Oak Bluffs Homes for Sale

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  $1,200,000

  • Land
  • 10,890 Sq Ft
  • $4,800,000 per Acre

  0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568

  Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs.Build Your Martha’s Vineyard Dream Home.Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha’s Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

  

  Rene Ben David

  Ocean Park Realty Inc

  0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
• Explore Oak Bluffs

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  /40

  $3,675,000

  • 4 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  28 Beach Rd, Oak Bluffs, MA 02557

  Enjoy Spectacular Views From This Chic Island Retreat. Wake up to panoramic Vineyard Sound views, watch the Steamship ferries cross to Woods Hole, and enjoy sunsets stretching down the Lagoon. This turnkey 4-bedroom, 2.5-bath home is designed to embrace its remarkable waterfront setting, with covered decks on both sides capturing ocean breezes and water views from nearly every room. The first

  

  Wendy Harman

  Compass

  28 Beach Rd, Oak Bluffs, MA 02557
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  /8

  $1,200,000

  • Land
  • 10,890 Sq Ft
  • $4,800,000 per Acre

  0 Temahigan Ave & Dover St Unit 22602202, Oak Bluffs, MA 02557

  Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs. Build Your Martha's Vineyard Dream Home. Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha's Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

  

  Rene Ben David

  Ocean Park Realty, Inc.

  0 Temahigan Ave & Dover St Unit 22602202, Oak Bluffs, MA 02557
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  /18

  $1,199,000

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  47 Winemack St, Oak Bluffs, MA 02557

  Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one

  Lisa Lucier Anchor Realty of MV

  47 Winemack St, Oak Bluffs, MA 02557
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  /6

  $975,000

  • Land
  • 1.07 Acres
  • $911,215 per Acre

  68 Pond View Dr, Oak Bluffs, MA 02557

  Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process. The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development. Subject to the Town of Oak

  Casandra Hyland Sandpiper Realty, Inc.

  68 Pond View Dr, Oak Bluffs, MA 02557
• 

  

  /23

  $1,800,000

  Open Sat 10AM - 12PM

  • 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

  Janna O'Loughlin Portfolio Properties

  18 Wood Duck Way, Edgartown, MA 02539
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  /28

  $1,850,000

  Open Wed 12PM - 1:30PM

  • 3 Beds
  • 6 Baths
  • 2,641 Sq Ft

  33 Tia Anna Ln, Oak Bluffs, MA 02557

  33 Tia Anna Lane has so much to offer; a charming, bright, renovated main and guest house on a half-acre in Oak Bluffs with proximity to town and walking distance to Lagoon Pond for swimming, fishing, boating and sunset enjoyment. The property is ready to enjoy, offering a turn-key home on a quiet side street as well as a detached guest house with its own yard and deck. The inviting main house

  Elissa Lash Tea Lane Associates

  33 Tia Anna Ln, Oak Bluffs, MA 02557
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  /4

  $625,000

  • Land
  • 14,997 Sq Ft
  • $1,815,277 per Acre

  0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

  Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

  Andrew McElhinney Compass LLC

  0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
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  /6

  $975,000

  • Land
  • 1.07 Acres
  • $912,921 per Acre

  68 Pond View Dr Unit 2, Oak Bluffs, MA 02557

  Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process.The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development.Subject to the Town of

  Casandra Hyland Sandpiper Realty

  68 Pond View Dr Unit 2, Oak Bluffs, MA 02557
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  $1,599,000

  • 2 Beds
  • 1 Bath
  • 981 Sq Ft

  13 Beach Rd, Oak Bluffs, MA 02557

  OAK BLUFFS Beach Road: VINEYARD HAVEN OUTER HARBOR WATERFRONT WITH DOCK... 1860’s Beach House with substantial 60’ dock built in 2004, is situated on OUTER HARBOR in private waterfront setting. Enjoy all variety of watersports, dramatic sunsets every evening, refreshing swims, or just relax on your back porch and watch the colorful boating activity unfold. Property features 2 bedrooms, 1 full

  Alan Schweikert Ocean Park Realty Inc

  13 Beach Rd, Oak Bluffs, MA 02557
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  /27

  $869,000

  • 1 Bed
  • 1 Bath
  • 797 Sq Ft

  37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

  In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled

  Lisa Lucier Anchor Realty of MV

  37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
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  /4

  $809,000

  • Land
  • 16,988 Sq Ft
  • $2,074,359 per Acre

  7 Highland Ave, Oak Bluffs, MA 02557

  Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

  Shera Toledo eXp Realty, LLC

  7 Highland Ave, Oak Bluffs, MA 02557
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  /12

  $3,400,000

  New Construction

  • 3 Beds
  • 4.5 Baths
  • 3,260 Sq Ft

  27 Double Ox Rd, Oak Bluffs, MA 02557

  Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living

  Lesley Heidt Sandpiper Realty, Inc.

