Sheila O’Leary



About Sheila O’Leary

As the firm’s managing partner and an affordable housing advocate and attorney for over 25 years, I have extensive experience working with clients in developing, preserving, and operating their federally-assisted affordable housing portfolios. I regularly advise clients on HUD programs including:

  • Section 8 contract renewals, modifications, bifurcations, and 8bb budget authority transfers
  • Post Mark-to-Market transactions
  • Rental Assistance Demonstration Program (RAD) rental subsidy conversions
  • Expiring and new HUD use restrictions under Section 202, Section 236, RAD, and FHA loans
  • Low Income Housing Preservation and Resident Homeownership Act (LIHPRHA)
  • Section 202 Capital Advance/PRAC

I also work routinely with clients to assess new development opportunities, evaluate recapitalization options for assets in their existing portfolios, and strategize about how to access HUD programs for maximum programmatic and financial potential. Prior to joining HAO, I was an associate at Nixon Peabody and a research associate at The Urban Institute.


Bar Admissions

  • District of Columbia
  • Maryland
  • Massachusetts


  • JD, American University’s Washington College of Law, cum laude
    BS, Georgetown University

Representative Matters

  • Represented a client in a Post Mark-to-Market transaction in Atlanta involving obtaining HUD approvals to transfer the Mark-to-Market use restriction that was restricting rents in order to facilitate a redevelopment of the project funded with new debt, low-income housing tax credits, and a Mark-Up-To-Market rent increase.
  • Represented a client in ownership structuring issues and obtaining HUD approvals needed for the acquisition and redevelopment of a portfolio of five properties in Connecticut involving a combination of Section 202/PRAC contracts and project-based rental assistance contracts. HUD approvals included HAP assignments, new long-term HAP contracts, transfer of physical asset (TPA) approvals, and post-rehabilitation rent increases for deals financed with conventional debt and low-income housing tax credits.
  • Represented a client in the redevelopment of a hurricane damaged and vacant property in North Carolina that included reconstruction of the project, significant tenant relocation issues, and obtaining HUD approvals for a HAP assignment and post-rehabilitation rent increase.
  • Represented a client in obtaining HUD TPA approvals and HUD form 2530 clearance for corporate restructuring of the client’s entire HUD-assisted portfolio.
  • Represented a client in the acquisition and redevelopment of a portfolio of eight properties in North Carolina involving HUD approvals for HAP assignments, long term HAP contract renewals, post-rehabilitation rent increases, LIHPRHA budget-based rent increases, and modifications of LIHPRHA use agreements to eliminate owner distributions.
  • Represented a client to obtain a project-based voucher contract and rent increase for a former Section 236 property with an expiring use agreement in New Jersey with scarce affordable housing, thereby preserving the asset and protecting tenants.

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