Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers just over 2,800 square feet of living space, plus an additional 700+ square feet of newly finished recreation space above the two-car garage, with its own private entrance and second-floor deck. The inviting first floor is designed for both comfortable living and entertaining, featuring a spacious kitchen with a center island and abundant counter space. The adjacent dining room offers a warm gathering space with a wood stove, while glass doors open to a wood deck and bluestone patio for seamless indoor-outdoor living. Multiple sitting areas, a living room with a gas fireplace, and a private office provide plenty of space to relax or work. Upstairs, two guest bedrooms share a recently updated bathroom, while the spacious primary suite offers a walk-in closet and a large, light-filled bathroom with a soaking tub and tiled shower. The primary bedroom and bathroom feature radiant-heated floors, adding an extra level of comfort and warmth. Additional amenities include a two-car garage and half basketball court, making this a versatile home with plenty of space for guests and entertaining. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this property offers an ideal setting for enjoying all that the Island has to offer.

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Wake up to breathtaking ocean views and the soothing rhythm of waves from this charming two-bedroom oceanfront cottage on East Chop. Set on approximately .21 acres of waterfront property with more than 50 feet of shoreline, this special retreat offers a rare opportunity to own a true piece of the island's coastline. Positioned directly on the water, the cottage captures the beauty of the ever-changing ocean from sunrise through sunset. Inside, the cozy two-bedroom cottage offers an inviting island escape with an intimate connection to its spectacular surroundings. Step outside and experience the salt air, gentle sea breezes, and the unmistakable magic of waterfront living. Whether you're enjoying your morning coffee while watching the boats pass, gathering with family and friends, or simply listening to the waves from your own waterfront property, this is a place designed to create lasting Martha's Vineyard memories. A rare East Chop opportunity—over 50 feet of oceanfront, .21 acres of waterfront land, and an enchanting two-bedroom cottage in an extraordinary setting. Just imagine what you could build with proper permitting on this special lot.

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33 Vineyard Avenue Oak Bluffs offers immense investment and flexible living opportunity with TWO UNITS on a fully irrigated appx 5200 sq ft lot. Fully gut renovated with all BRAND NEW; electric, plumbing, roof, septic system, and structural engineering - highlighted by elevated finishes, classic aesthetics and high quality construction. Supreme location close to downtown Oak Bluffs - two blocks to the Oak Bluffs Arts District, Public Library, MVCMA cottages- just moments to downtown, harbor, beaches and ferries. PRIMARY Two bedroom, two bathroom primary home showcases a light-filled interior, solid wood floors, exquisite beamwork, and elevated finishes. First floor open living with gourmet kitchen, suede-finish Quartz counters, all Bosch appliances, propane range, dining counter, walk-in pantry. Two spacious second floor bedrooms, a skylit bath with glass and stone shower, and a private balcony. Abundant outdoor spaces afford luxury of outdoor living & dining; covered farmers porch and side deck and second story bedroom balcony. ACCESSORY DWELLING UNIT The one bedroom, one bathroom attached Accessory Dwelling Unit offers a fully separate secondary suite - perfect for extended family, staff housing, guest accommodations. Spacious and luxurious open floow plan with stainless Bosch appliances, propane range, quartz counters, solid oak flooring, plus a bedroom and luxurious full bath. Private entrance, additional parking, and separate utilities. Sliding glass doors open to a well appointed deck and adjacent patio.

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Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features Victorian charm, featuring a beautiful stained glass window, painted beam ceilings, wainscoting, and built-in shelves. The second floor has 3 bedrooms, each with its own character, including a generous primary bedroom suite with vaulted ceilings, skylights, a walk-in closet, plus a full bathroom and an extra built-in closet. The 2nd bedroom has an open and airy feel with a vaulted ceiling and a screened porch affording views of the neighborhood. The final room has its own private balcony for viewing the backyard garden oasis. The lower level consists of a finished bonus room, laundry, and a full bathroom with tub and storage area. This home and its established gardens have been lovingly maintained, and its location in a delightful neighborhood of highly sought-after East Chop, gives you all that Martha's Vineyard living can offer. Passed Title V Inspection.

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Hidden Cove Retreat — Water Access, Tennis & Pickleball Set within the sought-after Hidden Cove community, a 65-acre private enclave with direct access to Sengekontacket Pond, this contemporary retreat offers an exceptional Martha’s Vineyard lifestyle. Residents enjoy a private community boat dock, scenic walking trails, pickleball and tennis courts, all just moments from Oak Bluffs and Edgartown. Set on a private, wooded lot, the home blends classic Vineyard character with relaxed coastal living. Cedar siding, an expansive wood deck, screened porch, and outdoor shower create inviting spaces for everything from quiet mornings to long summer evenings and post-beach afternoons. Inside, 1,898 square feet of above-grade living space unfolds around a striking two-sided gas and wood-burning fireplace, with large windows bringing the surrounding landscape indoors. Four bedrooms offer comfortable space for family and guests, while a 512-square-foot finished lower level adds exceptional versatility — currently configured as a media room and home office, with an unfinished portion ready to become a private gym, wine cellar, or whatever you envision. With water access, exceptional community amenities, and a private setting close to the Island’s favorite towns, Hidden Cove offers a rare combination of active outdoor living, privacy, and quintessential Vineyard ease.

