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.

Questions about buying a home in Oak Bluffs?

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.

r=1-10
3 Checama Path

Price$799,000

Est. Mortgage: $/month

MLS ID 34755

  • Residential
  • Square Feet 1818
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 1.527

This light-filled, post and beam saltbox home is comfortable, move-in ready, and full of charm. Updated and very well-maintained, the house is worry-free and ready to enjoy both year round and seasonally. The first floor features the living room with a wood-burning fireplace and brick chimney built in 2005 - perfectly cozy on a brisk day. Also on the first floor is the cheerful, granite kitchen with a walk-in pantry, a full bathroom, and the spacious dining room. The second floor has four bedrooms and a full bathroom. Plus there are stairs to a bonus insulated attic space on the third level, which could be transformed to be another living space. The full, dry basement has both interior and exterior egresses. Also, there is refreshing central air and efficient central heat installed in 2005, as well as Harvey windows also installed in 2005. Set on 1.5 acres, it has a generous deck overlooking the large back yard and gardens. The neighborhood has substantial homes and lot sizes. All this plus a very short walk to serene Little Duarte's Pond, perfect for kayaking and canoeing. The central location is convenient to several towns and it is close proximity to miles of bike paths in the State Forest. Don't miss out on this uniquely wonderful property!

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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

27 Bayes Hill Road

Price$1,189,000

Est. Mortgage: $/month

MLS ID 34713

  • Residential
  • Square Feet 3500
  • Bedrooms 4
  • Bathrooms 4
  • Half Bath 1

A builder's own custom colonial home nestled in a private setting of the Bayes Hill Association in Oak Bluffs. A desirable community of substantial homes with private tennis and easy access to the Lagoon & Sailing Camp. This home is situated on a .76 acre lot with an abundance of mature landscaping offering privacy. This home comfortably accomodates multi-family living with its four floors of finished space. A spacious open kitchen with a eatin bar and lots of cabinetry and dining area leading to the a TV room which includes custom built-ins for storage. The first floor also has a gracious living room with woodburning fireplace and a formal dining room ( or 1st fl bdrm) with glass doors that lead to the back deck and patio area. The second floor is comprised of a master bedroom suite , three guest bedrooms with a shared bath, and a separate wing that functions as a perfect “in- law suite” or 2nd master suite. The suite is complemented with a beautiful atrium window, wet bar and full bathroom. Designed for year around living, with gas FHA heating zones and central A/C,ample storage ,huge garage and laundry room with sink. In addition,the attic has been converted into a spacious and bright office space with large skylights and built in shelving. The basement is fully finished with a second washer / dryer & bath and plenty of storage. Well sited on the lot with a back deck, patio, big yard and garden.Surrounded by an abundance of mature trees and colorful rhododendroms & hydrangeas. This home was thoughtfully designed to comfortably accommodate all the family and friends that will come to visit!

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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 Quail Run

Price$1,299,000

Est. Mortgage: $/month

MLS ID 34677

  • Residential
  • Square Feet 2877
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

Custom Contemporary Design!! ! This home shows like a new home! IMMACULATE Residence impeccably maintained is in the desirable Sengekontacket Community of Oak Bluffs! This Exquisite custom design, comfortably on one level, is situated on almost an acre of land with mature landscaping, stone walls and colorful perennial flower beds. Enter an impressive foyer into an OPEN BRIGHT living room highlighted with a beautiful stone European wood burning fireplace and 12 ft ceilings. CENTRAL AC ! The interior design is complemented by attractive furnishings that add to the graceful flow of the floor plan. Gracious Master Suite and 2 additional bedrooms are all spacious and inviting with custom closets, the kitchen is large with high end appliances, and there is a cozy separate den, and a dining room with sunsets. SURPRISE! There is a lower level, fully finished, offering a large media/rec room and multiple gathering spaces along with a full tiled bathroom & spacious workshop with walk out access! TERRIFIC LOCATION with private amenities that include access to both fresh and salt water ponds, community dock, mooring available, with kayak storage and boat ramp, a community clubhouse on the fresh pond (available for private events), tennis courts, and community services such as curbside trash pick-up and snow removal. MUST SEE HOME!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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

10 Prospect Park

Price$995,000

Est. Mortgage: $/month

MLS ID 34585

  • Residential
  • Square Feet 1691
  • Bedrooms 4
  • Bathrooms 1
  • Half Bath 1

Classic turn-of-the-century Victorian cottage with beachstone fireplace and distant water views, faces out on to a charming park. The property is located in the heart of East Chop and just a short stroll to the beach, tennis courts,the harbor and downtown. This wood framed house, aptly named The Haven of Bliss, has been lovingly maintained through the years and has two covered porches, a deck off the master bedroom, and a screened, stormed porch off the kitchen. The house has four bedrooms, one and 1/2 bathrooms, and sinks in three of the bedrooms. The living room and dining/sitting rooms have large windows and double doors which are screened or stormed with plexiglass, as are all the windows in the house allowing 3 season use with electric heaters. The outdoor shower is surrounded by mature trees and a landscaped yard.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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

