Bulldozers arrived at Church Street South last week to raze the first of the 300-unit apartment complex’s concrete structures — poorly maintained remnants of a 50-year-old housing project, which is due for demolition after the city condemned them last fall.

Northland Investment Corporation, the private development firm that purchased Church Street South in 2008, demolished the complex’s laundromat and day care center last Monday. Northland and the New Haven Building Department now seek licenses to complete demolition once the remaining families — which numbered 273 in January of the original 300 — still living at the complex are relocated. The city, Northland and the federal Department of Housing and Urban Development aim to move all families out of the complex by September, regional HUD spokeswoman Rhonda Siciliano said.

Residents at Church Street South endured unlivable conditions such as moldy water and chronic leakages for at least the past decade. After several residents filed litigation last summer against Northland, the company began relocating residents before announcing complete demolition.

“[The demolition] begins the next chapter for this Church Street South development and its residents,” Mayor Toni Harp said in a statement last Monday afternoon. “While no one is celebrating the overdue relocation of these families, there’s some consolation knowing they’ll now be in healthier living quarters and HUD-subsidized apartments nationwide which will be inspected using new guidelines and standards.”

Jordan Yorks, marketing assistant at Northland Investment Corporation, said Friday that Northland had no comment regarding its plans for the Church Street South property, which sits across the street from Union Station. Northland — which specializes in market-value and high-end residential buildings — bought the complex in 2008 when former New Haven Mayor John DeStefano Jr. urged the company to rebuild Church Street South as a mixed-income apartment complex. The Board of Alders stalled Northland’s plans in 2012 when it requested that Northland add more affordable housing units than the company said would be profitable.

While Northland prepares for Church Street South’s complete demolition, it is working with HUD and the Housing Authority of New Haven, the local arm of federal housing programs, to distribute housing vouchers over the next few months to the 198 families who opted for them. An additional 43 families wait — either at Church Street South or at a temporary residence due to health concerns — for HUD to identify federally funded affordable housing units as their future homes, Siciliano said.

She added that HUD has identified two apartment complexes in the Elm City willing to accept a federal grant to provide affordable housing for Church Street South families. HUD cannot release the names and details of those deals while parties negotiate, Siciliano said. She said HUD is continuing to identify more potential landlord partners.

As residents trickle out of Church Street South and the complex’s concrete walls crumble, New Haven loses an icon — a poorly maintained remnant of the federal government’s 1960 housing programs. Prominent 20th-century architect Charles Moore designed the building and was lauded for his designs, said Jonathan Hopkins, a New Haven resident who wrote his master’s thesis in architecture on Church Street South.

But the complex suffered from a lack of funds and routine maintenance after construction began. The city lacked funds to complete an additional building that would have housed more expensive market-price apartments and added socioeconomic diversity to the complex. In the 1980s and the 1990s, crime rates in the complex skyrocketed due to the rise of a gang called the Jungle Boys. In the 1990s, residents of the Elm Haven complex won a lawsuit against HANH, which managed Church Street South at the time, for mismanagement.

But Hopkins added that the demolition of Church Street South could benefit the city economically. Former Mayor Richard Lee, who led the Elm City in the 1960s, intended for the complex’s land to house commercial developments and market-rate housing, as real estate near a city’s train station often does, Hopkins said. Lack of investor interest led Lee to propose Church Street South instead.

“It should have been a place of investment,” Hopkins said. “But it has not benefitted from investment in a long time. So it’s a positive that this area might become new and usable for a large portion of the city’s residents.”

Correction, March 28: A previous version of this article “Demolition Begins at Church Street South” incorrectly stated that Church Street South residents filed a lawsuit against HANH in the 1990s. In fact, residents of the Elm Haven complex filed the suit against HANH, which also managed Church Street South at the time.