About Sterling Insurance Group | Independent Insurance Agency, Martha's Vineyard, MA
Sterling Insurance Group is an independent insurance agency serving Martha’s Vineyard, Nantucket, Cape Cod, and Boston, Massachusetts. We focus on helping clients understand and explore coverage options for homeowners, flood, auto, and commercial insurance with reputable insurance companies.
Martha's Vineyard Independent Insurance Agency — Coastal & Island Property Experience
Finding the right insurance on Martha's Vineyard isn't like buying coverage on the mainland. Coastal exposures, seasonal properties, and a shrinking pool of carriers willing to write on the island make it genuinely hard to know where to start — or whether what you have is enough.
Sterling Insurance Group is an independent insurance agency based in Vineyard Haven. Because we're independent, we're not tied to a single company. We work with multiple insurers that are familiar with island and coastal properties, which gives us a wider view of what's available in a market where options can be limited.
Our job is to help you understand your options, connect you with carriers that may be able to cover your property or business, and make the process as straightforward as possible.
Insurance Coverage Options for Martha's Vineyard Homeowners & Businesses
Homeowners & Coastal Property Insurance
Coverage for primary residences, seasonal homes, and high-value properties — including coastal and waterfront locations that many standard carriers no longer write.
Flood Insurance on Martha's Vineyard
Separate flood coverage through private carriers or the National Flood Insurance Program (NFIP). Many lenders require it, and some properties benefit from it even when it's not mandatory.
Auto Insurance
Personal auto coverage for island residents, including year-round and seasonal vehicles.
Commercial & Business Insurance
Coverage options for local businesses, professional offices, and organizations, including general liability, commercial property, and business owner's policies.
Umbrella & Excess Liability Coverage
Additional liability protection that can sit above your home or auto policies for broader peace of mind.
How Our Insurance Process Works
Working with an independent agent is different from going directly to a single insurance company. Here's what that looks like with Sterling:
We start by getting to know your situation.
We ask about your property, your business, or what you're looking to protect — not to upsell you, but because the right coverage options depend on the details. A beachfront home in Aquinnah has different considerations than a rental property in Oak Bluffs.
We identify which carriers and policy types may apply.
Based on what you share with us, we can point you toward the insurers and policy structures that are most likely to be a fit for your situation. Availability depends on each carrier's underwriting guidelines, which we'll be upfront with you about.
We submit your information and present your options.
When you're ready to move forward, we gather what the carriers need, submit it on your behalf, and walk you through what comes back — pricing, coverage structure, and anything notable in the terms.
We stay available after the policy is in place.
Questions about your bill, your policy documents, certificates of insurance, or what to do after an incident — we're here for that, too.
Serving Martha's Vineyard, the Cape & Greater Boston Area
Our main office is at 31 Beach Road, Unit 203, in Vineyard Haven, Massachusetts. We work with clients across the island — Vineyard Haven (Tisbury), Edgartown, Oak Bluffs, West Tisbury, Chilmark, Menemsha, and Aquinnah.
We also assist clients with properties and exposures connected to Nantucket, the Cape, and the greater Boston area. And because many of our island clients have homes, vehicles, or businesses in other states — Connecticut, Virginia, New Hampshire, Maine, Rhode Island, New York, New Jersey, Maryland, Florida, California, and beyond — we can often help bridge those needs where carriers and underwriting guidelines allow.
Wherever your property is, if you have a connection to Martha's Vineyard, there's a good chance we can help.
Our Carrier Relationships & Market Accessiders
Over time, we've built working relationships with a range of insurance companies that understand the unique dynamics of coastal and island properties. That means we know which markets are actively writing on Martha's Vineyard, which ones have appetites for high-value or waterfront homes, and which carriers tend to work well for local businesses.
That said, every insurer makes its own underwriting decisions. Having access to a market doesn't guarantee placement — but it does mean you're working with an agency that knows where to look, especially when standard carriers aren't an option.
How We Communicate & What to Expect
When you reach out to us, you'll hear from a licensed team member — not an automated queue. We're available Monday through Thursday, 10am–5pm, and Friday, 10am–3:30pm. Text and email work, too.
If you have a question about your policy, need a certificate of insurance, or want to understand what your current coverage actually covers — that's exactly what we're here for.
The content on this page is for general informational purposes and doesn't replace the terms of any insurance policy. Coverage availability, pricing, and eligibility are always determined by the insurer — not by anything on this website. Coverage cannot be bound, changed, or cancelled through this site, by email, or by voicemail. To make any changes to your coverage, please speak directly with a licensed Sterling Insurance Group agent and refer to your actual policy documents.
Questions? Call or text (508) 687-2750 or email ask@insurewithsterling.com