Oak Bluffs Homes for Sale

Oak Bluffs has a wonderful array of single family homes on Martha’s Vineyard. From beach cottages and waterfront homes to homes within walking distance to downtown, shops, and restaurants, you’re sure to find the perfect Martha’s Vineyard home in Oak Bluffs.

Scroll down to explore Oak Bluffs houses for sale on Martha’s Vineyard and reach out to us with questions. You can also sign up for an account to save all of your favorite houses and properties.

40 Tiffany Drive, Oak Bluffs, MA

Price$889,000

Est. Mortgage: $/month

MLS Number 34214

  • Residential
  • Square Feet 1948
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1.91

Private Contemporary Saltbox situate on a nicely treed lot and abutting conservation. Bright, gracious, beautifully maintained home with oak hardwood floors in the living areas. Beamed dining area and kitchen with plenty of counter space and all appliances. Living room with cathedral ceiling and skylight, brick fireplace with wood stove w/ heatilator w blower, plus three sliders to deck. Master suite/ sitting area w/ ensuite bath, another bedroom w bathroom off the hall. On the second level one finds another generous master suite with ensuite bath and private deck w slider. On this floor also, a spacious sky lit loft overlooking the living room, now used as an office and sitting room. All living areas and bedrooms have paddle fans. The walk out basement contains a water filtration system, dehumidifier, work bench that includes most tools and washer and dryer. Over sized one car garage completes the offering. Exterior of house was painted in 2017, and irrigation system updated. This lovely house comes mostly furnished and almost turnkey. Property has deeded rights to Lagoon Pond where you can keep a kayak/canoe and do some fishing! 2015 Toyota for sale also.

Listed by Hughes & JC Murphy R.E.

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Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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385 County Road, Oak Bluffs, MA

Price$525,000

Est. Mortgage: $/month

MLS Number 34289

  • Residential
  • Square Feet 954
  • Bedrooms 1
  • Bathroom 2
  • Acreage 0.3266

Raised ranch, set up off the road on a knoll, near Farm Neck Golf. Large side and rear yard. Main level contains open plan living, dining, kitchen, master bedroom and full bath with laundry facilities. Lower level contains 3 additional rooms and full bath. A large deck runs the length of the house. House needs work; being sold "as is".

Listed by Martha's Vineyard Island-Wide Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29 Simpson Avenue, Oak Bluffs, MA

Price$655,000

Est. Mortgage: $/month

MLS Number 34299

  • Residential
  • Square Feet 1460
  • Bedrooms 2
  • Bathroom 2
  • Acreage 0.1

Ideally located above Sunset Lake and Oak Bluffs Harbor in the desirable Copeland District, this 2+bedroom Vintage Island Home is in a lovely residential neighborhood. If the walls of the charming screened in porch could talk you would hear stories of how many generations have enjoyed this beach house. Close to beaches, ferries, shops, restaurants and all that the harbor and downtown Oak Bluffs have to offer. Plans for a four bedroom septic are in place and awaiting approval. This home has been rented to friends and family for 30 years. Your friends and family, and others will love it! ***AGENT MUST BE PRESENT FOR ALL SHOWINGS***

Listed by Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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78 Isaac Avenue, Oak Bluffs, MA

Price$610,000

Est. Mortgage: $/month

MLS Number 34302

  • Residential
  • Square Feet 1568
  • Bedrooms 1
  • Bathroom 2
  • Acreage 0.25

Brand New in Oak Bluffs. This thoughtfully designed home is spacious and bright with gleaming hardwood floors throughout the open living room, dining area and kitchen complete with new stainless steel appliances. Lovely bedroom with full bath, two additional bonus rooms and another full bath. Full unfinished basement, large maintenance free deck and out door shower complete this home. Centrally Located, Just minutes to the harbor, town beaches, restaurants and shops.

Listed by Laer Realty Partners

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41 School Street, Oak Bluffs, MA

Price$590,000

Est. Mortgage: $/month

MLS Number 34246

  • Residential
  • Square Feet 1007
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 1

Walk to Oak Bluffs center, beaches, and restaurants from this renovated bungalow. This is a rare opportunity to get an affordable home so close to town. This cozy 3 bedroom 2 1/2 bathroom home is suited for year-round living and is connected to town sewer. Secluded yard includes a deck grassy yard and shed. Private driveway provides plenty of off street parking. Spacious living area with sliding glass doors opening onto the wrap around deck and front porch. The open kitchen and dining area also has a door opening onto the deck. The utility room with laundry and a half bathroom complete the first floor. Upstairs are three bedrooms and 2 full bathrooms. The front bedroom with it's own private balcony and bathroom off the hall. Two other bedrooms each with direct access to a "Jack and Jill" Bathroom.

