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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3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 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 your mortgage. The main house features a stunning solarium or sunroom, a cheerful efficient kitchen, and a sweet living room anchored by a beautiful stone fireplace. The main house has been emptied out 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, radiating a clean and bright atmosphere. Situated on a spacious lot, a 4-bedroom septic design is currently being finalized by Sourati Engineering (buyer to be financially responsible for the upgrade). Other features include oak floors, two decks for outdoor enjoyment, a vintage garden shed, and a full dry basement for additional storage.

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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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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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Set on a private, wooded lot in Vineyard Haven, this recently built home offers a rare combination of immediate enjoyment and exceptional future potential. Built in 2021, the thoughtfully designed 1-bedroom residence features a bright, modern interior, energy-efficient solar panels, and a peaceful setting surrounded by nature. The true value lies in the property’s remarkable expansion possibilities. A 6-bedroom septic system is already installed, allowing for the future construction of a substantial 5-bedroom main house while retaining the existing home as a guest house, rental property, or secondary dwelling. The lot also has ample room for a pool and outdoor entertaining spaces, creating an ideal Vineyard compound opportunity. Ideally located just over a mile from both the West Chop Club and Mink Meadows Golf Club, as well as downtown Vineyard Haven, the property offers convenient access to golf, boating, dining, shops, and ferry service while still maintaining a quiet, tucked-away feel. Nearby walking trails and conservation land further enhance the property’s unique sense of privacy and connection to the outdoors. Whether you are seeking a turnkey Vineyard retreat, an investment opportunity, or the perfect canvas for a future estate, this offering presents incredible flexibility in one of the island’s most sought-after areas.

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This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other. Many attractive features include hardwood floors and Indian tile throughout, a large inviting mahogany deck off the front of the house overlooking a koi pond, fully owned solar panels that have covered the electrical costs for the past five years, a nitrogen reducing septic system, a full unfinished walkout basement and a large detached shed. This property is deed restricted to year-round housing and is part of the Daggett Ave. Homeowner’s Association which has a ninety-nine-year ground lease agreement.

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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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This cared for contemporary is located in a mature neighborhood abutting Sheriff's Meadow. It has a three bedroom, one bath reverse floor-plan design that captures ample natural light from a serene park-like setting. Hardwoods and ceramic tile flooring, A/C mini-split heat-pumps, a rear balcony deck, outdoor shower, and a delightful terraced patio compliment this new opportunity. *Seller is offering a closing credit of up to $50,000.00 toward the required nitrogen septic system upgrade.

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NESTLED ON AN OVERSIZED LOT in a highly convenient Vineyard Haven location, this classic 1972 center-entrance Colonial offers timeless charm and exceptional potential. Inside, an inviting open-concept living space is anchored by a wood-burning fireplace, while soaring vaulted ceilings over the dining area and kitchen create an airy, light-filled atmosphere ideal for gathering with family and friends. The thoughtfully designed floor plan features a desirable first-floor primary suite complete with an en suite bath and a private screened sitting porch—the perfect retreat for morning coffee or quiet summer evenings. Upstairs, two additional bedrooms share a full bath and are connected by an open balcony overlooking the main living area below, adding architectural interest and a sense of openness throughout the home. Outdoor living is equally inviting, with a spacious deck leading to the backyard and providing ample room for entertaining, dining al fresco, or simply enjoying the island breeze. Ideally situated with easy access to the Lagoon, downtown Vineyard Haven, beaches, shops, restaurants, and the Steamship Authority, this property presents an outstanding opportunity to create your own Martha’s Vineyard getaway or year-round residence. Offered as is, this home is ready for its next chapter and the vision of its new owner. Note: Septic will need to be brought into compliance with current regulations.

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Great Location! Cape Cod style year round home well maintained on a private dead end road close to Tashmoo Landing. Open concept kitchen to dining room. Three bedrooms and one full one half bath. Full clean basement adds additional 768 SF, with egress walkout door and large windows letting in sunshine. Includes two lots. The house has two propane monitors, one on the first floor and one in the basement. It has two mini splits for cooling as well as window A/C units on the second floor. Additional backup heat is electric baseboard. New roof 2025. The property is in the Tashmoo Watershed and will need an enhanced system installed by the buyer. This is a fantastic area just minutes to Tashmoo landing, tennis, pickleball, fishing, kayak storage, kayaking, and close to Mink Meadows Golf, Downtown Main Street and the year round Ferry Terminal.

NEW

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Vineyard Haven- Walk to the Ferry from this 2 bedroom condo with pool. Located near the downtown area a desirable place for a rental property or live there year-round. The property features common grounds, picnic tables, and seating by the pool to relax and enjoy the outdoors.

NEW

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