In the heart of Washington, D.C., where affordable housing options remain scarce, Richard Cunningham and Jésyl Crowdy-Cunningham are leading a quiet but powerful transformation to ensure veterans have a safe place to live. Through their firm, Cunningham Real Estate Holdings, the husband-and-wife team has become a steadfast presence in the city, operating 160 mixed-income rental homes across a dozen communities, and with more in development.
For the Cunninghams, it’s more than real estate — it’s a calling.
“It gives us a sense of joy and satisfaction to provide upscale affordable housing for lower-income individuals in our community,” said Richard Cunningham. “To see the growth and development of constituents in need means everything to us.”
Partnering for Impact
Cunningham Real Estate Holdings didn’t grow its footprint in isolation. Strategic partnerships — with Community Development Financial Institutions (CDFIs) like Enterprise Community Loan Fund, Mercy Community Capital, and city agencies — have played a vital role. Early on, the Cunninghams attended educational seminars hosted by Enterprise and others, which introduced them to new tools, contacts, and financial pathways to expand their mission.
One of the most transformational of those tools has been HUD-VASH, a joint program between the U.S. Department of Housing and Urban Development (HUD) and the Department of Veterans Affairs (VA). Designed to end veteran homelessness, the program provides housing vouchers alongside wraparound services like healthcare and mental health counseling.
The Cunninghams have emerged as local leaders in integrating HUD-VASH with their properties. Their latest effort, Legacy Lofts, is a 28-unit project created from the acquisition and rehabilitation of two multifamily buildings. Funded in part by a $10 million loan from Enterprise and Mercy Community Capital, the development will offer one-, two-, and three-bedroom units affordable to residents earning 30% of the area median income.
Through HUD-VASH, eligible tenants will receive rental assistance and supportive services coordinated by a dedicated VA case manager. Additional help is available offsite, reinforcing the safety net that makes recovery and progress possible.
Legacy Lofts comes after the Cunninghams’ 2018 project, Cunningham Apartments, a ground-up development of 37 veteran-focused affordable units in the Brightwood Park neighborhood. That project also received support from HUD-VASH, along with a $17.3 million construction and acquisition loan backed by Enterprise and Capital Impact Partners.
“These individuals served our country,” Cunningham said. “And it’s now time for us to serve them in return.”
An Urgent Crisis Demanding Solutions
The Cunninghams’ work is especially vital against a backdrop of mounting housing insecurity in Washington D.C. Nearly half of all D.C. households are cost-burdened, spending more than 30% of their income on housing. More than 80,000 residents experience some form of housing instability, according to a 2023 Urban Institute report.
Veterans are disproportionately affected. The National Alliance to End Homelessness reports that over 32,000 veterans experienced homelessness in 2024 —13,000 of whom had no shelter at all.
Meanwhile, the financial sustainability of affordable housing itself is under threat. The pandemic-era surge in nonpayment of rent has ballooned into a long-term challenge. In Washington, D.C., unpaid rent to affordable housing providers soared from $11 million in 2020 to an expected $147 million by the end of 2025. That kind of loss can cripple providers, making it impossible to maintain properties or keep rents affordable.
HUD-VASH helps bridge the gap. It ensures housing providers have a reliable revenue stream while giving residents a stable home base to rebuild their lives. In this delicate balance of mission and economics, the Cunninghams have found a model that works—and one that offers hope.
