Oak Bluffs
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Oak Bluffs - or 'OB' - is a classic beach town, filled with tons of fun! Enjoy the sandy beaches along the calm waters of Nantucket Sound, events held in Ocean Park and the Tabernacle, and the casual atmosphere of the harbor and Circuit Avenue. Popular attractions include the Flying Horses Carousel, the nation’s oldest operating platform carousel, and the Martha’s Vineyard Camp Meeting Association, a National Historic Landmark and community of over 300 charming Victorian gingerbread cottages surrounding a beautiful iron Tabernacle. Circuit Avenue is always bustling and has something for everyone – ice cream, coffee shops, eateries, bars and boutiques. The Harbor is entirely walkable and is a great place to relax and watch the boats coming and going. Outside of the downtown area, there are many areas in OB that offer a quieter atmosphere. Contact us and we'll help you find the perfect getaway!
130 properties available
Welcome to your dream vacation home! This stunning 4 bedroom, 2-story home is located on the lagoon and offers breathtaking water views and stunning sunsets. With more than 150 feet of private beach frontage, you'll enjoy privacy and ample space to relax and unwind. TDesigned for comfort and convenience, the home features two en suite bedrooms on t
Oak Bluffs 824
Welcome to your dream vacation home! This stunning 4 bedroom, 2-story home is located on the lagoon and offers breathtaking water views and stunning s... Read More
Welcome to your dream vacation home! This stunning 4 bedroom, 2-story home is located on the lagoon and offers breathtaking water views and stunning s... Read More
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house, and oversized deck, perfect for entertaining, grilling and memorable evenings. The nearby guest house includes a king bed, kitchenette, and full bath. This home includes many amenities for all to enj
Oak Bluffs 812
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house,... Read More
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house,... Read More
This neighborhood, with an Oak Bluffs address, is one of the best-kept secrets. It's located down a quiet road while still providing easy access to Oak Bluffs, Edgartown, West Tisbury, and other points up island. You'll find biking and walking trails nearby that connect to the State Forest bike path network.
The home features a thoughtful floor pla
Oak Bluffs 819
This neighborhood, with an Oak Bluffs address, is one of the best-kept secrets. It's located down a quiet road while still providing easy access to Oa... Read More
This neighborhood, with an Oak Bluffs address, is one of the best-kept secrets. It's located down a quiet road while still providing easy access to Oa... Read More
This stunning single-level condo, situated on the second floor of the Seaview Condo complex, boasts two bedrooms and two bathrooms, along with a small additional room featuring a convenient desk. Perfectly positioned just across from the picturesque Inkwell beach and a leisurely stroll away from the charming Village of Oak Bluffs, this property is
Oak Bluffs 8025
This stunning single-level condo, situated on the second floor of the Seaview Condo complex, boasts two bedrooms and two bathrooms, along with a small... Read More
This stunning single-level condo, situated on the second floor of the Seaview Condo complex, boasts two bedrooms and two bathrooms, along with a small... Read More
Experience the best that Martha's Vineyard has to offer with wonderful privacy and minutes to stunning beaches at this contemporary cottage nestled in landscaped surroundings. This home is centrally located a located with Oak Bluffs, Edgartown, and Vineyard Haven town centers nearby. Appreciate the modern flare with up to date amenities which make
Oak Bluffs 823
Experience the best that Martha's Vineyard has to offer with wonderful privacy and minutes to stunning beaches at this contemporary cottage nestled in... Read More
Experience the best that Martha's Vineyard has to offer with wonderful privacy and minutes to stunning beaches at this contemporary cottage nestled in... Read More
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room with vaulted ceilings, kitchen, living and dining area with French doors that open to an expansive patio and pool. Separate wings on each side of the great room house another living/sitting room and p
Oak Bluffs 8134
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room ... Read More
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room ... Read More
Escape to an exceptional retreat on Martha's Vineyard with this magnificent four-bedroom beach house, perfectly located across the street from a park with stunning harbor views. With an unbeatable location, this property is conveniently within easy reach of the town, the ferry, and the charming Oak Bluffs Village, as well as public beaches. As you
Oak Bluffs 8162
Escape to an exceptional retreat on Martha's Vineyard with this magnificent four-bedroom beach house, perfectly located across the street from a park ... Read More
Escape to an exceptional retreat on Martha's Vineyard with this magnificent four-bedroom beach house, perfectly located across the street from a park ... Read More
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beautiful beaches of Edgartown, Oak Bluffs, and Vineyard Haven. The house features cozy furnishings and lovely wood floors on both the first and second levels.
Amenities include high-speed wireless intern
Oak Bluffs 860
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beau... Read More
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beau... Read More
Enjoy this expansive five bedroom home, ideal for extended family or friends. Spanning four levels, there is ample space for everyone to spread out. The main level includes the kitchen, dining, half bath and a couple of sitting areas with access to the back deck. The deck is perfect for outdoor dining and ample room in the backyard for those outdoo
Oak Bluffs 8109
Enjoy this expansive five bedroom home, ideal for extended family or friends. Spanning four levels, there is ample space for everyone to spread out. T... Read More
Enjoy this expansive five bedroom home, ideal for extended family or friends. Spanning four levels, there is ample space for everyone to spread out. T... Read More
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for gathering. The open living and dining areas create a welcoming atmosphere, while the thoughtful layout provides quiet retreats for guests. The home sleeps seven and features three bedrooms and four and
Oak Bluffs 8013
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for ga... Read More
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for ga... Read More
A classic East Chop summer house, featuring multiple bedrooms and situated just minutes away center of town. Step outside to enjoy a generous deck and patio areas, ideal for warm summer evenings. Inside, you'll discover a cozy living area, dining space, and spacious kitchen. The first floor also includes a twin bedroom and a full bathroom. Upstairs
Oak Bluffs 8056
A classic East Chop summer house, featuring multiple bedrooms and situated just minutes away center of town. Step outside to enjoy a generous deck and... Read More
A classic East Chop summer house, featuring multiple bedrooms and situated just minutes away center of town. Step outside to enjoy a generous deck and... Read More
All the charm of Oak Bluffs in an updated, clean and comfortable gingerbread cottage. This house is perfect for families with children. The neighborhood is quiet and relaxing with all of the action just a stroll away. Ocean Park, the beach and Circuit Avenue are no more than two short blocks. Everyone can do their own thing. Depart out the front do
Oak Bluffs 815
All the charm of Oak Bluffs in an updated, clean and comfortable gingerbread cottage. This house is perfect for families with children. The neighborho... Read More
All the charm of Oak Bluffs in an updated, clean and comfortable gingerbread cottage. This house is perfect for families with children. The neighborho... Read More
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