Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with the comfort, privacy, and functionality of a thoughtfully modernized home. Two-car off-street parking—an exceptional Campground amenity—adds everyday convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away. Encompassing 1,135 square feet, the home feels surprisingly spacious, with painted wood floors, abundant natural light, and vintage details throughout. The flexible floor plan offers multiple living and bonus spaces suitable for a home office, den, guest overflow, or additional gathering areas. The generous first-floor bathroom includes ample storage and a full-size washer and dryer. Unlike many seasonal Campground cottages, this home is fully winterized for comfortable year-round use. A four-zone heat-pump system provides efficient heating and full air conditioning, complemented by a modern propane on-demand water heater with backup heating capability. Additional improvements include substantially updated electrical wiring and lighting, newer appliances, added kitchen built-ins, and major foundation work completed after temporarily lifting the home. The crawlspace is fully sealed and dry, improving long-term comfort and durability. Outside, the fenced yard and expanded brick patio offer a degree of privacy and outdoor living space rarely found in the Campground. Shade sails, a cooling fan, and an outdoor television create an inviting setting for dining, entertaining, and relaxing. A large shed provides abundant storage for bicycles, beach equipment, and seasonal belongings. With its coveted location, double lot, two-car parking, year-round systems, private outdoor spaces, and extensive upgrades, this is a truly uncommon Campground offering.

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Tucked away on a quiet side street just 0.7 miles from Circuit Avenue, this charming Oak Bluffs cottage offers the rare combination of privacy and proximity to town. The original two-bedroom, one-bath home was thoughtfully expanded to include a bright great room that opens directly to a large fenced yard — ideal for outdoor dining, pets, or simply enjoying Vineyard summers. The property is enhanced by mature, thoughtfully curated plantings including Japanese maple, cherry, and magnolia, creating a peaceful, garden-like setting with seasonal color and texture. A separate storage shed with its own small deck presents exciting potential for a studio, home office, creative space, or even a future sauna. A comfortable year-round residence, vacation retreat, or investment opportunity close to beaches, ferries, restaurants, and all that downtown Oak Bluffs has to offer — without the noise of being in the middle of it.

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Welcome to this FULLY FURNISHED, private, 2-bedroom, end-unit townhouse offering 1,208 sq ft of effortless coastal living. With seasonal rentals already in place this opportunity is the defenition of TURN KEY. Thoughtfully designed with both comfort and style in mind, this coastal retreat blends relaxed island charm with modern convenience—perfect for year-round living or as an established rental investment. Sunlight pours in through two walls of sliding glass doors, opening to an expansive 288 sq ft private deck. Ideal for al fresco dining, morning coffee, or evening gatherings, this inviting outdoor space creates a seamless indoor-outdoor lifestyle. The half bathroom, along with the added convenience of first-floor laundry complete the first floor. Upstairs you will find two generously sized bedrooms with lofted ceilings, beautiful patio views and a full bath. If simplicity is what you’re craving in your island home, this condo offers a low-maintenance lifestyle with community services such as trash removal and snow clearing—so you can spend more time enjoying the island and less time managing it. Located within the sought-after Sengekontacket community, residents enjoy an array of amenities including a saltwater dock with kayak and canoe storage, a freshwater pond with clubhouse, tennis and pickleball courts, and a playground area. Centrally positioned, the property offers easy access to downtown Oak Bluffs, Farm Neck Golf Club, pristine public beaches, and the island’s scenic bike paths—placing the very best of island living right at your doorstep. Additional conveniences include a two-car carport and a private owner storage closet. A refined island escape with strong investment potential—this is coastal living at its best. More information about the Sengekontacket Community can be found at: https://www.sengekontacket.com/

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In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom with glass enclosed shower, and a large primary bedroom that's over 16'x21'. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it!

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Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to the beach, town, bike path, and more, this home sits in a special location. Enjoy this house as it is or work through the process to create something new. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but not on the MACRIS registry. Buyers should research the process for making major renovations.

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In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view of Downtown Oak Bluffs. Sit back and watch the boats come into the harbor at one of the many seating areas or enjoy diner al fresco under the stars. This spacious unit has many custom wooden features including a staircase leading to the rooftop deck creating a storage area and sleep nook with daybed. Take a step down to the comfortable living area. With hardwood floors throughout, the kitchen and dining area are divided with custom cabinetry. The spacious bedroom has an additional alcove area with pull down skylight, ideal for an exercise area or office. A tiled bathroom with full tub and shower can be entered off the hall or bedroom. A separate Laundry room is shared by 2 other units.

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Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. This year-round home is filled with natural light and features a spacious deck —perfect for relaxing or entertaining. Additional highlights include in-unit laundry, dedicated parking, a storage area, a new septic system (2025), and low HOA fees. Ideally located near Farm Neck Golf Club, Felix Neck Wildlife Sanctuary, scenic bike paths, and the down-island towns, this inviting property offers the best of coastal living.

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OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut Avenue and Oak Avenue, increases flexibility for design options, access and privacy. Walking distance to Oak Bluffs Harbor, Oak Bluffs Library, Sunset Lake, Campground cottages, shops, restaurants, Oak Bluffs Ferry, beaches and local entertainment. This property is ideal for seasonal enjoyment, multigenerational living, or a strong rental in one of Martha’s Vineyard’s most desirable markets. A chance to acquire a ready to build lot with tons of potential, substantial bedroom capacity, options for two structures, offering long-term and enduring value & BUILDING PERMIT in place for an ADU. This could be yours! Ready to go.

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This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with tons of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in compliance with Massachusetts ADU regulation - 760 CMR 71.00. Only .6 of a mile to Oak Bluffs Harbor and .5 mile to the top of Circuit Avenue! Title 5 Certification in place. Lot is in Zone II and will allow a total of two bedrooms with upgrade to an advanced treatment system. Just one house from Wesleyan Park or stroll to Harbor and Town. Empty and easy to show.

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Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

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Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

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Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features a living area and kitchen with breakfast bar. Ample storage and a stackable washer/dryer complete the kitchen. The home has two comfortable bedrooms and one full bath. Enjoy seamless indoor-outdoor living from the expansive wrap-around deck. After a day at the beach, rinse off in the requisite Vineyard amenity, the outdoor shower. A barn-style shed provides an enormous amount of storage or it can be a workshop space/she-shed. Conveniently located near downtown, access to the Lagoon, bike path, the hospital, public library and more, this property offers both practicality and charm in a sought-after Oak Bluffs neighborhood. An adorable home to make your own. The septic system has passed Title V inspection and is certified for two-bedrooms. Located in the R1 zoning district and in Zone 2, the property is subject to 20-foot setbacks on all sides. It is a pre-existing, non-conforming lot, so any additions to the structure will require approval from the Zoning Board of Appeals.

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