Martha’s Vineyard continues to attract buyers with its timeless coastal charm, limited inventory, and enduring value, continually remaining one of the Northeast’s most desirable markets for both lifestyle and legacy buyers. We sat down with Managing Partner of The Agency Martha’s Vineyard, Paul Pertile, to find out more about this iconic seaside market, known for its historic architecture and undeniable character.
What keeps drawing people to Martha’s Vineyard year after year?
There’s an authenticity to Martha’s Vineyard that is increasingly hard to find. People come here for the beaches and natural beauty, of course, but what brings them back is the sense of place. Each town has its own personality, there’s a real connection to the land and the water, and despite the Island’s profile, it has retained a wonderful understated quality. For many of our clients, the Vineyard is also deeply emotional—it’s where their families have spent summers, where traditions were created, and ultimately where they want to establish something lasting for the next generation.
What types of homes are most in demand right now — classic shingle-style estates, waterfront compounds, or something else entirely?
At the upper end of the market, waterfront properties with exceptional privacy will always command attention because they are inherently scarce. But we’re also seeing buyers place tremendous value on turnkey homes. They want beautiful architecture and a sense of Vineyard character, but they also want modern systems, thoughtful renovations, great outdoor living spaces, pools, guest accommodations, and very little that needs to be done after closing. What’s interesting is that buyers aren’t necessarily looking for the largest house anymore. They’re looking for the right property, one with privacy, location, outdoor space, water access or views, and a lifestyle they can immediately step into.
Which neighborhoods or towns on the Vineyard are seeing the most demand right now?
Edgartown continues to be exceptionally strong because it offers several very different lifestyles within one town, in-town properties where you can walk to restaurants and the harbor, waterfront estates, and larger compounds with privacy just outside the Village.
Chilmark remains highly desirable for buyers seeking acreage, privacy and a more understated Vineyard experience, particularly when there is water access or a view involved. West Tisbury is also compelling for people who want more land and a quieter setting.
What we’re seeing, though, is that sophisticated buyers are increasingly less rigid about town lines. When inventory is limited, an extraordinary property in the right setting can create its own market.
How has the mix of seasonal versus year-round residents shifted, and what’s driving that change?
The Vineyard is still predominantly a seasonal-home market, but the definition of “seasonal” has changed quite a bit. Remote and hybrid work have allowed people who once spent six or eight weeks here to spend several months here, and in some cases transition to living here most or all of the year. That has helped extend the Island’s season and created more year-round activity.
At the same time, housing for the Vineyard’s year-round workforce remains a significant challenge. A large majority of the Island’s housing stock is still devoted to seasonal or occasional use, so there is an important distinction between second-home owners spending more time here and the availability of true year-round housing.
“The buyers who ultimately succeed here tend to be decisive on the things that truly matter and flexible on the things that can be changed. You can renovate a kitchen. You cannot recreate five acres of privacy, a harbor view, or a location you love.”
Paul Pertile
the agency Martha’s vineyard
With inventory as limited as it is, what advice do you give buyers who are eager to find a home?
Preparation matters tremendously in this market. Before the right property appears, buyers should know their financing, understand which elements are absolute priorities and which are negotiable, and have an agent who is actively connected to the market rather than simply watching new listings come online.
On Martha’s Vineyard, some of the best opportunities begin with conversations long before a property is formally marketed. Relationships matter. We are constantly speaking with homeowners, other brokers, and people throughout the community so that when something potentially fits a client, we can move quickly.
I also tell buyers not to wait for a property that checks every box. On an Island with finite land and limited inventory, those properties are extraordinarily rare.
Where (and when) should they be looking? How flexible do they need to be?
They should be looking year-round. There’s a misconception that the Vineyard real estate market begins in the spring, but opportunities can surface at any point, and sometimes the quieter months are when you can have the most productive conversations.
I would also encourage buyers to think first about the lifestyle they want rather than starting with a particular town or zip code. Do you want to walk into Edgartown Village? Do you want acreage and privacy? Are water access and boating important? Do you want a property that can accommodate multiple generations?
Once we understand those priorities, we can often broaden the search considerably.
The buyers who ultimately succeed here tend to be decisive on the things that truly matter and flexible on the things that can be changed. You can renovate a kitchen. You cannot recreate five acres of privacy, a harbor view, private beach access, or a location you love.
Thinking of making a move to Martha’s Vineyard?
Get in touch with Paul Pertile, Managing Partner of The Agency Martha’s Vineyard,
to learn more about the market and available properties.
