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”, it is a classic beach town. 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

56 Head Of The Pond, Oak Bluffs, MA

Price$795,000

Est. Mortgage: $/month

MLS Number 32694

  • Residential
  • Square Feet 2095
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.64

Bright 3 bedroom Contemporary Saltbox with an inground swimming pool on 1.64 serene & pastoral acres that abutt Thimble Farm. Nearby Land Bank trails access the State Forest, and Little Duarte's Pond is a short walk. The main floor has 3 spacious living areas to relax or entertain. The updated kitchen with Corian counters is flanked by a Post & Beam den and light-filled family room. Three sets of sliders open to the spacious deck and pool beyond, all surrounded by mature landscaping. This year round property offers gracious living, and exceptional investment value with its strong rental history. Offered turnkey.

Listed by Martha's Vineyard Seacoast Properties

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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

4 Quail Run, Oak Bluffs, MA

Price$459,000

Est. Mortgage: $/month

MLS Number 32773

  • Condominium
  • Village Sengy
  • Square Feet 1182
  • Bedrooms 1
  • Bathroom 1

The best of the best; access to all Sengekontacket Community amenities, a newly renovated condominium with impeccable taste and high quality finishes at a price many can consider. The well-planned Community is centered around a fresh pond for swimming, canoeing or fishing. The Community Club House sits directly on the pond and is available for private and community functions. Tennis courts are located opposite the Club House and the list continues....there is an association dock on Sengekontacket Pond, racks for canoes and kayaks and the potential of a mooring in the Pond. Being sold turnkey. This has it all.

Listed by Sandpiper Realty

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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

122 Tellette Street, Oak Bluffs, MA

Price$495,000

Est. Mortgage: $/month

MLS Number 32785

  • Residential
  • Village Central
  • Square Feet 896
  • Bedrooms 2
  • Bathroom 1

Ranch style residence situated on large gently sloping lot in quiet residential neighborhood features an open kitchen/living/dining area with brick fireplace, hardwood flooring, high ceilings, lots of natural wood detail, slider to exterior deck, two bedrooms, full bathroom, and a finished 2 room walkout basement. Seller is getting an approved 3 bedroom septic design and buyer is responsible for septic installation.

Listed by Ocean Park Realty Inc

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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

42 Meadow View Road, Oak Bluffs, MA

Price$865,000

Est. Mortgage: $/month

MLS Number 32332

  • Residential
  • Village Sengy
  • Square Feet 2480
  • Bedrooms 4
  • Bathroom 2

This immaculate 3 level contemporary presides over one of the most desirable neighborhoods in Oak Bluffs. Newly renovated and offered to include beautiful furnishings and appointments, this property is ready to become your family gathering spot for all seasons (think Thanksgiving and Christmas on the island!). The layout is perfect for multi-generational living, with 3 bedrooms on the first level and bright, open living space with fireplace and separate den on the second floor. A large sunny deck and screened porch beckon summer relaxation and cookouts. The entire third floor comprises a master suite with separate living space with fireplace and small kitchenette. It features a private deck to enjoy your morning coffee or afternoon libation overlooking the back yard and common lands behind. If summer rentals are part of your plan, the property has a strong rental history, with many repeat tenants who would love to continue coming back. Great quality and location in this price range!

Listed by Sandpiper Realty

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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$749,500

Est. Mortgage: $/month

MLS Number 32771

  • Residential
  • Village Central
  • Square Feet 1238
  • Bedrooms 3
  • Bathroom 2

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 bedroom and full bath. 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

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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$4,995,000

Est. Mortgage: $/month

MLS Number 32756

  • Residential
  • Village East Chop
  • Square Feet 6441
  • Bedrooms 6
  • Bathroom 5

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

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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 Lagoon Road, Oak Bluffs, MA

Price$535,000

Est. Mortgage: $/month

MLS Number 32754

  • Residential
  • Village Central
  • Square Feet 1176
  • Bedrooms 3
  • Bathroom 2

This 3 Bedroom 2 Bath Cape Style home is located in the desirable Lagoon area of Oak Bluffs. Close to Schools, Town, Library and all Ferries. Kitchen features newer appliances, lots of cabinet and counter space. Hardwood flooring throughout the Dining, Living Area and Staircase. Thoughtfully planned second floor bedrooms feature a full dormer to offer more space. Updates include new mini split heating/air conditioning system throughout the house and basement, Radiant heat has been roughed in living area and bedroom on the first floor. Full basement partially finished to a play room area. A nice wrap around deck overlooks the private backyard. Outdoor shower and Plenty of Parking. This house is JUST WAITING for your personal touches. Perfect home for First Home buyer or Investor!

Listed by Island Real Estate

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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

90 South Circuit Avenue, Oak Bluffs, MA

Price$1,679,000

Est. Mortgage: $/month

MLS Number 32760

  • Residential
  • Village Downtown
  • Square Feet 2780
  • Bedrooms 3
  • Bathroom 3

Oak Bluffs: Custom design in special location just a short walk to town and public beach...but offering Up Island Privacy with views over Farm Pond, barrier beach and Nantucket Sound to the Southeast and over a cedar meadow to the Southwest. Bright great room with high ceilings lots of South facing glass, intimate sitting arrangements, large beamed dining room, great kitchen and pantry, broad sunny deck, huge bedrooms, new roof, marble vanities in the bathrooms, 2 car garage with loft storage, wonderful outside shower.

Listed by Ocean Park Realty Inc

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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

28 Beach Road, Oak Bluffs, MA

Price$1,749,000

Est. Mortgage: $/month

MLS Number 32743

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1800
  • Bedrooms 4
  • Bathroom 2

VIEWS GALORE! Dramatic views of Vineyard Haven Harbor, Outer Harbor, Vineyard Sound and a penetrating vista right up the length of Lagoon Pond. This property stands out alone, without competition, and offers easy access to a sandy beach across the street and to Vineyard Haven Town Center. Features a sunny bright open living/dining/kitchen area with powder room and out side decks, a master suite with private bath, exterior deck, and sunset view over Harbor, 3 more bedrooms, another full bathroom, family room, and plenty of storage below. Professionally built with state of the art efficient heat pump system, ash flooring, propane fireplace, Thermador kitchen appliances, Silestone counters, over 800 square feet of decks, and so much more!

Listed by Ocean Park Realty Inc

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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

28 Beach Road, Oak Bluffs, MA

Price$1,749,000

Est. Mortgage: $/month

MLS Number 32752

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1800
  • Bedrooms 4
  • Bathroom 2

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.

Listed by Island Real Estate

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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