It’s been some two centuries since the roads of Martha’s Vineyard were traversed by horse-drawn carriages, whaling was the dominant industry and the Island was controlled by the Peases, Mayhews and Gosnolds.

These days, other families are the power players of downtown Edgartown, Oak Bluffs and Vineyard Haven.

It’s a challenging — and profitable — time to own commercial properties on the Island. An analysis of publicly available assessors records by the Gazette found that from 2019 to 2023, assessed property values on the main streets in the three down-Island towns rose by 40 per cent in Edgartown and Oak Bluffs, and by 19 per cent in Vineyard Haven, respectively.

All told, that’s a whopping $272.4 million worth of real estate on the main streets of the three towns, their history, ownership and architectural character as varied as the towns themselves. The highest values are found in Edgartown, while the lowest are in Vineyard Haven, with Oak Bluffs in the middle.

For its analysis, the Gazette examined land values, building values and total values for more than 100 properties that house Main street businesses, including landmark buildings such as the Capawock Theatre in Vineyard Haven, Giordano’s restaurant in Oak Bluffs, the Richard Hotel in Edgartown and many, many more. We also interviewed the down-Island towns’ largest commercial landlords as well as several property owners who operate businesses in the buildings they own.

Edgartown's Main Street has the highest real estate value of the down-Island towns. — Ray Ewing

A map and key containing details about each property accompany this story.

Increasingly, commercial buildings are held by trusts and limited liability companies rather than families. Where possible, the Gazette has listed some or all of the names of individuals associated with these entities.

In part the project set out to answer the question: who, exactly, owns the downtowns?

The analysis found that while ownership is varied and covers a wide spectrum, certain family names jumped out of local assessor’s databases, among them Hall, Courtney and Hajjar. Some have main street real estate holdings that date back for many decades, while others are relative newcomers to the downtowns.

And beyond all the names and numbers, a picture emerges of two Martha’s Vineyard main streets. One is still controlled by the old guard, their way of doing business rooted in the old ways.

But a new guard is coming in too, bringing with it new wealth and also fresh ideas, including about the responsibility to the community that comes with being a property owner.

Bunch of Grapes bookstore in Vineyard Haven has changed locations over the years. — Ray Ewing

More than once over the years, the vitality of main streets has been a point for discussion and concern. In 1990, town leaders in Edgartown and Vineyard Haven convened separate summits, alarmed at the growing commercial sprawl on the outskirts of their town. Anchor businesses were leaving main street and few were moving in to take their place.

But that would change again. Today the three down-Island main streets are vibrant, with new owners and businesses such as Larkin Stallings at the Ritz on Circuit avenue taking their place alongside longtime anchors such as Bob Pacheco at Reliable Market and Annie Schwenk at Laughing Bear. In Edgartown Andrew and Sarah Aliberti, longtime owners of Summer Shades, bought their own building in 2005, then the building next door six years later. Anne and Charles Hajjar have created a strong footprint with their boutique hotels, including The Richard on Main street.

There are generational shifts too. Geno Courtney’s two sons are leading restaurateurs and businessmen in Edgartown. In Vineyard Haven, Emily Bramhall’s daughter, Ty Sinnett, recently opened a store, The Seven Sisters, in a Main street building Emily owns near where she ran her own business Bramhall and Dunn for a quarter century. A fourth generation of Giordanos now run the popular Oak Bluffs Italian-American eatery started by Edwardo and Mary Giordano in the 1930s.

daRosa's on Circuit avenue has stood the test of time. — Ray Ewing

Still, there are few signs that radical change will come to the main streets anytime in the near future. Although the real estate market has been active, downtown properties don’t come up for sale often. It varies slightly by town — in Oak Bluffs and Vineyard Haven some longtime owner/operators who bought their buildings 30 and 40 years ago are getting older and may be interested in selling. Edgartown’s main street includes many long-term players, including the town, the Preservation Trust and two banks, Rockland Trust and Martha’s Vineyard Bank. The Courtneys and the Halls are dominant landlords who appear to be content to hold on to what they have, making the opportunity for new investment limited.

It’s perhaps an irony that the Hall family name was the gold standard on Martha’s Vineyard in the first half of the 20th century, owing to the late Alfred Hall, who was a widely admired Island businessman and philanthropist. But that changed over the years, and today the family reputation in Main street real estate has grown tarnished, with more than one building in poor repair, vacant or both.

In an interview with the Gazette, Benjamin Hall Jr. claimed town policies and procedures have posed obstacles, pointing to limits on wastewater capacity and other issues.

“The economic vitality of the downtowns is not just the responsibility of the land owners — it’s also the responsibility of the townships. They need to . . . not to discourage people from doing business,” he said.

At the beginning of the summer, Rosewater Market and Edgartown Lululemon franchise owner Christopher Celeste penned a provocative commentary for the Gazette, describing sadness at what he called “an acceleration of profit-driven development conveniently described in a narrative of faux historical stewardship.”

Christopher Celeste owns multiple properties in Edgartown. — Jeanna Shepard

“When we buy something, we think of it as ours. It’s a particular issue in America, this sense of ownership,” he wrote.

In an interview, Mr. Celeste elaborated on the idea.

“When you buy property within a community, you belong to something, it’s not just that something belongs to you,” he said.

“If we don’t care for the Main street, we lose a central place. I think of it as the heartbeat. Blood is flowing all through your body. The stronger the main street, the stronger the overall community.”


For this project, the Gazette focused on the central business districts in each town. In Edgartown, this included the commercial properties from the top of Main street at Pease’s Point Way to Dock street; in Oak Bluffs, from the foot of Circuit avenue to the intersection with Kennebec avenue; and in Vineyard Haven, from the Beach street intersection to Drummer lane.

What follows are brief profiles and interviews with six main street owners.

Holly Pretsky, Noah Asimow, Landry Harlan, Emily Gajda and Halina Bennet contributed to this project.

Benjamin Hall Jr.

The Hall family history of Island real estate ownership runs deep in all three down-Island main streets and beyond. 

Eugene (Geno) Courtney

Sitting on a bench in front of Vineyard Scoops ice cream shop, Geno Courtney spends his days surveying Edgartown’s downtown. He owns 40 per cent of it, by his estimate. 


Claudia Canerdy

Claudia Canerdy founded Claudia in Vineyard Haven in 1971. She is one of a handful of female owners of downtown properties. 

Larkin Stallings

Larkin Stallings said he was walking down Circuit avenue in 2014 when he saw a "for sale" sign in the window of the Ritz. He took ownship of the bar four months later. 


Josh Goldstein

Josh Goldstein, with his parents, owns the Mansion House. Sherman and Susan Goldstein purchased it in 1986.  

Charles and Anne Hajjar

Charles and Anne Hajjar have named the Island hotels they own after their children. They purchased the Sydney in 2015.