Heavy on Island hotels with a handful of fun and games in the mix, Boston-based developer Charles Hajjar and wife Anne own the Edgartown Inn, the Richard, Sydney and Christopher hotels in Edgartown, as well as the staple Arcade at 19 Circuit avenue in Oak Bluffs. They also own the Black Dog store building on 11 Main street in Edgartown.

“If it’s a good deal, we buy it,” Ms. Hajjar said.

The Hajjars first built a home at Farm Neck 15 years ago.

“As my kids got older, I got bored,” she said.

Noting to her husband that many of her friends traveled to boutique hotels in Nantucket, the former mental health counselor said “let me have a chance with this” feeling she could try her hand at bringing them to Martha’s Vineyard.

With the Edgartown hotels named after each of their children, (another property is named after eldest son Charles in Boston) the couple has treated the business as an extension of their family, purchasing the Sydney, first, in 2015, naming it after their only daughter. The Christopher and The Richard followed. The Hajjars also purchased the Edgartown Inn, originally built as a whaling residence for Capt. Thomas Worth, from the Radford family for $5 million in late 2017.

The Richard Hotel, at $5.7 million, stands today as one of Edgartown’s most expensive Main street properties, just as the Arcade, assessed at $3.4 million, remains one of the most expensive in Oak Bluffs.

Ms. Hajjar said she “loves the architecture of the historic buildings,” and feared had they not been bought by hoteliers, they would have been purchased and renovated to be single family homes.

Along with a mission of keeping up both the town’s beauty and character, Ms. Hajjar said she feels fortunate that she and her husband were able to build housing at the hotels for 24 of their 30 employees.

“It’s a mission of ours to restore the integrity and natural beauty of these buildings,” she said. “I treat them like my homes.”

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.


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