Who is Pioneer Realty Group?

We provide real estate leasing, property management, sales, and investment consulting for renters and owners in the Chicagoland area. We offer smart, trustworthy, personalized services to our customers and to our agents. We are continuing to expand our own portfolio while partnering and building relationships with quality investors who share our same mission.


Helen Bailey & Sean Flynt

After meeting at Grinnell College (Go Pioneers!) Helen and Sean moved to her home town of Chicago. They started as renters and worked their way up to landlords while gaining experience in various aspects of multifamily real estate investment.  During his nine years in Chicago, Sean gained his real estate experience in property management.  Helen completed her MBA in Real Estate Finance at DePaul University while excelling as a real estate broker.  More recently she honed her finance skills working at Freddie Mac in the multifamily mortgage industry.  These skills have proven useful as the partners continue to invest in multifamily in the Lakeview neighborhood.

Equipped with encouragement from friends and family along with love for the local community, Helen and Sean opened Pioneer Realty Group: a full-service apartment leasing, property management, and real estate investment firm specializing in multifamily real-estate.