Oak Bluffs Homes for Sale

• 

  

  

  /15

  $510,000

  • 1 Bed
  • 1.5 Baths
  • 591 Sq Ft

  21 39G Island Inn Rd Unit 39G, Oak Bluffs, MA 02557

  Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

  Sheila Morse Island Real Estate

  21 39G Island Inn Rd Unit 39G, Oak Bluffs, MA 02557
• 

  

  

  /23

  $899,000

  • 1 Bed
  • 1.5 Baths
  • 1,182 Sq Ft

  4 Quail Run Unit 1, Oak Bluffs, MA 02557

  Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. This year-round home is filled with natural light and features a spacious deck —perfect for

  Jarrett Hurwitz Keller Williams Realty

  4 Quail Run Unit 1, Oak Bluffs, MA 02557
• 

  

  

  /41

  $8,900,000

  • 8 Beds
  • 9 Baths
  • 8,170 Sq Ft

  150 E Chop Dr, Oak Bluffs, MA 02568

  BIG BLUFF- Recognized for its architectural significance and featured in leading design publications, this home stands as one of the Vineyard’s most notable coastal residences. Set along the prestigious shoreline of East Chop, this estate represents a rare convergence of architectural pedigree, craftsmanship, and irreplaceable setting. Designed by Hutker Architects, built by J.G. Early, and

  Andrew McElhinney Compass LLC

  150 E Chop Dr, Oak Bluffs, MA 02568
• 

  

  

  /22

  $899,000

  • 2 Beds
  • 0.5 Baths
  • 953 Sq Ft

  50 Canonicus Ave, Oak Bluffs, MA 02557

  Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and

  Michele Moore Island Real Estate

  50 Canonicus Ave, Oak Bluffs, MA 02557
• 

  

  

  /14

  $5,100,000

  • Land
  • 2.34 Acres
  • $2,182,285 per Acre

  7 Overview Ln Unit 47, Oak Bluffs, MA 02557

  A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

  Alyssa Halisky Wallace & Co. Sotheby's

  7 Overview Ln Unit 47, Oak Bluffs, MA 02557
• 

  

  /14

  $5,100,000

  • Land
  • 2.34 Acres
  • $2,179,487 per Acre

  7 Overview Ln, Oak Bluffs, MA 02557

  A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association on Martha's Vineyard. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck,

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  7 Overview Ln, Oak Bluffs, MA 02557
• 

  

  /8

  $695,000

  • Land
  • 11,417 Sq Ft
  • $2,651,660 per Acre

  35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

  GOING, GOING... GONE!This is the LAST 3-bedroom lot available in Cluster C.12 lots SOLD 9 homes already built.Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes.The lot is ready

  Marilyn Moses Ocean Park Realty Inc

  35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
• 

  

  /30

  $1,245,000

  • 3 Beds
  • 2 Baths
  • 1,752 Sq Ft

  66 Barnes Rd, Vineyard Haven, MA 02568

  Oak Bluffs~ Classic Cape charm meets modern efficiency in this move-in-ready 3-bedroom home. Thoughtfully maintained and beautifully presented, the home features sun-filled living spaces, an updated kitchen, and comfortable bedrooms designed for easy everyday living. Enjoy year-round comfort with energy-efficient mini-split systems providing both heating and air conditioning, offering

  Marilyn Moses Ocean Park Realty Inc

  66 Barnes Rd, Vineyard Haven, MA 02568
• 

  

  /20

  $1,390,000

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  5 Seth's Path, Oak Bluffs, MA 02557

  Desirable picturesque Deer Run location. Just steps from the bike path, this centrally located home is a perfect island retreat. You can enjoy the multi level deck and patio overlooking a wonderful in ground pool. The large lot provides for plenty of room for gardening or games and backs up to an idyllic open field. This house is perfectly set back off of the small cul de sac. Wonderful location

  Robin Perschel Feiner Real Estate

  5 Seth's Path, Oak Bluffs, MA 02557
• 

  

  /59

  $1,325,000

  • 3 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  101 Tradewinds Rd, Oak Bluffs, MA 02557

  Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creating a warm and inviting space. The interior features hardwood floors in the dramatic great room

  Nya Clarke Martha's Vineyard Island-Wide Realty

  101 Tradewinds Rd, Oak Bluffs, MA 02557
• 

  

  /7

  $599,000

  • Land
  • 3,049 Sq Ft
  • $8,557,143 per Acre

  112 Dukes County Ave, Oak Bluffs, MA 02557

  Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha’s Vineyard’s most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park.This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved

  Rose Ryley Wallace & Co. Sotheby's International Realty

  112 Dukes County Ave, Oak Bluffs, MA 02557
• 

  

  /4

  $465,000

  • Land
  • 9,997 Sq Ft
  • $2,026,144 per Acre

  0 California Ave Unit 76 42933, Oak Bluffs, MA 02568

  Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for a one bedroom home of any size. Water and electric are nearby.

  Jim Joyce Carroll & Vincent R.E.

  0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
• 

  

  /18

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  10 Winthrop Ave, Oak Bluffs, MA 02557

  Oak Bluffs- Fully renovated and just completed, this three-bedroom, two-bath home is ready for immediate occupancy! Ideally located just moments from downtown Oak Bluffs and the vibrant harborfront, you’ll enjoy easy access to shops, dining, beaches, and ferry connections. Featuring modern updates throughout, this home offers the perfect blend of comfort and convenience.

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  10 Winthrop Ave, Oak Bluffs, MA 02557
• 

  

  /36

  $1,275,000

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft

  9 Brunswick Ave, Oak Bluffs, MA 02557

  PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully & extensively UPDATED INSIDE AND OUT. Enjoy peace of mind w/ NEW septic system, siding, windows, water line from the street, & upgraded electrical & plumbing. Interior boasts new flooring, insulation, fresh paint, a stylishly

  Alice Pierce Coldwell Banker Realty - Hingham

  9 Brunswick Ave, Oak Bluffs, MA 02557
• 

  

  /36

  $4,695,000

  • 7 Beds
  • 4.5 Baths
  • 5,320 Sq Ft

  8 Fresh Pond Rd, Oak Bluffs, MA 02557

  The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

  Jarrett Hurwitz Keller Williams Realty

  8 Fresh Pond Rd, Oak Bluffs, MA 02557
• 

  

  /15

  $950,000

  • 2 Beds
  • 1 Bath
  • 1,074 Sq Ft

  22 Firehouse Ln, Oak Bluffs, MA 02557

  Tucked away on a quiet side street just 0.7 miles from Circuit Avenue, this charming Oak Bluffs cottage offers the rare combination of privacy and proximity to town. The original two-bedroom, one-bath home was thoughtfully expanded to include a bright great room that opens directly to a large fenced yard — ideal for outdoor dining, pets, or simply enjoying Vineyard summers. The property is

  Jennifer O'hanlon Compass LLC

  22 Firehouse Ln, Oak Bluffs, MA 02557
• 

  

  /37

  $2,495,000

  • 6 Beds
  • 2.5 Baths
  • 2,577 Sq Ft

  16 Atlantic Ave, Oak Bluffs, MA 02557

  Oak Bluffs | East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The stately five-bedroom main residence is rich in character and nostalgic charm, thoughtfully updated to enhance comfort for year-round living. Tucked privately at the rear of the

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  16 Atlantic Ave, Oak Bluffs, MA 02557
• 

  

  /18

  $799,000

  • 2 Beds
  • 1 Bath
  • 623 Sq Ft

  1 Pease Ave, Oak Bluffs, MA 02557

  Tucked away on a quiet no-thru street near the Tabernacle and Trinity Park, this meticulously maintained year-round Martha’s Vineyard Camp Meeting Association cottage blends charm and convenience. Thoughtful 2023 updates—including a new kitchen with stainless steel appliances, refreshed bathroom, upgraded insulation and electrical, three mini-splits, onsite laundry, spiral staircase, and new

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  1 Pease Ave, Oak Bluffs, MA 02557

Showing Results 41 - 58, Page 2 of 2