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!
126 properties available
This lovely pond front property is situated in the private and peaceful association called Sengekontacket. This association offers tennis, a boat launch, dock and small club house and is overall a great neighborhood. On the first floor is the primary suite with a shower and separate tub. All remaining bedrooms are on the second floor and are connec
Oak Bluffs 8067
This lovely pond front property is situated in the private and peaceful association called Sengekontacket. This association offers tennis, a boat laun... Read More
This lovely pond front property is situated in the private and peaceful association called Sengekontacket. This association offers tennis, a boat laun... Read More
This classic colonial home in Oak Bluffs offers the perfect Martha's Vineyard getaway for families and small groups. With five comfortable bedrooms accommodating up to eight guests, the home blends timeless charm with relaxed coastal living. Inside, you'll find inviting, well-appointed bedrooms designed for restful nights after a day of island expl
Oak Bluffs 8123
This classic colonial home in Oak Bluffs offers the perfect Martha's Vineyard getaway for families and small groups. With five comfortable bedrooms ac... Read More
This classic colonial home in Oak Bluffs offers the perfect Martha's Vineyard getaway for families and small groups. With five comfortable bedrooms ac... Read More
Located at the end of a quiet, dead-end road just one mile from Oak Bluffs center, this renovated four-bedroom, three-bath home offers comfort, convenience, and plenty of charm. Enjoy new furnishings, updated appliances, and modernized bathrooms throughout. The open living and dining area features a cathedral ceiling that enhances the spacious feel
Oak Bluffs 8020
Located at the end of a quiet, dead-end road just one mile from Oak Bluffs center, this renovated four-bedroom, three-bath home offers comfort, conven... Read More
Located at the end of a quiet, dead-end road just one mile from Oak Bluffs center, this renovated four-bedroom, three-bath home offers comfort, conven... Read More
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from the town landing on Lagoon Pond. It is ideal for accommodating your extended family. The efficient kitchen provides access to the back deck, perfect for outdoor dining and gatherings. The home feature
Oak Bluffs 877
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from ... Read More
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from ... Read More
Step back in time with a stay in this 1850s Victorian-style home, nestled in the heart of downtown Oak Bluffs. Overlooking the scenic Ocean Park and Nantucket Sound, this charming property offers the perfect blend of historic elegance and modern convenience. With seven bedrooms—one on the first floor and six on the second. On this floor is another
Oak Bluffs 8163
Step back in time with a stay in this 1850s Victorian-style home, nestled in the heart of downtown Oak Bluffs. Overlooking the scenic Ocean Park and N... Read More
Step back in time with a stay in this 1850s Victorian-style home, nestled in the heart of downtown Oak Bluffs. Overlooking the scenic Ocean Park and N... Read More
Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architecturally designed with two primary suites, a chef's Kitchen, open and sprawling dining and living spaces all on the main level with peaceful water views of Farm Pond and a distance view of the Atlantic
Oak Bluffs 807
Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architect... Read More
Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architect... Read More
Located on over three acres of conservation land with views of Sengekontacket Pond and seconds away from Farm Neck Golf course...three bedrooms two bathrooms, two kitchens, and outdoor back deck - a great way to spend your time on Martha's Vineyard. Two of the bedrooms are on the main living floor and the lower level offers one bedroom with a pullo
Oak Bluffs 8177
Located on over three acres of conservation land with views of Sengekontacket Pond and seconds away from Farm Neck Golf course...three bedrooms two ba... Read More
Located on over three acres of conservation land with views of Sengekontacket Pond and seconds away from Farm Neck Golf course...three bedrooms two ba... Read More
Lovely Oak Bluffs home located in Sengekontacket. This home offers great space and multiple amenities to enjoy your summer get away. Association tennis courts, fresh pond frontage and access to saltwater pond that leads out to the Vineyard Sound. Your vacation begins the moment you enter the property with an updated kitchen, lovely views of the fr
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Oak Bluffs 8174
Lovely Oak Bluffs home located in Sengekontacket. This home offers great space and multiple amenities to enjoy your summer get away. Association tenni... Read More
Lovely Oak Bluffs home located in Sengekontacket. This home offers great space and multiple amenities to enjoy your summer get away. Association tenni... Read More
This cozy well maintained and tastefully decorated Martha's Vineyard summer home is perfect for vacationers. It is located on a carriage road in a quiet neighborhood with association tennis, just minutes away. The large yard is fenced in to accommodate a heated in ground pool with lots of chairs for lounging. The lovely screened porch, right off th
Oak Bluffs 8143
This cozy well maintained and tastefully decorated Martha's Vineyard summer home is perfect for vacationers. It is located on a carriage road in a qui... Read More
This cozy well maintained and tastefully decorated Martha's Vineyard summer home is perfect for vacationers. It is located on a carriage road in a qui... Read More
This classic 3 bedroom Oak Bluffs home is perfect for relaxing, entertaining and spending quality time with family. All 3 of the bedrooms are on the Main Level and there is bonus living space and 2 Twin beds on the Lower Level. The kitchen, living, and dining spaces flow seamlessly from one area of the Main Level to the next and have access to the
Oak Bluffs 838
This classic 3 bedroom Oak Bluffs home is perfect for relaxing, entertaining and spending quality time with family. All 3 of the bedrooms are on the M... Read More
This classic 3 bedroom Oak Bluffs home is perfect for relaxing, entertaining and spending quality time with family. All 3 of the bedrooms are on the M... Read More
A jaw-dropping restoration of a classic Gingerbread Cottage by the ocean - melding a sophisticated bohemian style with the nostalgia of yesteryear.
The modern decor reflects an aesthetic that is masterfully California: refined and tailored - but not overly fussy. Sleek, sophisticated fixtures adorn clean and simple surfaces - wood vanities and bu
Oak Bluffs 834
A jaw-dropping restoration of a classic Gingerbread Cottage by the ocean - melding a sophisticated bohemian style with the nostalgia of yesteryear. ... Read More
A jaw-dropping restoration of a classic Gingerbread Cottage by the ocean - melding a sophisticated bohemian style with the nostalgia of yesteryear. ... Read More
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkwell Beach or into town. The five bedrooms are located on the second floor and share two bathrooms. There is an additional half bath and an outdoor shower. Your favorite part of your vacation will be
Oak Bluffs 833
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkw... Read More
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkw... Read More
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