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

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

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40 Tiffany Drive

Oak Bluffs, MA40 Tiffany Drive

Price$869,000

Est. Mortgage: $/month

MLS ID 36412

  • Residential
  • Square Feet 1948
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 1.847

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

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%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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.

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225 East Chop Drive

Oak Bluffs, MA225 East Chop Drive

Price$2,790,000

Est. Mortgage: $/month

MLS ID 36309

  • Residential
  • Square Feet 2449
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

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. Rentals in place for summer 2020

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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.

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6 Mourning Dove Way

Oak Bluffs, MA6 Mourning Dove Way

Price$969,000

Est. Mortgage: $/month

MLS ID 36333

  • Residential
  • Square Feet 1728
  • Bedrooms 4
  • Bathrooms 1
  • Half Bath 2

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: 3.15% last updated on May 28, 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.

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232 Massachusetts Avenue

Oak Bluffs, MA232 Massachusetts Avenue

Price$1,799,000

Est. Mortgage: $/month

MLS ID 36118

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

East Chop -- Expansive 5-bedroom/4-bathroom (3-ensuite) home, 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: 3.15% last updated on May 28, 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.

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111 New York Avenue

Oak Bluffs, MA111 New York Avenue

Price$1,395,000

Est. Mortgage: $/month

MLS ID 36072

  • Residential
  • Square Feet 4015
  • Bedrooms 6
  • Bathrooms 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 approx. 7,234 sq ft of land (including 4,161 sq ft running the length of the driveway side of the lot will be included to rectify the setbacks, and another 3,071 sq ft behind the house will be included to expand the back yard), will be submitted as a subdivision plan subject to buyers approval (see subdivision plan in the documents section).

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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.

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395 Barnes Road

Oak Bluffs, MA395 Barnes Road

Price$4,350,000

Est. Mortgage: $/month

MLS ID 36053

  • Residential
  • Square Feet 4330
  • Bedrooms 4
  • Bathrooms 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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.

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40 Hidden Cove Road

Oak Bluffs, MA40 Hidden Cove Road

Price$1,100,000

Est. Mortgage: $/month

MLS ID 36017

  • Condominium
  • Village Sengy
  • Square Feet 2690
  • Bedrooms 3
  • Bathrooms 2

This newly renovated Hidden Cove condo unit is located in an area that includes private pool, tennis, and access to a boat launch on Sengekontacket Pond. Many nice features include all new kitchen and baths, new flooring, carpeting and a new heat pump system for heating and cooling. The main level offers an open kitchen and dining room, living room with fireplace both that open to a private deck and offering stunning ocean and pond views. Second floor is the master suite, lower level includes 2 bedrooms, both with access through sliders to a private patio. Stunning ocean and pond views from each floor. There is also an oversized 1-care garage that includes additional storage of bikes and out door furniture.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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.

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34 Waterview Road

Oak Bluffs, MA34 Waterview Road

Price$1,125,000

Est. Mortgage: $/month

MLS ID 35933

  • Residential
  • Village Sengy
  • Square Feet 1559
  • Bedrooms 3
  • Bathrooms 3

Waterview Farm - Waterfront neighborhood with association beach, boating, and common lands is an ideal location. The architecturally fabulous three season home is set on a quiet meadow with water views of Sengekontacket Pond and Nantucket Sound. A short walk takes you to the association beach. The owners lovingly renovated the home, creating the ultimate Vineyard experience. With ship lap cathedral ceilings and walls, six skylights, large windows, and three sets of sliders to an oversized deck, the house lives large. It offers incredible natural light throughout the day. The open living room, dining room, and kitchen are intentionally at the back of the house to enjoy the views and exceptional wraparound deck. The master en suite is tucked away from the heart of the house for privacy, with sliders to the deck and outside shower. A cozy guest room, full bath, and laundry complete this floor. A delightful second floor suite will keep your guests coming back to visit. There is a large bedroom with unique angles, skylights, full bath and a relaxing loft to take in the panoramic water views. This property has a strong rental history and unique Vineyard appeal. Check out the Virtual Tour in the External Links section of the listing.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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.

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5 Upper Meadow Lane

Oak Bluffs, MA5 Upper Meadow Lane

Price$1,135,000

Est. Mortgage: $/month

MLS ID 35923

  • Residential
  • Village Central
  • Square Feet 2072
  • Bedrooms 3
  • Bathrooms 3

This Meadow View Farms home offers tremendous value with lots of family space, 3+ bedrooms, and a spectacular, oversized post & beam garage with over 800 sq feet of additional living space above. Solar panels on the garage installed by South Mountain have significantly reduced year-round electric expenses. Meticulously maintained inside and out, this delightful home is attractively sited on .81 acres on a private cul-de-sac. The first floor offers a formal living room with gas fireplace and cathedral ceiling, dining room opening to a sun-filled kitchen, family room with tray ceiling, and glass doors leading to an inviting three-season screened porch. The first floor also features 2 guest bedrooms and a full bath. The second floor offers a master bedroom with en suite bath and large loft with full bath and laundry room. The beautifully landscaped yard features a striking Belgian block-lined driveway and front walk, garden shed, and a variety of trees, flowers gardens, and wild flowers. Located in a Private Association with tennis courts, near miles of walking trails, bike paths, Farm Neck Golf Club, and easy access to downtown Oak Bluffs. Look no further, this home has it all!

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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.

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38 Tiffany Drive

Oak Bluffs, MA38 Tiffany Drive

Price$869,000

Est. Mortgage: $/month

MLS ID 35936

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1892
  • Bedrooms 4
  • Bathrooms 3

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: 3.15% last updated on May 28, 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 TourAsk A QuestionMore Details