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Oak Bluffs Properties

Originally called “Cottage City”, Oak Bluffs is a classic beach town, filled Downtown Oak Bluffs Martha's Vineyardwith fun restaurants, bars, shops and beaches. It’s one of the island’s principal points of arrival for summer tourists, and is home to the Camp Meeting Association, or “Campgrounds”; a renowned area consisting of hundreds of colorful, unique “gingerbread” cottages in the center of town. Also in Oak Bluffs is Circuit Avenue, the commercial heart of the town with restaurants, souvenirs, and ice cream shops, as well as the spacious waterfront grounds of Ocean Park, and the long stretch of Joseph A. Sylvia State Beach that extends into Edgartown.

Within Oak Bluffs you’ll find properties along the winding roads on East Chop, historic cottages in Ocean Park and the Campground, and waterfront properties along the long stretch of Lagoon Pond.

Contact Sandpiper Realty to learn more about one of the Oak Bluffs real estate listings below. Register with our site if you would like to stay up to date on your favorite Oak Bluffs homes.

You might also like to view Vineyard Haven properties or Chilmark properties.

90 South Circuit Avenue, Oak Bluffs, MA

MLS Number 28960

  • Residential
  • Village Oak Bluffs
  • Square Feet 2780
  • Bathroom 2
  • Bedrooms 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 marble vanities in the bathrooms, 2 car garage with loft storage, wonderful outside shower...HEY, LOOK AT THE PICTURES!

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

79 Pond View Drive, Oak Bluffs, MA

MLS Number 28948

  • Residential
  • Village Oak Bluffs
  • Square Feet 2128
  • Bathroom 2
  • Bedrooms 3

Oak Bluffs: Classic Cape style residence with attached 2-car garage and farmer's porch is well maintained and situated in a private community with protective covenants on over a half acre of landscaped land that abuts greenbelt. This wonderful residence has bright open spaces with lots of sunlight, extra intimate living areas, full basement and even more storage over the garage. Features a spacious living area with warm brick fireplace, separate dining room with view over the gardens and woodlands, working kitchen with cherry cabinets, cozy den/tv room, full bathroom, and another parlor room that can be used for overflow. Upstairs is a large master, full bathroom and 2 more ample bedrooms. There is a lot of living space in this house and its just a short walk to the beach on Lagoon Pond!

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

9 Tori Lane, Oak Bluffs, MA

Oak Bluffs MA9 Tori Lane

Price$459,000

Est. Mortgage: $/month

MLS Number 28945

  • Residential
  • Village Oak Bluffs
  • Square Feet 1344
  • Bathroom 2
  • Bedrooms 3

Oak Bluffs Cape Style home located in a central location convenient to all 3 down island towns! The home is situated on a .50 acre lot nestled back offering plenty of privacy.The farmers porch is a perfect place to read and relax ..Step into the open living room with wood burning fireplace and wood beam ceilings make this home quite comfortable..The kitchen has newer stainless steel appliances and there is a first floor bedroom..Two additional bedrooms on the second floor with full bathroom.. Lots of closets and full basement ..Title 5 has passed.! The open common lands in the Deer Run Association offer a beautiful vista of privacy..This home is a TERRIFIC VALUE !

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

8 Harvester Way, Oak Bluffs, MA

Oak Bluffs MA8 Harvester Way, Sengy

Price$1,720,000

Est. Mortgage: $/month

MLS Number 28902

  • Residential
  • Village Oak Bluffs
  • Square Feet 2581
  • Bathroom 2
  • Bedrooms 4

Elegance and privacy define this spacious 4+ bedroom, 5 bath waterview contemporary in the desirable community of Hidden Cove. Constructed and recently updated by one of our Island's preeminent builders, the quality is everywhere - from the custom oak built-ins to the huge wraparound deck with retractable awning. The upper level master bedroom suite boasts views of Hidden Cove and Sengekontacket Pond. With minimal clearing, water views may be expanded at the owner's discretion so that water vistas are restored to the dining room, kitchen, and deck. Two-car garage, PBX phone system, large hot tub, irrigation system, guest bedroom suite with separate living area and office complete this offering. Association privileges include dock, private mooring, and tennis. Move-in condition!