  27 Double Ox Rd, Oak Bluffs, MA 02557
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  /46

  $2,400,000

  • 5 Beds
  • 3.5 Baths
  • 3,873 Sq Ft

  50 Hidden Cove Rd, Edgartown, MA 02539

  Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering

  Sean Federowicz Landmarks at TODAY Real Estate

  50 Hidden Cove Rd, Edgartown, MA 02539
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  /15

  $1,925,000

  • 5 Beds
  • 1 Bath
  • 2,232 Sq Ft

  8 Pequot Ave, Oak Bluffs, MA 02557

  Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time. Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends. The front porch has been a gathering place for 50+ years, and the views have not been expanded. So much

  Kerry Quinlan-Potter Breakwater MV

  8 Pequot Ave, Oak Bluffs, MA 02557
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  $839,000

  $60K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 804 Sq Ft

  26 Winthrop Ave, Oak Bluffs, MA 02557

  This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with tons of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  26 Winthrop Ave, Oak Bluffs, MA 02557
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  $2,260,000

  $335K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,810 Sq Ft

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by

  Kate Burnside Portfolio Properties

  4 High Meadow Ln, Oak Bluffs, MA 02557
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  /2

  $425,000

  • Land
  • 7,840 Sq Ft
  • $2,361,111 per Acre

  0 Heather Ln Unit 56, Oak Bluffs, MA 02568

  Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

  Jennifer DaSilva Compass | Point B

  0 Heather Ln Unit 56, Oak Bluffs, MA 02568
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  $3,750,000

  • 4 Beds
  • 3 Baths
  • 2,204 Sq Ft

  9 Weston Ave, Oak Bluffs, MA 02568

  This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor

  Gerrett Conover Landvest MV

  9 Weston Ave, Oak Bluffs, MA 02568
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  $1,599,000

  • 3 Beds
  • 2.5 Baths
  • 1,645 Sq Ft

  7 Ploughshare Ln, Oak Bluffs, MA 02557

  Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

  Emma Kennedy Sandpiper Realty, Inc.

  7 Ploughshare Ln, Oak Bluffs, MA 02557
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  /42

  $4,600,000

  $350K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 3,998 Sq Ft

  15 Tamarack Ln, Oak Bluffs, MA 02557

  Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic

  Stephanie Roache Donnelly + Co.

  15 Tamarack Ln, Oak Bluffs, MA 02557
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  /18

  $239,000

  • 1 Bed
  • 1 Bath
  • 316 Sq Ft

  33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568

  Want to own a slice of Martha's Vineyard? As an owner of this studio style "Condo-tel", you will enjoy the convenience of worry free ownership. This unit has newer flooring, an updated bathroom, updated kitchenette and a cathedral ceiling. This is casual resort style living that includes association pool, 3 tennis courts, playground, and shared grilling area. This wonderful location borders Farm

  Rene Jackson Island Real Estate

  33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
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  $5,450,000

  • 4 Beds
  • 5.5 Baths
  • 3,300 Sq Ft

  8 Paddock Rd, Oak Bluffs, MA 02557

  Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combination of privacy, elegance, and seamless indoor-outdoor living. At its core, an expansive great room

  Lesley Heidt Sandpiper Realty

  8 Paddock Rd, Oak Bluffs, MA 02557
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  /10

  $3,750,000

  $245K PRICE DROP

  • Land
  • 1.92 Acres
  • $1,956,182 per Acre

  98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568

  Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha’s

  Andrew McElhinney Compass LLC

  98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
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  /32

  $1,595,000

  • 3 Beds
  • 3.5 Baths
  • 2,739 Sq Ft

  40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557

  Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

  Rose Ryley Wallace & Co. Sotheby's International Realty

  40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
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  /2

  $794,000

  • 2 Beds
  • 1 Bath
  • 624 Sq Ft

  60R Carol Ln, Oak Bluffs, MA 02557

  Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features a living area and kitchen with breakfast bar. Ample storage and a stackable washer/dryer complete

