Oak Bluffs Homes For Sale

Oak Bluffs, MA, is Martha Vineyard’s original summer resort, dating back to the late Victorian era. Oak Bluffs real estate includes a wide range of homes including quaint capes, charming bungalows, and waterfront estates. You’ll also find homes in Oak Bluffs with the hallmark colorful "gingerbread" aesthetic and views of the ocean.

Oak Bluffs residents revel in the lively scene of Circuit Avenue and the harbor front, day and night, while the outlying neighborhoods contrast in serenity. Find some of the most in-demand Martha’s Vineyard real estate including luxurious waterfront houses and vacation condos in Oak Bluffs. 

Learn more about Oak Bluffs.

Our team at Coldwell Banker Landmarks takes great pride in connecting home buyers with the perfect Martha's Vineyard vacation home. Contact us today to learn more.

29 Simpson Avenue

Price$655,000

Est. Mortgage: $/month

MLS ID 34299

  • Residential
  • Square Feet 1460
  • Bedrooms 2
  • Bathrooms 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 Dawson, Katie of 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

Price$610,000

Est. Mortgage: $/month

MLS ID 34302

  • Residential
  • Square Feet 1568
  • Bedrooms 1
  • Bathrooms 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 Twiss, Barbara of 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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91 Dukes County Avenue

MLS ID 31761

  • Condominium
  • Village Downtown
  • Square Feet 1107
  • Bedrooms 1
  • Bathrooms 1

This unique condo offers the best of retail and/or residential living. Set on the corner with easy access to Circuit Ave, Ferries and all that "In Town" has too offer. Spacious "L" shaped open concept first floor plan that leads to NEWLY renovated kitchen with all stainless appliances. The second floor has a Bedroom and half Bath. Hardwood Floors throughout, outdoor shower and beautiful perennial gardens surrounding the courtyard. Off street parking for 4 cars. Currently being used as an Art Gallery but you can make it your own! Great space for retail or personal residence. This is a must see for the savvy investor.

Listed by Jackson, Rene of Island Real Estate

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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

Price$590,000

Est. Mortgage: $/month

MLS ID 34246

  • Residential
  • Village Downtown
  • Square Feet 1007
  • Bedrooms 3
  • Bathrooms 2

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 Lucier, Lisa of 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

MLS ID 34239

  • Residential
  • Village Central
  • Square Feet 1960
  • Bedrooms 3
  • Bathrooms 2

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 Smadbeck, Art of 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

Price$4,995,000

Est. Mortgage: $/month

MLS ID 34138

  • Residential
  • Village State Beach
  • Square Feet 3460
  • Bedrooms 6
  • Bathrooms 5

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 Katherine Donahue of Sandpiper 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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71 Pennacook Avenue

Price$1,149,000

Est. Mortgage: $/month

MLS ID 33425

  • Residential
  • Village Downtown
  • Square Feet 2108
  • Bedrooms 6
  • Bathrooms 2

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 Alan Schweikert of Ocean Park 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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10 Paddock Road

Price$2,520,000

Est. Mortgage: $/month

MLS ID 33638

  • Residential
  • Village Central
  • Square Feet 4000
  • Bedrooms 5
  • Bathrooms 4

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 Pierce, Bonnie of Wallace & Co. Sotheby's

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$
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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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33 Beach Road

Price$1,500,000

Est. Mortgage: $/month

MLS ID 34185

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1622
  • Bedrooms 4
  • Bathrooms 2

Smell it! Feel it! Taste it...the sea that is! Waterfront 3 season cottage looking westerly over Vineyard Haven Harbor. Sunsets and sailboats everyday plus a DEEPWATER DOCK for all your boating needs. Originally known as "Station #7" of the NY Yacht Club, this historic home was used "back in the day" to give club members a comfortable place to tie up their tenders and step ashore while sailing the waters around the Vineyard. Classic cottage appeal inside and out.

Listed by Reece, Doug of RE/MAX on Island

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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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15 June Avenue

Price$629,000

Est. Mortgage: $/month

MLS ID 34169

  • Residential
  • Village Central
  • Square Feet 1274
  • Bedrooms 3
  • Bathrooms 2

Move in ready! This comfortable 3 bedroom 2 bath home has been lovingly maintained through the years. The first floor features an open floor plan with hard wood floors, wood burning fireplace in the living room, dining area and kitchen. The windows throughout the house and the kitchen slider and storm door have all been replaced within the past 2 years. Off the kitchen is a bedroom and full bathroom with stall shower. The second floor has two additional bedrooms and a full bathroom. The home is heated by propane, forced air and has a full basement and outdoor shower. There is central air conditioning on the first floor only. The second floor has electric heat. The yard is beautifully manicured with plantings and flower gardens around the perimeter of the house as well as a split rail fence along the front of the property. A large deck off the kitchen completes the home. The rock driveway clearly defines an area for 2+ cars. This property is close to the Lagoon and bike path. Come take a look!

Listed by Jardin, Nora of Island Real Estate

$
$
%
$/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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