Centrally located at the top of Daggett Avenue, just blocks from the harbor and town beach, sits this charming turn of the century Cape. The covered porch graces the front of the home welcoming friends and family. Light spills into the living room that stretches across the front of the house featuring vintage architectural details and the warm patina of newly refinished Carolina pine floors. Continue through the framed wide entrance to the dining room featuring a built-in corner China cupboard. The sweet country kitchen has been updated with new appliances and flooring. The laundry with new large capacity washer and dryer and shower bath is conveniently located on the first floor. A central hall on the second floor opens to four corner bedrooms and a full bath. The walk-up attic provides plenty of storage. Step into the newly landscaped yard with a new driveway and off-street parking. Other improvements include a new electrical service and wiring, dual heat/AC mini splits for the entire house, new Rothe fuel tank, newly shingled exterior and gutters, and the requisite outdoor shower. The windows were replaced by the previous owner.

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Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers require a deed restriction that prevents the property from ever being used as a bike rental shop. Seize this unique chance to establish your business in a highly visible area.

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Nestled on a quiet street just moments from the heart of Vineyard Haven, this well-maintained 4 BR, 3 BA home offers a winning blend of comfort, privacy, and classic island appeal. The sun-filled main level features an open-concept living area flowing seamlessly into a bright, updated kitchen with center island, ideal for everyday living and casual entertaining. Two 1st floor bedrooms and a full bath provide excellent flexibility for guests, home office space, or convenient one-level living, while upstairs offers two spacious en-suite bedrooms designed for privacy and relaxation. Outdoor living shines with a deck overlooking the yard, plus a lower-level bonus with laundry, storage, and workshop potential. Peacefully set yet close to it all, enjoy easy access to public beaches, Tisbury School, and just 0.5 miles to Main Street Vineyard Haven with shops, dining, and ferry access. Perfect as a year-round residence, second home, or investment opportunity—this property checks all the boxes!

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Discover the opportunity to make this spacious Vineyard Haven home your own, ideally located on the desirable lower end of Lambert’s Cove Road. Just across from Pilot Hill Road and approximately one mile from the pristine shores of Lambert’s Cove Beach, this well-positioned property offers a wonderful blend of convenience, privacy, and potential. Spanning three levels, this charming home offers over 2,000 square feet of living space on a generous 0.26-acre lot. The thoughtful layout includes four bedrooms, with the primary bedroom conveniently located on the first floor and three additional bedrooms on the second floor. The finished lower level provides even more versatility, featuring a bonus bedroom along with additional finished rooms that can be used for guests, a home office, recreation, or other living needs. Painted wood floors and inviting living spaces showcase the home's enduring character and timeless appeal. Outside, the property features ample parking, with additional parking and open space both above the home and to the rear of the property, offering plenty of room for entertaining, recreation, or future enhancements. An approved six-bedroom septic system presents an outstanding opportunity for expansion and allows the next owner to maximize the property's potential. Whether you're looking for a year-round residence, a seasonal getaway, or an investment opportunity, this property is ready to be enjoyed today while offering the space, flexibility, and possibility to create something truly special for the future.

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Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful renovation, the property offers an excellent foundation to create long-term value. An attic and basement offer generous storage and space for updated mechanical systems, while an interior staircase provides the opportunity to reconnect the two residences into a single-family home if desired. The seller will provide a $50,000 credit at closing toward the installation of a new septic system.

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Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this beautifully maintained three-bedroom home combines distinctive character with thoughtfully updated spaces, modern comforts, and a peaceful residential setting. The home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An updated custom kitchen by French Accent, with a walk-in pantry, opens to the dining area, while a first-floor powder room with laundry adds everyday convenience. A substantial 2010 addition expanded the home with a spacious, light-filled living room and a generous second-floor primary suite. Two additional bedrooms and a full bath comfortably accommodate family and guests. Outside, a large deck overlooks landscaped grounds with native plantings, stonework, and a fire pit gathering area. A full walk-out basement is perfect for both a work space and storage. Whether you’re searching for a year-round home, vacation retreat, or investment opportunity, this property offers something increasingly rare on Martha’s Vineyard: a home with genuine character, generous living space, and the comforts of modern living.

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HOUSE + APARTMENT NEAR LAGOON! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This clean and bright, move-in ready property features a 3 BR, 1 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset the mortgage. The main house, featuring a wonderful sun-room, a cheerful efficient kitchen, and a comfortable living room anchored by a beautiful stone fireplace, has been emptied and awaits the new owner's touch (please refer to images showing digital staging). Both the main house and the apartment have been freshly painted throughout. Situated on a spacious corner lot, and located a short distance to down town and public Lagoon access, this property is a super value. SELLER WILL CREDIT BUYER THE COST OF A BRAND NEW 4BR SEPTIC SYSTEM AT CLOSING.

