When Brook Katzen moved to the Vineyard two years ago, it was not with the specific intention to buy a miniature golf course, a year-round restaurant, a taco truck, a retail building, an ice cream chain, and now a gourmet market.

“My career has evolved rapidly since I came here,” Mr. Katzen said this week over his daily breakfast of eggs, greens and lentils at Little House Café, the 12-year-old State Road restaurant he bought in the summer of 2020.

Mr. Katzen also owns and operates The Cove Golf & Grill, on the other side of State Road, and is landlord for the Island Time cannabis dispensary on Mechanic’s street.

With chef Spring Sheldon, Mr. Katzen co-owns the El Gato Grande taco truck, and he has partnered with investor Jim Shane of Edgartown to buy Mad Martha’s Ice Cream, as well as the former Glass House on Union street and, now, the Larder, directly across State Road from Little House.

“I’m uniquely qualified to seize some of these opportunities,” said Mr. Katzen, who studied hospitality management at Cornell before earning a master’s degree in real estate from the university.

A former Washington, D.C. housing developer and seasonal Island visitor originally from Worcester, Mr. Katzen was already planning a move to the Vineyard to be closer to his parents, who live here year-round, when the pandemic lockdowns began in Massachusetts.

“I kind of freaked out and didn’t really know what this meant to me, [so] I threw everything into my car and started driving north,” he said. “I wanted to get here in case travel was restricted.”

Initially planning to use his D.C.-area experience in developing workforce housing, Mr. Katzen had already identified a promising location at Island Cove, the longtime miniature golf resort at 386 State Road.

“I guess I’m a real estate investor, [and] sometimes you have to buy the operating business as well,” he said.

“I grew up going there,” he added.

Little House was Mr. Katzen's second purchase. — Albert O. Fischer

Mr. Katzen’s second purchase was Little House, a profitable business popular with year-round Islanders.

“I signed the contracts to purchase the mini golf business and Little House before the pandemic hit,” he said.

By the time the sale went through, he said, the restaurant’s founding owners had successfully shifted from dine-in to takeout as the pandemic continued.

“They did a darn good job,” Mr. Katzen said.

Through Little House, he met Ms. Sheldon, even traveling to meet with her in Oaxaca to discuss the joint venture that became El Gato Grande.

“She showed me around and fed me,” Mr. Katzen recalled. “We had pretty good professional chemistry.”

Adding the taco truck, which operates at the Cove, also provides his food businesses with an additional commercial kitchen, Mr. Katzen added.

“Having a commercial kitchen is extremely valuable,” he said.

Acquiring the Island Time building came about because cannabis entrepreneur Geoff Rose, who had an option on the building, didn’t want to own the property as well as his business, Mr. Katzen said.

The Mad Martha’s purchase was spurred by Mr. Shane, whom he’d met through mutual friends.

“I was not thinking that I wanted to buy it,” Mr. Katzen said of the iconic, 50-year-old ice cream chain, with locations in all three down-Island towns. “It was way too big a deal for me to pursue on my own.”

But when Mr. Shane proposed a partnership, the resulting deal — sealed for $6 million in May, 2021 — opened even more doors.

In December, Mr. Katzen and Mr. Shane bought the Vineyard Haven retail space most recently occupied by the Glasshouse, where they plan to relocate the Mad Martha’s from Main street.

“Of the Mad Martha’s locations, the Vineyard Haven location had always been the weakest performer because the store wasn’t as large as the other two and [had] some physical restraints,” Mr. Katzen said.

While Mad Martha’s moves to its new, highly visible Union street location across from the ferry terminal, Ms. Sheldon will take over the Main street shop, a former restaurant where she already leases the commercial kitchen downstairs.

“She’s going to open up a new business at 48 Main [called] S&S Kitchenette,” Mr. Katzen said.

“She will sell prepared foods, including taco kits and pizza kits, [and] host special events [such as] private dinners.”

Mr. Katzen and Mr. Shane have most recently purchased the Larder, formerly Tisbury Farm Market, where their tenant will be Rose Willett of North Tisbury Farm and Whippoorwill Farm.

Ms. Willett plans to sell gourmet meats and cheeses and other specialty foods at the Larder, in collaboration with chef Tyler Potter.

Mr. Katzen said he decided early on that Vineyard Haven, and the State Road business corridor in particular, was his best bet for the kind of “smart development” he favors. In the future, he sees housing within walking distance of the local businesses.

“I’m sold on this neighborhood,” he said. “I think this neighborhood is going to be an important part of Vineyard Haven’s future.”

But he said the area’s full potential will not be available until it is tied into to the town sewer system.

“The two most pressing issues on my mind are housing and wastewater,” said Mr. Katzen, whose own living arrangements reflect the Island’s housing crisis.

“I’m moving into my parents’ basement,” he said.