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

r=1-10
90 South Circuit Avenue, Oak Bluffs, MA

Price$1,669,000

Est. Mortgage: $/month

MLS Number 33863

  • Residential
  • Square Feet 2780
  • Bedrooms 3
  • Bathroom 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 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

105 Eastville Avenue, Oak Bluffs, MA

Price$997,000

Est. Mortgage: $/month

MLS Number 33848

  • Residential
  • Square Feet 1879
  • Bedrooms 4
  • Bathroom 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 Martha's Vineyard R.E.

{$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

50 Circuit Avenue, Oak Bluffs, MA

MLS Number 33856

  • Commercial
  • Area Downtown
  • Bathroom 1
  • Bedrooms 1
  • Half Bath 1

The Slice of Life, a long-established restaurant at 50 Circuit Avenue in Oak Bluffs, is being offered for the first time in 15 years. The existing structure, circa 1900, underwent a complete renovation in 2003 and features 3,036 square feet of restaurant operating space. An additional 340 square foot, one-bedroom apartment upstairs provides an ideal opportunity for chef / owner. There is potential for a second apartment upstairs (with permitting). The Slice of Life is a year-round restaurant offering breakfast, lunch, dinner and take away items that is popular with locals and tourists alike. There are total of 42 seats with 18 seats on the winterized porch overlooking Circuit Avenue. The space is adaptable to many restaurant settings, i.e. a bistro, intimate formal, café, casual dining, pizzeria, bakery or coffee shop. The property is located in Oak Bluffs B1 zoning district and other non-restaurant, retail uses are possible. The Slice of Life fully equipped restaurant business is offered separately. Restaurant equipment, furnishings, current inventory, goodwill, branding, logo and website are being offered. The restaurant operates with an annual beer and wine license. See listing broker for more details on the sale of the business.

Listed by Russell Maloney 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

331 East Chop Drive, Oak Bluffs, MA

Price$895,000

Est. Mortgage: $/month

MLS Number 33868

  • Residential
  • Area East Chop
  • Square Feet 444
  • Bedrooms 1
  • Bathroom 1

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. Why buy a beach key when you can buy the beach!!??!

Listed by Martha's Vineyard Vacation Rentals

{$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

7 Old Harbor Lane, Oak Bluffs, MA

Price$2,925,000

Est. Mortgage: $/month

MLS Number 33797

  • Residential
  • Area Sengy
  • Square Feet 2488
  • Bedrooms 4
  • Bathroom 4

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)

Listed by Island Home 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

8 Rock Avenue, Oak Bluffs, MA

Price$465,000

Est. Mortgage: $/month

MLS Number 33821

  • Residential
  • Area Downtown
  • Square Feet 955
  • Bedrooms 3
  • Bathroom 1

Location Location Vacation ~ Magical Setting in the Martha's Vineyard Camp Meeting Association! Rare offering with 2 side yards and large Farmers Porch! This Charming Victorian Gingerbread Cottage is located a block to public beaches, shopping & dining on a famous Circuit Avenue, Oak Bluffs Harbor, ferry ports and all the Oak Bluffs Town Parks! There are 3 bedrooms, 1 full bathroom and a SPACIOUS & BRIGHT LIVING & DINING AREA!

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

1 Fairmont Avenue, Oak Bluffs, MA

Price$699,000

Est. Mortgage: $/month

MLS Number 33805

  • Residential
  • Area Central
  • Square Feet 2808
  • Bedrooms 3
  • Bathroom 4

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 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

311 East Chop Drive, Oak Bluffs, MA

Price$2,250,000

Est. Mortgage: $/month

MLS Number 33800

  • Residential
  • Area East Chop
  • Square Feet 1496
  • Bedrooms 4
  • Bathroom 2

Smell the sea and touch the sky from this unique vintage waterfront home on East Chop. Extraordinary views of Vineyard Sound from every room with ocean breezes flowing through to Crystal Lake. You can watch the sun rise as you bathe in the antique tub and then watch the sun set from the patio or master suite. Your private 120' dock, mooring and sandy pebbled beach are the perfect place to enjoy all the beauty and water activities that make the Island a special place for generations of family memories. On the ground floor there is an open floor plan with a central kitchen, living and dining area flanked by two bedrooms. The master bedroom is en-suite with a sitting area that opens up to spectacular views of the blue water. The second bedroom on the first floor is a cozy enclave with a private half bath. The open kitchen has ample room to prepare breakfast, lunch and dinner - eat in the attached dining nook or alfresco on the brick patio. Upstairs there are two additional bedrooms and a full bath. There is a detached garage with a large cedar-lined closet for storage. This magnificent home is located within walking or biking distance of downtown Oak Bluffs. Being offered turnkey and has a solid rental history.

Listed by Coldwell Banker Landmarks

{$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

98 Park Street, Oak Bluffs, MA

Price$698,000

Est. Mortgage: $/month

MLS Number 33802

  • Land
  • Village East Chop
  • Acreage 0.24

Find your perfect foothold in Oak Bluffs with this adorable property in East Chop! Enjoy all that Oak Bluffs has to offer - the lighthouse is just moments away, as are beaches, tennis, downtown and the harbor. Offered with plans for a much larger home with attached garage, this property has outstanding potential, just waiting for your vision. At the same time, the existing home, a quaint cottage, is charming as-is, ideal as a cozy Vineyard retreat. The location is superb, with a number of elegant homes in the immediate surrounds. A fantastic opportunity. Note: there is an existing waterview of the Sound and ferries that was established by clearing, with permission, on a neighboring property.

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

137 Circuit Avenue, Oak Bluffs, MA

Price$680,000

Est. Mortgage: $/month

MLS Number 32750

  • Residential
  • Village Downtown
  • Square Feet 864
  • Bedrooms 3
  • Bathroom 2

Fantastic downtown Oak Bluffs location, walk to everything! Beaches, restaurants, parks, ferry, harbor. A rare opportunity for downtown OB. Meticulously maintained by the same family for over 50 years this home has hardwood and cork floors, newer Marvin windows, covered porch, finsished basement and fantastic yard! The home comes fully furnished including a Jeep Cherokee for your Island adventures! 3 first floor bedrooms with full bath, eat in kitchen and living room. Walkout basement is partially finished with another sleeping area, living area full bathroom and extra unfinished space for storage. The home sits perched on a hill overlooking Hiawatha park with a huge 24'x14'covered porch. The home is deceivingly larger than it looks and you have a spacious front and back yard..A great opportunity for downtown living.

Listed by Martha's Vineyard Island-Wide 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