Listed by Anchor Realty of Martha's Vineyard

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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56 Pennacook Avenue, Oak Bluffs, MA

Price$739,000

Est. Mortgage: $/month

MLS Number 34250

  • Residential
  • Square Feet 1285
  • Bedrooms 4
  • Bathroom 1
  • Acreage 0.08

Classic Victorian home located in the heart of Oak Bluffs. Situated across from lovely tranquil park, one block from Niantic Park recreation, just 3 blocks from the beach and a 5 minute walk to shops, restaurants, ferries. Lovely, shaded wrap around porch and upper level balcony overlooking Pennacook Park across the street. Expansion possibilities with proper permitting!

Listed by Anchor Realty of Martha's Vineyard

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 School House Village, Oak Bluffs, MA

MLS Number 34239

  • Residential
  • Square Feet 1960
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.76

Three bedroom two bath house with two first floor bedrooms. Downstairs includes the kitchen, living room, and large dining room. Upstairs is the third bedroom and family room. The property is built on two full size lots, a one bedroom guest house can be built adjacent to the garage.

Listed by Priestley Smadbeck & Mone

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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274 Sea View Avenue, Oak Bluffs, MA

Price$4,995,000

Est. Mortgage: $/month

MLS Number 34138

  • Residential
  • Square Feet 3460
  • Bedrooms 6
  • Bathroom 5
  • Half Bath 1

HARTHAVEN WATERFRONT WITH PRIVATE DOCK- An Undeniably special and unique property this Harthaven compound is one of only four homes situated on the picturesque and protected harbor with private dock. Elegant yet casual, vintage yet chic you'll find it all here at this tastefully renovated Oak Bluffs home. The expansive six bedroom property delivers all the amenities one would expect while retaining the charm and character of days gone by. The sprawling first floor boasts commanding water views with access to an expansive covered porch and deck overlooking the protected inlet, barrier beach, and Vineyard Sound - bound to ignite your inner explorer. The private first floor guest wing, complete with deck and beach stone fireplace, combined with the four additional bedrooms and baths on the second level provide the ideal layout for all your family and friends, evident in properties strong rental history. A large boathouse/garage, perched on the water's edge, great for storage of all beach and boating gear, is the perfect complement to this seaside escape. The expansive lawn, beckoning for yard games and laughter, slopes gently to a private dock, offering boaters both protection and easy access to the deeper waters of Nantucket Sound and nearby harbors. The highly sought after location, within the Harthaven community, provides you and your guests with access to tennis and a long stretch of association sandy beach on the calm waters of the sound. A magnificent offering!

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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71 Pennacook Avenue, Oak Bluffs, MA

Price$1,149,000

Est. Mortgage: $/month

MLS Number 33425

  • Residential
  • Square Feet 2108
  • Bedrooms 6
  • Bathroom 2
  • Half Bath 1

CLASSIC BEAUTY IN THE HEART OF OAK BLUFFS, The Pennacook House is set on a slight hill on a large landscaped yard. this YEAR ROUND 6 bedroom, 2.5 bath home has a lovely eat-in kitchen, formal dining and living rooms with bay windows, den/study, hardwood flooring, outdoor shower, gorgeous period details and many updates throughout. Brand new propane hot water and heating system. Full walk-out basement with laundry and plenty of storage space. Home is sunny and warm in the winter and catches the cool summer breezes. GREAT LOCATION just a few blocks to town center, ferry, Ocean Park, and beaches. VERY STRONG RENTAL HISTORY!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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10 Paddock Road, Oak Bluffs, MA

Price$2,520,000

Est. Mortgage: $/month

MLS Number 33638

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

Under Construction: 4000 sq ft of brand-new construction tucked nicely on a beautiful lot in the prestigious subdivision of "The Preserve". This home meets all the modern buyer's needs with its open floor plan, 1st and 2nd floor master bedroom suites, chef's kitchen, hardwood floors throughout, custom tile bathrooms, expansive outside entertaining space, and lush landscaping. This is a "family compound in the making," a swimming pool and poolhouse may also be installed if a buyer chooses to do so. With its generous living spaces this home is ideal for entertaining friends and family. There is also lots of opportunity for privacy, thanks to the separate bedroom suite and bathroom above the garage. This is the summer house of your dreams, and can also be your escape during the cooler months thanks to the modern, efficient systems. This spectacular home will be the ideal place to host large family dinners at Thanksgiving or the holiday season with the fireplace as the perfect setting to gather round at the end of the day. To be completed in the Fall of 2018. ***** interior pictures shown are of a similar house built by the builder to give you an idea of quality and finishes.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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