Oak Bluffs Homes for Sale

Oak Bluffs has a wonderful array of single family homes on Martha’s Vineyard. From beach cottages and waterfront homes to homes within walking distance to downtown, shops, and restaurants, you’re sure to find the perfect Martha’s Vineyard home in Oak Bluffs. Scroll down to explore Oak Bluffs houses for sale on Martha’s Vineyard. 

View Oak Bluffs Real Estate

Call Ocean Park Realty at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour.

Time Saving Tip - Sign up for a search account (it's free) to save your favorite Martha's Vineyard real estate listings and get notified when similar properties become available.

232 Massachusetts Avenue Oak Bluffs MA

Oak Bluffs, MA232 Massachusetts Avenue

Price$1,825,000

Est. Mortgage: $/month

MLS Number 36118

  • Residential
  • Square Feet 5269
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.44

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: 3.65% last updated on Jan 16, 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 MA

Oak Bluffs, MA111 New York Avenue

Price$1,395,000

Est. Mortgage: $/month

MLS Number 36072

  • Residential
  • Square Feet 4015
  • Bedrooms 6
  • Bathroom 6
  • Acreage 0.23

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 2,500 sq ft of land (25' x 100') running the length of one side of the lot may be purchased separately, for an additional side yard/parking area.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

395 Barnes Road Oak Bluffs MA

Oak Bluffs, MA395 Barnes Road

Price$4,350,000

Est. Mortgage: $/month

MLS Number 36053

  • Residential
  • Square Feet 4330
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

RARE OPPORTUNITY ON THE LAGOON WITH A DEEP WATER DOCK - It is rare to find a home in a setting like this on Martha's Vineyard. Tucked away just off Barnes Road, it feels as if you are in a remote locale, yet you are so close to all the Island has to offer. Invite your friends and family. This home boasts room to absorb many people without feeling crowded and has plenty of private retreats for the generations to come. West facing views and glorious sunsets help make this a perfect place to spend - and end - a day. Entertaining is a breeze throughout the open concept main floor. Take in a glorious sunset from the screened porch or out near the dock. Clams and scallops are within your reach just offshore. A ball game or two have been known to erupt on the front yard. Sit back and soak in the natural setting - the fish and fowl will keep you entertained. A deep water dock and deep water access, with the added comfort of the protected location. Come for a visit. You will want to stay for a lifetime.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

14 South Street Oak Bluffs MA

Oak Bluffs, MA14 South Street

Price$1,895,000

Est. Mortgage: $/month

MLS Number 34860

  • Residential
  • Square Feet 2576
  • Bedrooms 6
  • Bathroom 5
  • Acreage 0.2921

Walk to town, ferry, harbor and beach. A beautiful family compound or investors dream! Pristine newly renovated 4 bedroom 3 bath main home and brand new modern 2 bedroom 2 bath detached guest home. Both dwellings boasts solid hardwood floors, ducted heat and A/C, gas fireplaces, granite and quartz stone counters and tiled bathrooms, open concept floor plan, first floor master bedrooms, walk-in closets, the second floor features vaulted ceilings, a master bedroom with private bath. The dwellings radiates with morning and afternoon sun. The yard includes mature oak trees, custom landscaping, hydrangeas bordering a wrap-around porch, a spacious rear deck with built-in benches, two private parking lots that can accommodate up to 8 vehicles, two private outdoor showers, an automated irrigation system. The property is being sold fully furnished for a complete turnkey solution. The main dwelling has a very strong rental history. Agent is the owner.

Listed by Premier Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

9 Stone Pound Way Oak Bluffs MA

Oak Bluffs, MA9 Stone Pound Way

Price$985,000

Est. Mortgage: $/month

MLS Number 35827

  • Residential
  • Square Feet 2839
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 1

An ideal location with pleasant waterviews and an opportunity to remodel a home to your specifications. Located in Hidden Cove Community, close to the bike path, offering tennis courts, and coveted for its incredible water experience to enjoy boating and kayaking on Sengekontacket Pond. With access to the association dock, boat storage and launch, what could be better? This three story home takes advantage of the views on all levels. Great living space on the main level with fireplace and sliders to the spacious deck overlooking the pond. The extensive master suite with fireplace, oversized walk in closet, and bath occupy the upper level. The lower level is dedicated to two guest rooms and a full bath. A detached one car garage for all the tools and toys finishes the property. Priced appropriately to allow you to design and update the interior in time for next season.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

38 Tiffany Drive Oak Bluffs MA

Oak Bluffs, MA38 Tiffany Drive

Price$869,000

Est. Mortgage: $/month

MLS Number 35936

  • Residential
  • Square Feet 1892
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.38

On a beautiful 1.38 acre lot in a quiet subdivision off Barnes road lies this private four bedroom 3 bath home. There is a lofted great room with a warm fireplace for entertaining which opens to a dining large kitchen area so that whether your in the kitchen dining room or great room your in the conversation! Two first floor bedrooms for easy living and two large master bedroom suites make for very comfortable living with everything only a short ride away! A full poured basement will store all the summer toys!

