Tucked away on 4.5 private acres, this West Tisbury retreat offers a 3-bedroom main home plus a private guest cottage—outdoor showers, peaceful setting, and just minutes to beaches, towns, and island adventures.
Welcome to 40 Orchard Road, an exceptional West Tisbury retreat offering the rare combination of privacy, space, and classic Martha’s Vineyard charm. Set on 4.5 lush acres of rolling woodland and open lawn, this peaceful escape is ideal for families or friends seeking room to spread out while remaining conveniently close to the island’s beloved beaches, village centers, and dining spots.
This property features a beautifully appointed main residence along with a separate guest sleeping cottage, creating the perfect setup for multi-generational groups or families traveling together who appreciate both connection and personal space. (A second guest house on the grounds is rented separately and maintains full privacy.)
The main house offers three comfortable bedrooms and two and a half baths, thoughtfully designed for relaxed Vineyard living. Open and sun-filled living spaces flow naturally for easy gathering after days at the beach or exploring town. The well-equipped kitchen supports casual breakfasts and memorable family dinners, while the inviting living area provides the ideal spot to unwind with a book, games, or movie nights. Step outdoors to enjoy the island tradition of an open-air outdoor shower, a favorite ritual after sandy beach days.
Just steps away yet wonderfully private, the guest cottage serves as its own tranquil escape. Featuring one bedroom, a full bathroom, and its own outdoor shower, this charming space is perfect for visiting grandparents, a couple traveling with your group, or anyone seeking a little extra serenity during their stay.
The expansive grounds deliver something increasingly rare on the Vineyard: true seclusion paired with outdoor freedom. Children can explore, adults can relax with morning coffee or evening cocktails under the trees, and everyone can savor the unhurried pace that defines the island’s quieter side.
From this central West Tisbury location, guests are perfectly positioned to explore the best of Martha’s Vineyard. Enjoy easy access into Vineyard Haven’s ferry terminal, shops, harborside dining, and art galleries, or venture toward the island’s renowned beaches, nature trails, and conservation areas. Farm stands, coastal bike rides, and sunset dinners are all part of the nearby island lifestyle waiting just minutes from your doorstep.
Whether you're envisioning slow mornings in the garden, family game nights under the stars, outdoor showers after beach days, or peaceful evenings surrounded by nature, 40 Orchard Road offers the space, comfort, and Vineyard authenticity that elevate a simple vacation into a truly unforgettable island retreat.
