Episode 16

October 06, 2025

01:04:17

Regina Stilp on Chicago Development, Mag Mile Revival & $4.9B in Projects

Hosted by

Joe Smazal
Regina Stilp on Chicago Development, Mag Mile Revival & $4.9B in Projects
Real Estate Chicago Style Podcast
Regina Stilp on Chicago Development, Mag Mile Revival & $4.9B in Projects

Oct 06 2025 | 01:04:17

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Show Notes

Join us for an insightful conversation with Regina Stilp, founding principal of Farpoint Development, one of Chicago's most innovative real estate development firms. Since co-founding Farpoint in 2016, Regina has spearheaded development projects totaling $4.9 billion across the Midwest and Southeast, including transformative Chicago landmarks.

In This Episode:

Regina shares her journey from traveling the world (Japan, London, adventure tours across America) to becoming a key player in Chicago real estate. Starting at Sterling Bay in 1996 when it was just four people, she helped grow the company through landmark projects including Google's first Midwest headquarters at 1000 West Fulton and McDonald's global headquarters at 400 South Jefferson.

Key Topics Discussed:

  • Bronzeville Lakefront - The 48-acre mixed-use redevelopment of the former Michael Reese Hospital site, navigating three mayoral administrations and community engagement
  • Sola Michigan City - A 252-key Renaissance Hotel with 188 condos/townhomes bringing new life to the Indiana lakefront
  • 1308 North Elston - Farpoint's new office in a converted light factory with unobstructed city views
  • Southeast Expansion - Building industrial projects along the I-85 corridor, including a facility that brought 150 jobs to rural Alabama
  • Working with communities and navigating public-private partnerships
  • The current state of Chicago development and capital markets
  • Why the "Chicago is dangerous" narrative frustrates her
  • Advice for young professionals entering real estate

Regina's philosophy centers on community engagement, creating economic impact, and maintaining an abundance mindset in a competitive industry. Her projects span from high-profile urban developments to industrial facilities creating meaningful employment in rural communities.

Connect with Farpoint Development to learn more about their portfolio of transformative projects across Chicago and the Southeast.

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