In his annual State of the City address Tuesday, Boston Mayor Marty Walsh called for new investments, including a major influx of new revenue, to bolster, expand and create new housing initiatives.

Walsh said he wants to more than quadruple spending on housing — a new investment of some $500 million over five years. Those investments, he said, will allow the city to create and preserve thousands of units of affordable housing around the city, as well as create, for the first time in the city's history, a city-funded rent voucher program to directly help vulnerable renters pay for housing.

Walsh has already staked his administration's record on carrying out a promise to address the city's growing affordability crisis by creating housing across the city.

He touted those accomplishments Tuesday, but said housing remains "the biggest economic challenge our residents face."

The new goals represent a significant, even historic boost in investment in housing — roughly five times current city spending, according to figures released by Walsh's office — and one that could bring in new city revenue for decades to come.

But fully funding the mayor's plan is also highly contingent on favorable action by the state legislature that is by no means certain.

The chief vehicle of that new revenue would be a proposed "transfer" fee, or tax, on high-end real estate sales. Such a tax, even if aimed only at real estate sales over $2 million, could raise as much as $50 million in new revenue, according to Walsh's office.

To do that, however, requires that the state legislature pass a home rule petition, first introduced in Boston's City Council and signed by the mayor last fall, that would allow Boston to create such a fee.

Similar transfer taxes have gone before the state legislature before — and have died on Beacon Hill.

On Tuesday, Walsh used his bully pulpit to pressure state legislators not to let that happen this time.

"I urge the legislature to take this step, so we can ease housing pressures in neighborhoods like Brighton, Chinatown and East Boston," Walsh told an audience that included those he seeks to reach, including many state legislators, like House Speaker Robert DeLeo, Senate President Karen Spilka and Gov. Charlie Baker.

Walsh is also proposing to add to the funds a transfer tax that would raise by the one-time sale of the city-owned Lafayette Garage in downtown Boston. Administration officials aren't sure how much that sale would raise, especially as the city owns only the subterranean garage and not the right to build on top of it.

Walsh also highlighted education, pledging to provide $100 million in new funding for Boston classrooms.

The funding, Walsh said, "will reach every school, and it will be carefully targeted so every dollar makes a difference."

Calling Boston Public Schools "a tale of two districts," Walsh said the city needs to do more to even the gap between high-performing and lower-performing public schools.

"Too much potential is still being lost for the students who face the toughest challenges," Walsh said.

Walsh also spoke of the city's complicated relationship with its transportation infrastructure — specifically the MBTA, which is controlled by the state.

Walsh repeated calls he's made before for the city of Boston to have a seat on the MBTA's board, noting that "our city and residents are the largest payer into the MBTA," and called on state legislators to provide the funding needed to improve and expand service.

"We need more reliable subway service, we need better bus service in our neighborhoods, and we need [a] commuter rail that is frequent and affordable," Walsh said.

Walsh touted his administration's work on city streets, including repaving some 30 miles of roads, repainting crosswalks and adding bike and bus lanes. But he also acknowledged ongoing challenges.

"Traffic jams, delayed trains, not enough buses ... it's not just a headache. It's a threat to the future of our economy," Walsh said.

He also noted that the city has a ways to go toward achieving his "Vision Zero" goal of ending traffic-related fatalities and serious injuries.

Walsh also called on the legislature to change state laws that prevent cities and towns from enacting ballot initiatives to directly fund capital projects like transportation.

"If you can't move forward, then let us lead," he said.