Listed by Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

7 East Meadow Lane Oak Bluffs MA

Oak Bluffs, MA7 East Meadow Lane

Price$1,089,900

Est. Mortgage: $/month

MLS Number 35873

  • Residential
  • Square Feet 2500
  • Bedrooms 5
  • Bathroom 4
  • Acreage 1.08

Meadow View Farms- Perched on top of the hill sits this contemporary home with room for all. The first level offers two bedrooms and two full bathrooms with access to the fully finished basement. As you ascend up the stairs you will find a great mix of living and dining. In addition to that, a full bathroom, laundry, and one bedroom. The third level is the master's quarters with stunning views of the meadows and partial distant pond view. Close proximity to beaches, Oak Bluffs town, and Farm Neck Golf Club.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

19 Old Harbor Lane Oak Bluffs MA

Oak Bluffs, MA19 Old Harbor Lane

Price$3,850,000

Est. Mortgage: $/month

MLS Number 35849

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1
  • Acreage 1.9491

Rare Opportunity to build 3 separate dwellings or to build your dream home near the water with private beach access and .3 miles to Farm Neck Golf Club! These properties are currently 3 individual lots which can be combined to offer a large estate lot. A summer home is already in place on lot 7, but is not winterized for year-round living. Renderings shown in photos are for visualization purposes and do not necessarily reflect the HOA specifications for Waterview Farms. For Information regarding 4th lot shown please contact listing agent. Two of these parcels adjoin conservation land offering unobstructed views of Sengy Pond, State Beach and beyond. Waterview Farms provides beach access with boat storage and docking available. Explore quaint nearby walking trails to Pecoy Point, or use your paddle boards or kayaks to enjoy Felix Neck & State beach! The MV biking trails access is at entrance to the community with an easy ride to town! This listing includes 7 Old Harbor Lane which is also listed separately.

Listed by Sierra Properties & Investments

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

3 North Meadow Lane Oak Bluffs MA

Oak Bluffs, MA3 North Meadow Lane

Price$859,000

Est. Mortgage: $/month

MLS Number 35785

  • Residential
  • Square Feet 2304
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.63

This 4 bedroom, 4 bath home is located in a nice area, Meadow View Farms, and sited on just over a 1/2 acre. Nice features include a new kitchen with stainless appliances and granite counters, a living room with fireplace and bay window. Nicely landscaped yard with many mature plantings overlooking one of the common meadows and just a short distance to association tennis.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

11 Myrtle Avenue Oak Bluffs MA

Oak Bluffs, MA11 Myrtle Avenue

Price$569,000

Est. Mortgage: $/month

MLS Number 35525

  • Residential
  • Square Feet 1050
  • Bedrooms 2
  • Bathroom 2
  • Acreage 0.2206

Oak Bluffs Ranch Style home located in a very desirable private setting in the East Chop Highlands! There are 2 bedrooms and 2 bathrooms along with a galley style kitchen. This year round house will keep you cozy in the winter with fuel efficient propane heat and a wood burning stove (including a woodshed chock-full of seasoned wood), and summer in comfort with wall unit A/C's. A heated partial basement also offers additional storage and/or living space and a charming garden shed is also on the property. The large lot offers an abundance of parking and private intimate spaces to relax with a private deck and outdoor shower on each side facing nicely landscaped yards. There are no abutting properties as you are surrounded by three streets (the back one a paper road ) and a park. The original house was under 400 square feet with additions (including basement) done by previous owner, including modern wiring and plumbing, so it is effectively a fully modern house. This property is in a great location for renting and has a strong Air bnb rental history. Rent it out partially and still maintain owner privacy or fully for maximum income, this will easily pay for some or all of your mortgage. It is turn key and low maintenance, ready to produce income early in the Spring! Easy stroll to Oak Bluffs Harbor, public beaches, East Chop Lighthouse, restaurants and galleries! TITLE 5 Report in hand for 2 bedrooms and recently pumped septic! Recent improvements include interior & exterior painting with new roof on the back side, an updated kitchen with new fridge, cabinets and beautiful butcher block counter-tops and a new hot water heater. A very versatile house that lives larger than it looks and is move-in ready!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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