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Incredible opportunity for workforce housing, live in one/rent the other, or multi generational family living. Main house has 4 levels of living space. Main floor living/kitchen/dining/full bath and laundry. 2nd floor has two bedrooms and full bath. 3rd floor is a large finished bonus room. The full walkout basement in the main house is finished with private entry, full bath, separate rooms and laundry. The guest house was completely renovated top to bottom in 2023, new everything! Included but not limited to: new kitchen, baths, windows, roof, siding, electrical and plumbing. Landscape around guest house has new stone walls, patio, and pea stone driveway. Guest house is 1 bedroom, 1.5 bath and really is a gem. Main house has been fully rented year-round for years and may need a little TLC for the next owner, a new asphalt roof on main house was installed in 2025. Guest house has been rented via airbnb and has all 5 star reviews. A new septic system was installed in 2018. This property has TONS of potential.

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Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style. First showings 7/12/26.

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Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style. First showings 7/12/26.

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A wonderful opportunity to enjoy island living within one of Oak Bluffs’ most desirable private communities. Set on over 65 acres, Hidden Cove offers the perfect combination of privacy, recreation, and easy Vineyard living. This contemporary three-bedroom and three bath home has been thoughtfully renovated and is offered fully furnished. The modern aesthetic complements the home’s architectural design, with a lofty living room ceiling and a fireplace, and an open kitchen and dining area with multiple glass sliders to the back deck. The back deck is buffered by mature trees, that creates a private setting for outdoor dining and entertaining. The comfortable floor plan features a first-floor primary suite, with two spacious bedrooms, a full bath, and an open loft area upstairs, plus ample eave storage. Offered turnkey with a solid rental history in place. This home works equally well as a personal Vineyard retreat or investment property. Hidden Cove residents enjoy private access to Sengekontacket Pond, an association dock and kayak/boat storage, tennis and pickleball courts, and scenic walking trails. Centrally located between Oak Bluffs and Edgartown, the location offers convenient access to beaches, bike paths, shopping, and dining.

NEW

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Renovated Cape style home in the desirable East Chop neighborhood of Oak Bluffs, offering the perfect combination of coastal charm, modern updates and an exceptional location. This bright and inviting 3-bedroom, 2-bath home features a spacious open floor plan, coastal-inspired décor throughout, and comfortable spaces designed for relaxed Vineyard living and entertaining. A first-floor bedroom provides added flexibility, while the enclosed 120-square-foot sun porch creates a wonderful extension of the living space. Outdoor living shines with a newer mahogany outdoor shower, bluestone patio and beautifully designed walkway, all surrounded by a private setting. An unfinished basement provides approximately 720 square feet of additional space for storage and future possibilities. Walk or bike to Jetty Beach and the East Chop Lighthouse, enjoy the nearby East Chop Beach Club, or stroll to Oak Bluffs Harbor, downtown restaurants and shops. With a proven rental history and a desirable East Chop location, this move-in-ready property is equally suited as a Vineyard retreat, year-round home or investment opportunity. Please include a pre approval letter with all offers and or proof of funds for cash.

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New listing tucked away on a dead end road in Oak Bluffs ~Enjoy the best of Vineyard living from this beautifully renovated Oak Bluffs home, ideally located just a short walk from a private Lagoon beach—perfect for swimming, kayaking, paddleboarding and all your favorite water activities. The inviting living area features a dramatic vaulted ceiling and gas fireplace, creating a warm and spacious gathering space. The thoughtfully designed layout offers a private first-floor primary suite, while the second floor features two additional spacious bedrooms and a full bath. Step outside to a spacious back deck, ideal for outdoor dining, entertaining or relaxing after a day at the beach. Beautifully updated for today’s lifestyle, this home offers a wonderful blend of comfort, coastal living and Vineyard charm.

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Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch — ideal for entertaining on warm summer evenings. A welcoming front porch provides additional outdoor living space. The main level is completed by a gracious primary suite with a full bath and a convenient half bath. The walk-out lower level features two additional bedrooms, a full bath, and laundry. A one-car garage offers excellent storage for your car, kayaks, or beach gear. Perfectly positioned between Edgartown and Oak Bluffs. **Additional bedrooms possible with septic upgrade per BOH.

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