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.

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52 Head of the Pond Road

MLS ID 34050

  • Residential
  • Square Feet 3100
  • Bedrooms 5
  • Bathrooms 3
  • Half Bath 1

This contemporary 5 bedroom home is located in a nice area of fine homes and close to farm fields and conservation walking trails. The open floor plan includes a newly renovated kitchen, spacious living ,dining room with sliders to a screened-in porch and deck. First floor master bedroom and bath. The second floor includes 2 bedrooms, an office and great room with cathedral ceiling and skylights. An efficiency apartment can be accessed from the main house as well as it's own entry. The third floor has been finished for additional studio space with skylights. 2-car garage and an attached office space for an in-home business. A great value in this market.

Listed by Galligan, Brenda of Karen M. Overtoom R.E.

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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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227 Buddys Drive

Price$1,070,000

Est. Mortgage: $/month

MLS ID 33978

  • Residential
  • Square Feet 2762
  • Bedrooms 6
  • Bathrooms 3
  • Half Bath 1

The perfect choice for your family vacation home/year round residence ! One owner ~custom colonial offering an updated & renovated bright & sun filled great room with expansive living/dining area and newer kitchen with stainless steel appliances & gleaming granite counters! The interior of the home is inviting and generous with an abundance of rooms! This open design has striking natural wood ship lap ceilings. Glass doors offer access to a huge exterior deck and penetrating views into the abutting state forest ...The attention to detail includes the luxury of 2 master suites, on the first floor and second floor.There is a total of 6 bedrooms, 3. 5 bathrooms and a huge unfinished space above the two bay garage!..Strong existing rental history in place! Outstanding location & terrific value! Room for a pool too!

Listed by Marilyn Moses 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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446 County Road

Price$779,000

Est. Mortgage: $/month

MLS ID 33957

  • Residential
  • Square Feet 1959
  • Bedrooms 2
  • Bathrooms 2
  • Half Bath 1

OAK BLUFFS: WATERVIEW FARMS!! Sweeping MEADOW VIEWS and some distant peek views of Nantucket Sound and Sengekontacket Pond from this spacious year round residence. Short walk to community beach and dock area and potential for a mooring in The Pond with access to the OCEAN for small boats. LOTS OF BANG FOR YOUR BUCK! Open sun-filled living/dining room with cathedral ceilings and access to deck, large eat-in kitchen, 2 ample bedrooms and 2 full bathrooms on the first floor and a finished second floor with a half bathroom, and a full basement. Exterior is good condition with newer cedar shingle roof. A MUST SEE!!!!

Listed by Michael 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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115 Dukes County Avenue

MLS ID 33969

  • Residential
  • Square Feet 1435
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.08

Located near the Arts district just a short walk to downtown Oak Bluffs, this home features two first floor bedrooms with a third bedroom on the second floor. Walk in to an open kitchen/dining area with a large pantry off the kitchen. Down the hallway there is a full bathroom and a den/living room. The basement is partially finished with a full bathroom and separate laundry room with a washer and dryer. The backyard is fenced in with a large deck and a shed. There is off-street parking in the gravel driveway with room for 2 cars. Please give 24 hour notice for all showings

Listed by Michael Schweikert of Ocean Park Realty

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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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225 East Chop Drive

Price$3,950,000

Est. Mortgage: $/month

MLS ID 33942

  • Residential
  • Square Feet 2449
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

Top of the Chop ~ A stunning contemporary with dramatic sweeping views of Vineyard Sound. A complete transformation by South Mountain & Company of the former residence resulted in a masterpiece of modern living and superb style. Upon entering you are immediately greeted with water views and the breathtaking landscape and it continues to unfold as you go through the home. The single story home was designed with the living and entertaining area at the core with the master wing tucked privately away and a two bedroom guest wing down its own corridor. The baths are luxurious, the kitchen a work of art and the finishes throughout are simply exquisite. East Chop is an upscale summer community, a most ideal location with the beach, harbor and town just a short distance away.

Listed by Lesley Heidt 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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90 South Circuit Avenue

Price$1,669,000

Est. Mortgage: $/month

MLS ID 33863

  • Residential
  • Square Feet 2780
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 0.33

Oak Bluffs: Custom design in special location just a short walk to town and public beach...but offering Up Island Privacy with views over Farm Pond, barrier beach and Nantucket Sound to the Southeast and over a cedar meadow to the Southwest. Bright great room with high ceilings lots of South facing glass, intimate sitting arrangements, large beamed dining room, great kitchen and pantry, broad sunny deck, huge bedrooms, new roof, marble vanities in the bathrooms, 2 car garage with loft storage, wonderful outside shower. Heat Pump AC mini splits throughout! RARE OFFERING & ONE of A KIND LOCATION!

