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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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

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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$
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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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$789,000

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. 2019 Assessment does not reflect renovations.

Listed by RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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: 4.07% last updated on May 16, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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: 4.07% last updated on May 16, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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10 Eastville Avenue

Price$1,149,000

Est. Mortgage: $/month

MLS ID 34837

  • Residential
  • Square Feet 1966
  • Bedrooms 4
  • Bathrooms 3
  • Half Bath 1

Walk to Town from this lovely 'Like new' four bedroom Home, with 2 Master Bedroom Suites (6 Bedroom Septic System) on an oversized 15,000 sq.ft. lot. Main living level has an open floor plan with clearly defined spaces. Living room has an Aspen Fieldstone clad fireplace, Bluestone hearth, crown molding, custom cabinetry for audio/visual equipment, recessed downlighters and beautiful rustic American Cherry floors that only get better with age. Breakfast area adjacent to the Kitchen leads directly to mahogany deck. Kitchen cabinets are a lovely Caramel Colored Maple with Giallo granite counter tops. The matching island provides great additional space to work on, or to sit at to keep the chef company. Kitchen leads to a separate dining room with built-in mirror feature and rustic cherry floors. Half bath w/travertine tiles, wainscoting and laundry. Also direct access to a one car garage with an automatic garage door opener. Second floor has two Master Bedrooms each with an ensuite. Two additional guest bedrooms share a guest bathroom. Each bathroom has travertine flooring, custom tiled baths/shower and granite counters. Berber carpet provides a soft touch in each bedroom, along with ceiling fans and recessed downlighters. Propane forced Central Air and Heat throughout. Basement is framed to accommodate two more bedrooms and a bathroom. Egress windows are already place for safety and additional light and ventilation! Town approval required in order to complete. Guest house potential when owner complies with town requirements. Asphalt driveway. Irrigation system around perimeter of house. Mahogany clad outdoor shower! Minutes to Eastville Beach, Oak Bluffs Harbor, the Ferry, Hospital and downtown restaurants and activities. Contents available for purchase separately. Room for a POOL! Easy to show.

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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8 Circuit Avenue Extension

MLS ID 25824

  • Condominium
  • Village Downtown
  • Square Feet 366
  • Bathrooms 1

No question that this property is the most affordable, turnkey, WATERVIEW property on the Vineyard. Everyone will be talking about how this one got away. Perched up high overlooking Oak Bluffs Harbor, the ferry boats and all the action.This Victorian style architecture studio suite with wood and tile flooring, stove top, fridge, shower, bathroom and water views of Nantucket Sound, O.B. Harbor, and Sunset Lake is located in the heart of Town. Walk to the Steamship authority, beaches, restaurants and or your private boat at the harbor. Also for sale is another unit with a Penthouse. Property is recognized as an office/retail space. Currently being used as a residential rental. Seller is participating in a 1031 tax deferred exchange. At the present time, we can only show condo unit on Saturday and Sunday.

Listed by Dockside Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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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71 Pennacook Avenue

Price$1,149,000

Est. Mortgage: $/month

MLS ID 34791

  • Residential
  • Village Downtown
  • Square Feet 2108
  • Bedrooms 6
  • Bathrooms 2

CLASSIC BEAUTY IN THE HEART OF OAK BLUFFS, The Pennacook House is set on a slight hill on a large landscaped yard. YEAR ROUND 6 bedroom, 2.5 bath home has a lovely eat-in kitchen, formal dining and living rooms with bay windows, den/study, hardwood flooring, outdoor shower, gorgeous period details and many updates throughout. Brand new state of the art propane hot water heating system and new electrical panel. Full walk-out basement with laundry and plenty of storage space. Home is sunny and warm in the winter and catches the cool breezes in the summer. GREAT LOCATION just a few blocks to town center, ferry, Ocean Park, and beaches. VERY STRONG RENTAL HISTORY!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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