61 Bayes Hill Road

Price$1,295,000

Est. Mortgage: $/month

MLS ID 22464

  • Residential
  • Square Feet 2745
  • Bedrooms 5
  • Bathrooms 3
  • Acreage 1

A must see in Bayes Hill! This spacious two story home on an acre of land with a fantastic backyard is the perfect place to call home. Traditional in style with formal and casual spaces that flow nicely to the multiple gathering areas. The dining room, kitchen and family room span the back of the house and all feature glass doors to the pool area. The outside spaces are amazing - heated gunite pool with pebble tec finish with patio surround and cabana for lounging in the shade. A screened porch offers more outside yet sheltered space, and the expansive decking unifies it all. Four great sized bedrooms occupy the second level including a grand master with walk-in closet and luxuriously appointed bath. A first-floor office/den can also serve as a fifth bedroom. The lower level is nicely finished and offers an additional 700+ square feet of space - perfect for movie watching and gaming. This home has it all - laundry room/mud room, two car garage, attic for storage and more. Bayes Hill is an attractive neighborhood with substantial homes and large parcels providing good privacy; and enjoy association tennis!

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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

31 Tuckernuck Avenue

Price$1,050,000

Est. Mortgage: $/month

MLS ID 34488

  • Residential
  • Square Feet 1738
  • Bedrooms 4
  • Bathrooms 1
  • Half Bath 1

A rare opportunity to own a property bordering Waban Park looking out to the ocean beyond. This spacious house with over 1700 square feet of interior space is tied into town sewer. Sit back and relax on the wrap around porch as you gaze over one of the most famous of Oak Bluffs parks an open grassy field and the ocean beyond. The sandy beach is just a block away. The house has been updated with a large kitchen, dining room with built in cabinets, a sun porch and spacious living room that runs the width of the house. Lovingly maintained wood floors and freshly painted walls throughout. Presently there are 4 bedrooms with with an additional second floor sitting room that could be another bathroom or another bedroom. The two front bedrooms have doors that open onto the 2nd floor large porch. Just a short distance to all the shops restaurants and entertainment of downtown Oak Bluffs.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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

267 Barnes Road

Price$3,900,000

Est. Mortgage: $/month

MLS ID 34265

  • Residential
  • Square Feet 4046
  • Bedrooms 3
  • Bathrooms 5
  • Half Bath 1

Well appointed 4000+ sq ft Contemporary home surrounded by a little more than one acre of lush landscaped greenery on Lagoon Pond with private beach and potential for a dock. Spacious 3 bedroom 5.5 bathroom with high ceilings, two first floor offices, open living/ dining areas all with views of the Lagoon. The large gourmet kitchen. Sweeping waterviews from every room. A wrap around deck and a screened sun room adjoins the upstairs bedrooms. Full basement ready to be finished. This house has spacious rooms perfect for entertaining . Being sold mostly furnished.

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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

11 Winthrop Avenue

Price$659,000

Est. Mortgage: $/month

MLS ID 34342

  • Residential
  • Square Feet 1286
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.1595

Charming oak bluffs in town location! Walk to beaches, galleries, restaurants & harbor! Ranch style home offering 3 bedrooms 2 bathrooms a spacious bright living & dining area! Walk in pantry and eat in kitchen! The home has been well cared for and offers a warm loving feeling throughout! The furnace is approximately 4 years old along and a newer stainless roth double walled oil storage tank!. Newer roof & windows! Sellers in process of designing & installation of a brand new title 5 septic system! Perfect location for year round & summer vacations!! ! Terrific value!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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

Price$869,000

Est. Mortgage: $/month

MLS ID 34214

  • Residential
  • Square Feet 1948
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 1.91

Contemporary Saltbox in Lagoon Estates w deeded rights to the Lagoon. Situated on a knoll w mature shrubs and abutting greenbelt. Wrap around deck perfect for summer socializing. This house has never been rented and has been meticulously maintained. Plenty of skylights and patio doors to let the light in. Two huge master bedroom suites w/ baths on each floor. Guest bedroom on the first floor. Large kitchen w plenty of counter space. Brick fireplace w wood stove w/ heatilator and blower, cozy in the winter. Large loft overlooking living room for office, etc. One car garage completes the offering with a 2015 Toyota for sale This lovely house can come mostly furnished, almost turnkey ready for you to use. Private and quiet setting. Please give 24 hours notice for showings.

Listed by Hughes & JC Murphy R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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

385 County Road

Price$525,000

Est. Mortgage: $/month

MLS ID 34289

  • Residential
  • Square Feet 954
  • Bedrooms 1
  • Bathrooms 2
  • Acreage 0.3266

Raised ranch, set up off the road on a knoll, near Farm Neck Golf. Large side and rear yard. Main level contains open plan living, dining, kitchen, master bedroom and full bath with laundry facilities. Lower level contains 3 additional rooms and full bath. A large deck runs the length of the house. House needs work; being sold "as is". Square footage does not include lower level.

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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