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
Oak Bluffs, MA

Price$649,000

Est. Mortgage: $/month

MLS Number 34334

  • Land
  • Acreage 2.177

Harthaven - One of the last remaining parcels of land available within the Harthaven association, this 2.1 acre parcel will allow for a house and guest house (after 5 years) with up to 9 bedrooms. Enjoy all that the association has to offer including private beach, small boat harbor and tennis. Surrounded by conversation land with walking trails. Easy access to town, ferries and more. Perc test has been completed. Staking and a plot plan are be finalized and then paths will be created for easy viewing.

Listed by 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

4 Meshaket Way, Oak Bluffs, MA

Price$499,000

Est. Mortgage: $/month

MLS Number 34323

  • Land
  • Area Central
  • Acreage 1.38

Build your very own custom Island getaway or year-round home in this desirable neighborhood of attractive homes. This level 1.38 acre lot can accommodate a 5 bedroom home with a future 1 bedroom guest house. Approved 6 bedroom disposal system permit, soil test and septic design completed in 2014. This level corner parcel allows for privacy buffers from roads and neighbors. You've even got plenty of room for a pool. Very convenient to all three down-island towns.

Listed by Laer Realty Partners

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

7 Pennacook Avenue, Oak Bluffs, MA

Price$1,950,000

Est. Mortgage: $/month

MLS Number 34316

  • Multi-Family
  • Village Downtown
  • Location 41.452340,-70.555809
  • Bedrooms 8
  • Bathroom 4

Own a bit of history in the Copeland district! The Dunmere by the Sea has one hundred fifty years of hospitality behind it's name and under its roof. Built as a small hotel, it was converted to apartments by an architect in 1970. It has been family owned and operated for over 40 years. It is ideally situated, 150' from the famous Inkwell beach and minutes from shops and restaurants of "downtown" Oak Bluffs and the ferries. The town playground and tennis courts are two whole blocks away. Off road parking. Water views from every floor. Enjoy the ocean breeze and sunrise over Inkwell beach as you relax on the deep wrap around porch.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

29 Simpson Avenue, Oak Bluffs, MA

Price$655,000

Est. Mortgage: $/month

MLS Number 34299

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1460
  • Bedrooms 2
  • Bathroom 2

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

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

78 Isaac Avenue, Oak Bluffs, MA

Price$610,000

Est. Mortgage: $/month

MLS Number 34302

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1568
  • Bedrooms 1
  • Bathroom 2

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

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

8 Melrose Avenue, Oak Bluffs, MA

Price$675,000

Est. Mortgage: $/month

MLS Number 34274

  • Multi-Family
  • Village Lagoon/Harbor
  • Bedrooms 3
  • Bathroom 4

House and guest house privately set back off the street. The main house contains 2 bedrooms plus large loft area and two full baths. Hardwood floors in kitchen/dining room and living room. First floor laundry room.The full basement is finished with additional rooms and full bath with separate entry. The cute guesthouse has open plan living, dining, kitchen and laundry. Upstairs a large bedroom. Plenty of off street parking for both residences. Excellent rental history.

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

91 Dukes County Avenue, Oak Bluffs, MA

MLS Number 31761

  • Condominium
  • Village Downtown
  • Square Feet 1107
  • Bedrooms 1
  • Bathroom 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 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

41 School Street, Oak Bluffs, MA

Price$590,000

Est. Mortgage: $/month

MLS Number 34246

  • Residential
  • Village Downtown
  • Square Feet 1007
  • Bedrooms 3
  • Bathroom 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 Anchor Realty of Martha's Vineyard

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

1 School House Village, Oak Bluffs, MA

MLS Number 34239

  • Residential
  • Village Central
  • Square Feet 1960
  • Bedrooms 3
  • Bathroom 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 Priestley Smadbeck & Mone

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

274 Sea View Avenue, Oak Bluffs, MA

Price$4,995,000

Est. Mortgage: $/month

MLS Number 34138

  • Residential
  • Village State Beach
  • Square Feet 3460
  • Bedrooms 6
  • Bathroom 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 Sandpiper Realty, Inc.

$
$
%
$/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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details