Oak Bluffs Cottages

Scroll down to find the latest cottages for sale in Martha's Vineyard, MA's town of Oak Bluffs. Look through a variety of listings to find your new home. Register with our site to save your favorite properties, and you can get email updates when new listings match your search criteria. For more information, questions, or to schedule a showing, please contact us today!

103 Winemack Street, Oak Bluffs, MA

Price$990,000

Est. Mortgage: $/month

MLS Number 32781

  • Residential
  • Square Feet 1536
  • Bedrooms 4
  • Bathroom 1
  • Acreage 0.35

East Chop Gem: Ranch style 4 Bedroom Vintage Cottage with a gable roof, patio, and charming windows. The center great room boasts a soaring ceiling and separates two wings of the house. There is a grand stone fireplace with wood stove insert, which can be accessed from the rear of the house. The house sits on one third acre of land in a prime neighborhood. There are two small garage buildings and ample room for expansion. This house faces on two streets, Winnemack and West Streets. This property is being sold AS IS.

Listed by Martha's Vineyard Seacoast Properties

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

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$
$
%
$/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.

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27 Eastville Avenue, Oak Bluffs, MA

Price$539,000

Est. Mortgage: $/month

MLS Number 32786

  • Residential
  • Square Feet 720
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.1147

Centrally located is this adorable Oak Bluffs year round cottage within walking distance to Oak Bluffs Harbor. Property is move in condition with recent replacement of roof shingles and painted exterior. Open floor plan to kitchen, dining, and living with full basement. There is a 3 bedroom Title 5 septic on site so the possibility of an additional bedroom exists.

Listed by Dockside 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.

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8 Rural Circle, Oak Bluffs, MA

Price$425,000

Est. Mortgage: $/month

MLS Number 32845

  • Residential
  • Square Feet 648
  • Bedrooms 2
  • Bathroom 1

Oak Bluffs ONE OF A KIND CAMPGROUND COTTAGE INSULATED with HEAT! Soaring cathedral ceilings with large windows throughout! This campground cottage was totally re built in the 1980's and offers newer updates throughout! Gorgeous hard wood floors in the living & loft area, stylish black & white kitchen floor tile and glass cabinetry complete kitchen area! First floor bonus "den" sleeping area( no door) and full bathroom with laundry! The loft area bedroom fits queen size, love seat sofa and lots of closet space! THIS IS A MUST SEE! A BLOCK to CIRCUIT AVENUE, a STROLL to Oak Bluffs Beaches, Ocean Park, Oak Bluffs Harbor, public transportation and all the in town parks! THIS IS TRULY A MAGICAL PLACE TO LIVE & ENJOY YEAR ROUND! BETTERMENT FEE IS PAID in FULL..!

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.

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76 Trinity Park, Oak Bluffs, MA

Price$525,000

Est. Mortgage: $/month

MLS Number 32837

  • Residential
  • Square Feet 640
  • Bedrooms 2
  • Bathroom 1

Year Round Campground Cottage located on Trinity Circle in HISTORIC MARTHA'S VINEYARD CAMP MEETING ASSOCIATION. Open spacious living area with high painted ceilings, 2 bedrooms one bedroom area is " loft style" with wood floors! Enjoy all the wonderful tabernacle events front your porch overlooking large lawn on Trinity Park and The Tabernacle. Onsite parking outside the back door. Oil forced hot water and a newer hot water heater, cottage is fully insulated. Only a short walk to Circuit Avenue, beaches and ferry ports! NEW PHOTOS COMING SOON! VACANT EASY TO SHOW!!

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.

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9 Victorian Park, Oak Bluffs, MA

Price$579,000

Est. Mortgage: $/month

MLS Number 32556

  • Residential
  • Square Feet 1015
  • Bedrooms 4
  • Bathroom 1

RARE OFFERING in the Martha's Vineyard Camp Meeting Association! This beautiful Victorian Gingerbread Cottage has been in the same family for over 50 years! Terrific location a block to Circuit Avenue easy stroll to public beaches, shopping & dining on a famous Circuit Avenue, Oak Bluffs Harbor, ferry ports and all the Oak Bluffs Town Parks! Classic Camp Ground Cottage located a in quiet section of the Martha's Vineyard Camp-Meeting Association has all of its original charm and character. Relaxing front porch looking out on Victorian Park, living room, dining room, kitchen, full bathroom and bedroom on the first floor. Upstairs are three more ample bedrooms. Private backyard with landscaping a storage shed and on site parking. Unique opportunity! EASY to SHOW! You will love this MAGICAL SETTING! ON -SITE PARKING for 2+ CARS !

