Oak Bluffs Real Estate

Downtown Oak Bluffs Martha's Vineyard

Search all listings for sale in this Martha's Vineyard village. Originally called “Cottage City”, the town is known for its historic gingerbread cottages. The classic beach town is home to the largest marina on Martha's Vineyard. Oak Bluffs is also home to the popular East Chop neighborhood.

Learn more about Oak Bluffs >>

Browse All Real Estate For Sale In Oak Bluffs, Martha's Vineyard

Contact us for all your questions and for more information about Oak Bluffs. Create an account to save your favorite listings and to receive email updates for similar properties.

Narrow Your Search

r=1-10
30 Fairmont Avenue, Oak Bluffs, MA

Price$559,000

Est. Mortgage: $/month

MLS Number 32699

  • Residential
  • Square Feet 1365
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.2299

This three bedroom beautifully landscaped Cape has a four bedroom septic allowing for expansion. At the end of a dead end road, it is quiet , yet close to Farm Neck and a baseball field for kids to play in. It has a new roof and three different heating sources which include a Propane Moniter, Wood Stove and Electric heat for back up. There is an oversize deck which wraps the house with access to and sturdy outside shower. The house has a nice flow to it with an open kitchen dining area and a cozy living room. The basement is partially finished as works as a large play room for both kids and adults! Outside the home there are many different levels of landscaping made with the wood from the original Jaws bridge! At the entrance there are three spectacular burning bushes followed by an exotic mature yellow tea rose shrub. Surrounded by a nice woods belt, there is a comfortable feeling of privacy!

Listed by Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

54 Pond View Drive, Oak Bluffs, MA

Price$634,000

Est. Mortgage: $/month

MLS Number 32771

  • Residential
  • Square Feet 1238
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.17

Charming cape in Vineyard Hills neighborhood, set on an ample 1.17 gorgeous acres with immense potential. Vineyard Hills is a sought after, private community, offering paved roads, easy access to Sailing Camp Park, the Lagoon, and less than three miles to Oak Bluffs town center, harbor and beaches. The 5 bedroom septic, on 1.17 acres, allows for expansion of the 3 bedroom house OR, this enormous lot, with the large 5 bedroom septic design, offers the potential to build a two bedroom guest house. This wonderful residence offers 3 bedrooms and 2 full baths. The living room is bright and offers a warm brick hearth with a wood stove hookup. The kitchen and dining room are open and flows outside via sliders to the rear deck for grilling and outside dining. Also, on the first floor, is a full bathroom , and a bedroom with two large closets. The second floor offers two more spacious bedrooms and a bath. Walk out basement with a one car garage offers fabulous potential to finish this space into more living area. This private 1.17 lot is gently sloping to the south. Please check with the Oak Bluffs building inspector to confirm any future building plans for this great opportunity.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

32 Temahigan Avenue, Oak Bluffs, MA

Price$4,750,000

Est. Mortgage: $/month

MLS Number 32756

  • Residential
  • Square Feet 6441
  • Bedrooms 6
  • Bathroom 5
  • Half Bath 2

HISTORIC EAST CHOP WATERFRONT ESTATE WITH BOATHOUSE AND DEEP WATER DOCK. Originally built in 1870 with all of the grandeur of a 19th century seaside estate, this grand historic home features over 6,000 square feet of finished interior living space which was meticulously renovated from top to bottom in the year 2000, under the direction of noted architect, Joseph Dick and island builder, Everett Whorton. Today, this luxurious home maintains all of the original character and architectural details of the era, including beautiful coffered ceilings, gorgeous custom wood paneling, and finely crafted millwork throughout. The property boasts sweeping views from three floors of living space -- plus a spacious outdoor deck -- across the 3.2-acre property with rolling lawn, patio with stone fireplace and beautifully landscaped grounds to Vineyard Haven Harbor and Vineyard Sound beyond. A wooden boardwalk crosses over a small pond, leading to the water's edge where a 750-sf boathouse with stone fireplace, kitchen and bath sits adjacent to a deep water dock and moorings. The property also includes a detached 2-car garage with unfinished living space above which can be easily transformed into a beautiful Guest House, also with water views. This iconic property is the ultimate place to gather family and friends and create treasured Vineyard memories for years to come. Furnishings are available separately.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

28 Beach Road, Oak Bluffs, MA

Price$1,595,000

Est. Mortgage: $/month

MLS Number 32752

  • Residential
  • Square Feet 1800
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

VIEWS, VIEWS & MORE VIEWS! Designed to not only capture the views of Vineyard Sound and beyond to Woods Holes as well as a straight shot down the Lagoon, but this home was also created to be a comfortable home for year-round and summer living. Newly built 4 bedroom/2.5 bath home has commanding views from almost EVERY room with 2-levels of covered decks on the Vineyard Sound side of the home and 2-levels of decks on the Lagoon side. First level features 3 bedrooms, spacious family room, a full bath with laundry and ample storage. The second level features a sun-drenched open floor plan with a gourmet kitchen with stainless Thermador appliances, Silestone counters and an abundance of cabinets. Take in the long view down the Lagoon from the living area with gas fireplace and custom mantel. The master en suite has high ceilings with bathroom features that include a double-sink vanity with marble counters and glass shower enclosure finish this level of the home. There are sliding doors on both levels that open to the front and side decks. High-efficiency heat pump system, central air and more. Home is ready for you to pack your bags and move in. Did we mention the views? Come tour this unique home and see them for yourself. Home is being sold furnished.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

10 Elliott Avenue, Oak Bluffs, MA

Price$474,900

Est. Mortgage: $/month

MLS Number 32661

  • Residential
  • Square Feet 996
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.1

