Oak Bluffs, MA Homes

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  $1,799,999

  • 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

  NorthStar Real Estate, LLC

  (508) 850-0854

  43 N Slope Ln, Chilmark, MA 02535
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  /21

  $7,000 total monthly price

  • 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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  /46

  $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 $4,101,962

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

  140 Pond Rd, Vineyard Haven, MA 02568
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  /30

  Est $2,464,428 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  10 Crow Hollow Rd, Vineyard Haven, MA 02568

  10 Crow Hollow Rd, Vineyard Haven, MA 02568
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  /18

  $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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  /20

  $6,000 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • House for Rent

  11 Hammett Ln, Chilmark, MA 02535

  ** WEEKLY SUMMER RATE** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  11 Hammett Ln, 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 $1,603,863

  Last Listing Agent Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
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  /2

  Est $2,548,131 Not Listed For Sale

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

  230 Pond Rd, Vineyard Haven, MA 02568

  230 Pond 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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  /10

  $8,500 total monthly price

  • 3 Beds
  • 2 Baths
  • House for Rent

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

  Karen Overtoom Karen M. Overtoom R.E.

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
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  /18

  $4,250,000 Sold Sep 09, 2025

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 4,125 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $1,030/SF
  • 21 Days On Market

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /4

  Est $3,009,324 Not Listed For Sale

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

  188 Pond Rd, Vineyard Haven, MA 02568

  188 Pond Rd, Vineyard Haven, MA 02568
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  $4,695,000 Pending

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

  97 Longview Rd, Vineyard Haven, MA 02568

  This beautifully designed post-and-beam home features stunning views of the Vineyard Sound, Elizabeth Islands, and unforgettable sunsets. Surrounded by beautiful stone walls and perfectly sited on 2.2 acres, this serene property offers a combination of luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels, all opening onto generous decks ideal for

  Stephanie Roache Donnelly + Co

  97 Longview Rd, Vineyard Haven, MA 02568
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  /8

  $11,800 total monthly price

  • 4 Beds
  • 4 Baths
  • 2,612 Sq Ft
  • House for Rent

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

  Karen Overtoom Karen M. Overtoom R.E.

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
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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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  Est $2,473,034 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 1 Sq Ft

  248 Pond Rd, Vineyard Haven, MA 02568

  248 Pond Rd, Vineyard Haven, MA 02568
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  /7

  $400,000

  • 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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  /8

  $16,000 total monthly price

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

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

  Karen Overtoom Karen M. Overtoom R.E.

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
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  /7

  $650,000 Sold Aug 14, 2025

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

  • Land
  • 0.2 Acre
  • $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 $2,104,866 Not Listed For Sale

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

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  131 Shubael Weeks Path, Vineyard Haven, MA 02568
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  /29

  $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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  /12

  $6,180 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft
  • House for Rent

  44 Music St Wt153, West Tisbury, MA 02575

  PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

  Karen Overtoom Karen M. Overtoom R.E.

  44 Music St Wt153, West Tisbury, MA 02575
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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

  Last Listing Agent Candy DaRosa Feiner Real Estate

  140 Longview Rd, Vineyard Haven, MA 02568
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  /2

  Est $1,809,681 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,102 Sq Ft

  26 Old Coach Rd, Vineyard Haven, MA 02568

  26 Old Coach Rd, Vineyard Haven, MA 02568
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  /4

  $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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  /8

  $8,250 total monthly price

  • 7 Beds
  • 5 Baths
  • 3,528 Sq Ft
  • House for Rent

  227 S Gate Rd Wt120, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

  Karen Overtoom Karen M. Overtoom R.E.

  227 S Gate Rd Wt120, West Tisbury, MA 02575
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  $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 $6,307,216

  Last Listing Agent Deb Hancock Hancock Real Estate

  25 Osprey Ln, Chilmark, MA 02535
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  /79

  Not Listed For Sale

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

  260 South Rd, Chilmark, MA 02535

  260 South Rd, Chilmark, MA 02535
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  /25

  $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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  /8

  $4,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • House for Rent

  33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

  THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
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  /22

  $435,000 Sold Aug 26, 2025

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

  • Land
  • 0.1 Acre
  • $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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  /36

  Est $2,360,766 Not Listed For Sale

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

  377 State Rd, Vineyard Haven, MA 02568

  377 State Rd, Vineyard Haven, MA 02568
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  /21

  $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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  /8

  $4,800 total monthly price

  • 3 Beds
  • 3 Baths
  • 3,279 Sq Ft
  • House for Rent

  165 Christiantown Rd, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

  Karen Overtoom Karen M. Overtoom R.E.

  165 Christiantown Rd, West Tisbury, MA 02575
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  /2

  $1,645,000 Sold Feb 21, 2025

  49 Oak Ln, West Tisbury, MA 02575

  • 4 Beds
  • 3.5 Baths
  • 2,576 Sq Ft
  • Built 1974

  Last Sold Summary

  • 10% Above List Price
  • $639/SF
  • 6 Days On Market

  Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  49 Oak Ln, West Tisbury, MA 02575
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  /14

  Est $2,771,008 Not Listed For Sale

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

  30 Pond Ln, Vineyard Haven, MA 02568

  30 Pond Ln, Vineyard Haven, MA 02568
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  /50

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  20 Brook Hollow Rd, Vineyard Haven, MA 02568

  This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

  Jim Feiner Feiner Real Estate

  20 Brook Hollow Rd, Vineyard Haven, MA 02568
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  /8

  $8,000 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 3,600 Sq Ft
  • House for Rent

  56 Chilmark Rd, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master

  Karen Overtoom Karen M. Overtoom R.E.

  56 Chilmark Rd, 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

  Last Listing Agent Stephanie Roache Donnelly + Co.

  1054 State 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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