Oak Bluffs Real Estate

Downtown Oak Bluffs Martha's Vineyard

Search all listings for sale in this Martha's Vineyard village. Originally called “Cottage City”, the town is known for its historic gingerbread cottages. The classic beach town is home to the largest marina on Martha's Vineyard. Oak Bluffs is also home to the popular East Chop neighborhood.

Learn more about Oak Bluffs >>

Browse All Real Estate For Sale In Oak Bluffs, Martha's Vineyard

Contact us for all your questions and for more information about Oak Bluffs. Create an account to save your favorite listings and to receive email updates for similar properties.

Narrow Your Search

Oak Bluffs, MA

Price$285,000

Est. Mortgage: $/month

MLS Number 34010

  • Land
  • Acreage 0.2699

A Sweet Spot to Call Home - Just 1.1 miles to the bottom of Circuit Avenue or Inkwell Beach sits this level 1/4 acre lot. A blank canvas for you to create your dream home. Property should support a minimum 3 bedroom home. Close to town, bike path, ferries and more, this lovely piece of the Vineyard could be your future home.

Listed by Island Real Estate

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

80 County Road, Oak Bluffs, MA

Price$1,170,000

Est. Mortgage: $/month

MLS Number 33297

  • Residential
  • Area Central
  • Square Feet 2196
  • Bedrooms 3
  • Bathroom 3

Custom built in 2007 and recently renovated, this 2 story Colonial offers a modern kitchen, 3 large bathrooms, a fully finished basement, and shotcret heated in-ground swimming pool with LED lighting, deck fountains and whirlpool bench seat. Conveniently situated on the bike path and walking distance to downtown Oak Bluffs, the hospital, beaches, and both ferries. Professionally landscaped yard boasting mature trees, a well groomed lawn and an array of colorful flowers. Large raised blue stone patio with a built in grill, sink and custom blue stone bar top that is perfect for barbecues. The large modern kitchen has stainless steel, granite and flows right into the dining room with plenty of space for entertaining. 8kW sun power solar system that generates a substantial amount of power for the entire house hold throughout the year.

Listed by Elevated Realty LLC

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

4 Quail Run, Oak Bluffs, MA

Price$479,000

Est. Mortgage: $/month

MLS Number 34009

  • Condominium
  • Village Sengy
  • Square Feet 1182
  • Bedrooms 1
  • Bathroom 1

The best of the best; access to all Sengekontacket Community amenities, a newly renovated condominium with impeccable taste and high quality finishes at a price many can consider. The well-planned Community is centered around a fresh pond for swimming, canoeing or fishing. The Community Club House sits directly on the pond and is available for private and community functions. Tennis courts are located opposite the Club House and the list continues....there is an association dock on Sengekontacket Pond, racks for canoes and kayaks and the potential of a mooring in the Pond. Being sold turnkey. This has it all.

Listed by Sandpiper Realty

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

46 Meshacket Way, Oak Bluffs, MA

Price$825,000

Est. Mortgage: $/month

MLS Number 34007

  • Residential
  • Village Central
  • Square Feet 1456
  • Bedrooms 4
  • Bathroom 3

Attractive and newly renovated Cape on a spacious and centrally located property in Oak Bluffs! With numerous recent upgrades, including brand new kitchen, updated bathrooms, central forced air/AC system, and refreshed living spaces, this property is ideal for summer or year-round occupancy. Set quietly on over an acre of land, the location is superb, with great proximity to Farm Neck, the YMCA, and all down-island towns. Bike paths nearby allow for cycling and easy enjoyment outdoors. Easy to show and a delightful offering!

Listed by Wallace & Co. Sotheby's

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

227 Buddys Drive, Oak Bluffs, MA

Price$1,070,000

Est. Mortgage: $/month

MLS Number 33978

  • Residential
  • Village Central
  • Square Feet 2762
  • Bedrooms 6
  • Bathroom 3

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 Ocean Park Realty Inc

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

446 County Road, Oak Bluffs, MA

Price$799,000

Est. Mortgage: $/month

MLS Number 33957

  • Residential
  • Village Sengy
  • Square Feet 1959
  • Bedrooms 2
  • Bathroom 2

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 Ocean Park Realty Inc

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

16 Atlantic Avenue, Oak Bluffs, MA

Price$899,000

Est. Mortgage: $/month

MLS Number 33972

  • Residential
  • Village East Chop
  • Square Feet 1785
  • Bedrooms 5
  • Bathroom 1

Exceptional East Chop cottage located near the Lighthouse and tennis club. Antique home (circa 1890) has many recent improvements including roof, sidewall shingles, 7 bedroom septic system, refinished wood floors and more! This is a work in progress so you are afforded the opportunity to complete the home to your "taste". The wrap around front porch and rear screened porch extend the living area outside. Plus there is a 2 car garage and room for a guest house. Included with the sale are architectural plans for the guest cottage.

Listed by RE/MAX on Island

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

115 Dukes County Avenue, Oak Bluffs, MA

MLS Number 33969

  • Residential
  • Village Downtown
  • Square Feet 1435
  • Bedrooms 3
  • Bathroom 2

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 Ocean Park Realty Inc

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

225 East Chop Drive, Oak Bluffs, MA

Price$3,950,000

Est. Mortgage: $/month

MLS Number 33942

  • Residential
  • Village East Chop
  • Square Feet 2449
  • Bedrooms 3
  • Bathroom 3

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 Sandpiper Realty

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

48 Cannahoot Street., Oak Bluffs, MA

Price$429,500

Est. Mortgage: $/month

MLS Number 33901

  • Residential
  • Village East Chop
  • Square Feet 616
  • Bedrooms 1
  • Bathroom 1

An all-seasons, compact cottage, complete with appliances, furniture and furnishings - move in condition. A ruggedly built quaint cottage on wooded lot that has charm, warmth and cuteness. Located on a nicely treed lot, with off-street parking and only a bike ride to town. Mostly fenced which, gives a feeling of privacy. The first floor is open with a combined living room, kitchen & dining area plus a full bath(tub & shower) and one bedroom. The second floor has two loft sleeping areas that are bright and airy with windows and skylights. The first floor is heated by a ac/heat split and the 2nd level (reached via a living-rm stairway) has baseboard electric. To the rear is an attached deck w/sun awning. To the rear of the residence is a 12x15ft shed which is used mostly for storage. This home comes fully furnished and is ready to move into.... Ideal starter home or income producer.

Listed by Towne & Country Realty

{$office->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details