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.

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42 Paddock Road

Price$1,999,000

Est. Mortgage: $/month

MLS ID 35025

  • Residential
  • Square Feet 4200
  • Bedrooms 5
  • Bathrooms 4
  • Half Bath 1

OAK BLUFFS - new, luxury enclave - The Preserve at the Woodlands! Enjoy the best of both worlds in this lovely area abutting 200 acres of conservation land yet centrally located off County Road near Farm Neck Golf Club with bike paths that provide EASY ACCESS into downtown Oak Bluffs, Edgartown and Vineyard Haven. Relax and enjoy POND VIEWS and panoramic meadow views. This HIGH QUALITY NEW CONSTRUCTION offers 5 bedrooms and 4.5 bathrooms with 9 foot high ceilings. The wooded 1.8 acre lot offers a spacious backyard with a bluestone patio for entertaining, outdoor shower and borders conservation land for complete privacy. The option to add a POOL is available upon request. An OPEN FLOOR PLAN features a large gourmet kitchen with a Sub-Zero fridge, Wolf range and other professional stainless steel appliances. The living and dining area has lovely views of the pond, custom built-ins and a gas fireplace. A first floor master bedroom contains an en suite bath, dressing area and walk-in closet. For your convenience, there is a first floor laundry room, mud room and powder room. Upstairs there are four SPACIOUS bedrooms - two of which are master bedrooms with en suite baths and vaulted ceilings. The two additional bedrooms share a hallway bathroom with double sinks. Two of the bedrooms offer pond views. There is an additional washer and dryer upstairs. Enjoy UP-ISLAND PRIVACY with DOWN-ISLAND CONVENIENCE! Don't miss this opportunity to enjoy this beautiful INVESTMENT property and begin to earn income right away. Or enjoy it all year round yourself with family and friends!! MOVE IN READY!!

Listed by Ocean Park Realty Inc

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$
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$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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439 Neal Way

Price$859,000

Est. Mortgage: $/month

MLS ID 34999

  • Residential
  • Square Feet 2368
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 1.437

Oak Bluffs located at the entrance of Meadow View Farms in Oak Bluffs~Custom Contemporary Design located in desirable sunny location on a sprawling 1.43 acre lot and abuts greenbelt! This attractive residence offers an abundance of light throughout the open spacious living dining area and a sun filled solarium offering picturesque views over a tastefully landscaped backyard! Peaceful setting and meticulously maintained,and recently painted inside! Walk out basement with workshop,office, laundry area and utility room! Strong RENTAL POTENTIAL! Room for a pool and or garage with town approvals! Easy to show call for an appointment to see this unique BEAUTIFUL home!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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15 Peter M. Williamson Boulevard

MLS ID 34857

  • Residential
  • Square Feet 3100
  • Bedrooms 6
  • Bathrooms 5
  • Half Bath 1

BRAND NEW!!! Custom design will be Ready for Occupancy this SEASON. Features over 3100 square feet with another 1000 in finished walkout basement including another bedroom. Beautiful marble/tile work in all bathrooms, wide oak hardwood flooring, gas fireplace with marble mantle, first floor en suite master, 8' sliders with access to sweeping deck, 9' ceilings and cathedral in the living room, and an open kitchen/dining area with Wolf stove, Sub Zero fridge, Bosch dishwasher, large center island. Also, attached 2 car garage with unfinished space above. This house flows comfortably through the intimate spaces offering easy living, privacy, and the yard has room for a pool. A must see!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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21 Mill Square Road

Price$2,250,000

Est. Mortgage: $/month

MLS ID 34973

  • Residential
  • Square Feet 2905
  • Bedrooms 4
  • Bathrooms 4
  • Half Bath 2

EAST CHOP - WATER VIEWS - GREAT LOCATION! -- Totally renovated, year-round, 4-bedroom, Victorian, overlooks Nantucket Sound. Walk to beaches, harbor, yacht club, tennis courts, ferries and restaurants. Tastefully renovated in 2002 to retain its Victorian charm, its extensive renovations included replacement of all electric, plumbing, heating, many windows, and roof. Features include beachstone fireplace in living room, wrap around front porch, gourmet kitchen appliances, garage and parking for multiple vehicles.

