Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you’ll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha’s Vineyard so special. Martha’s Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home’s usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities. A newly completed “doghouse”-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own. Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living. Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs. Title 5 System failed, Seller is offering a credit at closing to cover costs(to be determined). Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.

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Create an extraordinary Martha's Vineyard estate in the exclusive Lagoon Ridge community of Oak Bluffs. This mostly wooded estate parcel of over one acre features gently rolling topography, providing an exceptional canvas for a custom-designed luxury residence. Privately situated within an intimate enclave of just four estate parcels, the property is accessed by a welcoming paved approach. This thoughtfully planned neighborhood will feature distinctive architect-designed residences, creating a refined and cohesive community setting. Approved for connection to the neighborhood's private Amphidrome® (you will avoid the high expense of a septic system a savings of almost $50,000)on-site wastewater treatment system the parcel is approved for a three-bedroom residence and may offer the potential for additional flex spaces, expansive outdoor living areas, a pool, and attached or detached garages, subject to applicable approvals. Embrace the timeless Martha's Vineyard coastal lifestyle, with beaches, boating, children's sailing programs, the harbor, ferries, boutique shopping, restaurants, and the charm of Oak Bluffs just minutes away. This exceptional offering presents a rare opportunity to create a private Island retreat in one of Oak Bluffs' most desirable neighborhoods. Buyers are encouraged to conduct their own due diligence regarding building plans and intended use.

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Living is easy in this beautifully maintained 3-bedroom, 2-bath air-conditioned Ranch located just one mile from the center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace, an updated kitchen with granite countertops and stainless-steel appliances, and a dining area with sliders leading to a spacious deck and outdoor shower overlooking the yard. The generous backyard offers plenty of room for gardens, pets, or play. The home features three generously sized bedrooms, including a primary suite with a private en-suite bath. Oak hardwood flooring runs throughout most of the home, and a large rear storage shed provides additional storage and convenience. Set in a peaceful, private location just minutes from beaches, ferries, restaurants, and all that Oak Bluffs has to offer, this property is ideal as a year-round residence, summer getaway, or investment opportunity. A new septic system has been installed. Strong rental history. Easy to show by appointment.

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Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back deck. The second floor has a huge front-to-back primary bedroom, a large landing, full bathroom and two guest bedrooms. Although the property is in need of updates, it will be well worth the effort. There is a ton of potential here. Being offer "as is".

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Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs. Build Your Martha’s Vineyard Dream Home. Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha’s Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a possible future pool. Located in the sought-after Eastville area, where many homes enjoy beautiful water views, this lot offers the potential to capture stunning views of Vineyard Sound and beyond from a thoughtfully designed home. Create a custom residence that embraces all the beauty and lifestyle Martha’s Vineyard has to offer. Enjoy a short walk to Eastville Beach, where you can take in spectacular sunsets, watch the ferries come and go, and experience the charm of island living. Just a short drive away, you’ll have access to everything that makes Oak Bluffs so special — additional beaches, shellfishing, swimming, boating, and the vibrant energy of Circuit Avenue, featuring boutique shopping, diverse restaurants, and convenient ferry service to and from the island via the iconic Oak Bluffs Harbor and nearby ports. This is more than just land — it’s an opportunity to create something truly special. Don’t just dream it — make it reality. Owning a piece of Martha’s Vineyard is an investment in a lifestyle you’ll never regret. Please include a pre approval or proof of funds with offer. Seller is offering a buyers broker consideration.

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Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process. The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development. Subject to the Town of Oak Bluffs' zoning regulations and permitting requirements, the property offers the potential for a main residence and a guest house, with a combined maximum of six bedrooms. Whether you're envisioning a year-round residence, a seasonal getaway, or an investment property, this parcel presents an outstanding opportunity to build in one of Martha's Vineyard's most sought-after communities.

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A Gem of a Marthas Vineyard Camp Meeting House Association Home, 3 Dukes County Ave. Located down from the Oak Bluffs Harbor. A couple house from Sunset Pond. Convenient to Beaches,Harbor, Resturants, Shopping, Dancing Music and walk to and from the Steamship Authority. 2 bedroom,1 queen bedroom 1 full bed and twin bunk room with built in wardrobe and desk bathroom. Bathroom shower bath combo cast iron tub, sink and toilet, Kitchen gally stone and marble counter top with a 2 seat breakfeast nock. vintage wood cabinets, living room with wood burning fireplace. and access to small attic storage space. attach bunk laundry room with washer and dryer brand New hotter on demand 2025. Town hook up to septic 2015 with update electric and isulation for yearround living. Back outside shower tub and sink all with hot and cold runnning water. lots of yard space front sides and back for your privacy. lots of on site parking. beautiful Lawn, lots of trim replace with axec trim. can be purchased with furnishings if needed. a very private campground house with water shed on one side and parking lot on the other and front side. Come make this beauty your own. Being sold as is

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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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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 Oak Bluffs' desirable East Chop neighborhood, this 10,000± sq. ft. R2-zoned property offers an exceptional opportunity to renovate or build new (subject to applicable approvals). The existing two-bedroom, one-bath home is being sold as is. The level lot features a spacious yard and is ideally located just 0.9 miles from the East Chop Lighthouse, 1.3 miles from the East Chop Beach Club, and only minutes from downtown Oak Bluffs, the harbor, beaches, ferries, restaurants, and shops. The property is currently served by a failed cesspool and will require installation of a Title 5-compliant septic system. Buyers are encouraged to perform their own due diligence regarding zoning, permitting, redevelopment potential, and septic requirements.

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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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