Oak Bluffs School principal Jeremy Light has witnessed the struggles teachers have when trying to secure housing.

The school system is one of the largest employers on the Island, but with the median sale price of a home at $1.6 million, it can be difficult to find candidates.

Many must commute from off-Island, unable to get a place to stay here. Others might be able to find housing in the off-season, but often have to move out come May when summer rentals seek higher-paying tenants.

“I think what is stressful for a lot of teachers is the shuffle,” said Mr. Light, who previously was the assistant principal at the regional high school. “They’ll have to be out by June 1 and school doesn’t end until June 18.”

A new law passed last year, however, could make it easier not just for the schools, but all municipal employees to get housing on the Island. As part of Affordable Homes Act, towns on the Vineyard and other tourist destinations can opt in to a “seasonal communities” designation, which gives them a suite of new housing options not available to other communities. Voters are being asked to sign off on the designation at the upcoming town meeting.

West Tisbury project could resemble Kuehns way development. — Mark Alan Lovewell

If residents give the green light, towns could then dedicate public money to develop municipal employee housing for the first time.

The first potential project with a municipal employee preference will also head to town meeting floor this year, with Island Housing Trust asking if the towns are willing to help pay for a teacher housing project in West Tisbury. Plans are still being developed for the project at 48 Old Courthouse Road, but Philippe Jordi, the executive director of Island Housing Trust, said the proposal is expected to include eight rental apartments in four duplexes, similar to other projects at Scott’s Grove and Kuehn’s Way.

The land for the project was donated to Island Housing Trust by developer William Cumming, who attended Island schools and wanted to give back by making housing more available to school employees.

The towns’ community preservation committees are expected to submit $1.3 million in town meeting funding requests for the project, which will also seek private and state funding.

Edgartown is also taking the first steps towards developing municipal employee housing at the former Martha’s Vineyard Land Bank headquarters on Upper Main street, asking voters to dedicate $10,000 for a study on future options.

Staffing town hall, especially high-level positions, can be difficult for municipalities across the state, said James Hagerty, the Edgartown town administrator. With the pool of qualified individuals already limited, the Vineyard’s real estate market doesn’t make it any easier.

“The municipal field is difficult,” Mr. Hagerty said. “It’s hard to find municipal employees on the South Shore, and even hard on the Vineyard.”

The development of employee housing comes after many private businesses have, at times reluctantly, become landlords of their own. Several employers last year said that providing housing is one of the only ways to ensure they have enough staff.

Until the seasonal communities designation, towns have been hamstrung with what they can do. While some towns offer housing stipends, they previously couldn’t dedicate public funds to the development of housing for their employees.

Despite the new allowances, there are still challenges and choices to make. Developing housing is new to many towns on the Island, and the kind of housing could attract different kinds of employees.

“It seems to me that Town leaders will want to weigh the potential merits and drawbacks of creating, say, two single-family units — which might attract and keep an employee with a family — vs. somewhat smaller townhouse-style units that could offer more housing but may not appeal to people seeking ‘roots’ in Edgartown,” Judi Barrett, a planning consultant, wrote to the town when they sought her advice earlier this year.

As the West Tisbury and Edgartown projects go through the planning stages, other towns are considering adding municipal slots to projects that have already been approved.

Oak Bluffs has asked Island Housing Trust about dedicating units at the permitted Takenash Knoll project, formerly known as Southern Tier, near the high school for public employees.

“That’s the first step, seeing where we can go with the projects we already have going,” said Mark Leonard, an Oak Bluffs select board member.

Mr. Light at the Oak Bluffs school hoped that Islanders would rally around the housing projects to create a more stable future for the school system. “As retirements come and people leave, it is a worry of principals across the Island to get them replaced,” he said. “It’s only getting more and more expensive.”