Oak Bluffs, MA Homes

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  /42

  $7,950,000

  • 5 Beds
  • 7 Baths
  • 4,531 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  /8

  $7,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • House for Rent

  2 Paddock Cir, Chilmark, MA 02535

  Karen Overtoom Karen M. Overtoom R.E.

  2 Paddock Cir, Chilmark, MA 02535
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  /3

  $3,100,000 Sold Jul 03, 2025

  • 1,500 Sq Ft
  • $2,067/SF

  • 6 Beds
  • 3 Baths
  • Built 1975

  10 Basin Rd, Chilmark, MA 02535

  Unique compound in the heart of Menemsha - one of a kind!The cottage (520 sq.ft.), the chandlery buikding(5968 sq.ft.) and deli with an apartment(2172 sq.ft.) on just under an acre of land has tremendous potential for the right buyer!Special permits are required from the town to operate a business but they have approved a deli/restuarant, small stores and a commercial kitchen in the past.

  Julianna Flanders Flanders Real Estate

  10 Basin Rd, Chilmark, MA 02535
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  /16

  Est $1,211,244 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
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  /59

  $2,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,983 Sq Ft

  157 Ben Chase Rd, West Tisbury, MA 02575

  You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

  Madelyn Silvia Wallace & Co. Sotheby's

  157 Ben Chase Rd, West Tisbury, MA 02575
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  /36

  $1,950,000 Sold Jul 02, 2025

  • 2,691 Sq Ft
  • $725/SF
  • 30 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1976

  51 Black Brook Crossing Rd, West Tisbury, MA 02568

  This charming 4 bed/2.5 bath Cape style home is set in a perfect setting, carefully sited on 1 acre bordered by a beautiful stone wall with mature plantings. Newly renovated kitchen with plenty of cabinets and storage, quartz counters and dining room with sliders to a screened-in porch. There is a den and living room with access to a spacious deck. The Great Room features cathedral ceilings,

  Brenda Galligan Karen M. Overtoom R.E.

  51 Black Brook Crossing Rd, West Tisbury, MA 02568
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  /37

  Est $1,172,287 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  43 Skiffs Ln, Vineyard Haven, MA 02568

  43 Skiffs Ln, Vineyard Haven, MA 02568
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  /7

  $2,500,000

  • Land
  • 1.4 Acres
  • $1,785,714 per Acre

  2 Other House Rd Unit 173, Chilmark, MA 02535

  Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

  Russell Maloney Russell Maloney Real Estate

  2 Other House Rd Unit 173, Chilmark, MA 02535
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  /2

  $1,595,000 Sold Jul 01, 2025

  • 1,176 Sq Ft
  • $1,356/SF

  • 2 Beds
  • 1.5 Baths
  • Built 1998

  10 Red Pony Rd, West Tisbury, MA 02568

  Pastoral and perfect. Room to grow or just move in.

  Lisa Da Silva Compass | Point B

  10 Red Pony Rd, West Tisbury, MA 02568
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  /26

  Est $5,313,502 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
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  /8

  $1,425,000

  • Land
  • 3.01 Acres
  • $473,422 per Acre

  38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568

  The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

  Elissa Lash Tea Lane Associates

  38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
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  /32

  $3,925,000 Sold Jul 01, 2025

  • 5,603 Sq Ft
  • $701/SF
  • 238 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 1995

  140 Merry Farm Rd, Vineyard Haven, MA 02568

  Site of the original Rainbow Farm, this 8.05-acre parcel is one of the most beautiful pieces of land in West Tisbury. The warm and convivial 5,000 sq ft home with its 4 bedrooms looks out onto a setting that is as if from a bygone era, the vast fields stretching into the distance. The spring-fed pond is a centerpiece of the pastoral view. The home itself has many surprising and charming design

  Mark Jenkins Wallace & Co. Sotheby's

  140 Merry Farm Rd, Vineyard Haven, MA 02568
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  /26

  Est $1,484,787 Not Listed For Sale

  • 5 Beds
  • 2.5 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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  /26

  $1,345,000

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  9 Galway Rd, Vineyard Haven, MA 02568

  Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

  Julianna Flanders Flanders Real Estate

  9 Galway Rd, Vineyard Haven, MA 02568
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  /6

  $430,000 Sold Jun 30, 2025

  • Land
  • 1.4 Acres
  • $307,143 per Acre

  • 0 Days On Market

  0 Quansoo Beach Lot Unit 76 43513, Chilmark, MA 02535

  Not listed in LINK.

