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. View all real estate for sale on the Vineyard here.

Oak Bluffs Real Estate

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View by Property Type: Waterfront Homes | Water View Homes | Single Family | Condos

3 Hidden Cove Road

Oak Bluffs, MA3 Hidden Cove Road

Price$1,600,000

Est. Mortgage: $/month

MLS ID 36927

  • Residential
  • Square Feet 3016
  • Bedrooms 4
  • Bathrooms 3
  • Half Bath 1

If you have been waiting for your opportunity to live in Hidden Cove, this beautiful contemporary house is the answer. It is complete with four bedrooms and three and one half bathrooms plus an outdoor shower to accommodate the needs of a busy three generation household. Custom modern kitchen with high end appliances. granite countertops, and backsplash; large tiled floor bathrooms, central air, efficient propane heat and electric heat as a back up, hardwood floors, marble floors on the lower level, central vacuum system throughout. The landscaped backyard has an irrigation system plus an invisible fence for your dog. There is a kayak on the rack at the community dock that goes with the house. The tennis courts are a short walk away. There is a one car garage. Many impressive features that make life on the Vineyard the ideal place to call home.

Listed by Martha's Vineyard Seacoast Properties

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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, MA14 Rose Avenue

Price$639,000

Est. Mortgage: $/month

MLS ID 36854

  • Residential
  • Square Feet 1034
  • Bedrooms 2
  • Bathrooms 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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90 Dukes County Avenue

Oak Bluffs, MA90 Dukes County Avenue

Price$2,195,000

Est. Mortgage: $/month

MLS ID 36887

  • Multi-Family
  • Village Downtown
  • Bedrooms 5
  • Bathrooms 5
  • Half Bath 1

ULTRA CHIC + LUXE IN-TOWN MIXED-USE COMPOUND. Located within walking distance to Oak Bluffs town center and harbor, this luxurious designer's own property offers a one-of-a-kind opportunity -- with three residential living spaces, multiple commercial office spaces, plus off-street parking spaces for up to nine (9) cars. Ideal for a savvy investor or business person looking for a condominium conversion OR a live-work situation with opportunity to do use rental income to offset ownership costs. The property currently generates $120,000+/year in combined commercial and residential rental income. The compound is anchored by a private and beautifully landscaped courtyard. The different spaces are as follows: THE TREE HOUSE (1,668 sq. feet) 3-Bedroom | 3-Bath second-floor unit with private deck; THE GARDEN HOUSE (797 sq. feet): 1-Bedroom | 1-Bath ground-floor unit; THE GATE HOUSE (1,350 sq. feet) 1-Bedroom | 1-Bath ground floor unit; LOWER LEVEL (1,466 sq. feet - not included in total SF shown) and featuring 12-foot ceilings, multiple rooms and a half bathroom. There is also a 1-car garage or storage shed on the first floor of the compound. There are superlative architectural and designer touches throughout this amazing property. Select furnishings are available for separate purchase. There is no other offering like this unique property . . truly a must see!

Listed by Point B Realty LLC

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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, MA22 Old Harbor Lane

Price$1,100,000

Est. Mortgage: $/month

MLS ID 36734

  • Residential
  • Village Sengy
  • Square Feet 1833
  • Bedrooms 4
  • Bathrooms 2

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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18 Paddock Road

Oak Bluffs, MA18 Paddock Road

Price$2,399,000

Est. Mortgage: $/month

MLS ID 36170

  • Residential
  • Village Central
  • Square Feet 4329
  • Bedrooms 5
  • Bathrooms 5

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, MA8 Mourning Dove Way

Price$780,000

Est. Mortgage: $/month

MLS ID 36666

  • Residential
  • Village Sengy
  • Square Feet 1600
  • Bedrooms 3
  • Bathrooms 2

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

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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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5 Winona Avenue

Oak Bluffs, MA5 Winona Avenue

Price$1,450,000

Est. Mortgage: $/month

MLS ID 35684

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 1524
  • Bedrooms 4
  • Bathrooms 2

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 21st and after with notice!

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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5 John Wesley Avenue

Oak Bluffs, MA5 John Wesley Avenue

Price$1,450,000

Est. Mortgage: $/month

MLS ID 36768

  • Residential
  • Village East Chop
  • Square Feet 2600
  • Bedrooms 4
  • Bathrooms 4

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

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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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17 Jessica Lane

Oak Bluffs, MA17 Jessica Lane

Price$1,500,000

Est. Mortgage: $/month

MLS ID 36761

  • Residential
  • Village Central
  • Square Feet 3020
  • Bedrooms 4
  • Bathrooms 3

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

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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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9 West Clinton Avenue

Oak Bluffs, MA9 West Clinton Avenue

Price$549,000

Est. Mortgage: $/month

MLS ID 36123

  • Residential
  • Village Downtown
  • Square Feet 827
  • Bedrooms 3
  • Bathrooms 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

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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.

Save FavoriteSchedule TourAsk A QuestionMore Details