Oak Bluffs Homes for Sale

Learn More About Oak Bluffs MA

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.

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Oak Bluffs, Massachusetts is a vibrant destination on Martha's Vineyard renowned for its Victorian architecture and bustling downtown area. The town features an array of attractions and activities, including the Flying Horses Carousel, one of the oldest operating carousels in the country. Other notable landmarks in Oak Bluffs include the Tabernacle, a historic performance venue, and the picturesque Gingerbread Cottages, which are adorned with vibrant colors and intricate details. Visitors to the town can also explore its diverse food scene, with a variety of restaurants offering everything from fresh seafood to classic American cuisine. Beyond its historic charm and culinary delights, Oak Bluffs also boasts beautiful beaches, such as Inkwell Beach and East Chop Beach, which offer stunning views of the Atlantic Ocean. Overall, Oak Bluffs is a captivating destination that combines the best of history, culture, and natural beauty.

2 East Side Road & 60 Bay View Avenue Oak Bluffs MA 02557

MLS Number 41587

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.25

Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the covered porch. Watch the ferries come and go and delight in the dazzling colors of the setting sun. Recent renovations include raising the house and the pouring of a foundation offering an additional 930 square feet of lower level living area. Experience true Vineyard living at its best, just steps away is easy access to the Lagoon with clamming, swimming, and boating. Bring your vision to the open and airy studio/ bunkhouse that is included in this offering at 60 Bay View Avenue and features the same wonderful vistas. Two unbuildable lots abut this property so you will never lose sight of the breathtaking scenery. This classic home is a rare Vineyard offering and not to be missed.

Listed by Carol Shore of Donnelly + Co

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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4 High Meadow Lane Oak Bluffs MA 02557

Oak Bluffs, MA4 High Meadow Lane

Price$2,650,000

Est. Mortgage: $/month

MLS Number 41548

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.8899

Set back and overlooking a sprawling front yard from the quintessential farmer’s porch you can envision family and friends enjoying the outdoors! Soaring cathedral ceilings and beautiful craftsmanship will immediately capture your attention upon entering this expansive cape style home. Many upgrades make this a gracious charmer from the get go.. The floor plan is fabulous, from the bright large kitchen outfitted with ample granite counters, rugged commercial Wolf stove, wine fridge and eat-in counter plus table eating is perfect for family gatherings and entertaining. SOLID is the best way to describe what you will experience when you visit this home. Post and Beam construction levels up with Energy Efficient SIP style of insulation plus Radiant heat through the floors. Central AC and great use of sized windows lets all the light in! First floor primary bedroom is spacious with walk in closet and full bathroom with tub. There is a 2nd bedroom that is currently being used as a TV room. 2 more sizeable bedrooms ensuite and closets complete the 2nd floor. The Lower level is partially finished with key and perfect for multigenerational flex space and or a game room or office. Bring your imagination and personalize the possibilities! There is more! A large Garage with additional space above that can be finished for other creative use. Situated on .89 acres of land, so much yard for all occasions. Lawn games, get togethers outdoor fun all surrounded by beautiful landscaping and Abutting a buffer of Common Land! This is an impressive home base perfect for year-round, a fabulous vacation spot and or generate impressive rental income. Meadow View Farms is a lovely welcoming community that offers beautiful walking paths, along with Association Tennis courts. Perfectly convenient to the bike paths, bus routes central to the down island towns. Title V inspection has been completed and passed.

Listed by Martha Smith of C McManus Realty Group

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$
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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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2b Lauras Way Oak Bluffs MA 02557

Oak Bluffs, MA2b Lauras Way

Price$1,295,000

Est. Mortgage: $/month

Active With Contract

MLS Number 41546

  • Residential
  • Bedrooms 2
  • Bathroom 3
  • Acreage 0.3525

Centrally located to shops, restaurants, beaches, and schools, this completely renovated home will satisfy the most discerning buyer. The first floor offers an open concept floor plan with a state of the art kitchen, dining area, and living room. There is also a large bedroom and full bathroom. The second floor offers a den, bonus room / office, full bathroom, and primary bedroom suite. The finished lower level offers endless possibilities. Highlights include a large fenced in yard, outdoor shower, oak hardwood flooring, storage shed, renovated bathrooms, and stainless steel Bosch appliances. Move right in and enjoy.