  Michele Moore Island Real Estate

  60R Carol Ln, 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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  /2

  $789,000

  $68K PRICE DROP

  • Land
  • 16,892 Sq Ft
  • $2,034,554 per Acre

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

  OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
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  /20

  $899,000

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

  In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest

  Lisa Lucier Anchor Realty of MV

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
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  $925,000

  • 2 Beds
  • 1.5 Baths
  • 1,208 Sq Ft

  4 Quail Run Unit 21, Oak Bluffs, MA 02557

  Welcome to this FULLY FURNISHED, private, 2-bedroom, end-unit townhouse offering 1,208 sq ft of effortless coastal living. With seasonal rentals already in place this opportunity is the defenition of TURN KEY. Thoughtfully designed with both comfort and style in mind, this coastal retreat blends relaxed island charm with modern convenience—perfect for year-round living or as an established rental

  Emma Bryant Studio Realty

  4 Quail Run Unit 21, Oak Bluffs, MA 02557
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  $1,850,000

  • 4 Beds
  • 2 Baths
  • 1,833 Sq Ft

  22 Old Harbor Ln, Oak Bluffs, MA 02557

  Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

  Lisa Stewart Sandpiper Realty, Inc.

  22 Old Harbor Ln, Oak Bluffs, MA 02557
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  /70

  $5,295,000

  $200K PRICE DROP

  • 3 Beds
  • 7 Baths
  • 3,608 Sq Ft

  385 Barnes Rd, Vineyard Haven, MA 02568

  SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and

  Stephanie Roache Donnelly + Co

  385 Barnes Rd, Vineyard Haven, MA 02568
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  /45

  $1,765,000

  • 2 Beds
  • 2 Baths
  • 890 Sq Ft

  2 Great Rock Rd, Oak Bluffs, MA 02568

  Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property

  Susan Lemoie-Zarba Premier Properties

  2 Great Rock Rd, Oak Bluffs, MA 02568
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  /20

  $1,745,000

  • 2 Beds
  • 1 Bath
  • 560 Sq Ft

  11 Beach Rd, Oak Bluffs, MA 02568

  Oceanfront Cottage on .21 acre of waterfront property and over 50ft of shoreline on East Chop. Wake up to breathtaking ocean views and the soothing sound of waves from this charming two-bedroom oceanfront cottage. Perfectly positioned along the shoreline, this inviting coastal retreat offers the rare opportunity to own a slice of waterfront paradise. Designed for relaxed seaside living, the home

  Carleen Cordwell Anchor Realty of Martha's Vineyard

  11 Beach Rd, Oak Bluffs, MA 02568
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  /28

  $839,000

  • 1 Bed
  • 1 Bath
  • 804 Sq Ft

  26 Winthrop Ave, Oak Bluffs, MA 02557

  This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with lots of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in

  Alisan Lohan - Conway Alisan Lohan - Conway Properties

  26 Winthrop Ave, Oak Bluffs, MA 02557
• 

  

  /40

  $1,750,000

  • 3 Beds
  • 3.5 Baths
  • 2,376 Sq Ft

  28 Grovedale Rd, Oak Bluffs, MA 02557

  GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate

  David White OwnerEntry.com

  28 Grovedale Rd, Oak Bluffs, MA 02557
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  /64

  $2,579,000

  • 4 Beds
  • 2 Baths
  • 1,399 Sq Ft

  34 Windemere Rd, Oak Bluffs, MA 02557

  Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  34 Windemere Rd, Oak Bluffs, MA 02557
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  /32

  $1,755,000

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,695 Sq Ft

  68 Front St, Oak Bluffs, MA 02557

  Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan with large windows that frame views of the surrounding property. The generously sized kitchen features

  Jayne Isford Ocean Park Realty, Inc.

