Oak Bluffs Homes For Sale

Oak Bluffs, MA, is Martha Vineyard’s original summer resort, dating back to the late Victorian era. Oak Bluffs real estate includes a wide range of homes including quaint capes, charming bungalows, and waterfront estates. You’ll also find homes in Oak Bluffs with the hallmark colorful "gingerbread" aesthetic and views of the ocean. Oak Bluffs residents revel in the lively scene of Circuit Avenue and the harbor front, day and night, while the outlying neighborhoods contrast in serenity. Find some of the most in-demand Martha’s Vineyard real estate including luxurious waterfront houses and vacation condos in Oak Bluffs. We will help you find the right vacation home or year round residence! Learn more about Oak Bluffs.

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40 Tiffany Drive

Price$889,000

Est. Mortgage: $/month

MLS ID 34214

  • Residential
  • Square Feet 1948
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 1.85

Contemporary Saltbox w deeded rights to the Lagoon. Situated on a knoll w mature shrubs and abutting greenbelt. Wrap around deck in the back of the house overlooking the woods, perfect for summer socializing. This house has never been rented and has been meticulously maintained. Plenty of skylights and patio doors to let the light in. Two huge master bedroom suites w/ baths on each floor. Guest bedroom on the first floor. Large kitchen w plenty of counter space. Brick fireplace w wood stove w/ heatilator and blower, cozy in the winter. Loft overlooking living room for office, etc. Over sized one car garage completes the offering with a 2015 Toyota for sale This lovely house comes mostly furnished and almost turnkey ready for you to use.Please give 24 hours notice for showings.

Listed by Hughes & JC Murphy R.E.

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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385 County Road

Price$525,000

Est. Mortgage: $/month

MLS ID 34289

  • Residential
  • Square Feet 954
  • Bedrooms 1
  • Bathrooms 2
  • Acreage 0.3266

Raised ranch, set up off the road on a knoll, near Farm Neck Golf. Large side and rear yard. Main level contains open plan living, dining, kitchen, master bedroom and full bath with laundry facilities. Lower level contains 3 additional rooms and full bath. A large deck runs the length of the house. House needs work; being sold "as is". Square footage does not include lower level.

Listed by Martha's Vineyard Island-Wide Realty

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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 School Street

Price$590,000

Est. Mortgage: $/month

MLS ID 34246

  • Residential
  • Square Feet 1007
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 1

Walk to Oak Bluffs center, beaches, and restaurants from this renovated year-round home. This is a rare opportunity to get an affordable home so close to town. This cozy 3 bedroom 2 1/2 bathroom home is suited for year-round living and is connected to town sewer. Secluded yard includes a deck grassy yard and shed. Private driveway provides plenty of off street parking. Spacious living area with sliding glass doors opening onto the wrap around deck and front porch. The open kitchen and dining area also has a door opening onto the deck. The utility room with laundry and a half bathroom complete the first floor. Upstairs are three bedrooms and 2 full bathrooms. The front bedroom with it's own private balcony and bathroom off the hall. Two other bedrooms each with direct access to a full bathroom.

Listed by Anchor Realty of Martha's Vineyard

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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10 Paddock Road

Price$2,370,000

Est. Mortgage: $/month

MLS ID 33638

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathrooms 4
  • Half Bath 1

4000 sq ft of brand-new construction tucked nicely on a beautiful lot in the prestigious subdivision of "The Preserve". This home meets all the modern buyer's needs with its open floor plan, 1st and 2nd floor master bedroom suites, chef's kitchen, hardwood floors throughout, custom tile bathrooms, expansive outside entertaining space, and lush landscaping. This is a "family compound in the making," a swimming pool and poolhouse may also be installed if a buyer chooses to do so. With its generous living spaces this home is ideal for entertaining friends and family. There is also lots of opportunity for privacy, thanks to the separate bedroom suite and bathroom above the garage. This is the summer house of your dreams, and can also be your escape during the cooler months thanks to the modern, efficient systems. This spectacular home will be the ideal place to host large family dinners at Thanksgiving or the holiday season with the fireplace as the perfect setting to gather round at the end of the day.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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225 East Chop Drive

Price$3,950,000

Est. Mortgage: $/month

MLS ID 33942

  • Residential
  • Square Feet 2449
  • Bedrooms 3
  • Bathrooms 3
  • Half Bath 1

Top of the Chop ~ A stunning contemporary with dramatic sweeping views of Vineyard Sound. A complete transformation by South Mountain & Company of the former residence resulted in a masterpiece of modern living and superb style. Upon entering you are immediately greeted with water views and the breathtaking landscape and it continues to unfold as you go through the home. The single story home was designed with the living and entertaining area at the core with the master wing tucked privately away and a two bedroom guest wing down its own corridor. The baths are luxurious, the kitchen a work of art and the finishes throughout are simply exquisite. East Chop is an upscale summer community, a most ideal location with the beach, harbor and town just a short distance away.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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311 East Chop Drive

