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. We will help you find the right vacation home or year round residence! Learn more about Oak Bluffs.

Oak Bluffs Real Estate

Questions? Call Coldwell Banker Landmarks Real Estate: 508-693-6866

Save time & effort! Create an account to save your favorite listings & get notifications when similar properties become available.

View by Property Type: Waterfront Homes | Water View Homes | Single Family | Condos

21 Kennebec Avenue

Oak Bluffs, MA21 Kennebec Avenue

Price$659,000

Est. Mortgage: $/month

MLS ID 36460

  • Condominium
  • Village Downtown
  • Square Feet 985
  • Bedrooms 1
  • Bathrooms 1

Rare Opportunity to own an in-town condo with private parking and NANTUCKET SOUND WATER VIEWS! In excellent condition, this lovingly maintained sun-filled Condo features high ceilings, hardwood flooring, stunning views over the sound and Ferry dock, separate basement storage and deeded parking lot. Center of Town, Steamship, Harbor and Public Beaches just steps away. Must see.

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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

21 Kennebec Avenue

Oak Bluffs, MA21 Kennebec Avenue

Price$659,000

Est. Mortgage: $/month

MLS ID 36486

  • Condominium
  • Village Downtown
  • Square Feet 985
  • Bedrooms 1
  • Bathrooms 1

FANTASTIC CONDO UNIT WITH WATER VIEWS. In the heart of town, this prime location is steps from Ocean Park, the ferry, Inkwell beach, the harbor, shops and the lively restaurants of Oak Bluffs. Watch the boats and ferries coming and going from this beautifully appointed third floor unit. There's a private balcony with water views, perfect for relaxing with a book or entertaining guests. While great for a year round residence, the unit would also make for a smart investment. Rental history available upon request. Of added value is the parking space just behind the building that is included in the sale.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

179 Edgartown Vineyard Haven Road

MLS ID 36459

  • Residential
  • Village Central
  • Square Feet 1092
  • Bedrooms 2
  • Bathrooms 1

MAKE PLANS TO EXPAND OR ENJOY AS IS. This gem of a property has many options, as it is set on 1.84 acres in a wonderful central location. The 2 bedroom carriage house with one bay garage and office on the main level has been beautifully designed with lovely interior finishes and a chef's kitchen. There is a large covered deck that overlooks the expansive yard. A Land Bank trail from the house leads down to the head of the Lagoon and most of the property is surrounded by the Weahtaqua Srings Preserve, a 35 acre Land Bank parcel. This is a peaceful setting just minutes to all down Island town centers.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

13 Shirley Avenue

Oak Bluffs, MA13 Shirley Avenue

Price$759,000

Est. Mortgage: $/month

MLS ID 36457

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1508
  • Bedrooms 3
  • Bathrooms 3

New LISTING in Oak Bluffs! Contemporary Ranch Style Home conveniently located off BIKE PATH and only 2 BLOCKS easy STROLL to the LAGOON SANDY BEACH! This home is very charming and has many special finishes and nooks! There are 2 large cheerful bedrooms with walk in closets and 2 updated bathrooms..The kitchen, dining and living areas are all open and are perfect for entertaining ! The built in window seat is an ideal place to read and relax! There are sliders off the living room that open to a pleasant patio. There are 3 bedrooms and 3 bathrooms. Two of the bedrooms are on the main living floor and the third bedroom suite is in the walk out basement which is bright and cheerful! TERRIFIC VALUE ! SHORT WALK BIKE RIDE TO TOWN, FERRIES, BEACHES and OAK BLUFFS HARBOR!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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

67 Trinity Park

Oak Bluffs, MA67 Trinity Park

Price$550,000

Est. Mortgage: $/month

MLS ID 36428

  • Residential
  • Village Downtown
  • Square Feet 810
  • Bedrooms 2
  • Bathrooms 1

You can enjoy year round or vacation living in this Martha's Vineyard Camp Ground Cottage. Lovingly Renovated, insulated and full of charm, this two bedroom one and one half bath cottage has beautiful wood floors, custom made kitchen counter tops, mini spits for heating and air conditioning, two second floor bedrooms with vaulted ceilings, full bath on first floor with half bath on the second, a she-shed for storage and summer laundry. Enjoy the views of the park in front and the tabernacle along with it's many events all from the front porch. There are a few weeks rented this summer but the best week of the summer has been reserved for your use as the new owner. Betterment fee has been paid in full.

