TISBURY MARKETPLACE offers an active and well-established setting for this beloved eatery. The year 'round destination hub draws proven foot traffic and a healthy commercial environment. Rocco’s Pizzeria anchors the corner of the water view plaza with sustained history and a devoted following. Open throughout every season, the operation inhabits two connecting condo units as well as an additional second floor al fresco dining area. Front facing exterior areas include the raised first level outdoor deck seating as well as a stairway accessing the rooftop dining area with views of Tisbury Harbor and the Lagoon. Rear access provides an easy delivery entrance directly into the kitchen, storage and a rear second staircase up to the outdoor dining area. Permits for seating (81) and beer and wine licenses are transferable with application and approval. Sale package includes commercially appointed kitchen and food prep appliances, fixtures and furnishings. Full inventory and equipment lists available. With 20 years of successful service and consistent offerings no matter the season, it’s easy to envision ownership!

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Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready for your plans or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or future investment. An easement is being established along the existing driveway to provide access to the residence while allowing the buildable lot to remain an independent parcel. Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this rare offering combines the convenience of in-town living with a peaceful residential setting. The beautifully maintained home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An updated kitchen with walk-in pantry opens to the dining area, while a first-floor powder room with laundry adds 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 beautifully landscaped grounds with native plantings, stonework, and a fire pit gathering area. A detached studio provides flexible space for an office, art studio, or hobbies, while the full walk-out basement offers abundant 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 move-in-ready home paired with a separate buildable lot, all in one purchase.

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Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect after a day at the beach. Also on this level is a comfortable guest bedroom with peaks of the harbor, a stylish full tile bath with a glass-enclosed shower, a cozy living area, and washer/dryer for convenience. Upstairs, cathedral ceilings and a gas fireplace create an inviting open-concept living space. The gourmet kitchen is outfitted with sleek Bosch appliances, a large center island ideal for entertaining, and an adjoining dining area. Enjoy panoramic water views of the harbor, passing ferry boats, and Vineyard Sound from the entire second floor, or step out onto your private deck, perfect for alfresco dining or morning coffee. Just steps from your door, a private path leads to the association’s sandy harbor beach where you can store your kayak or launch your boat. This condo also includes a dedicated parking space and an enclosed storage area under the house ideal for bikes, beach gear, or seasonal items. With easy access to downtown shops, restaurants, ferry terminal, and local beaches, this condo offers the ultimate combination of luxury, convenience, and island charm. A rare opportunity for carefree coastal living on Martha’s Vineyard.

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Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect after a day at the beach. Also on this level is a comfortable guest bedroom with peaks of the harbor, a stylish full tile bath with a glass-enclosed shower, a cozy living area, and washer/dryer for convenience. Upstairs, cathedral ceilings and a gas fireplace create an inviting open-concept living space. The gourmet kitchen is outfitted with sleek Bosch appliances, a large center island ideal for entertaining, and an adjoining dining area. Enjoy panoramic water views of the harbor, passing ferry boats, and Vineyard Sound from the entire second floor, or step out onto your private deck—perfect for alfresco dining or morning coffee. Just steps from your door, a private path leads to the association’s sandy harbor beach, where you can store your kayak or launch your boat. This condo also includes a dedicated parking space and an enclosed storage area under the house ideal for bikes, beach gear, or seasonal items. With easy access to downtown shops, restaurants, ferry terminal, and local beaches, this condo offers the ultimate combination of luxury, convenience, and island charm. A rare opportunity for carefree coastal living on Martha’s Vineyard.

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This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical, evidenced by the well-appointed kitchen which offers direct access to the rear deck for an eat-in or eat-out option. With separate finished living quarters on the garden level, the home easily accommodates guests and multi-generational living. The expansive deck invites morning coffee, summer gatherings, and peaceful evenings surrounded by nature. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. You are just moments from the harbor, shops, and ferry, and yet this property also offers seclusion and privacy - this is a rare combination in this price point.