Charming two bedroom Cape style ranch property located on a dead end street within close proximity to downtown Oak Bluffs, public transportation, beaches, and East Chop tennis courts. Upon entry, you are welcomed into the sunlit living room with fireplace, kitchen with lots of cabinet and counter space includes small dining area. Front deck running the length of the house and and grassy yard are the perfect compliments to this move in ready home. New Title V septic for 2-bedroom house installed April 2018. Property cannot be shown until Nov. 1st, 2018, tenants in residence.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

12 Isaac Avenue, Oak Bluffs, MA

Price$859,000

Est. Mortgage: $/month

MLS Number 32602

  • Residential
  • Square Feet 1902
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 1

NEW CONSTRUCTION - OAK BLUFFS - COMPLETED!! By Michael Frank Designs. This is a Michael Torcia house. Custom Built home by highly regarded Island Builder. Issac Avenue is 4 minutes walk to Sailing Camp Park, sited up a short, quiet road, in a great location, minutes to downtown Oak Bluffs and easy access to all island towns! Front Porch with Mahogany Decking. Elegant Interior with Custom Details. Main living area has flows with an open floor plan, yet clearly defined areas. Painted White Maple Kitchen Cabinets with Carrara Marble Countertops and subway tile backsplash. Contrasting Espresso cabinets in center island with Carrara Marble Counter! All Stainless Steel appliances, including a Gas Stove for the Cook, a Pot Filler and Cafe style refrigerator! Second story has Master Bedroom with En-Suite bathroom, Two Guest Bedrooms and another Full Guest Bathroom. Half Bath on ground floor with Laundry. Beautiful American Cherry floors throughout....on both floors, no carpets! All bathrooms have beautiful Marble floors, Wainscoting - Custom Woodwork throughout. Master Bedroom with Ensuite Bathroom, Seamless Glass shower and walk in Closet. Forced Hot Air heat with Central Air-Conditioning. Full basement ~ Would make a great finished space for a playroom or recreation room. Central Vacuum. One Car Garage! Huge Mahogany Deck and Outdoor Shower! Low maintenance exterior. Less than a 5 minute walk to the water! Grounds landscaped with plantings and irrigation system around perimeter of house, cobble stone lined and crushed shell driveway. EASY TO SHOW AND MUST BE SEEN.

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

6 Mourning Dove Way, Oak Bluffs, MA

Price$965,000

Est. Mortgage: $/month

MLS Number 32529

  • Residential
  • Square Feet 1312
  • Bedrooms 4
  • Bathroom 1
  • Half Bath 2

Sengekontacket Association: This stylish, year-round bungalow is the perfect spot to begin your vacation. This low maintenance home is not your traditional mainland house - as you ascend the entryway stairs, you leave the daily stress behind. In front of you is the simple elegence that vacation dreams are made. Designed as a classic one-story cottage, it has 4 comfortable bedrooms that surround the centrally located living / dining / kitchen space. The window-lined cupola and vaulted ceiling add to the openness of the living area. Nestled in a private neighborhood, all you see from the windows is the green canopy of trees on the nearly acre lot. Escape to one of the two large decks with your morning coffee or evening cocktail is the true essence of the house. This house is ideal whether you are looking for a private get-a-way during the off-season or a great space to entertain your friends on a warm summer evening. The amenities within the lovely Sengekontacket Association only enhance your experience. Centrally located between Edgartown, Oak Bluffs and Vineyard Haven, the association has 2 tennis courts, a clubhouse, an association beach, a boat launch with kayak storage and dock. Bring your boat; there are moorings available through the Town of Oak Bluffs.

Listed by Martha's Vineyard R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

14 Temahigan Avenue, Oak Bluffs, MA

Price$2,950,000

Est. Mortgage: $/month

MLS Number 32282

  • Residential
  • Square Feet 4821
  • Bedrooms 7
  • Bathroom 3
  • Half Bath 2

Historic Water View Home with views of endless sunsets and sailboat races! On the market for the first time in over 50 years. Originally built in 1915, this stately Dutch Colonial has been enjoyed as a family gathering and celebration place every summer. Everything about this house....the 7 bedrooms, grand foyer, imposing dining and living rooms (both with water view), the original hand crafted woodwork details and the full length wrap around covered veranda overlooking West Chop and Vineyard Sound....will help you create your own family legacy and memories on the island. You will be amazed by the classic architecture of the home and the sweeping back yard inviting games for the young and old alike. A deeded walkway to the beach is included where you can keep a dingy to row out to your moored boat, sit and watch the sun set over West Chop or take a quick dip in the Sound. Remember...this is a home where porch parties are a must!

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

37 Puritan Drive, Oak Bluffs, MA

Price$934,900

Est. Mortgage: $/month

MLS Number 32330

  • Residential
  • Square Feet 2780
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

Impeccably maintained custom cape in the conveniently located Tower Ridge development.This property features a open floor plan with dining room galley kitchen and living room with a gas fireplace. A bonus family room over the garage with a gas fireplace and full bath. A three level deck which faces east provides a comfortable place for family gatherings and entertaining.

Listed by Ledden Properties LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

2 Sengekontacket Road, Oak Bluffs, MA

Price$875,000

Est. Mortgage: $/month

MLS Number 32240

  • Residential
  • Square Feet 1900
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

JUST REDUCED - Motivated Seller! This property has a lot going for it. Located in the desirable community of Sengekontacket, with access to tennis courts, dock, boat launch and storage, mooring potential, and use of the community Club House located on Fresh Pond. These amenities enhance the many options available with the property. A pleasant four bedroom home that includes a finished lower level and bonus room with full bath above the 2 car garage for expanded living space. This property can be used for personal use with plenty room for extended family and friends, or as an investment property. There is rental history in place. NEW 4 BEDROOM SEPTIC INSTALLED!

Listed by Sandpiper Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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