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

71,77, 79 Edgartown Vineyard Haven Rd & 10 Gamba Rd., Oak Bluffs, MA

MLS Number 28569

  • Residential
  • Village Oak Bluffs
  • Square Feet 692
  • Bathroom 1
  • Bedrooms 2

Centrally located 7.78+/- acres subdivided into 4 separate parcels with 500ft+ frontage on Edgartown-Vineyard Haven Rd. Features existing 2 bed/1 bath home, 2 story garage/workshop, and several additional outbuildings - see below for more details. Lightly wooded lots with varying topography, established plantings of arborvitae, cedar and Leland cypress and fencing provide ample privacy screening, brick walkway surrounding the house. Curb cut access on Edgartown-Vineyard Haven Rd. and Gamba Rd. Within walking distance to many Island community organizations, easy access to the cross-island bike trail, VTA routes 7, 9 & 1 and public conservation trail systems. Call for more details and to view - all viewings must be accompanied by listing broker!

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

71,77, 79 Edgartown Vineyard Haven Rd & 10 Gamba Rd., Oak Bluffs, MA

MLS Number 28950

  • Land
  • Village Oak Bluffs
  • Acreage 7.7800

Centrally located 7.78+/- acres subdivided into 4 separate parcels with 500ft+ frontage on Edgartown-Vineyard Haven Rd. Features existing 2 bed/1 bath home, 2 story garage/workshop, 2 story barn and several additional outbuildings Lightly wooded lots with varying topography, established plantings of arborvitae, cedar and Leland cypress and fencing provide ample privacy screening, brick walkway surrounding the house. Curb cut access on Edgartown-Vineyard Haven Rd. and Gamba Rd. Within walking distance to many Island community organizations, easy access to the cross-island bike trail, VTA routes 7, 9 & 1 and public conservation trail systems. Call for more details and to view - all viewings must be accompanied by listing broker!

Listed by Conroy & Company R.E., Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

12 Monahegan Avenue, Oak Bluffs, MA

Oak Bluffs MA12 Monahegan Avenue

Price$699,000

Est. Mortgage: $/month

MLS Number 28879

  • Residential
  • Village Oak Bluffs
  • Square Feet 2168
  • Bathroom 3
  • Bedrooms 5

Great investment opportunity within walking distance to the harbor, ferries and all of the wonderful shops and restaurant's of downtown Oak Bluffs. The guest house was built in 2007, and boasts central air conditioning, stainless steel appliances and a sunny and bright three season room. The main house is a wonderful seasonal home with a generous sized living room and two levels of decks just perfect for entertaining and enjoying your summer guest.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

15 Tamarack Lane, Oak Bluffs, MA

Oak Bluffs MA15 Tamarack Lane

Price$3,400,000

Est. Mortgage: $/month

MLS Number 28637

  • Residential
  • Village Oak Bluffs
  • Square Feet 3998
  • Bathroom 5
  • Bedrooms 5

Sited on over three and a half acres and offering views of the seventh fairway and green across to Sengekontacket Pond, this Farm Neck property is a true delight. The main house, offering four bedrooms and four full baths, exudes all the charm and character you would expect in fully restored 1780's farm house. A perfectly appointed one bedroom guest house is the perfect accompaniment to this bucolic retreat. Take full advantage of all this exclusive community has to offer, whether dining at the clubhouse after a round of golf, paddling around Sengekontacket via the association water access or perhaps challenging friends to a match of tennis. Your purchase is more than just a home on the Vineyard, it is a lifestyle.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

15 Island Inn Road, Oak Bluffs, MA

MLS Number 28854

  • Commercial
  • Modification Date 2015-06-22 10:01:52
  • Village Oak Bluffs
  • Bathroom 1

What an opportunity! Famous and Beautifully Scenic LOLA'S is now for sale. That's the building, land and the whole business, everything included! The exception is some art, other than that everything is included! It is located right off the water and next to the prestigious Farm Neck golf course. This easily accessible establishment has $750,000 on the books for annual events, and current management will stay on if needed! Operated currently as a restaurant, night club, wedding and event destination. Don't let this opportunity pass you by!

Listed by Towne & Country Realty

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

20 Pocasset Avenue, Oak Bluffs, MA

Oak Bluffs MA20 Pocasset Avenue

Price$724,900

Est. Mortgage: $/month

MLS Number 28810

  • Residential
  • Village Oak Bluffs
  • Square Feet 1152
  • Bathroom 2
  • Bedrooms 3

This 7 year old Victorian is a 3 bedroom 2 bath home with all the bells and whistles. One of the few properties in this area that does not need a renovation. Desireable location to Walk to Town, Beach, Shops and Boats. The home was constructed in 2007 with an an open floor plan, 1 st floor bedroom, Andersen bay windows, Cherry hardwood flooring, Granite countertops, Jacuzzi tub, Cherry cabinets, FHA propane, and Central AC. Relax on your wooden rockers with that glass of wine on your farmers porch.

Listed by Sandpiper Realty, Inc.

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

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.87% last updated on 2015-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.