Price$2,250,000

Est. Mortgage: $/month

MLS ID 33800

  • Residential
  • Square Feet 1496
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Smell the sea and touch the sky from this unique vintage waterfront home on East Chop. Extraordinary views of Vineyard Sound from every room with ocean breezes flowing through to Crystal Lake. You can watch the sun rise as you bathe in the antique tub and then watch the sun set from the patio or master suite. Your private 120' dock, mooring and sandy pebbled beach are the perfect place to enjoy all the beauty and water activities that make the Island a special place for generations of family memories. On the ground floor there is an open floor plan with a central kitchen, living and dining area flanked by two bedrooms. The master bedroom is en-suite with a sitting area that opens up to spectacular views of the blue water. The second bedroom on the first floor is a cozy enclave with a private half bath. The open kitchen has ample room to prepare breakfast, lunch and dinner - eat in the attached dining nook or alfresco on the brick patio. Upstairs there are two additional bedrooms and a full bath. There is a detached garage with a large cedar-lined closet for storage. This magnificent home is located within walking or biking distance of downtown Oak Bluffs. Being offered turnkey and has a solid rental history.

Listed by Coldwell Banker Landmarks

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$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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507 Barnes Road

Price$899,000

Est. Mortgage: $/month

MLS ID 33389

  • Residential
  • Square Feet 2592
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 1.3842

BEST VALUE ON MARTHA'S VINEYARD! HOUSE, BARN, 2 CAR GARAGE on 1.38 ACRES! A convenient central "down-island" location (Oak Bluffs-Barnes Road), complete with a 24' x 30' Horse Barn, Main house and an oversized Garage plus enclosed storage area, all on 1.38 acres of land abutting 35.3 acres of conservation land. Great property for anyone that wants a large lot, abundant storage and a 4 bedroom house, all within a 5 minute drive to town or the Ferry. Much of the value lies in the excellent location, degree of privacy, amount of land, and Brand New 4 bedroom Septic System has just been installed. Very close to Featherstone Art Gallery and the Lagoon Pond Herring Run. Only minutes to the VH Ferry. Please call a minimum of 24 hrs. before a requested showing. House occupied. Dog on premise.

Listed by Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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3 Nahomon Street

Price$695,000

Est. Mortgage: $/month

MLS ID 33679

  • Residential
  • Square Feet 1131
  • Bedrooms 2
  • Bathrooms 2
  • Acreage 0.1199

Don't miss this opportunity to own the perfect Oak Bluffs get-away with a pool. Every inch of this Cape-style home has been well cared for. The home features brazilian cherry floors, updated kitchen with stainless appliances, spacious living room with brick fireplace, first floor bedroom and tile bath. Second floor offers a bedroom suite with jacuzzi tub and tile shower. Enjoy lush gardens, large farmers porch, outdoor deck plus a second grilling area all overlooking an in-ground pool. Just a short distance to Oak Bluffs center and Harbor. Excellent rental history!!

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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32 Iron Hill Road

Price$799,000

Est. Mortgage: $/month

MLS ID 33283

  • Residential
  • Square Feet 2934
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 1.517

A must see hidden gem this home lies on 1.52 acres featuring over 100k of reclaimed antique stone work. Located in a very private setting down island, 10 minutes from ferry and 15 minutes from beaches, this home has the feel and tranquility of being up island. The main house offers 3 bedrooms 2 baths with an airy and open floor plan. Beautiful reclaimed wide antique oak flooring as well as other artistic touches truly gives this home the authentic feel of Marhtas Vineyard. An attatched 1400 sq ft 2 story addition with beautiful large stain glass windows ( 4x6ft ) is ready to be easily finished and offers an opportunity to almost double the homes square footage at 2900 sq ft. In addition to added living space it would also make a great home office or artist studio.The property setting is on high ground and overlooks a 9 acre pasture with rights to graze two horses. Access to Little Duarts Pond also accompanies ownership. This property is a great opportunity as a rental/investment home with the additional opportunity to add substantial value with finished addition. Difficult to capture this home in pictures, truly a must see !! And ,YES !, the clock works and keeps perfect time. It is fully modernized with a gps unit for accuracy.

Listed by Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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103 Winemack Street

Price$850,000

Est. Mortgage: $/month

MLS ID 32781

  • Residential
  • Square Feet 1536
  • Bedrooms 4
  • Bathrooms 1
  • Half Bath 2

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. Approved four bedroom septic design plan in place. This property is being sold AS IS.

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 2019
* 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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