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.

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:

58 New York Avenue Marthas Vineyard MA

MLS Number 30327

  • Residential
  • Village Oak Bluffs
  • Square Feet 1922
  • Bedrooms 5
  • Bathroom 2

Just a short walk to Oak Bluffs center from this renovated Victorian home. This classic home with mansard roof has been beautifully maintained throughout the years. The recent renovations include a new kitchen, deck, shed, and outdoor shower to name a few. The house features 5 bedrooms and 2 bathrooms with over 1900 sq ft. of interior space. Being sold furnished this turn-key investment property has 10 weeks of rental income for the 2016 season in place for future owner.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

325 East Chop Drive Marthas Vineyard MA

MLS Number 30278

  • Residential
  • Village Oak Bluffs
  • Square Feet 1709
  • Bedrooms 4
  • Bathroom 2

Fall asleep to the sound of a gently breaking surf in this carefully renovated and meticulously maintained turn of the century East Chop beach house. Nestled between the shore of the Vineyard Sound to the west and Crystal Lake to the east, this unique property boasts water views from every window. Enjoy spectacular sunrises from your breakfast table and sunsets over West Chop. Watch maritime activity of all kinds or just listen to the waves from numerous first and second floor oceanside porches. Nearly 150 feet of private beach permits direct access to the water for fishing, swimming, kayaking or paddling. The main living area of this exceptional summer home features a brick fireplace and is lined with large windows and French doors that open to a spacious, enclosed sun porch overlooking the water. The first floor also includes a sun drenched dining room, a home office or first floor bedroom, a half bath and an updated kitchen with high-end appliances, oversized antique porcelain sink and zinc countertops with copper accents. The staircase to the second floor leads to two guest bedrooms with a shared bath, a spacious hallway with built-in closets, laundry and extra storage space. The master bedroom suite features a private bath and sun porch. Other amenities include an enclosed drying yard with a cedar deck, a grilling area off the kitchen, a private outdoor shower on the beach and a one-car garage with a cabana for towels, chairs and beach toys. This wonderful location is also an easy bike ride to the East Chop tennis, beach and yacht clubs and to downtown Oak Bluffs. Frequently featured in island artwork, this spectacular waterfront home provides you with the best of Martha's Vineyard.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

50 & 9 Farm Pond & Harthaven Roads Marthas Vineyard MA

MLS Number 30302

  • Residential
  • Village Oak Bluffs
  • Square Feet 2250
  • Bedrooms 4
  • Bathroom 2

This truly is a "one of a kind" Water View, Pond Side, Property. Custom Techbuilt A-Frame that needs a total renovation. Owner took much care with this house when it was originally constructed to save as many trees and Blueberry Bushes as possible, so the deck was constructed around them and aptly named "Blueberry Bottom" for all that lie below.(some of which were taken out with Septic installation). Built by one of the originals Bronislaw (Bronie) Lesnikowski.! ...A brand NEW 4 Bedroom Enhanced Septic System has been installed by owner. The appeal to this Property, besides being in the Private Community of Hart Haven, is the 2 footprints and over 3 acres (2 Properties being sold together for $895,000) near the water. Hart Haven is right outside of Oak Bluffs proper, heading towards Edgartown, where Lola's Restaurant is. Private Association Beaches, Tennis and Harbor with 3 Docks (one pictured above) help make these 2 Lots, (1 with the 2 footprints, house and garage) even more in demand. This listing and assessment is on both properties together (50 Farm Pond Rd.) located on 0.69 acres, and the 2.39 acre lot (9 Hart Haven Rd.) abutting Farm Pond and ONLY BEING SOLD TOGETHER. The total package was assessed at over 1.5 Million a few years ago, and with a Buyer who has "A lot of Vision", it could be a 2,800,000 Property. Not a bad "Investment" ! It is now assessed at $900.000. The photos show the beauty and serenity that comes from this property and it's surroundings........ Come take a look at a unique opportunity to create your "Dream Home", or a" Dream House" for someone else to enjoy.

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

116 Dukes County Marthas Vineyard MA

MLS Number 30271

  • Commercial
  • Area Oak Bluffs
  • Bathroom 1

Rare opportunity to purchase land in a flexible commercial location just a short walk to town, harbor, and beaches. There is an existing 560 sq.ft. studio apartment in good condition, and approval from the Oak Bluffs ZBA allowing for the construction of 3 more buildings each with a footprint of 530 sq.ft., at least 2 stories high, and can be used for either residential or commercial use. There are 5 designated on site parking spaces for this property.

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

176 County Road Marthas Vineyard MA

MLS Number 30292

  • Residential
  • Village Oak Bluffs
  • Square Feet 1040
  • Bedrooms 3
  • Bathroom 1

Going, Going…be the lucky one that says Gone! Surrounded by mature plantings along the perimeter for privacy, this shingle-style ranch home is situated in a convenient location in Oak Bluffs. The home's layout includes three comfortable bedrooms, and an open-design living, dining, kitchen area which accesses an ample outdoor entertaining deck with retractable awning. Beautiful wood floors are throughout the home, and the soothing coastal colors and central a/c provide a relaxing escape. The manicured yard offers an underground irrigation system, deck, an enclosed outdoor shower and a small storage shed. There is quick and easy access to the bike paths which network through Oak Bluffs, Edgartown and the State Forest. This property is perfect for year-round living and also boasts a solid vacation rental history if considering for a terrific rental investment opportunity. A pristine home and ready to enjoy right away!