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Prime commercial opportunity in Vineyard Haven, Martha’s Vineyard’s vibrant year-round community! This 2,614± sq. ft. corner commercial condominium in popular Woodland Center Marketplace —one of the largest in a well-managed association—offers outstanding visibility and versatile space. Currently configured for a tile and flooring business, Unit 8 features a showroom with office area, a workroom/warehouse storage section, kitchenette, and half bath. The flexible layout easily adapts for retail, design, or professional use. With ample parking, professional management, and a high-traffic location, this property is a standout investment. The successful Karpet Kare tile and flooring business is also available separately for those seeking a turnkey operation in a thriving commercial hub.

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Minutes to downtown and the ferry, this updated year-round home checks every box buyers are asking for right now: space, flexibility, and a move-in ready setup in a highly convenient location. 3 bedrooms, 4 bathrooms, and over 3,000 sq ft of living space, including a private lower-level apartment ideal for guests, extended family, or income potential. The main level offers hardwood floors, a renovated kitchen with granite countertops and stainless appliances, and an open living/dining area with fireplace that flows effortlessly for everyday living and entertaining. The primary suite features a private bath and balcony access. The lower level adds a second living/media room, fireplace, laundry, and direct access to the garage. So many upgrades are already done: new roof (2019), 7 mini-splits, updated kitchen and baths, new windows and doors, plus a bright enclosed sunroom. Outside, enjoy a fenced yard, multiple balconies, outdoor shower, firepit, and grilling area, along with a detached garage for boat or vehicle storage. Set on a quiet cul-de-sac with access to 109 acres of trails just beyond your doorstep. Waterloo Biofilter septic system in place (no upgrade required). Title V passed. Water line tested and passed. 4,568 gross sq ft. A rare combination of size, condition, and location this close to town.

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Tucked away on a quiet cul-de-sac, this beautifully maintained multi-family property offers the perfect blend of privacy, flexibility, and convenience. Built in 2020, the home encompasses 2,884 square feet of thoughtfully designed living space, featuring a total of 5 bedrooms and 4 full bathrooms. The walkout lower level is a fully permitted Accessory Dwelling Unit (ADU), creating an ideal opportunity for multigenerational living, guest accommodations, or rental income while maintaining privacy between living spaces. Situated on a generous 15,593-square-foot lot, the property offers abundant outdoor space with exceptional future potential. A six-bedroom septic system is already in place, providing flexibility for expansion. The home could continue to function as a single-family residence with the addition of a detached guest house/ADU, or it could remain a multi-family property with the potential to add a freestanding ADU, subject to Martha's Vineyard Commission and Zoning Board of Appeals (ZBA) review and approval. Ideally located just a short distance from downtown Vineyard Haven, the Lake Tashmoo boat landing, and town tennis courts, this property combines peaceful cul-de-sac living with convenient access to the island's amenities and recreational opportunities. Note: The property is located within the Tashmoo Watershed District and is equipped with a NitROE wastewater treatment system.Note: property is located in the Tashmoo Watershed District, but has a NitROE system.

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Charming Property in the Heart of Vineyard Haven. A rare opportunity to own a beautifully maintained main house and guest house nestled on a generous 25,100 square foot lot in Tisbury. This special offering combines charm, privacy and versatility, surrounded by a stunningly landscaped yard with irrigation. The main house has three full bedrooms and two full bathrooms. The one-bedroom and one-bathroom guest house has a kitchen, loft, private deck, and outside shower. Enjoy easy access to the town's vibrant waterfront, boutique shops, local restaurants, cafés, galleries, and the ferry terminal, making it an ideal location for both year-round living and seasonal escapes. Per the Board of Health, there is no land area restriction; therefore, if a new septic system can be installed without variances, the approved bedroom capacity may be increased. The main house and the guest house both have their own basements with a washer and dryer and plenty of storage. The Main house has a very clean, large/dry area for storage.

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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 the perfect blend of convenience, privacy, and potential. Spanning three levels, this five-bedroom, two-and-a-half-bath home offers over 2,000 square feet of living space on a generous 0.26-acre lot, providing an exceptional combination of space, flexibility, and future possibilities. 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 endless possibilities for entertaining, recreation, or future enhancements. An approved six-bedroom septic system presents an outstanding opportunity for expansion, allowing the next owner to maximize the property's full 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 opportunity 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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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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