Oak Bluffs Homes for Sale

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  $1,075,000

  • 3 Beds
  • 2 Baths
  • 1,135 Sq Ft

  21 Butler Ave, Oak Bluffs, MA 02557

  Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with the comfort, privacy, and functionality of a thoughtfully modernized home. Two-car off-street parking—an exceptional Campground amenity—adds everyday convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away.

  Jennifer O'hanlon Compass LLC

  21 Butler Ave, Oak Bluffs, MA 02557
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  $5,225,000

  $100K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,890 Sq Ft

  4 Canonicus Ave, Oak Bluffs, MA 02557

  With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

  Katherine Donahue Sandpiper Realty

  4 Canonicus Ave, Oak Bluffs, MA 02557
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  $1,155,000

  $40K PRICE DROP

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

  3 Kims Way, Oak Bluffs, MA 02557

  Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  3 Kims Way, Oak Bluffs, MA 02557
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  $1,250,000

  • 1 Bed
  • 1 Bath
  • 855 Sq Ft

  0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

  Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

  Peyton Wallace Studio Realty

  0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
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  $599,000

  • Land
  • 3,197 Sq Ft
  • $8,160,763 per Acre

  112 Dukes County Ave Unit 209, 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

  112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557
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  $2,250,000

  • 3 Beds
  • 3.5 Baths
  • 2,475 Sq Ft

  35 Double Ox Rd, Oak Bluffs, MA 02557

  Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase $695,000 and building contract approximately $1,550,000.This 3-bedroom dream home is set

  Marilyn Moses Ocean Park Realty Inc

  35 Double Ox Rd, Oak Bluffs, MA 02557
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  $1,299,000

  $100K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  61 Ocean Ave Unit 4, Oak Bluffs, MA 02557

  THE BEST SEAT IN TOWN! This one-bedroom, one-bathroom condo offers incomparable, panoramic views of Vineyard Sound and the open ocean beyond, across the green expanse of Ocean Park with the Steamship Authority dock in the distance. Door to door, the ferry dock is 392 yards away. This perfect pied-a-terre is convenient to long stretches of beach, numerous shops, great and varied restaurants and

  Buder Team Sandpiper Realty, Inc.

  61 Ocean Ave Unit 4, Oak Bluffs, MA 02557
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  /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
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  /22

  $899,000

  $71K PRICE DROP

  • 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
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  $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
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  $695,000

  $55K PRICE DROP

  • 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
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  $3,250,000

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft

  6 Brewster Ave, Oak Bluffs, MA 02557

  Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home’s original charm. Tucked privately at the rear of the property, the guest cottage

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  6 Brewster Ave, Oak Bluffs, MA 02557
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  $825,000

  • 2 Beds
  • 1 Bath
  • 985 Sq Ft

  19 Perkins Ave, Oak Bluffs, MA 02557

  Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

  Katherine Donahue Sandpiper Realty

  19 Perkins Ave, Oak Bluffs, MA 02557
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  $2,295,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  312 E Chop Dr, Oak Bluffs, MA 02557

  “The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts

  Alyssa Halisky Wallace & Co. Sotheby's

  312 E Chop Dr, Oak Bluffs, MA 02557
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  $1,755,000

  $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,406 Sq Ft

  17 John Wesley Ave, Vineyard Haven, MA 02568

  Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features

  kyle Neyer Tea Lane Associates

  17 John Wesley Ave, Vineyard Haven, MA 02568
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  $1,250,000

  $185K PRICE DROP

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

  101 Tradewinds Rd, Oak Bluffs, MA 02557

  Motivated sellers - a great opportunity for a savvy buyer! 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

  Nya Clarke Martha's Vineyard Island-Wide Realty

  101 Tradewinds Rd, Oak Bluffs, MA 02557
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  $429,000

  $66K PRICE DROP

  • Land
  • 9,997 Sq Ft
  • $1,869,281 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
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  $1,275,000

  $20K PRICE DROP

  • 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
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  $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
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  $940,000

  $10K PRICE DROP

  • 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
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  /23

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 2,864 Sq Ft

  18 Wood Duck Way, Edgartown, MA 02539

  Welcome to your coastal retreat in sought-after Sengekontacket, offered fully turnkey and ready to enjoy from day one. This light-filled contemporary home blends comfort, style, and exceptional community amenities in one of Martha's Vineyard's most desirable central Island locations.Designed with soaring vaulted ceilings and oversized windows, the home is flooded with natural sunlight throughout.

  Janna O'Loughlin Portfolio Properties

  18 Wood Duck Way, Edgartown, MA 02539
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  $1,349,000

  • 3 Beds
  • 2 Baths
  • 1,863 Sq Ft

  3 Troy St, Oak Bluffs, MA 02557

  Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  3 Troy St, Oak Bluffs, MA 02557

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