Oak Bluffs Homes for Sale

Oak Bluffs has a wonderful array of single family homes on Martha’s Vineyard. From beach cottages and waterfront homes to homes within walking distance to downtown, shops, and restaurants, you’re sure to find the perfect Martha’s Vineyard home in Oak Bluffs. Scroll down to explore Oak Bluffs houses for sale on Martha’s Vineyard. Learn about the town of Oak Bluffs >>

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Call Ocean Park Realty at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour.

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9 Beecher Park Oak Bluffs MA

Oak Bluffs, MA9 Beecher Park

Price$1,295,000

Est. Mortgage: $/month

MLS Number 36834

  • Residential
  • Square Feet 1819
  • Bedrooms 5
  • Bathroom 2
  • Acreage 0.22

East Chop -- Meticulously maintained 5+ bedroom/2-bathroom, 3-season home with water view, sits on a beautifully landscaped yard with 2-car garage. This fabulous cottage should be at the top of your list because of its close proximity to beaches, tennis courts, the Oak Bluffs harbor and downtown areas. Overlooking Plymouth Park and the harbor beyond, the first floor features two living rooms with dining area in between, that have sliding glass doors and walls of windows that bring the park setting to your doorstep. Completing the first floor is a large wrap around deck, first floor bedroom, full bath and kitchen, plus a small bonus room that could be used as an overflow bedroom, storage space or office. Second floor includes four bedrooms and a full bathroom. The home comes partially furnished. Bring your renovation, remodeling and expansion ideas to make this a year-round family gathering place for the years to come. Septic upgrade to Title V for 5-6 bedrooms is buyer's responsibility. Family requests closing after October 1st, prior day notice for showings, and no showings week of July 19-25th.

Listed by RE/MAX on Island

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%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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14 Rose Avenue Oak Bluffs MA

Oak Bluffs, MA14 Rose Avenue

Price$639,000

Est. Mortgage: $/month

MLS Number 36854

  • Residential
  • Square Feet 1034
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.21

Classic bungalow style residence, circa 1937, updates in the 1980's. Tucked away in the Highlands section of East Chop situated in a quiet residential location just across the road from the Baptist Camp Grounds offering more wooded protection, this property sits across the street from Tabernacle Park thus you have the feeling of wooded privacy yet your only a couple blocks from OB harbor and the beach. Town is just a picturesque stroll along the harbor. The house has a roomy living room, up-to-date kitchen/dining area, two bedrooms, bath, enclosed porch room, laundry- room/pantry and a spacious deck. To the rear is an oversized 2 car garage w/electric. A Title V septic system is in place. This home also offers a rental history

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 Old Harbor Lane Oak Bluffs MA

Oak Bluffs, MA22 Old Harbor Lane

Price$1,100,000

Est. Mortgage: $/month

MLS Number 36734

  • Residential
  • Square Feet 1833
  • Bedrooms 4
  • Bathroom 2
  • Update Type NONE

Year-round living in Waterview Farm! This 4 bedroom home is a short distance to the association beach and dock, and enjoys spectacular sunset views over a beautiful 10 acre, forever wild meadow. Many upgrades over the past few years make it move-in ready, and it has a very strong rental history, grossing over $40,000/season. Extend your own season or enjoy the peaceful bliss and stark beauty all year long. SHOWINGS ON SUNDAYS BETWEEN 10 & 2 - MASKS AND GLOVES MUST BE WORN.

Listed by Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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24 Paddock Road Oak Bluffs MA

Oak Bluffs, MA24 Paddock Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 36525

  • Residential
  • Square Feet 3450
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

BEST VALUE IN THE PRESERVE!!! New Custom Built Residence, 2019, by Dubin Construction situated in OAK BLUFFS' most desirable Community that features large home sites and lots of conservation land with a pond. Contemporary design offers upstairs and downstairs master bedroom suites as well as a first and second floor living room and includes two additional bedrooms with a shared bath. Kitchen has gorgeous cabinetry with high end appliances, there is wide oak flooring throughout and gleaming marble tile detail in entrance, laundry and bathrooms. Other highlights include luxurious bathrooms, large deck off living and dining room, stone patio off first floor master, and a very special stone fireplace anchors the great room. Call for an appointment to view this wonderful property!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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18 Paddock Road Oak Bluffs MA

Oak Bluffs, MA18 Paddock Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 36170

  • Residential
  • Square Feet 4329
  • Bedrooms 5
  • Bathroom 5
  • Half Bath 1

Your luxury oasis awaits in Oak Bluffs' most sought after enclave, “The Preserve At The Woodlands.” This new construction luxury home sits on over two acres, surrounded by generous setbacks that provide added privacy among tall pines and oaks. This property truly accommodates the Vineyard lifestyle in a distinctive and beautifully maintained setting perfect for entertaining in the summer and beyond. For the sports and outdoor enthusiast, The Preserve is just a minute from the renowned Farm Neck Golf Club and connects to walking and biking trails that lead to the three down island beaches. With more than 4200 sq. ft., five-bedroom/bathroom ensuites, and 10 ft. ceilings, this stunning home defies expectations! Nestled at the end of a softly curving driveway, hidden from the road by a stretch of mature trees, the house provides coveted privacy coupled with a spacious modern interior that boasts high-end amenities, top of the line appliances, and all the requisites for a home to be enjoyed year-round. Specific features include: First and second-floor master bedroom suites, guest suite, chef's kitchen with Thermidor appliances, hardwood floors, custom tile bathrooms, multiple balconies and patios, luxe closets and storage throughout the home, spacious third-floor loft, massive unfinished basement with 10-foot ceilings, expansive outdoor entertaining spaces, and lush landscaping. As the home approaches the last stages of construction, the new buyers may opt to have the developers oversee the addition of an already-permitted 16'x34' inground pool and/or customize closets and basement. Completion of 18 Paddock is set for September 2020. With few lots remaining in this exclusive neighborhood, don't miss out on this incredible opportunity to fulfill the dream of luxury homeownership on the Vineyard.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 Mourning Dove Way Oak Bluffs MA