  LINK Email Cache LINK

  0 Quansoo Beach Lot Unit 76 43513, Chilmark, MA 02535
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  /30

  Est $2,417,153 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,540 Sq Ft

  41 Hidden Village Rd, Vineyard Haven, MA 02568

  41 Hidden Village Rd, Vineyard Haven, MA 02568
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  /2

  $799,000

  • Land
  • 0.92 Acre
  • $870,181 per Acre

  22 Bramble Path Unit 214, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path Unit 214, West Tisbury, MA 02568
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  /47

  $1,595,500 Sold Jun 23, 2025

  • 1,822 Sq Ft
  • $876/SF
  • 73 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2003

  21 Coffins Field Rd, Edgartown, MA 02539

  EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well

  Helena Kirschenbaum Studio Realty

  21 Coffins Field Rd, Edgartown, MA 02539
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  /30

  Est $1,541,820 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,560 Sq Ft

  12 Lily Farm Rd, Vineyard Haven, MA 02568

  12 Lily Farm Rd, Vineyard Haven, MA 02568
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  /2

  $799,000

  • Land
  • 0.91 Acre
  • $878,022 per Acre

  22 Bramble Path, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been done that supports a four bedroom title five system. It is the buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path, West Tisbury, MA 02568
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  /6

  $430,000 Sold Jun 18, 2025

  • Land
  • 1.4 Acres
  • $307,143 per Acre

  • 0 Days On Market

  0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

  Not listed in LINK.

  LINK Email Cache LINK

  0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
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  /29

  Est $1,689,499 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  7 Flanders Ln, Chilmark, MA 02535

  7 Flanders Ln, Chilmark, MA 02535
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  /42

  $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, sited on 2.2 acres, this serene property offers luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels with generous decks ideal for outdoor living and entertaining. The upper

  Stephanie Roache Donnelly + Co.

  97 Longview Rd, Vineyard Haven, MA 02568
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  /20

  $821,000 Sold Jun 17, 2025

  • Land
  • 1.4 Acres
  • $586,429 per Acre

  • 0 Days On Market

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

  Large 1.4 Acre Corner lot in Vineyard Meadow Farms South side of West Tisbury Road. Private, flat, level parcel, paved dead end road with no unnecessary through traffic. Six bedrooms, a 3,000SF Main House, a 2,000SF detached/attached Secondary Building allowed per the Town. Pool allowed with standard Special permit. Centrally located to all Island Towns. Great neighborhood. Great location with

  Janna O'Loughlin Portfolio Real Estate, Inc.

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
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  /13

  Est $1,465,652 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  12 Harbor Hill Rd, Chilmark, MA 02535

  12 Harbor Hill Rd, Chilmark, MA 02535
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  /27

  $1,495,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft

  42 Hidden Village Rd, Vineyard Haven, MA 02568

  Nestled off Hidden Village Road on 2.1 private wooded acres, this spacious 4-bedroom, 2-bath home offers the perfect blend of peace and convenience--just 1.5 miles from Lambert's Cove Beach and a short distance to Ice House Pond. Inside, enjoy an open-concept layout with cathedral ceilings, skylights, and an abundance of natural light. Sliding doors lead to a sunny, south-facing deck with

  Sheila Morse Island Real Estate

  42 Hidden Village Rd, Vineyard Haven, MA 02568
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  /18

  $1,219,000 Sold Jun 16, 2025

  • 1,512 Sq Ft
  • $806/SF
  • 99 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1986

  108 Charles Neck Way, Vineyard Haven, MA 02568

  This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room,

  Alyssa Halisky Wallace & Co. Sotheby's

  108 Charles Neck Way, Vineyard Haven, MA 02568
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  /18

  Est $3,695,146 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  1 Pond Mark, Chilmark, MA 02535

  1 Pond Mark, Chilmark, MA 02535
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  /12

  $1,250,000 Pending

  • Land
  • 4.32 Acres
  • $289,352 per Acre

  1 Crowberry Ln Unit 19, Chilmark, MA 02535

  Ready to build, private, 4.3 acres in Chilmark located just off of North Road and minutes from the iconic fishing village of Menemsha. This parcel comes equipped with a well, 4 bedroom septic system, electricity and cable all in place for seamless development. There is an existing garden house that can be repurposed as a construction site shed and perhaps later an ADU. The lot has recently been

