Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom tile bathrooms and seamless living both indoors and out. Enjoy water views from the living room, bedrooms and the inviting front porch, perfect for relaxing or entertaining, while the private backyard and spacious back deck provide the privacy many desire. The two-car garage provides a rare in-town convenience, for both parking and storage of your island car and beach gear. The property also boasts impressive rental history, look no further for your next in town purchase - an exceptional, well-rounded offering! Note: This property is also available for purchase with 29 Lagoon Pond Road as a combined offering for $3,295,000.

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Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential. The main residence features three bedrooms and an inviting open-concept floor plan, seamlessly connecting an updated kitchen, living room, and dining area, perfect for entertaining or relaxed island living. Expansive decks extend the living space outdoors, overlooking mature plantings and beautifully established garden areas throughout the property. The home is powered by an owned 5kw solar panel system serving the entire property, offering energy efficiency and reduced utility costs. Agent has a list of detailed upgrades upon request. Adding remarkable versatility, a 900 square foot barn style studio offers space for a home office, artist's studio, workshop, or creative retreat, while a private two bedroom garden apartment, complete with its own separate entrance, provides excellent rental income potential or comfortable accommodations for extended family and guests. Ample parking and move-in ready condition round out this rare combination of location, character, and income producing flexibility on Martha's Vineyard. Please note: the property is located within the Vineyard Haven watershed, and a new or upgraded nitrogen-mitigating septic system will be required.

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This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and heavily wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful neighborhood has seen many improvements and new construction in recent years, making it quite desirable. While being a tranquil neighborhood, you are still in close proximity to the shops and restaurants of Main Street, the Steamship Authority, Museum, and the MV Film Center.

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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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Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and bedroom—perfect for extended family or guests. There are two driveways. The home also features a garage and a finished basement offering excellent storage or future expansion potential. A detached studio at the rear of the property provides wonderful overflow space for a home office, art studio, or guests. The property is only 2/10ths of a mile to the town beach at the end of Grove Ave, and half a mile to the town beach on Owen Little Way. Ready for a new owner's vision and updates, this well-located property presents an exceptional opportunity to enjoy the convenience and charm of this desirable neighborhood. This property is being offered "as-is."

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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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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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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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Classic Vineyard Charm Meets Effortless Island Living! Brimming w/original character and timeless appeal, this delightful 3-bedroom, 3-bath home w/1BR, 1BA ADU offers a perfect blend of historic charm + thoughtful updates in one of Martha’s Vineyard’s most sought-after communities. Original hardwood floors flow throughout, setting a warm + inviting tone, while lovingly preserved original details reflect the home’s authentic Vineyard heritage.The renovated kitchen strikes a beautiful balance between modern convenience and classic charm, complemented by 1st fl bath w laundry + claw foot tub, one fully renovated bath and one updated bath up. Full basement provides ample storage+laundry, a two-car garage, grassy yard..Above the garage, a charming one-bedroom apartment features vaulted ceilings and hardwood floors, updated kitchen/bath + large composite deck,offering ideal space for guests or rental income. Perfectly situated a short distance to ferry, town amenities, beaches. Excellent rental history! Move in ready! Some furnishings may be available for purchase. Living area not measured, sq footage reported is based on property records. Buyers to perform their own due diligence to cerify accuracy.

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