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.

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34 Samoset Avenue, Oak Bluffs, MA

Price$925,000

Est. Mortgage: $/month

MLS Number 32629

  • Residential
  • Square Feet 2179
  • Bedrooms 6
  • Bathroom 2
  • Acreage 0.0899

One of the grand Victorian cottages that gives Oak Bluffs its distinctive character. This 6 bedroom home with over 2,100 sq.ft. of living space has all the charm and gingerbread detail of a Campground cottage writ large. Situated four houses up from the historic Union Chapel, Salty Towers is just a stone's throw from the town beach in one direction and Circuit Ave in the other. Located in the Copeland District and The Cottage City Historical District with peek views of Ocean Park, this 1870s Carpenter's Gothic house stands on the road just behind Ocean Park and features some peek views of the park and the ocean beyond. Enjoy a cocktail on the wraparound porch as you listen to the Sunday band concert in the gazebo or enjoy your own front row seats for the Oak Bluffs fireworks from the second story balcony or porch. Included is off street parking for up to 4 vehicles. A must see.

Listed by Dockside 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.

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8 Morgan Avenue, Oak Bluffs, MA

Price$499,000

Est. Mortgage: $/month

MLS Number 32178

  • Residential
  • Square Feet 816
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.1831

A Golden Nugget from the Oval Renaissance in East Chop! Located in the East Chop Highlands next to the historic Shearer Cottage is this 2+ bedroom/1 bath ranch-style year-round home. Kitchen has cathedral ceilings. Off of the kitchen is a small bonus room that is perfect for a home office/playroom. Hardwood floors throughout. Use the attic for storage or to continue the cathedral ceilings into other rooms in the house. There is a large storage shed at the back of the property. Abundant with a wide-variety of trees and mature plantings, the property will delight any horticulturalist. Watch the garden beds change with the seasons. Close to town, beach, ferries and more, this home has so much to offer for both year-round and summer living.

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.

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109 Barnes Road, Oak Bluffs, MA

Price$945,000

Est. Mortgage: $/month

MLS Number 32274

  • Residential
  • Square Feet 682
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.4932

"Vintage Vineyard" accurately describes this delightful cottage set on a bluff overlooking the Lagoon with views to the harbor and Vineyard Sound. Solidly constructed by a well known builder of yesteryear, this two-bedroom, 1-bath home features a comfortable living room with brick fireplace and west facing views of the Lagoon and spectacular sunsets. The porch has been enclosed to provide additional dining space. Step onto the patio, convenient for grilling and outdoor "meals with a view". The galley style kitchen is more than adequate for preparing meals. The requisite outdoor shower completes this charming Island get-away.

Listed by Coldwell Banker Landmarks

{$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.

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22 Siloam Avenue, Oak Bluffs, MA

Price$799,000

Est. Mortgage: $/month

MLS Number 31676

  • Residential
  • Square Feet 1520
  • Bedrooms 4
  • Bathroom 2

OAK BLUFFS 4BR 2 BATH IN the VILLAGE~Impeccable Pristine Year Round High End Campground Cottage located in the Historic Martha's Vineyard Camp Meeting Association a stroll to Oak Bluffs Harbor, waterviews over SUNSET LAKE and distant views of Washington Park..totally renovated throughout ..This home includes forced hot air and central AC , 2 brand new bathrooms with tile one shower one tub-one up one down; 4 bedrooms, a study with pull out twin sleeper couch, vaulted ceilings wood floors, completely gutted and rebuilt- all new electrical, plumbing etc. , front porch and balcony, two rear decks, outdoor shower , all new vinyl glad double pane tilt in Windows, cedar dipped exterior shingles, custom interior white oak doors, all white oak wood floors, brand new high end maple kitchen with glass built ins in kitchen and dining room, new period lights, sconces in all rooms, washer drier on 2nd floor, fenced in yard, beach stone hearth, gas stove for secondary heating- window blinds , wooden storm doors, security, landscaping in front with flowering plants and along side and back, two patio areas....MUST SEE! YOU WILL LOVE THIS PLACE! Basement accessible from house and from bulkhead.

