Oak Bluffs, MA Homes

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  /36

  $2,500,000

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft

  16 South Rd, Chilmark, MA 02535

  Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been updated

  Michele Casavant Vineyard Village Realty

  16 South Rd, Chilmark, MA 02535
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  /2

  $10,000 total monthly price

  • 6 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  15 Crowell Lane Wt119, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

  Karen Overtoom Karen M. Overtoom R.E.

  15 Crowell Lane Wt119, West Tisbury, MA 02575
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  /27

  $1,875,000 Sold Aug 27, 2025

  • 1,728 Sq Ft
  • $1,085/SF
  • 71 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  212 Charles Neck Way, Vineyard Haven, MA 02568

  This beautifully renovated South Shore retreat, located in a tranquil setting, features 3 bedrooms, 2 1/2 bathrooms, central air, all new Bosch appliances, in ground pool and mature perennial gardens galore! Sitting on 1.5 acres, this location provides easy access to Long Point Beach and the Red Pony Farm equestrian center and, includes access to the coveted Lamberts Cove Beach. The first floor

  Perry Patterson MV Luxury Homes LLC

  212 Charles Neck Way, Vineyard Haven, MA 02568
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  /41

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  566 Scrubby Neck Rd, Vineyard Haven, MA 02568

  566 Scrubby Neck Rd, Vineyard Haven, MA 02568
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  /36

  $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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  /25

  $13,600 total monthly price

  • 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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  /22

  $435,000 Sold Aug 26, 2025

  • Land
  • 0.1 Acre
  • $4,350,000 per Acre

  • 18 Days On Market

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

  Stunning Quansoo Beach Lot available NOW. With this ownership you will gain access to gated parking and endless beach days along the Islands expansive South Shore and Tisbury Great Pond! Skip the lines and parking worries and enjoy the freedom to come and go as you please. If you have been dreaming of endless beach days, long walks on private shores... here is your chance. ***Note: This is not a

  Emma Kiley Bryant Landmarks at TODAY Real Estate

  0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
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  /15

  Est $2,394,875 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 512 Sq Ft

  119 Old Thumb Point Rd, Vineyard Haven, MA 02568

  119 Old Thumb Point Rd, Vineyard Haven, MA 02568
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  /33

  $1,985,000

  • Land
  • 3.58 Acres
  • $554,469 per Acre

  4 Cedar Ln Unit 2.2, Chilmark, MA 02535

  Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with

  Jill Napior Tea Lane Associates

  4 Cedar Ln Unit 2.2, Chilmark, MA 02535
• 

  

  /18

  $10,000 total monthly price

  • 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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  /21

  $435,000 Sold Aug 26, 2025

  • Land
  • 0.1 Acre
  • $4,350,000 per Acre

  • 20 Days On Market

  0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

  Stunning Quansoo Beach Lot available NOW. With this ownership you will gain access to gated parking and endless beach days along the Islands expansive South Shore and Tisbury Great Pond! Skip the lines and parking worries and enjoy the freedom to come and go as you please. If you have been dreaming of endless beach days, long walks on private shores... here is your chance. ***Note: This is not a

  Emma Bryant Landmarks at TODAY Real Estate

  0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
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  /13

  Est $3,703,605 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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  /108

  $4,800,000

  • 6 Beds
  • 4.5 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

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /39

  $46,000 total monthly price

  • 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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  /7

  $650,000 Sold Aug 14, 2025

  • Land
  • 0.2 Acre
  • $3,250,000 per Acre

  • 7 Days On Market

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

  Spectacular Hancock beach lot on the Atlantic Ocean. Ownership of this lot allows you access to one of the world's most beautiful beaches, plenty of parking and away from the crowds. It is a most enjoyable spot to spend a relaxing day on the Vineyard, sunbathing, fishing, kayaking, canoeing, etc. as you also gain access to Chilmark Pond. Any property on the Vineyard would be greatly enhanced by

  Deb Hancock Hancock Real Estate

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
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  /42

  Est $1,904,690 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,172 Sq Ft

  44 Music St, Vineyard Haven, MA 02568

  44 Music St, Vineyard Haven, MA 02568
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  /45

  $19,500,000

  • 7 Beds
  • 5.5 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
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  /34

  $12,000 total monthly price

  • 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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  /24

  $1,200,180 Sold Aug 12, 2025

  • 1,144 Sq Ft
  • $1,049/SF
  • 13 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1972

  110 Otis Bassett Rd, Vineyard Haven, MA 02568

  MOVE-IN READY ISLAND HOME ON DOUBLE LOT WITH EXPANSION OPTIONS—Nestled in a highly desirable West Tisbury neighborhood, this 3-bedroom, 1-bath ranch offers the perfect blend of convenience, privacy, and access to some of Martha’s Vineyard’s most sought-after amenities.Set on a spacious and private 1.7-acre (double) lot, the property is just minutes from Down-Island towns while enjoying

  Jen O'Hanlon Compass | The O'Hanlon Group

  110 Otis Bassett Rd, Vineyard Haven, MA 02568
• 

  

