About Shawn Swift
Founder & Principal, City Roots Properties

Shawn Swift is a seasoned real estate professional with over a decade of experience in housing finance and property management. Before founding City Roots Properties, he served as a Senior Underwriter at the U.S. Department of Housing and Urban Development (HUD), where he specialized in complex commercial mortgage deals for new construction and existing apartment buildings—including both market-rate and affordable housing developments with layered subsidies and financing.

 

During his time at HUD, Shawn gained extensive experience conducting appraisal reviews and detailed market analysis specific to the Chicago area. He also reviewed capital needs assessments of multifamily properties, evaluating long-term maintenance and renovation requirements. His background includes asset management responsibilities such as reviewing financial reports, tracking property performance, and managing budgets. In addition, Shawn is highly knowledgeable in Chicago’s landlord-tenant ordinances and fair housing regulations—expertise that ensures City Roots Properties operates with full compliance while protecting both owners and residents.

After completing his service in the U.S. Air Force, Shawn earned his bachelor’s degree from Indiana University Bloomington and went on to receive a master’s degree from Ball State University. 

Shawn launched City Roots Properties to offer personalized, transparent property management services to investors and owners across Chicago. His unique background in federal housing underwriting, combined with a deep understanding of local market dynamics, allows him to deliver unmatched service, maximize returns, and bring peace of mind to every client.