  Russell Maloney Russell Maloney Real Estate

  1 Crowberry Ln Unit 19, Chilmark, MA 02535
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  /20

  $1,150,000 Sold Jun 13, 2025

  • 1,374 Sq Ft
  • $837/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  46 Old Coach Rd, Vineyard Haven, MA 02568

  Charming and Spacious 3-Bedroom Cape with large Loft and Deck Welcome to your dream West Tisbury home! This comfortable and spacious 3-bedroom, 2-bath Cape boasts a thoughtfully designed floor plan perfect for comfortable living. The first-floor features two bedrooms and a full bath, ideal for use as sleeping quarters or a home office. Moving to the second floor, discover privacy with a third

  Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
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  /19

  Est $2,478,758 Not Listed For Sale

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

  27 Ocean View Farm Rd, Chilmark, MA 02535

  27 Ocean View Farm Rd, Chilmark, MA 02535
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  /28

  $1,250,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  52 Old Coach Rd, Vineyard Haven, MA 02568

  Charming West Tisbury Home:*This charming country cape home is located in a private wooded association known as Island Farms in West Tisbury. The open floor plan kitchen, dining and living room area allow for comfortable living and convenience. Two French doors from the dining area open out onto a large deck with a dining table and chairs, couches and lounge chairs. Garden beds are plentiful

  Kathleen Kendrick Kendrick Real Estate

  52 Old Coach Rd, Vineyard Haven, MA 02568
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  /3

  $1,695,000 Sold May 30, 2025

  • 1,296 Sq Ft
  • $1,308/SF

  • 2 Beds
  • 2 Baths
  • Built 1960

  5 Vincent Rd, Vineyard Haven, MA 02568

  NOT LISTED IN LINK

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  5 Vincent Rd, Vineyard Haven, MA 02568
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  /69

  Est $2,333,534 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,034 Sq Ft

  276 South Rd, Chilmark, MA 02535

  276 South Rd, Chilmark, MA 02535
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  /26

  $1,950,000 Pending

  • 5 Beds
  • 3 Baths
  • 1,916 Sq Ft

  14 Rebekahs Way, Vineyard Haven, MA 02568

  Affectionately referred to as ‘The Treehouse', this property encompasses all the elements of a modern, sophisticated residence while providing the warmth and comfort of a private retreat. Professionally designed by Hutker Architects, this four-bedroom home, with a den/potential fifth bedroom, is sited in a private area, conveniently located with easy access to grocery store, pharmacy, and post

  Sheila Morse Island Real Estate

  14 Rebekahs Way, Vineyard Haven, MA 02568
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  /15

  $1,150,000 Sold May 30, 2025

  • 1,338 Sq Ft
  • $859/SF
  • 48 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1966

  14 Galway Rd, Vineyard Haven, MA 02568

  Welcome to 14 Galway Road, West Tisbury. The home and property have been lovingly maintained and used by the same family since the home was built. It offers an open eat-in kitchen/living room design with a masonry fireplace. On the first floor are two bedrooms, one full bathroom, a linen closet, and hidden washer and dryer along the hallway. The stairway brings you to a second floor which

  Michele Casavant Vineyard Village Realty

  14 Galway Rd, Vineyard Haven, MA 02568
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  /37

  Est $2,004,371 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,900 Sq Ft

  2 Rockrose Path, Chilmark, MA 02535

  2 Rockrose Path, Chilmark, MA 02535
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  /49

  $6,490,000 Pending

  • 6 Beds
  • 8 Baths
  • 5,660 Sq Ft

  60 Meetinghouse Rd, Chilmark, MA 02535

  This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

  Jim Feiner Feiner Real Estate

  60 Meetinghouse Rd, Chilmark, MA 02535
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  /32

  $1,050,000 Sold May 29, 2025

  • 1,701 Sq Ft
  • $617/SF
  • 28 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1960

  10 Rumpus Ridge Rd, Chilmark, MA 02535

  Discover this inviting two-unit property in the heart of Chilmark! Ideally situated near Chilmark General Store, Squibnocket, Menemsha, and the pristine shores of Lucy Vincent Beach, this home offers both convenience and charm. Thoughtfully updated for year-round comfort, the property features a new metal roof, new siding, solar panels, mini-split AC, and more. The main-level residence offers

  Peyton Wallace Studio Realty

  10 Rumpus Ridge Rd, Chilmark, MA 02535
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  /20

  Est $2,623,653 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  23 Black Point Rd, Chilmark, MA 02535

  23 Black Point Rd, Chilmark, MA 02535

Showing Results 161 - 200, Page 5 of 18