Regional Property Manager (Chicago Region)

At WinnCompanies, our work starts with people — the residents who call our communities home, the neighborhoods we help strengthen, and the 4,600+ team members across 30 states, Washington, D.C., and Puerto Rico who make it all possible. As an award-winning owner, developer, and manager of high-impact, mixed-income apartment communities, we are proud to be one of the nation’s leading managers of multifamily housing and one of the largest operators of affordable housing communities.

We bring together people who care about quality housing, meaningful service, and making a difference every day. Through our innovative resident services platform and commitment to exceptional communities, we offer career opportunities for individuals who want their work to create lasting impact.

Interested in learning more? Visit WinnCompanies to explore our benefits, mission, communities, and career opportunities.

About the opportunity

WinnCompanies is seeking an experienced Regional Property Manager to oversee a portfolio of multifamily and affordable housing communities across Chicago, IL.

In this role, you will lead property operations, support on-site teams, drive portfolio performance, and ensure compliance with LIHTC, HUD, and other affordable housing regulations where applicable. You will oversee a portfolio between 800-1000 units, focusing on occupancy, resident satisfaction, financial results, and asset preservation.

The salary range for this role is $120,000.00-$140,000.00 per year. The final pay rate will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors. The selected candidate will adhere to the following schedule: Monday through Friday from 8:30AM to 5:00PM.

Responsibilities:

• Manage a portfolio of multifamily and affordable housing communities, ensuring operational excellence and strong financial performance.
• Develop, present, and manage annual operating budgets, forecasts, and monthly financial reviews.
• Drive occupancy, rent collections, resident retention, and revenue growth strategies.
• Lead and support Property Managers and on-site teams across the region.
• Drive occupancy, rent collections, and revenue strategies, review rent schedules, renewals, and leasing performance.
• Ensure compliance with LIHTC, HUD, and other federal, state, and local housing regulations.
• Partner with maintenance teams to preserve assets, control expenses, and maintain safe communities.
• Build and maintain strong relationships with property owners, clients, residents, and internal stakeholders.
• Review property performance metrics and implement action plans to achieve portfolio goals.

Required Qualifications:

• High school diploma or GED equivalent required.
• 5+ years of residential property management, multifamily housing or real estate experience.
• 3+ years of leadership or supervisory experience.
• Experience with affordable housing programs, including LIHTC, HUD, HOME, or RD.
• Valid driver’s license in good standing and ability to meet company driving standards.
• Property management certifications such as CAM, ARM, RAM, SHCM, NAHP-CPL, CGPM, or equivalent.
• Experience managing multiple properties or a regional portfolio.
• Knowledge of property management operations and landlord-tenant regulations.
• Excellent customer service, client relations, conflict resolution, and relationship building skills.
• Strong financial management and budgeting skills.
• Advanced proficiency with Microsoft Office, including Excel.

Preferred Qualifications:

• Bachelor’s degree in Business, Real Estate, or related field.
• Experience using Yardi, RealPage, or other property management systems.
• Knowledge of marketing, leasing strategies, and resident retention strategies.

Benefits & Perks
Eligible full-time U.S. employees enjoy a competitive benefits package, including:

• Generous paid time off, paid holidays, sick time, a floating holiday, and a day of service
• Medical, dental, and vision coverage, plus HSA, FSA, and dependent care savings options
• 401(k) with company match and company-paid life, AD&D, and long-term disability insurance
• Tuition reimbursement, professional development opportunities, and career growth resources
• Wellness programs, employee assistance resources, commuter benefits, and employee discount programs
• Flexible work options for eligible positions

Learn more about our benefits at

If you are a California Resident, please see our Notice of Collection here.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.

Internal candidates, please apply here: Internal Careers Hub