At 29th Street Living, we are rewriting the rules of property management—raising expectations so that going above and beyond becomes the standard.

Headquartered in Chicago, we are a technology-enabled multifamily property management platform committed to creating value for owners, residents, and communities. We bring an all-in mindset to every property we manage, combining operational excellence, experience, and service.

We are creative, collaborative, and curious. We challenge routine, question convention, and look for ways to improve the resident experience, strengthen property performance, and operate more efficiently. This approach keeps us agile, accountable, and focused on consistent results.

29th Street Living manages properties for both affiliated ownership and third-party clients. That owner-operator perspective shapes everything we do. Whether the property is ours or entrusted to us by a partner, we think and act like owners—protecting the asset, maximizing value, controlling expenses, and making informed decisions with a long-term view.

Our third-party management platform applies the proven strategies, systems, and operating discipline developed across our own multifamily portfolio. Through data-driven decision-making, local market expertise, hands-on leadership, and a curated technology platform, we help ownership groups improve performance, enhance transparency, and create stronger resident experiences.

Technology supports every stage of the property lifecycle—from AI-powered lead management and self-guided tours to revenue management, business intelligence, reputation management, and resident engagement. These tools help our teams respond faster, make better decisions, reduce inefficiencies, and stay focused on what matters most: people, performance, and the communities we serve.

The bottom line is simple: we bring an owner’s mentality, an operator’s discipline, and a service-first commitment to every property we manage.

29th Street Living

Karen Plesh

This department focuses on building and managing relationships with community members to enhance participation and collaboration.

Community Engagement

This department oversees the operation, maintenance, and administration of properties to ensure optimal performance and tenant satisfaction.

Property Management

This department manages financial reporting, budgeting, and cost analysis related to property and capital projects.

Accounting Department

This department oversees training, assistance, and maintenance to ensure efficient organizational operations.

Operations Management

This department oversees regional operations and strategy implementation across various locations.

Regional Management

This department is responsible for identifying growth opportunities and managing strategic partnerships.

29th Street Living

Org chart

Teams

Community Engagement

Property Management

Accounting Department

Operations Management

Regional Management

Business Development

Offices

29th Street Living

Org chart

Teams

Community Engagement

Property Management

Accounting Department

Operations Management

Regional Management

Business Development

Offices

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