Leadership changes and a new winter shelter are on deck for Harbor Homes, the Island nonprofit dedicated to helping unhoused Islanders.
The past several weeks have seen transitions for the organization, which operates the Island’s only overnight winter shelter, as well as several long-term group residencies. Harbor Homes has said goodbye to its long-term winter shelter director, welcomed a new board president and identified a new property to permanently house the overnight shelter.
Interim executive director Jeannette De Jesús said that the changes will not interrupt Harbor Homes’s services, which have been crucial for unhoused Islanders amid a harsh winter of low temperatures and snow. She stressed that the organization is simply seeing natural growth.
“This is a fairly young organization, and I think that it’s had a tremendous amount of resilience,” Ms. De Jesús told the Gazette.
Harbor Homes’s new board president, Maura FitzGerald, started at the end of January. She replaced former board president Jennifer Frank, who had finished out her term and remains on the board.
Ms. FitzGerald, who splits her time between Aquinnah and Boston’s South End, met Ms. Frank at a fundraiser over the summer, where Ms. Frank invited her to join the organization. She said she jumped at the opportunity to step into the leading role.
“The work that Harbor Homes and the Harbor Homes staff is doing is really critical for a vulnerable population with the weather so unusually severe,” she said.
Ms. FitzGerald feels she came on at a critical time for the organization as a whole, which she noted is in the process of concluding its years-long search for a permanent property for its overnight winter shelter. This year, the shelter is operating out of a property Harbor Homes owns on New York avenue in Oak Bluffs that is typically used as a women’s group home.
“We’re about to close on a terrific property,” she said. “It’s been a struggle to find a place, but we finally have…. We have to raise a lot of money to build the structure out and to expand the programs that we’re doing.”
Ms. FitzGerald and Ms. De Jesús declined to share specifics of the new property or its location, citing the fact that Harbor Homes has not officially closed on the property. Ms. De Jesús said that the Island’s towns have been supportive of ongoing efforts to identify the new shelter.
Ms. FitzGerald’s arrival and the imminent purchase of the new shelter coincide with the resignation of Harbor Homes’s long-time shelter director, Lisa Belcastro. Ms. Belcastro became shelter director in 2020, but has been involved with serving the Island’s unhoused population for much longer.
“My decision to leave Harbor Homes wasn’t sudden,” she wrote in an email to the Gazette. “I notified Harbor Homes of my possible departure in December and confirmed it in January.”
Ms. FitzGerald said Ms. Belcastro was a valuable part of the Harbor Homes team.
“She was one of those people who always made sure that no matter what happened, our community was served, and served very well,” Ms. FitzGerald said. “I really wish her the best in her next endeavor, but she’ll be missed for sure.”
For the rest of this shelter season, longtime Harbor Homes volunteers Pat and Polly Toomey, owners of Among the Flowers Cafe, will fulfill leadership obligations at the shelter.
“They are going to provide the appropriate leadership until the end of this season, and we will then make some decisions about moving forward,” Ms. De Jesús said.
Meanwhile, Harbor Homes’s search for a long-term executive director continues.
“We’ve been making real progress in identifying the type of leadership that this organization needs going forward and the changes that need to happen in order for us to be able to do that,” Ms. De Jesús said.
Ms. De Jesús stressed that this year’s harsh winter weather has intensified the community’s need for the organization’s services.
“I’m at the shelter every day now, and I can tell you that the unhoused population in this community needs us more than ever,” she said. “And we plan to be there for them.”
This article appears in February 13, 2026.