Listed by Laer Realty Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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

40 Tiffany Drive

Oak Bluffs, MA40 Tiffany Drive

Price$869,000

Est. Mortgage: $/month

MLS ID 36412

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1948
  • Bedrooms 3
  • Bathrooms 3

Oak Bluffs Contemporary design located in desirable Lagoon Estates in a private setting over 1.84 acres and abutting acres of conservation land owned by the Land Bank! The interior of the home is OPEN, BRIGHT with HIGH WOOD BEAM CEILINGS and immaculate throughout. There are 3 bedrooms with one master en suite on first floor and one on the second floor along with a guest bedroom. Terrific location in PRISTINE condition throughout! Deeded access to Lagoon!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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, MA225 East Chop Drive

Price$2,790,000

Est. Mortgage: $/month

MLS ID 36309

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

Tempting buy on "Telegraph Hill"! This is the perfect “Nautical Neighborhood” to begin (or continue) your family legacy on Martha's Vineyard. Recently renovated to create a touch of class, this elegant, distinctive home overlooks Vineyard Sound and the East Chop Lighthouse. The home was completely re-designed and rebuilt (by South Mountain Company) in 2014-15 to take advantage of the never-ending water view and finished in custom detail to meet the high standards of the owner. From the moment you enter, you will be “wowed” by the view and quality of craftsmanship. There is beautiful Birch flooring that runs throughout most of the home including the upscale, gourmet “cooks” kitchen. And…What a difference a well-designed kitchen makes! This includes a center island work station where you can chop ingredients, roll out pizza dough or cut fresh flowers from the garden. All appliances are “top of the line” and the custom-built walnut cabinets are 2nd to none. From the kitchen, you will enjoy the water view, a glowing fire in the Stone fireplace and be part of all the activities in the wide-open dining/living room. The substantial rear deck and an expansive green lawn look over Vineyard Sound to Cape and beyond. You will enjoy the lighted evening shorelines along Vineyard Sound, glowing sunsets and sunrises and on the 4th of July, view the numerous firework displays from Edgartown to Falmouth and beyond…simply spectacular! Be sure to see the attached document "Marketing Material" for a list of the property features.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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

6 Mourning Dove Way

Oak Bluffs, MA6 Mourning Dove Way

Price$969,000

Est. Mortgage: $/month

MLS ID 36333

  • Residential
  • Village Sengy
  • Square Feet 1728
  • Bedrooms 4
  • Bathrooms 1

SENGEKONTACKET ASSOCIATION ~ CONTEMPORARY Island residence situated in the desirable water front community offers a unique Vineyard design featuring an OPEN BRIGHT GREAT ROOM with an ABUNDANCE of GLASS and SUN LIGHT from the lofty skylit cupola, and the sweeping EXPANSIVE MAHOGANY decks at each end of the room remind you that this is the place where festive people get together to celebrate Summer! Outdoor living with cookouts, sunbathing, entertaining and lots of amenities . The house with natural visuals is tastefully appointed, with an attractive kitchen and intimate sitting areas while the bedrooms and bathrooms conveniently surround this playful setting. This COASTAL CONTEMPORARY BEACH HOME is on the bike path to Town, has been BEAUTIFULLY MAINTAINED, NEW ROOF 3/25/2019, 5 BEDROOM SEPTIC, and includes a community salt water dock offering access to Nantucket Sound, mooring availability, tennis courts, and a spring fed freshwater beach.

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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

232 Massachusetts Avenue

Oak Bluffs, MA232 Massachusetts Avenue

Price$1,799,000

Est. Mortgage: $/month

MLS ID 36118

  • Residential
  • Village East Chop
  • Square Feet 5269
  • Bedrooms 5
  • Bathrooms 4

East Chop -- Distinctive, well-loved, multi-generational home, with 5-bedrooms (3-ensuite), looks out over Mill Square Park, with peeks of water in the distance, and surrounded by the best amenities East Chop has to offer -- beaches, yacht club, and tennis club. This graceful home features a large living room with paneled ceiling and beach stone fireplace, large dining room with Dutch tiled fireplace and, two large, sun-filled, family rooms (one upstairs and one downstairs). Ideally located with just a 7-minute walk to the beaches, tennis courts and harbor during the day, and 12-minutes walk to downtown restaurants and night life in the evening, this vacation home is ideal for those extended family stays! Upgraded to a 220 electrical system/circuit breakers '88-'89.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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

111 New York Avenue

Oak Bluffs, MA111 New York Avenue

Price$1,395,000

Est. Mortgage: $/month

MLS ID 36072

  • Residential
  • Village East Chop
  • Square Feet 4015
  • Bedrooms 6
  • Bathrooms 6

Exceptional and unique opportunity in East Chop -- walking distance to beaches, restaurants, galleries, harbor and ferries! Known for many years as the Martha's Vineyard Resort, this 6-bedroom/6-bathroom property with enormous 1st floor great room, 5-ensuite bedrooms upstairs (one with living room and fireplace), and connected property manager's office with 1-bedroom plus loft living quarters, speaks to its use as a rental property within walking distance to everything downtown. The inviting and spacious outdoor entertainment spaces include wrap around front covered porch, rear covered porch running the length of the house, and a 2nd floor balcony deck also running the length of the house. The full finished basement, with bar, and bathrooms, adds another 1,600 sq feet. The private property manager's quarters located off the main floor has an open living-kitchen-office area, bedroom and bathroom on the first floor, and a spiral staircase to the 2nd floor loft bedroom. House comes partially furnished. A great investment/rental property, or transform into your vacation or year-round home. Property does not include the tennis courts, which may be leased. An additional approx. 2,500 sq ft of land (25' x 100') running the length of one side of the lot will be included to rectify the setbacks.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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