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
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
A gorgeous home in an incredible location! This six-bedroom home offers water views, central air conditioning and a divine location, directly across from Ocean Park. The best spot for the annual Oak Bluffs Fireworks and Grand Illumination, outfitted with all of the modern amenities you could need.
There are two living areas, both on the first flo
Oak Bluffs 825
A gorgeous home in an incredible location! This six-bedroom home offers water views, central air conditioning and a divine location, directly across f... Read More
A gorgeous home in an incredible location! This six-bedroom home offers water views, central air conditioning and a divine location, directly across f... Read More
Spacious Colonial in Meadowview Farms with room for everyone to spread out. The well-equipped kitchen and indoor dining area open to the expansive rear deck with outdoor dining. The living room features a cathedral ceiling with open staircase to the second floor. Two of the three bedrooms are on the second floor, one King-primary suite and a se
Oak Bluffs 8115
Spacious Colonial in Meadowview Farms with room for everyone to spread out. The well-equipped kitchen and indoor dining area open to the expansive r... Read More
Spacious Colonial in Meadowview Farms with room for everyone to spread out. The well-equipped kitchen and indoor dining area open to the expansive r... Read More
Barnes Road, to Linden Avenue sits a three bedroom, three bathroom home with an open floor plan of stainless steel kitchen appliances, granite countertops and hardwood flooring throughout. The first floor has plenty of room for dining in or out on the front porch. Off the kitchen is a family room with flat screen tv and lots of overstuffed leather
Oak Bluffs 8135
Barnes Road, to Linden Avenue sits a three bedroom, three bathroom home with an open floor plan of stainless steel kitchen appliances, granite counter... Read More
Barnes Road, to Linden Avenue sits a three bedroom, three bathroom home with an open floor plan of stainless steel kitchen appliances, granite counter... Read More
Cozy Cottage at Coleman Corners is located on a quiet, peaceful road in the East Chop Highlands of Oak Bluffs, away from the hustle and bustle, yet only a ten-minute walk to shopping and restaurants in downtown Oak Bluffs and another ten minutes to town beaches. A place to relax and simply exhale, this homey, comfortable four-bedroom Cottage offers
Oak Bluffs 8169
Cozy Cottage at Coleman Corners is located on a quiet, peaceful road in the East Chop Highlands of Oak Bluffs, away from the hustle and bustle, yet on... Read More
Cozy Cottage at Coleman Corners is located on a quiet, peaceful road in the East Chop Highlands of Oak Bluffs, away from the hustle and bustle, yet on... Read More
Located in the serene Iron Hill Farm area just beyond the Islands' Alpaca Farm, this spacious four bedroom contemporary Cape offers large rooms, extensive outdoor living space, and close proximity to three island towns. The home is centrally located and +/- 4 miles from the townships and beautiful beaches of Edgartown, Oak Bluffs, and Vineyard Have
Oak Bluffs 831
Located in the serene Iron Hill Farm area just beyond the Islands' Alpaca Farm, this spacious four bedroom contemporary Cape offers large rooms, exten... Read More
Located in the serene Iron Hill Farm area just beyond the Islands' Alpaca Farm, this spacious four bedroom contemporary Cape offers large rooms, exten... Read More
Situated just about a mile from Oak Bluffs downtown and town beaches, is this charming four bedroom two bathroom home. It is comfortably furnished equipped with air conditioning, two sitting rooms, and updated kitchen and bathrooms. The fully equipped kitchen offers stainless steel appliances, gorgeous countertops, a butcher block island and bonus
Oak Bluffs 8132
Situated just about a mile from Oak Bluffs downtown and town beaches, is this charming four bedroom two bathroom home. It is comfortably furnished equ... Read More
Situated just about a mile from Oak Bluffs downtown and town beaches, is this charming four bedroom two bathroom home. It is comfortably furnished equ... Read More
Contemporary Cape in Oak Bluffs- Nestled between the Lagoon Sailing Camp Park and Farm Neck Golf Club, this contemporary Cape offers comfort, space, and classic Vineyard charm. Step onto the welcoming farmer's porch and into a bright, open living, dining, and kitchen area with hardwood floors and air conditioning. A charming sunroom just off the di
Oak Bluffs 8155
Contemporary Cape in Oak Bluffs- Nestled between the Lagoon Sailing Camp Park and Farm Neck Golf Club, this contemporary Cape offers comfort, space, a... Read More
Contemporary Cape in Oak Bluffs- Nestled between the Lagoon Sailing Camp Park and Farm Neck Golf Club, this contemporary Cape offers comfort, space, a... Read More
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, beach house with state of the art kitchen, gorgeous and comfortable furnishings throughout, fabulous decking to outdoor entertaining overlooking the Lagoon Pond. Most every room in the house has a wate
Oak Bluffs 8151
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, b... Read More
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, b... Read More
By the sea, by the sea! Picture yourself on the deck of this wonderful East Chop home with private beach, sweeping views of Vineyard Sound, huge flat yard and sunsets. The house has large eat-in kitchen, great living/dining room. Families, girlfriend weekends, Derby fishermen. A comfortable seaside home with privacy, yet convenient to Oak Bluffs an
Oak Bluffs 8065
By the sea, by the sea! Picture yourself on the deck of this wonderful East Chop home with private beach, sweeping views of Vineyard Sound, huge flat ... Read More
By the sea, by the sea! Picture yourself on the deck of this wonderful East Chop home with private beach, sweeping views of Vineyard Sound, huge flat ... 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
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
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