Listed by Jarrett Hurwitz of Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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54 Cannahoot Street Oak Bluffs MA 02557

Oak Bluffs, MA54 Cannahoot Street

Price$1,575,000

Est. Mortgage: $/month

MLS Number 41535

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.2295

Located on East Chop, in pristine condition and just a short walk to the beaches, tennis courts, yacht club/harbor, downtown restaurants and the ferries, is this contemporary style 2-bedroom main house, being sold partially furnished plus detached 1-bedroom/1-bathroom. The main house’ modern design features radiant floor heating, cathedral ceilings, modern kitchen, a central concrete block wall behind the floor to ceiling wood burning Rais-Wittus Shaker bench wood stove and access to exterior decks from both the main entrance and the downstairs bedroom. The steel staircase to the second floor is showcased by a wall of light from the hallway. The second floor features an ensuite master bedroom that has its own balcony deck with outdoor shower. It is located on 10,000 sq. ft. (0.23 acres), that includes a front and side yard and parking for 2-3 vehicles. New Title V septic installed 2022.

Listed by Perry Patterson of MV Luxury Homes

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$
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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 Canonicus Avenue Oak Bluffs MA 02557

Oak Bluffs, MA3 Canonicus Avenue

Price$2,495,000

Est. Mortgage: $/month

MLS Number 41509

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.0899

WATER VIEWS!!! Steps to the Beach - walk along the most scenic drive on Martha's Vineyard! This stunning property is a true gem, offering an exceptional combination of classic charm, modern amenities, and an ideal location for enjoying the island's relaxed lifestyle. Nestled in the heart of Oak Bluffs, this home is a short stroll to beaches, restaurants, and shops. The scenic harbor and parks are also just moments away, making it perfect for experiencing the best of the Vineyard. This renovated antique home boasts timeless architectural features and a welcoming front porch creating an inviting and picturesque curb appeal. The interior is a blend of elegance and modern convenience offering an inviting atmosphere for family and friends to gather. Enjoy the serene outdoor spaces, including a patio area for outdoor dining and rooftop deck (widow's walk) that features panoramic ocean views! With its prime location and strong rental income history, this property can serve as both your idyllic vacation retreat and a smart real estate investment. Don't miss the garage and surprise bonus area. Come experience the timeless allure of Martha's Vineyard, and make this extraordinary property your island haven. OWNER FINANCING IS AVAILABLE.

Listed by Jennifer B. DaSilva of Compass | Point B

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$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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71 Netock Avenue Oak Bluffs MA 02557

Oak Bluffs, MA71 Netock Avenue

Price$1,395,000

Est. Mortgage: $/month

Pending

MLS Number 40962

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 4.5
  • Acreage 0.23

Cape style home set on a .25 acre lot with close proximity to East Chop and OB harbor. Expansion possibilities for additional bedrooms. This 4 bedroom and 4.5 bathroom home with attached finished garage is being sold "AS IS" . Tenants are in place.

Listed by Paul Thoutsis of Dockside Real Estate

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%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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 Oak Bluffs MA 02557

Oak Bluffs, MA311 East Chop Drive

Price$3,250,000

Est. Mortgage: $/month

MLS Number 41412

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.25

This classic East Chop Drive gem lies on a 10,000 sq. ft. lot nestled in the sand dunes, just steps to the waters edge and private dock. The 4-bedroom/2.5-bath cottage went through a substantial renovation years ago with the majority of mechanicals, electrical and plumbing being updated. There is an open floor plan with kitchen, dining and living space with cathedral ceiling and wood burning fireplace. There is a ground floor master with private bath and lots of glass, a second bedroom with half bath and laundry/mudroom. The second-floor features 2-bedrooms and a shared bath. The cottage style structure is super charming inside and out and has a wonderful water facing brick terrace with built-in planter, a covered porch and a one-car garage. Beautiful landscaping with lawns and gardens complete this very special property. Let's not forget to mention, it offers some of the best seats on the Island to take in the incredible sunsets.

Listed by Gerrett Conover of Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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111 Eastville Avenue Oak Bluffs MA 02557

