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. View all real estate for sale on the Vineyard here.

Oak Bluffs Real Estate

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

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1 Winemack Street

Oak Bluffs, MA1 Winemack Street

Price$919,900

Est. Mortgage: $/month

MLS ID 35329

  • Multi-Family
  • Village Downtown
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Main house plus apartment above 2-car garage. Charming, Victorian style main house built in 1999, has 3 bedrooms, 1 ½ bathrooms, in great condition. Detached 2-car garage with a 1-bedroom/1-bathroom apt above it. Main house has a wrap-around farmer's porch, open floor plan on the first floor with kitchen and living room, and separate dining room, and a landscaped back yard with patio. Garage and guest apt built in 2017. Title V septic for 5-bedrooms installed 2017. Property comes mostly furnished, is located at the end of a quiet street, walking distance to Lagoon Pond and Eastville Point beach, downtown Oak Bluffs, restaurants, the ferries, and harbor. Rentals are all on a month-to-month basis. Please allow for 24-hour notice required for showings.

Listed by RE/MAX on Island

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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348 Sea View Avenue

Oak Bluffs, MA348 Sea View Avenue

Price$5,995,000

Est. Mortgage: $/month

MLS ID 35291

  • Multi-Family
  • Village State Beach
  • Location 41.436238,-70.555927
  • Bedrooms 12
  • Bathrooms 6

150 Feet of PRIVATE BEACH at this WATERFRONT COMPOUND IN HARTHAVEN - Perched high on a bluff with 180 degree views of Nantucket Sound and beyond, this property offers a rare opportunity for a waterfront family compound or an investor's dream with a private beach. The three homes that make-up this unique 13 bedroom property are as follows: The "Main Deck" is a sprawling cape-style home with 5+ bedrooms, 2 1/2 baths, oil forced hot water heat, air conditioning, wood-burning fireplace, large covered deck overlooking the bluff and a screened-in porch. This home was updated in 1996. This home is considered the main house of the property because of its commanding location perched on the bluff. The "Captain's House" was rebuilt in 1996. It has a reverse-style floor plan to take full advantage of the sweeping water views. Featuring 2 master suites and 2 additional bedrooms that share a bath, this home is light-filled, open and airy. Wood-burning fireplace. The craftsmen that created this home gave extra attention to the wood details throughout and made the house worthy of the finest sea "captain". You will notice these details from the moment you walk into the foyer and move your way through the home to enjoy the beamed ceiling in the living room. The "Cottage" completes this property...almost. This home was also fully rebuilt in 1996. It consists of a living room with wood-burning fireplace, eat-in kitchen, first floor bedroom, first floor laundry and bath. The second floor bedroom has breathtaking views from its private deck. A second large deck runs along the back side of the house. All 3 homes have been created to be independent of each other and all feature air conditioning, outdoor showers and more. With plenty of storage with additional space above, bath and outdoor shower, there is lots of possibilities to to be creative. The garage nicely completes this property. All homes have a solid rental histories with repeat tenants. Sellers would consider a full "turn-key" option. Please view Video of the Property to get a full feel for this one of a kind waterfront property.

Listed by Island Real Estate

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 John Wesley Park

Oak Bluffs, MA5 John Wesley Park

Price$1,499,000

Est. Mortgage: $/month

MLS ID 34510

  • Residential
  • Village East Chop
  • Square Feet 2600
  • Bedrooms 4
  • Bathrooms 4

EAST CHOP - This newly finished, custom built home will impress everyone looking for a modern East Chop experience. The coveted location is under ½ mile to the beach and gives you the ease of spending time downtown and on the harbor, while residing just moments away in this coveted neighborhood. This beautifully proportioned 2600 square foot home offers 4 bedrooms and 4.5 baths, as well as a full finished lower level that provides even more living space, and walkout access to the stone patio. Featuring 9 foot high ceilings, expansive wood and tiled floors on every level and tastefully modern hardware, this new home is both comfortable and perfect for entertaining. The gourmet kitchen has Thermidor and Bosch appliances, granite counter tops, and a center island with seating that flows easily to the dining room with dramatic coffered ceiling. The living room has multiple seating spaces. The attached garage conveniently stores your island car. The stone patio at the rear of the property is the perfect summer headquarters for grilling.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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15 Peter M. Williamson Boulevard

MLS ID 34857

  • Residential
  • Village Central
  • Square Feet 3100
  • Bedrooms 6
  • Bathrooms 5

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: 3.18% last updated on Jun 4, 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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10 Eastville Avenue

Oak Bluffs, MA10 Eastville Avenue

Price$1,149,000

Est. Mortgage: $/month

MLS ID 34837

  • Residential
  • Village Central
  • Square Feet 1966
  • Bedrooms 4
  • Bathrooms 3

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: 3.18% last updated on Jun 4, 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