Oak Bluffs, MA8 Mourning Dove Way

Price$780,000

Est. Mortgage: $/month

MLS Number 36666

  • Residential
  • Square Feet 1600
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.63

Renovated Contemporary Year Round Home located in the Waterfront Community of Sengekontacket conveniently located off the bike path equidistant to all the down island towns! TERRIFIC LOCATION with private amenities that include access to both fresh and salt water ponds, community dock, potential for a boat mooring , with kayak storage and boat ramp, a community clubhouse on the fresh pond (available for private events), tennis courts, and community services such as curbside trash pick-up and snow removal. There are 3 bedrooms with 2 on the first floor and 2 bathrooms on each floor. The Master Bedroom and loft are on the second floor! The HOME IS IN METICULOUS CONDITION! THERE is LIST OF IMPROVEMENTS in DOCUMENTS! HIGHLIGHTS include UPDATED NEWER KITCHEN 2015, BRAND NEW ROOF 2017, AZEC TRIM, EXTERIOR of the HOME was RE PAINTED in 2018! CENTRAL VACUUM! 4 bedroom TITLE 5 SEPTIC SYSTEM installed in 2010 ! ROOM FOR EXPANSION ! CALL TODAY this is a HIGHLY SOUGHT AFTER LOCATION with WATER ACCESS only STEPS AWAY!! LOOK AT THE PHOTOS ! 360 TOUR COMING SOON!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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5 Winona Avenue Oak Bluffs MA

Oak Bluffs, MA5 Winona Avenue

Price$1,450,000

Est. Mortgage: $/month

MLS Number 35684

  • Residential
  • Square Feet 1524
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.35

RARE WATERFRONT setting on the Lagoon - perched up high on the hill, facing westward with expansive views, views and more views! Private and tucked away yet surprisingly convenient, this vintage single level home and cottage "bunk house" is a dreamy island retreat. Welcoming and open from the first steps inside, the main great room leads to water view sliders and a deck across the entire back. Grassy yard and mature plantings enhance the truly beautiful views of the Lagoon, Hines Point and Vineyard Haven harbor beyond. Perfectly sited to take advantage of this unique setting. Direct access to the Lagoon waterfront beach by way of a sturdy, large timber staircase. Look no further - you've found Home Sweet Vineyard Home! Open for showing appointments July 20th with notice!

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details

5 John Wesley Avenue Oak Bluffs MA

Oak Bluffs, MA5 John Wesley Avenue

Price$1,450,000

Est. Mortgage: $/month

MLS Number 36768

  • Residential
  • Square Feet 2600
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

MOVE IN THIS SUMMER! BRAND NEW HOME located in East Chop within walking distance to Oak Bluffs Harbor, Jetty Beach, Town, Shops and Ferry Ports! Custom Design with 4 BEDROOMS 4.5 Tiled Bathrooms with a SPACIOUS living and dining area! Over 2600 square feet of living space ! The kitchen includes TOP of the line APPLIANCES and beautiful cabinetry throughout! There is a finished walk out basement with about 1000sqft with access to a huge patio for entertaining BONUS a walk up LARGE un finished attic space offer options for the SAVVY BUYER ! Attached one car garage completes this offering! MANY BEAUTIFUL TOUCHES THROUGHOUT ! RARE OFFERING in this LOCATION & SIZE!! ** single split rail fence framed with roses will line the front yard. There is a patio in the backyard more photos coming soon and 360 tour!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details

17 Jessica Lane Oak Bluffs MA

Oak Bluffs, MA17 Jessica Lane

Price$1,500,000

Est. Mortgage: $/month

MLS Number 36761

  • Residential
  • Square Feet 3020
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

Get the most for your money! Over 3,000 sq ft. with all the features you may desire...Open, great room floor plan complete with gas fireplace in the living area, radiant "in floor" heat plus central AC, main level master bedroom with private porch, a massive rear deck and inviting covered front porch providing extended living areas and an enchanting water feature that includes Koi fish of all colors & and a babbling waterfall! Also, SOLAR Panels and a refreshing outdoor shower. Nicely nestled at the end of a private country lane not far from everything that is "down island", this is the right place for vacation or year round living. Beautiful gardens galore and quick access to the many hiking trails nearby. Solar panels and outdoor shower too! Plenty of room on the 1.3 acres for a guest house (with town permits) or a pool. Close to bike bath and Farm Neck Golf Course. This is one "opportunity knocking" that you don't want to miss.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details

9 West Clinton Avenue Oak Bluffs MA

Oak Bluffs, MA9 West Clinton Avenue

Price$549,000

Est. Mortgage: $/month

MLS Number 36123

  • Residential
  • Square Feet 827
  • Bedrooms 3
  • Bathroom 1
  • Half Bath 1

Gingerbread Cottage Perfection. This sweet Oak Bluffs cottage is what dreams are made of! A short walk to beaches, ferries, harbor and Oak Bluffs town activities. Beautifully maintained and upgraded with whimsical details inside and out. A serene setting front to back, directly across from the Oak Park gardens plus rear access with convenient on-site parking. Fabulous new patio/BBQ area and an outdoor shower too! This treasured cottage home has high ceilings on the first and second floors, tons of windows and cross breezes and a lovely balcony. Comfortable and cozy, the epitome of vintage cottage charm!

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 TourAsk A QuestionMore Details