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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105 Eastville Avenue

Price$945,000

Est. Mortgage: $/month

MLS ID 33848

  • Residential
  • Square Feet 1879
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

This restored antique home is in pristine condition. Located near Eastville Beach, hospital and a short distance to downtown Oak Bluffs. Spacious manicured lawn, wraparound deck and outdoor shower. The inviting interior has wide plank floors, freshly painted walls, first floor bedroom, living room, family room, kitchen and formal dining area. There are three fireplaces on the first floor and a roomy bathroom with stand-up shower. The first floor bedroom has built-in wall storage, closet and ceiling fan. The living room is inviting and filled with natural light and centered fireplace with wood mantle. The family room has exposed wood beam ceiling and exquisite window and door moldings, a second fireplace and half bath tucked under the stairway. The formal dining area has beautiful built-in cabinets with glass doors, drawers and shelving. A third fireplace can be found in the dining area with a nice mantle and woodwork. The kitchen at the rear of the property is modern with adequate cabinet storage space, vaulted ceiling with exposed beams, skylight and hardwood oak flooring. The side door off kitchen leads to the large outside wraparound deck and access to the outdoor shower. A great spot to barbeque, read or just enjoy the outdoors. The second floor has a spacious landing and leads to the entry of all three 2nd floor bedrooms and the full bath with tiled flooring and claw foot tub. There is storage in the attic area and storage in the clean and dry basement. The expansive lawn and grounds are a pleasure to walk. Great rental history.

Listed by Dostal, Skip of Martha's Vineyard R.E.

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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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331 East Chop Drive

Price$895,000

Est. Mortgage: $/month

MLS ID 33868

  • Residential
  • Square Feet 444
  • Bedrooms 1
  • Bathrooms 1
  • Acreage 0.1796

LOWEST PRICED BEACH FRONT ON MARTHA'S VINEYARD. EAST CHOP COTTAGE, SPECTACULAR VIEWS, PERFECT GETAWAY COTTAGE. Beach cottage, a rare find these days and just perfectly cute. The cottage is located along the waterfront on East Chop Drive, a very desirable area of Oak Bluffs. The porch looks out over the beach and beyond to Vineyard Sound. Relax on the covered porch and take in the outstanding water views and the parade of boats heading to and from the harbor. The interior has been freshened with updated kitchen, an adjacent dining area and a bedroom with a bath with shower. There is also a loft area currently used for storage. An outside shower tops the list and is so loved by the family. Strong rental history and rentals in place for 2018.

Listed by Brown, Karen of Martha's Vineyard Vacation Rentals

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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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7 Old Harbor Lane

Price$2,632,500

Est. Mortgage: $/month

MLS ID 33797

  • Residential
  • Square Feet 2488
  • Bedrooms 4
  • Bathrooms 4
  • Acreage 1.547

Waterview Farms Opportunity: One of the most spectacular vistas of Sengekontacket Pond and Nantucket Sound. Beautifully landscaped with specimen plantings, perennial hydrangea, seasonal flowers, and semi bordered by stone walls. Open floor plan, large living room, kitchen with granite counter tops, and stainless appliances. Living room opens to a large deck with hot tub. Contemporary ranch with four bedrooms and four full baths. Three of which are suites. Adjacent to "Farm Neck” is the 3rd green… Short stroll through the meadow leads to the beach access for water sports. ( 24 hr notice required for showings due to summer rentals)

Listed by Lambert, JoJo of Island Home 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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1 Fairmont Avenue

Price$699,000

Est. Mortgage: $/month

MLS ID 33805

  • Residential
  • Square Feet 2808
  • Bedrooms 3
  • Bathrooms 4
  • Acreage 0.1147

Opportunity abounds with this large 3 story home, just off of Barnes Road. The first floor could be either a legal 1 bedroom apartment, or a main floor Master with large entertainment area. The 2nd and 3rd floors were added in 2009. The 2nd floor has an open living/dining/kitchen area with a full bath, and a Master en Suite. The floors throughout the 2nd floor are oak. Kitchen has cherry cabinets, granite countertops and a custom island. The 3rd floor is currently being used as two separate office areas, along with a full bath. It could easily be converted to another large bedroom with a sitting area/office. Extra care has been taken to make it a low maintenance home: Hardie Boarding siding has been installed on the 2nd/3rd floor, with new shingles on the 1st floor. The 2nd/3rd floor windows are Andersen 400 tilt out windows, and the stairs and decking are composite with a Lifetime Guarantee. The owners have taken meticulous care of the home, and have maintained the information on each improvement, along with receipts and warranty information. Truly move in ready.

Listed by Scott, Janet of 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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