  /23

  Est $1,974,665 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,370 Sq Ft

  50 Campbell Rd, Vineyard Haven, MA 02568

  50 Campbell Rd, Vineyard Haven, MA 02568
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  /32

  $22,950,000

  • 7 Beds
  • 8.5 Baths
  • 8,200 Sq Ft

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568

  This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design,

  Gerrett Conover Landvest MV

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568
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  /41

  $14,500 total monthly price

  • 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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  /32

  $2,278,000 Sold Aug 01, 2025

  • 2,685 Sq Ft
  • $848/SF
  • 139 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1998

  35 Woody Bottom Rd, West Tisbury, MA 02575

  This Cape style 5 bed/ 3.5 bath home is located in a nice area privately sited on 3 acres. This home features a nice floor plan thatincludes a fully equipped kitchen with center island, custom cabinetry and granite counters. Just off the kitchen is a sunny breakfastroom, a separate dining room, a spacious living room with fireplace and 2 sets of sliders to a backyard deck. There is a cozy

  Brenda Galligan Karen M. Overtoom R.E.

  35 Woody Bottom Rd, West Tisbury, MA 02575
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  /6

  Est $2,608,077 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
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  /37

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and

  Kerry Quinlan-Potter Breakwater MV

  4 Rock Pond Rd, Vineyard Haven, MA 02568
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  /22

  $3,000 total monthly price

  • 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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  /44

  $1,650,000 Sold Jul 29, 2025

  • 2,320 Sq Ft
  • $711/SF
  • 35 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1960

  26 Manaquayak Rd, Vineyard Haven, MA 02568

  Large comfortable and charming expanded Cape in a lovely setting very close to Lambert's Cove Beach and James Pond Preserve with special walking access to Swimming on Ice House Pond in the Manaquayak Preserve as well as deeded walking access to swim and boat on Seth's Pond. The living room is open to the beautiful newly-renovated kitchen and has an often-used wood-burning fireplace. There is a

  Candy DaRosa Feiner Real Estate

  26 Manaquayak Rd, Vineyard Haven, MA 02568
• 

  

  /31

  Est $1,353,687 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
• 

  

  /16

  $1,295,000

  • Land
  • 4.4 Acres
  • $294,318 per Acre

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535

  This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation. There are so many outstanding possibilities for a future Buyer to build their dream home on this

  Elissa Lash Tea Lane Associates

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
• 

  

  /22

  $10,000 total monthly price

  • 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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  /22

  $1,607,000 Sold Jul 10, 2025

  • 2,850 Sq Ft
  • $564/SF
  • 354 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1978

  10 N Abels Hill Rd, Chilmark, MA 02535

  A rare opportunity in the iconic Abel's Hill Association which offers private association beach access, three tennis courts and walking trails. This multi-level Chilmark home was designed and built as an homage to architect Frank Lloyd Wright's ethos of open living spaces with flowing sightlines from room to room. The main house has a pocket view to the Atlantic that opens in the fall and winter

  Elissa Lash Tea Lane Associates

  10 N Abels Hill Rd, Chilmark, MA 02535
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  /26

  Est $989,262 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,182 Sq Ft

  4 Elias Ln, Vineyard Haven, MA 02568

  4 Elias Ln, Vineyard Haven, MA 02568
• 

  

  /60

  $14,000,000

  • 6 Beds
  • 7 Baths
  • 6,967 Sq Ft

  8 Snail Rd, Chilmark, MA 02535

  This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

  Alyssa Halisky Wallace & Co. Sotheby's

  8 Snail Rd, Chilmark, MA 02535
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  /21

  $11,000 total monthly price

  • 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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  /44

  $37,000,000 Sold Jul 10, 2025

  • 7,846 Sq Ft
  • $4,716/SF
  • 39 Days On Market

  • 8 Beds
  • 5.5 Baths
  • Built 1993

  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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  /28

  Est $1,269,552 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
• 

  

  /30

  $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

  Tom Wallace Wallace & Co. Sotheby's International Realty

  25 Fulling Mill Rd, Chilmark, MA 02535
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  /9

  $10,800 total monthly price

  • 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
• 

  

  /42

  $2,900,000 Sold Jul 03, 2025

  • 4,476 Sq Ft
  • $648/SF
  • 347 Days On Market

  • 7 Beds
  • 5.5 Baths
  • Built 1997

  67 Hidden Village Rd, Vineyard Haven, MA 02568

  Picturesquely sited on a spacious 4.6-acre parcel this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels providing spacious yet private surroundings. The main living

  Stephanie Roache Donnelly + Co.

  67 Hidden Village Rd, Vineyard Haven, MA 02568
• 

  

  /23

  Est $1,905,437 Not Listed For Sale

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

  171 Otis Bassett Rd, Vineyard Haven, MA 02568

  171 Otis Bassett Rd, Vineyard Haven, MA 02568

Showing Results 121 - 160, Page 4 of 18