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.

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41 & 43 Ocean Avenue, Oak Bluffs, MA

Price$2,300,000

Est. Mortgage: $/month

MLS Number 30901

  • Residential
  • Square Feet 2451
  • Bedrooms 7
  • Bathroom 2
  • Acreage 0.1

Oak Bluffs ~2 homes with 2 separate deeds however sellers are selling both 43 & 41 Ocean Avenue.. 43 Ocean Ave -5 BR 1.5 baths! AMAZING BREATH TAKING COLORFUL SUNRISES from your wrap around porch! One of the 5 bedrooms is on the first floor and first floor laundry! Spacious and SUN FILLED living room and dining area! Beautiful STYLISH & RENOVATED eat in kitchen with lots of cabinets and cottage details throughout! This home is in impeccable condition and truly is a rare offering! 43 Ocean Avenue includes 1987 sq. feet..This RENOVATED HOME is a block to the Village of Oak Bluffs to explore and enjoy all the wonderful restaurants, galleries, shopping and ferry ports! 41 Ocean Ave is a Year Round Ranch Style home with 464 sq ft 1 bedroom and 1 bath & enclosed sun porch(an additional 184sq.ft.)! WONDERFUL WATERVIEWS OVER HISTORIC OCEAN PARK ALL the WAY TO VINEYARD SOUND! ACTIVE VIEWS OF PARK and located a block to Oak Bluffs Circuit Avenue, ferry ports and beach across the street! STUNNING VIEWS of FAMOUS GAZEBO..watch all the boats and Summer Activity from your porch!..Enjoy your wonderful private fenced in grassy yard..onsite parking in garage.. 2 houses 41 & 43 Ocean Avenue ...both houses are being sold together..for $2,300,000

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.

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348 Sea View Avenue, Oak Bluffs, MA

Price$6,490,000

Est. Mortgage: $/month

MLS Number 18014

  • Residential
  • Square Feet 3891
  • Bedrooms 10
  • Bathroom 5
  • Acreage 1.5

150 Feet of PRIVATE BEACH at this WATERFRONT COMPOUND IN HARTHAVEN - With 180 degree views of Nantucket Sound and beyond, this property offers a rare opportunity for a waterfront family compound or an investor's dream with a private beach. The three homes that make-up this unique 13 bedroom property are as follows: The "Main Deck" is a sprawling cape-style home with 5+ bedrooms, 2 1/2 baths, oil forced hot water heat, air conditioning, wood-burning fireplace, large covered deck overlooking the bluff and a screened-in porch. This home was updated in 1996. This home is considered the main house of the property because of its commanding location perched on the bluff. The "Captain's House" was rebuilt in 1996. It has a reverse-style floor plan to take full advantage of the sweeping water views. Featuring 2 master suites and 2 additional bedrooms that share a bath, this home is light-filled, open and airy. Two wood-burning fireplaces. The craftsmen that created this home gave extra attention to the wood details throughout and made the house worthy of the finest sea "captain". You will notice these details from the moment you walk into the foyer and move your way through the home to enjoy the beamed ceiling in the living room. The "Cottage" completes this property...almost. This home was also fully rebuilt in 1996. It consists of a living room with wood-burning fireplace, eat-in kitchen, first floor bedroom, first floor laundry and bath. The second floor bedroom has breathtaking views from its private deck. A second large deck runs along the back side of the house. All 3 homes have been created to be independent of each other and all feature air conditioning, outdoor showers and more. With plenty of storage and additional space to be creative with, the garage nicely completes this property. All homes have a solid rental histories with repeat tenants. Sellers would consider a full "turn-key" option.

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