  $1,900,000 Sold Oct 24, 2024

  • 2,172 Sq Ft
  • $875/SF
  • 66 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1984

  44 Music St, Vineyard Haven, MA 02568

  A rare opportunity to own in a cherished area of West Tisbury town center. Living is easy and peaceful on Music Street! Stroll to town for your morning paper and coffee at the general store, grab the yummiest breakfast sandwiches at 7A, enjoy the lively library, the Field Gallery or local events happening at the Grange Hall. This home offers country living close to fun town living. The main house

  Jill Napior Tea Lane Associates

  44 Music St, Vineyard Haven, MA 02568
• 

  

  /31

  Est $1,255,549 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 855 Sq Ft

  16 Elias Ln, Vineyard Haven, MA 02568

  16 Elias Ln, Vineyard Haven, MA 02568
• 

  

  /51

  $7,950,000

  • 4 Beds
  • 5 Baths
  • 3,490 Sq Ft

  308 South Rd, Chilmark, MA 02535

  Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers a rare blend of privacy, elegance, and modern comfort. Originally built by Tom Tate and renovated in 2018, it exudes contemporary sophistication while embracing its natural surroundings. A private dock on Chilmark Pond provides direct water access and stunning South Shore sunsets.

  Rose Ryley Sandpiper Realty Inc

  308 South Rd, Chilmark, MA 02535
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  /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
• 

  

  /19

  $1,800,000 Sold Oct 17, 2024

  • 1,822 Sq Ft
  • $988/SF
  • 224 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  7 Parsonage Woods Rd, West Tisbury, MA 02568

  This rare and cherished setting is truly in the heart of West Tisbury. With old growth cedar, oaks and evergreen trees this level 4.8 acre parcel includes a main house and timber barn, perfectly sited to enjoy serene views and southern exposure. Currently set up as a horse farm with a two stall barn, paddocks, full size arena, interconnecting grazing areas and multiple watering stations, it could

  Grace Bishop Compass

  7 Parsonage Woods Rd, West Tisbury, MA 02568
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  /28

  Est $1,275,006 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  175 Oak Ln, Vineyard Haven, MA 02568

  175 Oak Ln, Vineyard Haven, MA 02568
• 

  

  /46

  $39,000,000

  • 9 Beds
  • 9 Baths
  • 7,846 Sq Ft

  41 Cobbs Hill Rd, Chilmark, MA 02535

  One of the most exclusive estates across the Northeast, Blue Heron Farm on Martha's Vineyard is set on nearly 30 acres of lush landscaping along the shores of Tisbury Great Pond. The former summer residence of President Obama and family, chosen for its incredible privacy, serenity and significance, this multi-generational compound is protected by surrounding farmland and mature trees.

  Brian Dougherty Corcoran Property Advisors

  41 Cobbs Hill Rd, Chilmark, MA 02535
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  /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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  /34

  $6,100,000 Sold Oct 16, 2024

  • 3,859 Sq Ft
  • $1581/SF
  • 38 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 1941

  391 Middle Rd, Chilmark, MA 02535

  This iconic property and location is truly a once-in-a-lifetime opportunity. Exceptional house and guest house that is ready to move into . The exterior resonates with what is beloved about Chilmark but the interior is contemporary and fresh. The main house has views overlooking the Keith farm and the Atlantic Ocean beyond, old stone walls and open meadows. A new owner will have the gratification

  Jill Napior Tea Lane Associates

  391 Middle Rd, Chilmark, MA 02535
• 

  

  /23

  Est $1,959,900 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,026 Sq Ft

  171 Otis Bassett Rd, Vineyard Haven, MA 02568

  171 Otis Bassett Rd, Vineyard Haven, MA 02568
• 

  

  /20

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

  Brenda Galligan Karen M. Overtoom R.E.

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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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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  /6

  $430,000 Sold Oct 10, 2024

  • Land
  • 0.60 Acre
  • $716,667 per Acre

  • 0 Days On Market

  0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535

  Not listed in LINK.

  LINK Email Cache LINK

  0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
• 

  

  /16

  Est $1,338,410 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  35 Skiffs Ln, Vineyard Haven, MA 02568

  35 Skiffs Ln, Vineyard Haven, MA 02568
• 

  

  /51

  $5,295,000

  • 5 Beds
  • 4 Baths
  • 4,044 Sq Ft

  49 Gosnold's Way, Chilmark, MA 02535

  Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

  Meg Bodnar Tea Lane Associates

  49 Gosnold's Way, Chilmark, MA 02535
• 

  

  /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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  /29

  $1,680,000 Sold Oct 09, 2024

  • 1,200 Sq Ft
  • $1400/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  7 Flanders Ln, Chilmark, MA 02535

  Sweet, renovated cottage in Menemsha. Classic Vineyard home that is move-in ready! You'll find a renovated kitchen, central A/C, new bathrooms and fresh interior which still maintains the cottage charm of the original house. Open living room through to kitchen with all three bedrooms on the main level. The house is at the beginning of Flanders Lane just 1/4 mile from the Village of Menemsha

  Meg Bodnar Tea Lane Associates

  7 Flanders Ln, Chilmark, MA 02535
• 

  

  /26

  Est $4,720,473 Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 4,800 Sq Ft

  48 Forest Rd, Vineyard Haven, MA 02568

  48 Forest Rd, Vineyard Haven, MA 02568
• 

  

  /30

  $1,695,000

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

  251 State Rd, Vineyard Haven, MA 02568

  This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. The charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive family room off the sunny entrance

  Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, 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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  /8

  $660,000 Sold Oct 04, 2024

  • Land
  • 1.60 Acres
  • $412,500 per Acre

  • 175 Days On Market

  87 Longview Rd, West Tisbury, MA 02575

  This lovely 1.60 acre wooded parcel is located in an outstanding neighborhood off Lambert's Cove Road with paved roads and easy access to beautiful Lambert's Cove Beach, less than a mile away. This lot is ready to build on. It has been staked, there is an approved septic design for 4 bedrooms, well has been installed and electric and cable are to the lot. This is the chance to build the house of

  Brenda Galligan Karen M. Overtoom R.E.

  87 Longview Rd, West Tisbury, MA 02575
• 

  

  /26

  Est $1,555,406 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,968 Sq Ft

  33 Hidden Village Rd, Vineyard Haven, MA 02568

  33 Hidden Village Rd, Vineyard Haven, MA 02568

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