Insuring your Property on
Martha’s Vineyard is our Priority.

We Understand the Vineyard.

Owning a home on Martha's Vineyard is a truly special experience, and it comes with some unique aspects that are important to keep in mind. From scenic ferry rides to coastal weather patterns, and from land leases to homeowners associations, every property has its own story.

At Sterling Insurance Group, we’re here to help you navigate these Vineyard-specific details. Whether it's understanding insurance requirements for condominiums, considerations around septic systems and wells, or coverage for short-term rentals, we’ll walk you through your options. Our goal is to provide insurance solutions that suit your lifestyle and reflect the way you use your home.

  • Arial color image of Edgartown, Martha's Vineyard, Turkeyland Cove., with ocean in the distance.

    Edgartown - Turkeyland Cove

  • Color image of a beautiful high value home in Vineyard Haven, Martha's Vineyard, East Chop, overlooking the ocean.

    Vineyard Haven - East Chop

  • Color arial photo of a home in West Tisbury, Martha's Vineyard, Lambert's Cove.

    West Tisbury - Lambert's Cove

  • Color photo of homes in Aquinnah, Martha's Vineyard, dog fish Bar.

    Aquinnah - Dogfish Bar

  • Color photo of a home in Chilmark, Martha's Vineyard, Stonewall Pond - with a beautiful Sunset overlooking the ocean.

    Chilmark - Stonewall Pond

  • Photo of a home in Oak Bluffs, Martha's Vineyard, on Sengekontacket Pond.

    Oak Bluffs - Sengekontacket Pond

  • Image of a home in Vineyard Haven, Martha's Vineyard, on the Lagoon Pond.

    Vineyard Haven - Lagoon Pond

  • Image of a home in Downtown Edgartown, Martha's Vineyard.

    Edgartown - Downtown

  • Image of a home in Aquinnah, Martha's Vineyard, on Menemsha Pond.

    Aquinnah - Menemsha Pond

  • Arial image of homes on Chappaquiddick, Edgartown, Martha's Vineyard.

    Edgartown - Chappaquiddick

  • Image of a stonewall with a home in the distance, located in West Tisbury, Martha's Vineyard, North Road.

    West Tisbury - North Road

  • Image of a home in Chilmark, on Martha's Vineyard, Prospect Hill.

    Chilmark - Prospect Hill