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MOTIVATED SELLER. Please note substantial PRICE CHANGE. Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs to lower level and garage. 3 Bedrooms 2 full baths on the 2nd floor. Attic. Many windows. High Ceilings. Hardwood Floors throughout. Small front porch to entryway on the first floor level. Lower level above ground office/bedroom with half bath and private entrance from the exterior. Built in Garage and on site parking area. Propane FHW Heat pump A/C. Propane HW Heater. Sited on .23 acres bordered by grassy areas on the side and front of the property. Residential R10 zoning. Small Association. Easy access to Main St, Ferry, Shops, Restaurants, Schools, the Amphitheatre, the Tashmoo Overlook and a direct route to Up Island Towns. Town Water, Title V Four Bedroom Septic System. With the transfer of this property the Septic will need to be upgraded to a Nitrogen reducing Septic system. Owner to provide newly engineered approved septic design when completed.

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Set within an established island community, this spacious condominium offers tall ceilings, an open floor plan, abundant windows, and wonderful natural light, with views toward the surrounding woods. Its flexible layout and exceptional community amenities make it an inviting choice for year-round living or a seasonal Vineyard retreat. The first floor features open kitchen, dining, and living areas centered around a fireplace, plus a versatile study and full bath. The second floor offers two private bedroom suites, each with its own full bath, along with conveniently located laundry. An unfinished basement provides generous storage and future possibilities. Outdoor living includes a wraparound deck with wooded views, an outdoor shower, garage, additional storage, and established perennial plantings. Residents enjoy a heated pool, tennis courts, approximately 500 feet of Vineyard Sound beach, and a private boat landing—offering easy access to the water and the best of island living. *Located within the Tashmoo Watershed area.

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END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation and a more single-family feel—along with a one-car garage and additional storage for bikes and beach gear. Mature plantings enhance the sense of privacy. Inside, the layout is both functional and inviting. The kitchen features granite countertops and high-end appliances and opens seamlessly to the dining area and private deck overlooking peaceful woodlands. The living room, anchored by a wood-burning fireplace, offers a warm and comfortable gathering space, while a first-floor bedroom and full bath provide flexibility for guests or a home office. Upstairs, the primary bedroom includes a private en suite bath with both a soaking tub and separate shower, while the second bedroom is served by a nearby full bath—providing comfortable accommodations with good separation for family and guests. Recent improvements include a new 30-year roof and gutters. Tashmoo Woods is known for its exceptional amenities and ease of ownership, including access to association tennis courts, a heated pool, playground, basketball court, and a private dock on Lake Tashmoo for kayaking and paddle-boarding, along with association beach access on the Vineyard Sound. The community also provides maintenance of roads, building exteriors, landscaping, snow removal, and all shared outdoor spaces and facilities—offering a low-maintenance, turnkey lifestyle ideal for seasonal or year-round living. Mink Meadows Golf Club is just moments away. Seller will offer a credit at closing for septic upgrade. Several images include virtual staging.

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Welcome to 7 Fawndale Road in Vineyard Haven. Located just one mile from Main Street, this delightful property offers comfortable living and flexible spaces. The main level features offers single-story living featuring an open living and dining area with wood beams, a bay window, partial cathedral ceiling, skylight, and wood floors. The galley-style kitchen offers plenty of cabinetry and counter space, while sliding doors open to a partially covered deck overlooking the backyard—an inviting spot for outdoor dining and relaxing. The primary bedroom features an en suite bath, while two additional bedrooms share a hall bath. A unique finished stairway provides easy access to the expansive attic, offering additional storage and potential. The partially finished, walk-out lower level adds even more versatility, with a studio-style living area, alcove bedroom, kitchenette, and full bath. The remaining portion of the lower level houses the utilities and provides ample storage. The backyard is a blank canvas, ready for you to create an outdoor living space of your own. Conveniently located close to town, the ferry, and all that Vineyard Haven has to offer, this inviting home is ready for you to make it your own.

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Some properties you visit, and some properties you experience. Tucked behind mature gardens and a lush natural landscape, 41 Renear Street is a hidden Vineyard treasure — a classic 1927 cottage where timeless character, village convenience, and the beauty of the outdoors come together. Set on a generous .26-acre R10 parcel, this three-bedroom home offers the warmth and craftsmanship of an earlier era, with original architectural details, beautiful wood floors, classic moldings, built-ins, a fireplace, and sun-filled rooms framed by garden views. Thoughtfully cared for over the years, the home retains the authentic charm and easy elegance that make historic Vineyard cottages so beloved. The heart of the home is its connection to nature. Oversized windows invite the gardens inside, filling the living spaces with natural light and views of established plantings, stone pathways, and quiet outdoor sitting areas. Whether enjoying morning coffee overlooking the gardens, gathering by the fireplace, or relaxing among the private outdoor spaces, the property offers a sense of peace rarely found so close to town. With approximately 1,284 square feet of living space, three bedrooms, one and a half baths, an unfinished basement, and outdoor garden shed, the property provides comfortable year-round living today with opportunities to thoughtfully enhance or expand in the future. Just moments from Main Street, Vineyard Haven Harbor, restaurants, shops, beaches, and ferry access, 41 Renear Street offers the best of village living — a private garden sanctuary with the soul of old Martha’s Vineyard. NOTE: An enhanced Title V system will be required wihtin 6 months of purchase.

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