Oak Bluffs, MA111 Eastville Avenue

Price$3,200,000

Est. Mortgage: $/month

MLS Number 41243

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 4
  • Acreage 0.43

Welcome to Captain Shaw Norris House, where luxury meets coastal charm! Situated in the picturesque Nab’s Corner neighborhood, 111 Eastville Ave is a stunning property that is steps from the ocean. This historic whaling captain’s house boasts six bedrooms and four luxurious marble bathrooms. Plenty of room for friends and family or you can use the property as a high-end rental. An outstanding feature of this exceptional property is the expansive roof deck. Ascend to the top and be greeted by breathtaking harbor and ocean views that will leave you in awe. Imagine sipping your morning coffee or hosting unforgettable gatherings against this captivating backdrop, with the rhythmic sounds of the waves providing a soothing soundtrack to your life. Marvel at the ever-changing colors of the sky as the sun sets, illuminating the harbor with a golden hue. Watch as boats sail by, a gentle reminder of the maritime heritage that defines this island community. This roof deck is an exquisite refuge to relax and unwind, gathering memories that will last a lifetime. ---------------------------------------------------------------------------------------------------------- This is the perfect Oak Bluffs location! Walk to the beach or take a leisurely walk to downtown Oak Bluffs with its exciting and lively restaurants on the harbor. Enjoy strolling along the quaint historic gingerbread cottages or the charming shops of downtown Oak Bluffs. Or you can walk or bike on a new bike path to Vineyard Haven. The historic Captain Shaw Norris House, built in 1859, has been completely renovated and features, new insulation, electrical wiring, plumbing, bathrooms, roofing, siding, trim, windows, HVAC, and a custom-designed kitchen. There are many original architectural elements featured in this Greek Revival, such as an ancient brick hearth. Whether you are looking for a year-round residence or an exquisite vacation home, this property presents an unparalleled opportunity to create lifelong memories against a backdrop of stunning harbor and ocean views. Prepare to indulge in the island lifestyle and make this Martha's Vineyard gem yours today! Broker has an equity interest in the property.

Listed by Ed Charter of Arrowhead Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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15 Peter Williamson Boulevard Oak Bluffs MA 02557
Pending

MLS Number 41389

  • Residential
  • Mls Status Pending
  • Bedrooms 6
  • Bathroom 5.5
  • Acreage 1.37

Welcome to where elegance and tranquility meet! Nestled on a serene private lot, this exceptional property offers a lifestyle of luxury and comfort, making it the perfect island oasis for discerning homeowners. Step inside to discover an expansive open-concept floor plan flooded with natural light. High ceilings, hardwood floors, and elegant fixtures create an inviting atmosphere. The living area is perfect for entertaining, and a gourmet kitchen with top-of-the-line appliances makes cooking a pleasure. The property features 6 well-appointed bedrooms, including a luxurious master suite. Enjoy ample closet space, and unwind in the spa-like bathrooms. The beautifully landscaped grounds provide an outdoor paradise with lush gardens and mature trees adding to the ambiance. Enjoy al fresco dining on the spacious patio. This exquisite property promises an idyllic blend of comfort, style, and natural beauty, setting the stage for a lifetime of cherished memories. Comes fully furnished and boasts a strong rental income history!

Listed by Jennifer B. DaSilva of Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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2 Farm Path Oak Bluffs MA 02557

Oak Bluffs, MA2 Farm Path

Price$2,250,000

Est. Mortgage: $/month

MLS Number 41356

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.89

"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard and a pool! The large detached two-bay garage has a new attached studio with full bath, laundry, kitchen and a private deck. Newer exterior cedar shingles and trim, and a new 4 bedroom septic installed. Equidistant to each down-Island village, it resides within a mature neighborhood with attractive curb appeal.

Listed by Sean Federowicz of Landmarks at TODAY Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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7 Fairway Drive Oak Bluffs MA 02575

Oak Bluffs, MA7 Fairway Drive

Price$1,295,000

Est. Mortgage: $/month

MLS Number 41326

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.1918

Charming four-bedroom cape centrally located in Oak Bluffs. The well-maintained home offers inviting living spaces, generous-sized bedrooms, and a manicured yard with a large garden shed. The finished lower level, with a private walkout, serves as the perfect quiet office or additional recreation space. The best of both worlds as the quiet neighborhood provides easy access to all down island amenities- bustling main streets, beaches, and ferry!

Listed by Katherine Donahue of Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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11 Canonicus Avenue Oak Bluffs MA 02557

Oak Bluffs, MA11 Canonicus Avenue

Price$1,650,000

Est. Mortgage: $/month

MLS Number 41344

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 1.5
  • Acreage 0.16

LOCATION LOCATION LOCATION! Nestled on the picturesque island of Martha's Vineyard, this historic charming 3-bedroom, 1.5-bathroom single-family home is a tranquil oasis awaiting your arrival.The location of this home is truly exceptional. Oak Bluffs is known for its vibrant community, stunning beaches, and a wide array of dining and entertainment options. You'll be just moments away from the bustling downtown area with its shops, restaurants, and cultural attractions, making it easy to enjoy all that Martha's Vineyard has to offer.Visionaries take note!11 Canonicus Ave offers you a gorgeous water view with access to the beach, a wrap around porch and an expansive backyard. The heart of this home is the spacious sun filled dining area that offers tons of natural light. Whether you're looking for a year-round residence or a seasonal retreat, 11 Canonicus is a rare find that offers both comfort and convenience in one of New England's most coveted islands!

Listed by Amber Henry of Engel and Volkers Boston

$
$
%
$/month over payments
Federal 30-year interest rate: 7.22% last updated on Nov 30, 2023
* 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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Based on information submitted to LINKMV as of December 7, 2023 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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