Listed by RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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20 Buena Vista Street

Price$799,000

Est. Mortgage: $/month

MLS ID 34938

  • Residential
  • Square Feet 1400
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 0.25

Beautifully renovated 2 BR, 2 BA main house plus 1 BR/1 BA detached bedroom, on nicely landscaped yard in private setting. Features include propane fireplace in living room, open floor plan with counter top seating at kitchen center island, all new appliances and mix of wood floors and carpeting throughout. Mini-split/heat pump heat/AC, and on demand hot water. Outdoor shower and side deck off kitchen. Private patio off main bedroom. Flat cul de sac, private level lot, perfect for entertaining. Buena Vista St location is ideally located close to beaches and restaurants. Great house for airbnb investment, second home or primary residence. Lot is large enough for a garage of 400 sq. ft or less, but please verify with appropriate town departments.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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227 Buddys Drive

Price$999,000

Est. Mortgage: $/month

MLS ID 34943

  • Residential
  • Square Feet 3620
  • Bedrooms 6
  • Bathrooms 3
  • Half Bath 1

OAK BLUFFS CUSTOM COLONIAL SITUATED on.59 ACRES 1st floor sf 1820 2nd floor sf 1280 3rd floor sf 520 Total current finished SF 3620 Above garage unfinished sf 750 Basement sf 1428 Two car Garage sf 550 with an UPDATED & RENOVATED BRIGHT & SUN FILLED GREAT ROOM and an EXPANSIVE living/dining area and NEWER kitchen with STAINLESS STEEL APPLIANCES & GLEAMING GRANITE COUNTERS! The interior of the home is inviting and generous with an abundance of ROOMS! This open design has striking natural wood ship lap ceilings. Glass doors offer access to a huge exterior deck and penetrating views into the abutting State Forest ...The attention to detail includes the luxury of 2 Master Suites, on the first floor and second floor.There is a total of 6 bedrooms, 3. 5 bathrooms and a huge unfinished space above the two bay garage!..STRONG EXISTING RENTAL HISTORY in PLACE! OUTSTANDING LOCATION & TERRIFIC VALUE! ROOM for a POOL TOO!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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67 Trinity Park

Price$550,000

Est. Mortgage: $/month

MLS ID 34914

  • Residential
  • Square Feet 810
  • Bedrooms 2
  • Bathrooms 1
  • Half Bath 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.

Listed by Laer Realty Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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9 Victorian Park

Price$559,000

Est. Mortgage: $/month

MLS ID 34887

  • Residential
  • Square Feet 1015
  • Bedrooms 4
  • Bathrooms 1

RARE OFFERING in the Martha's Vineyard Camp Meeting Association! This beautiful Victorian Gingerbread Cottage is SPACIOUS & BRIGHT with an ABUNDANCE of SPACE & PARKING! Terrific location a block to Circuit Avenue easy stroll to public beaches, shopping & dining on a famous Circuit Avenue, Oak Bluffs Harbor, ferry ports and all the Oak Bluffs Town Parks! Classic Camp Ground Cottage located a in quiet section of the Martha's Vineyard Camp-Meeting Association has all of its original charm and character. Relaxing front porch looking out on Victorian Park, living room, dining room, kitchen, full bathroom and bedroom on the first floor. Upstairs are three more ample bedrooms. Private backyard with landscaping a storage shed and on site parking. Unique opportunity! EASY to SHOW! You will love this MAGICAL SETTING! ON -SITE PARKING for 2+ CARS !

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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283 East Chop Drive

Price$1,599,000

Est. Mortgage: $/month

MLS ID 34871

  • Residential
  • Square Feet 2456
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Private beach on East Chop with gorgeous water views of the Vineyard Sound from each room, including all bedrooms! Quintessential Vineyard shingled house right on the water; swim, kayak or watch the ferry and boats from your private deck or porch just a few steps to the Sound. 2456 square foot house with four bedrooms (two of them enormous), two and one half baths, large separate laundry room, open floor plan to include fully equipped kitchen, dining room and living room with a large stone fireplace, all with stunning water views. Second floor family room and ample closet space in every bedroom. Enjoy countless hours relaxing on the side deck with outdoor living space in addition to the new stone patio for all your grilling needs. Walk/bike to either Oak Bluffs or Vineyard Haven and to the Telegraph Hill Lighthouse. Perfectly situated within one mile of East Chop Beach Club, Yacht Club and Tennis Club. Great rental history too. This home will not disappoint.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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.

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9 Second Avenue and abutting lot

MLS ID 34515

  • Residential
  • Square Feet 836
  • Bedrooms 2
  • Bathrooms 1
  • Acreage 0.3353

Oak bluffs victorian style year round renovated home within walking distance to oak bluffs harbor, town, public beaches and ferry ports! The blue canoe is the perfect vacation home or year round residence! Offering 2 bedrooms 1 bathroom and a large exterior deck efficient floor plan and potential for expansion! Terrific rental history summer of 2019 is vacant! Ready for new owners!!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.2% last updated on Apr 25, 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