Chicago’s property market is one of the most competitive in the country — shaped by diverse neighborhoods, complex ordinances, and fast-moving demand. For property owners, success depends on partnering with a management firm that combines data, communication, and experience.
That’s what Landmark Property Management delivers. With an Excellent TrueMatch™ Score of 91.89%, Landmark has earned its position as one of Chicago’s most dependable and forward-thinking property managers. At the time of this blog, Landmark Property Management is ranked 23rd nationally.
Company Overview
- Company Name: Landmark Property Management
- Location: Chicago, IL
- Years in Business: 11 years
- Portfolio Size: 515 Doors
- Property Types Managed: Single-family homes, multi-family residences, mixed-use, and storage properties
- Markets Served: Chicago, Lakeview, Bridgeport, Chinatown, Lincoln Park, Avondale, Wicker Park, Logan Square, Pilsen, Bronzeville, Frankfort, Bolingbrook, New Lenox, Joliet, Lockport, Mokena, Tinley Park, Orland Park, Manhattan, Shorewood, Plainfield, Lemont, Romeoville, Homer Glen, Naperville, and Oak Park
- Services Offered: Marketing, tenant screening, rent collection, maintenance coordination, financial reporting
- Pricing List: https://www.chicagospropertymanagement.com/pricing
Why Landmark Property Management Stands Out in Chicago
- Decade-Long Market Presence – With over 11 years of experience, Landmark blends deep neighborhood knowledge with disciplined operations. Leadership previously managed thousands of units, giving owners seasoned guidance.
- Outstanding Reputation – A 4.8-star Google rating reflects consistent praise for responsiveness, professionalism, and fairness from both owners and residents.
- Education Hub for Owners & Tenants – The site offers blogs, explainer videos, and a robust FAQ library, plus interactive ROI, Rent-vs-Sell, and Vacancy Loss calculators that turn market data into actionable decisions.
- Accessible, Human Support – Direct contact options and Calendly scheduling make it easy to reach real people quickly—no black-box ticketing.
- Culture and Company Values – Landmark’s “About Us” page makes it clear they’re more than just a corporate team. Their down-to-earth, approachable culture filters through to every client interaction, building confidence and lasting relationships.
TrueMatch™ Score Breakdown for Landmark Property Management
Landmark Property Management earned an Excellent Tier ranking with a TrueMatch™ Score of 91.89%, driven by exceptional clarity in cost structure and trust performance.
💡 What does “Excellent” mean? The TrueMatch™ Tiers Guide explains how property managers are ranked across Performance, Cost, Trust, and Experience.
Performance
Landmark leans on data-driven pricing to set rents with precision using real-time comparables, showing feedback, and neighborhood trends. This strategy reduces vacancy days and keeps owner ROI competitive without over- or under-pricing assets.
Performance is reinforced by their educational ecosystem - blog articles, videos, and market guides that teach owners how to limit vacancy loss and monitor market fluctuations. The result is a partnership that helps owners make smarter, more profitable decisions throughout the leasing cycle.
Cost
Cost transparency is core to Landmark’s model. All fees are published clearly on their website, allowing owners to understand every line item before signing. There are no hidden markups or unnecessary charges.
The firm adds financial value through free rental analyses and ROI tools that quantify cash flow and vacancy impact. Their team also assists owners in navigating RLTO compliance, avoiding costly penalties. Together, these efficiencies transform transparency into true cost-to-value advantage.
Trust
Trust in Landmark comes from data and delivery. With 272 verified Google reviews averaging 4.8 stars, they’ve proven their consistency in communication and problem resolution. Owners and tenants alike commend the company for professionalism and follow-through.
Landmark is fully licensed and insured in Illinois, adhering to strict industry standards. Their direct communication channels and hands-on support team mean issues are resolved quickly and transparently—reinforcing the trust that keeps clients long-term.
Experience
With 11 years of operations and a portfolio of over 500 doors, Landmark demonstrates measured growth supported by experienced leadership. Their founders previously managed thousands of units, giving them a macro view of Chicago’s market and micro attention to each property.
They use AppFolio for real-time reporting and owner portals, delivering accurate financial insight and property visibility. That combination of technology and local expertise turns Landmark’s experience into an operational advantage that benefits every client.
A Trusted Partner for Chicago Property Owners
For property owners in Chicago, Landmark represents the ideal balance of scale, accessibility, and expertise. With more than a decade of experience, a reputation for openness, and a service approach that blends efficiency with human connection, Landmark makes managing rentals simpler and more profitable. Owners can count on them to handle the details while maintaining the transparency that builds long-term trust.
What Their Clients Are Saying
I am very happy with Jason and Landmark Property Management. Having been in real estate for a decade I have dealt with many bad property managers, and its always a real pleasure to be able to find one that I can recommend to my clients and also use for my own buildings! Highly recommend Jason and his team! - Lawrence
I have been with Landmark for about 3 years, and words could not describe how helpful they have been. They have completely taken away my stress from owning my property. Jill has been amazing to work with. She is a professional and an excellent communicator! She goes above and beyond, and I appreciate her! Would recommend this company! - Marc
Why This Matters
Chicago’s rental market is competitive, fast-moving, and diverse. To succeed, property owners need a management partner who can navigate neighborhoods, price properties strategically, and provide tools for long-term success. With their Excellent TrueMatch™ Score, Landmark demonstrates that they not only meet industry standards - they exceed them through transparency, accessibility, and educational resources that empower owners.
FAQs About Landmark Property Management
1) What types of properties does Landmark manage?
Single-family, multi-family, mixed-use, and storage properties in Chicago.
2) What services are included?
Marketing, tenant screening, rent collection, maintenance coordination, financial reporting.
3) How is the TrueMatch™ score calculated?
Based on verified performance metrics, including tenant satisfaction, maintenance efficiency, financial reporting accuracy, and operational consistency. Landmark’s score of 91.89% places them in the Excellent tier.
4) How does Landmark handle rent collection?
They use AppFolio, ensuring synchronized owner–tenant processes. Owners receive monthly statements and ACH transfers, while tenants have multiple digital options to pay (cash not accepted).
Find Your Property’s Best-Fit Manager
Looking for a Chicago property manager who combines transparency, accessibility, and deep market expertise? Use the TrueMatch™ to compare Landmark Property Management with other verified companies and find the best fit for your investment.