[2] The organization runs a chain of thrift shops, a bookstore café, and a dispensary[3] as social enterprises to support their work and lower dependence on grants and donations.

Founded in 1994 and located in Soho on Crosby Street, the bookstore cafe[4] is a successful entrepreneurial business raising money to support the Housing Works mission.

[12][13][14] Housing Works CEO Charles King auctioned off his trademark pony tail, and one bidder was Evangelical preacher Rick Warren.

[15] In October 2019, Housing Works organized a mass demonstration outside of the Supreme Court in support of LGBTQ civil rights, resulting in over 100 activists being arrested.

[16] In late 2019 and into 2020, Housing Works leadership began engaging in what many progressive leaders and labor organizations classify as union busting after the staff began a worker-led unionization effort to address a host of issues (such as workplace safety, benefits, and a lack of a living wage for many workers while some of the organization's executives receive six-figure salaries) impacting staff and the quality of service they provide to their community.

[17] Despite their assertion that they are not anti-union, Housing Works has retained a known "union busting" firm, Seyfarth Shaw LLP, "which prides itself as keeping workplaces 'union-free,' according to its website, and has a history of cases that include working against the 1960s agricultural labor activist Cesar Chavez and defending Harvey Weinstein’s film company against a slew of sexual harassment claims.