Listed by Martha's Vineyard Vacation Rentals

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

26 Grovedale Road Marthas Vineyard MA

MLS Number 30109

  • Residential
  • Village Oak Bluffs
  • Square Feet 1599
  • Bedrooms 4
  • Bathroom 2

Located on a seldom traveled street brings quiet to this convenient neighborhood. Close to town and walking distance to the sailing camp park on the lagoon. A great open floor plan with kitchen, dining and living room that flows to an outside deck. Cathedral ceiling adds to the spaciousness of this home. A great family home with a strong rental history. First floor bedroom for one floor living is possible. Third floor has 4th bedroom or a great play area for kids. Basement has inside and outside access and is dry.

Listed by Carroll & Vincent R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

115 Winemack Street Marthas Vineyard MA

MLS Number 30282

  • Residential
  • Village Oak Bluffs
  • Square Feet 2008
  • Bedrooms 4
  • Bathroom 2

Open house saturday may 28 1:00pm -3:00pm and sunday may 29 1:00pm -3:00pm east chop ~ generational home! Vintage vineyard residence ~a generational home Built, owned , and lovingly maintained by one family since 1928! .34 acre lot, a short walk to east chop beach club, jetty beach, oak bluffs harbor & in town activity! Includes 4 bedrooms, 2 baths, detached garage, Fireplace, sun porch / studio.. Many cottage details & renovations throughout! Mature plantings & gorgeous gardens surround this very special home! Easy to show! Call today for a private showing!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

33 Island Inn Road Marthas Vineyard MA

MLS Number 30267

  • Condominium
  • Village Oak Bluffs
  • Square Feet 319
  • Bedrooms 1
  • Bathroom 1

Recently upgraded 1-bedroom studio with two double beds at the Island Inn loaded with amenities -- pool, tennis, function rooms, adjacent to Farm Neck golf course and Lola's a fine island restaurant. Beaches just a walk or bike ride away! Upgrades include new wood floors, stone counter tops, new stove and refrigerator, mounted TV, new blind/wall hangings. Offered fully furnished. Enjoy a vacation -- and then rent for income -- management company on site. Good investment potential with solid rental history. A savvy investment opportunity at an attractive price. Unit can be used pet friendly at buyer's option.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

6 Anthiers Lane Marthas Vineyard MA

Price$4,495,000

Est. Mortgage: $/month

MLS Number 30081

  • Residential
  • Village Oak Bluffs
  • Square Feet 5710
  • Bedrooms 6
  • Bathroom 5

EXQUISITE FARM NECK LUXURY RETREAT WITH MAGNIFICENT WATER VIEWS. Set in a prestigious, private enclave along the northeastern side of Sengekontacket Pond and sited on over two acres of meadows, stone walls and beautifully landscaped grounds, this magnificent home blends spectacular water views, luxurious living and all of the amenities of Farm Neck Golf Club. A winding drive leads along the edge of a golden meadow to the full view of this classically styled home, which has been perfectly sited to maximize the magnificent water views, enjoyed by nearly every room in the house. The inviting foyer features a sweeping staircase and opens into a stunning, two-story Living Room with vaulted ceilings and an entire wall of glass windows and French doors that perfectly frame the water views. The Living Room is anchored by a wood-burning fireplace, flanked by custom built-in cabinets and bookshelves. An open-designed Dining Room, Kitchen and Family Room perfectly complements both casual living and entertaining. The gourmet cook's kitchen features custom milled cabinetry, soapstone countertops, an 8-burner Viking dual-fuel range, SubZero refrigerator and other top-notch amenities. The home is comprised of a total of six bedrooms and five and one-half baths, including a luxurious, first-floor Master Bedroom Suite with breathtaking views and master bath with double marble vanity, walk-in glass steam shower, claw foot soaking tub. Recent enhancements include an additional 1500 square feet of finished living space on the lower level -- including a spacious bedroom, full bath, an In-Home Theater with wet bar PLUS an Exercise Room/Gym. This offering also includes full stock ownership in Farm Neck Golf Club. You can literally drive your golf cart to the Farm Neck clubhouse for a round of golf or tennis -- or to the community dock at the end of the road, where you can board your own private kayak, canoe or power boat and enjoy a day out paddling, cruising or fishing on Nantucket Sound. Of course, State Beach and the bicycle path are also just a stone's throw away. This spectacular property truly offers all the finest of Vineyard living! ***Please see video for a tour through the house and Farm Neck Golf lifestyle.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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

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:

44 Windemere Road Marthas Vineyard MA

MLS Number 30201

  • Residential
  • Village Oak Bluffs
  • Square Feet 1984
  • Bedrooms 3
  • Bathroom 3

A Stunning & Impressive Location! Fabulous Water Views from almost every room in the house over the Lagoon, Brush Pond & Vineyard Haven Harbor, mixed w/quality construction, a terrific floor plan & lots of windows. A combination you always hope for but rarely find. Main living level has open floor plan w/views in every direction! Custom Kitchen, painted solid wood cabinetry, granite counters, stainless appliances, requisite gas stove & wide plank oak floors. Living room has riverstone, woodburning fireplace w/granite hearth. French doors, opening towards Lagoon onto 40ft wide covered, mahogany, wraparound deck w/outdoor fireplace. Upstairs, a 'real' master bedroom w/ensuite (two sinks!), private balcony & SUPER views of the Lagoon. Two guest rooms, one w/balcony, shared bath & separate laundry. Oak flooring throughout, Central Air Conditioning, Storm Watch windows, On Demand hot water, Seamless Glass showers (a bath tub also), ceiling fans, recessed down-lighters, colorful plantings..all this & only STEPS to the BEACH!! TRULY A MUST SEE....a Very Special property.

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.64% last updated on May 26, 2016
* 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