  68 Front St, Oak Bluffs, MA 02557
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  /40

  $1,350,000

  $45K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,305 Sq Ft

  46 Kennebec Ave, Oak Bluffs, MA 02557

  This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs'

  Cathy Gargiulo Ocean Park Realty Inc

  46 Kennebec Ave, Oak Bluffs, MA 02557
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  /31

  $2,800,000

  $445K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,023 Sq Ft

  44 Tiffany Dr, Oak Bluffs, MA 02557

  Tucked away in a serene setting and set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space with plenty of room for a backyard pool. The main portion of the house includes a gourmet kitchen, multiple entertaining areas including living room, family room, game room, a screened porch, ensuite bedroom and powder room. An attached one-bedroom

  Perry Patterson MV Luxury Homes

  44 Tiffany Dr, Oak Bluffs, MA 02557

Showing Results 1 - 40, Page 1 of 2

Why Live in Oak Bluffs

Oak Bluffs, located in the northeast of Martha’s Vineyard, is renowned for its whimsical gingerbread houses. This down-island town is a bustling port of entry during the summer season, where tourists disembark from ferry boats and explore attractions like Circuit Avenue, known for its T-shirts and fresh doughnuts. The town features gray-shingled beach houses overlooking the Nantucket Sound, and the commercial district offers pizza parlors, ice cream shops, and clothing stores. Oak Bluffs is home to the oldest platform carousel in the U.S., the Flying Horses Carousel, and hosts the Martha’s Vineyard African American Film Festival and a fireworks show every August. The Ritz Café provides nightlife with live music and karaoke, while the Sweet Life Café offers upscale dining year-round. Ocean Park, with its rolling hills and Victorian homes, and the Martha’s Vineyard Camp Meeting Association, with its brightly colored gingerbread houses, are notable landmarks. The town also has gray-shingled beach cottages, Cape Cods, and farmhouses. Martha’s Vineyard Regional High School, a highly rated institution, serves the island’s students. Health care is accessible at Mass General Brigham Martha’s Vineyard Hospital, which offers comprehensive services. Residents and visitors can enjoy sandy pathways along the Nantucket Sound, beaches like Inkwell Beach, and a skate park near the high school. Oak Bluffs is 10 minutes from Vineyard Haven, 15 minutes from Edgartown, and 15 minutes from Martha’s Vineyard Airport.

Learn more about living in Oak Bluffs

Oak Bluffs Home Prices vs. Nearby Marthas Vineyard, MA Neighborhoods

	Oak Bluffs	Vineyard Haven	West Tisbury
Median Home Price	$1,610,000	$1,790,000	$1,895,000
Median Sale Price	$1,317,500 +15% YoY	$1,470,000 +9% YoY	$1,537,500 -9% YoY
Median Single Family Price	$1,705,000	$1,795,000	$1,800,000
Median Condo Price	$899,000	$1,125,000	--
Total Active Listings	83 listings	76 listings	32 listings
Market Conditions	6 Months of Supply Balanced Market	8 Months of Supply Buyer's Market	8 Months of Supply Buyer's Market

Frequently Asked Questions

Is Oak Bluffs a good place to live?

Oak Bluffs is a good place to live. Oak Bluffs is considered very car-dependent and somewhat bikeable with some transit options. Oak Bluffs is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Oak Bluffs has 5 parks for recreational activities. It is sparse in population with 2.0 people per acre and a median age of 49. The average household income is $133,511 which is above the national average. College graduates make up 46.9% of residents. A majority of residents in Oak Bluffs are home owners, with 27% of residents renting and 73% of residents owning their home. A local real estate agent serving Oak Bluffs can help you decide if this neighborhood is the right one for you. Learn more on our Oak Bluffs neighborhood guide.

Is Oak Bluffs, MA a safe neighborhood?

Oak Bluffs, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.

How much do you need to make to afford a house in Oak Bluffs?

The median home price in Oak Bluffs is $1,610,000. If you put a 20% down payment of $322,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $8,300 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $356K a year to afford the median home price in Oak Bluffs. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Oak Bluffs is $134K.

What are the best public schools in Oak Bluffs?

The best public schools that serve Oak Bluffs are:

• Martha's Vineyard Regional High School has a B+ Niche grade, a student teacher ratio of 9:1 and an average review score of 3.6.
• Oak Bluffs Elementary School has a B Niche grade and a student teacher ratio of 8:1.

What are the best private schools in Oak Bluffs?

The best private schools that serve Oak Bluffs are:

• Vineyard Montessori School has a student teacher ratio of 5:1.

What are the most popular zip codes in Oak Bluffs, Marthas Vineyard, MA?

The most popular zip codes in Oak Bluffs, Marthas Vineyard, MA include 02568, 02536, 02539, 02575 and 02535.

What are the most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA?

The most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA are Vineyard Haven, Edgartown, West Tisbury, Chilmark and Woods Hole.