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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.

150 East Chop Drive, Oak Bluffs, MA

MLS Number 28610

  • Residential
  • Village Oak Bluffs
  • Square Feet 4170
  • Bathroom 5
  • Bedrooms 8

Known as "Big Bluff" this quintessential , authentic summer home offers an unparalleled "view from the top of East Chop" over Nantucket Sound to Cape Cod, Chappaquiddick and BEYOND! Bell buoys, fog horns and the timely "blink" from local and distant lighthouses will be your daily reminder of island life. A truly magnificent setting on ¾ of an acre of luscious lawn, this seaside home greets the morning sunrise with an easterly facing front porch and says "good evening" to the glowing sunsets from the westerly facing covered rear porch that has seen many great gatherings over the years. With 8 bedrooms(5 en-suite), there is no shortage of space for friends and family to visit. And...with 2 living areas, each one warmed by a classic BEACH STONE fireplace, entertaining is perfect, even on those cool evenings. The East Chop community offers boating, swimming, tennis, fishing and a social atmosphere that is hard to find. Impressive and in a class by itself

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: 3.84% last updated on 2015-05-21

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

317 East Chop Drive, Oak Bluffs, MA

MLS Number 28593

  • Residential
  • Village Oak Bluffs
  • Square Feet 2615
  • Bathroom 3
  • Bedrooms 6

East Chop Waterfront - Exceptional location with breathtaking views of the harbor and Vineyard Sound. Built in 1930 this rambling 2 story Cape enjoys approximately 200 feet of beach and deep water for a mooring. Lovingly maintained and in the same family ownership for several generations, this quintessential beach house features 6 bedrooms, 3.5 baths, hardwood floors, working fireplace, French doors leading to a beachfront patio, updated kitchen, detached 2 car-garage, and Title 5 septic.

Listed by Sandpiper Realty, Inc.

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

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.84% last updated on 2015-05-21

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

4 Canonicus Avenue, Oak Bluffs, MA

MLS Number 28573

  • Residential
  • Village Oak Bluffs
  • Square Feet 2890
  • Bathroom 4
  • Bedrooms 6

WATERVIEW FAMILY COMPOUND offers panoramic views over NANTUCKET SOUND and FARM POND...Public BEACH across the street! A few blocks to FERRY, HARBOR and SHOPPING...Features 4/5 bedroom Victorian residence offers lots of classic detail with a sun parlor and wrap-around porch, a beachy studio..warm and inviting, and a whimsical 1920's 1 bedroom garden cottage with lots of cheerful accents and views over Farm Pond...all structures suitable for YEAR-ROUND living! This wonderful property, with rental history, is the essence of Oak Bluffs, past and present.

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: 3.84% last updated on 2015-05-21

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

2 Ryans Way, Oak Bluffs, MA

Oak Bluffs MA2 Ryans Way, Central

Price$1,300,000

Est. Mortgage:$/month

MLS Number 28185

  • Residential
  • Village Oak Bluffs
  • Square Feet 6660
  • Bathroom 3
  • Bedrooms 3

2 Ryans Way: a superior location with easy access to all island towns from this versatile complex. Amenities include: plenty of parking, welcoming reception and waiting room, 6 exam/offices, existing lab and x-ray room, main living area with a new cooks kitchen, living room, den, breakfast room, two bedrooms, full bath, master suite with bath and walk-in closets, bonus room, multiple decks, 2 car garage with studio.

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: 3.84% last updated on 2015-05-21

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

496 County Road, Oak Bluffs, MA

Oak Bluffs MA496 County Road, Sengy

Price$1,175,000

Est. Mortgage:$/month

MLS Number 28568

  • Residential
  • Village Oak Bluffs
  • Square Feet 2200
  • Bathroom 2
  • Bedrooms 3

STORYBOOK OAK BLUFFS CHALET: This enchanting chalet-style home is nicely sited on 2.6 acres in a lovely, lush countryside location yet is centrally located with direct access to bike paths and less than a mile from the all-time favorite Farm Neck Golf Club and Restaurant. The spacious living room, reminiscent of an old-world country lodge, is graced by high ceilings with exposed beams, wood paneling, decorative woodwork and mural, and a soaring brick fireplace. The open floor design flows into the dining room. A second living room or library/den accessed from the dining area provides additional entertaining space. There are 3 bedrooms, two on the first floor and one off the"Sound of Music" balcony. This is truly a charming home filled with character, ideal for year-round living and as a vacation home. The large parcel welcomes expansion and also offers deeded easement to Fresh 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: 3.84% last updated on 2015-05-21

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

8 Pennacook Avenue, Oak Bluffs, MA

MLS Number 28571

  • Residential
  • Village Oak Bluffs
  • Square Feet 1727
  • Bathroom 2
  • Bedrooms 4

Step back in time when you walk into this cozy three season summer cottage. Enjoy the water views from the front porch as well as from the second floor balcony. The home has had a few upgrades over the years though has not been renovated. Work that has been done includes a new roof, upgraded electric, new windows, cedar siding, upgraded bathroom and gas monitor. The floor plan is an interesting blend of traditional Campground Victorian as well as more contemporary elements such as a master bedroom en-suite on the first floor. The home has a strong rental history of approximately $32,000 each season. It also offers a 5th sleeping area offering a spacious venue for large family gatherings. Though the water views and close proximity to Inkwell Beach make it the perfect setting for someone wanting to reinvent the home to suit their needs, the simple elegance of the period that one feels when moving thru the home will make it difficult for someone to abandon the history that the house conveys. Furnishings included except for heirloom pieces and artwork. Seller requests a September Closing. Tied into town sewerage. Priced to sell.

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: 3.84% last updated on 2015-05-21

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

114 Park Street, Oak Bluffs, MA

MLS Number 28507

  • Residential
  • Village Oak Bluffs
  • Square Feet 1872
  • Bathroom 3
  • Bedrooms 4

Oak bluffs - east chop - stunning waterviews over crystal lake ,vineyard & nantucket sound! Spectacular sunsets ! Outstanding location a stroll to east chop beach club, jetty beach, oak bluffs harbor & town ! Custom vineyard design bright & spacious throughout! 4 bedrooms & 3.5 baths ... Finished living space & second kitchen in the walk out basement! Large exterior deck is the perfect space for entertaining! Strong existing rental history 2015..Mini splits air conditioning ..In most of the rooms..Must see vineyard home! You will love this place! Panoramic 180 degree waterviews!!

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: 3.84% last updated on 2015-05-21

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

63 Webster Avenue, Oak Bluffs, MA

MLS Number 28117

  • Multi-Family
  • Village Oak Bluffs
  • Bathroom 3
  • Bedrooms 5

Water View Family Compound. East Chop area corner lot water view multi-family home. Recently remodeled with a new guest apartment this spacious family home is in move in condition and ready for occupancy. 5 bedrooms, 4.5 baths with multi sitting areas to accommodate summers, holidays and everything in-between. Year round living, wood burning fireplace and water views are added value to the oversized lot in a quiet area of sought after East Chop. A neighborhood of substantial homes, community and scenic vistas, this location is ideal for gatherings and celebration.

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: 3.84% last updated on 2015-05-21

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

10 Ploughshare Lane, Oak Bluffs, MA

MLS Number 28346

  • Residential
  • Village Oak Bluffs
  • Square Feet 1720
  • Bathroom 2
  • Bedrooms 3

This well maintained contemporary treasure is atop a hillside in Hidden Cove. The features of the first floor include a Master bedroom suite, laundry room, living room fireplace with cathedral ceilings and an updated kitchen with stainless steel appliances, custom cabinets with granite countertops. The second floor offers a full bath and two large bedrooms both with cathedral ceilings. Bonus loft space which overlooks living room space and additional storage. This private cul-de-sac within Hidden Cove affords you a prime location with association tennis courts and salt water access.

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: 3.84% last updated on 2015-05-21

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

134 Edgartown Vineyard Haven Road, Oak Bluffs, MA

MLS Number 28517

  • Residential
  • Village Oak Bluffs
  • Square Feet 2244
  • Bathroom 2
  • Bedrooms 6

Great Central Location!! House and Accessory building on a full acre of well landscaped property. Walk to the YMCA, Featherstone Center for the Arts, MV High School, Ice Arena and more... House offers 3 bedrooms, sunroom that opens to a patio facing the yard. Accessory structure also offers 3 bedrooms.

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: 3.84% last updated on 2015-05-21

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

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