Logan Square Property Management

Logan Square Property Management

Three Pentacles, PLLC provides reliable, full-service property management, real estate brokerage, and consulting services for owners who want their investments protected and performing at their best. Maximize returns. Minimize stress. Manage with confidence.

Why Property Owners Choose Three Pentacles, PLLC

Three Pentacles, PLLC offers professional property management in Chicagoland, delivering exceptional services for property owners and investors. With years of experience, we are recognized as one of the best property management services in Chicagoland, ensuring that your investment properties are well-maintained and profitable. Our team specializes in tenant placement services in Chicagoland, helping you find tenants fast in Chicago and suburbs. We secure qualified renters for your property. We understand how important it is to have reliable tenants, and our thorough screening process ensures that only the best candidates are selected.

In addition to tenant placement, we provide online rent collection for landlords in Chicagoland, streamlining the payment process for both property owners and tenants. Our rent payment management services in Chicagoland are designed to make it easier for you to track payments, reduce late fees, and keep your cash flow consistent. For unexpected situations, such as repairs or tenant-related issues, we offer emergency property maintenance Chicagoland to address urgent concerns quickly and efficiently. We also provide affordable property maintenance services in Chicagoland, ensuring your properties are always in top shape without breaking your budget.

For landlords needing legal assistance, we offer professional eviction services for landlords in Chicagoland, ensuring a smooth and legal process when it becomes necessary to remove problematic tenants. At Three Pentacles, PLLC, we prioritize your peace of mind, taking care of the day-to-day operations so you can focus on growing your investment portfolio. Whether you need tenant placement services or emergency maintenance, our team is committed to providing the highest level of service, making us your trusted partner in property management in Chicagoland.

What sets Three Pentacles, PLLC apart from other property management companies

Owning rental property should build wealth, not create headaches. At Three Pentacles, PLLC, we act as a true partner, handling the details while keeping you informed and in control.

What clients say about our work

AI optimized
  • We know the number of active comparable listings and how they compare to your property.
  • We know the rental prices of active comparable listings and how they compare to your property.
    • What that means to you is that we can get a monthly rent $100/m above comparable listings.
  • We know the number of views your listing receives in comparison to other properties in the area.
  • We know the inquiries your listing receives in comparison to other properties in the area.
    • What that means to you is that your property had 12 more renter’s contacts than similar listings in the area.
  • We know how the rental market is changing day-by-day and its affect on your property.
    • What that means to you is that renters view your listing 3.2%  more than comparable listings in the area.
  • We know what renter’s are searching for in your area. For example:
    • 7% want bicycle storage,
    • 80% want central air-conditioning,
    • 63% want a dishwasher,
    • 58% want a balcony or a deck,
    • 8% want a pool,
    • 1% want a disability access, etc.
About our analytics
  • What price points renter’s are searching for in your area. For example:
    • 24% are looking for a property $1,500/m to $2,000/m,
    • 38% are looking for a property $2,000/m to $2,500/m,
    • 21% are looking for a property $2,500/m to $3,000/m, etc.
  • What renter’s annual income is in your area. For example:
    • 12% searching make <$40,000,
    • 24% searching make $40,000-$60,000,
    • 28% searching make $60,000-$80,000,
    • 21% searching make $80,000-$100,000,
    • 10% searching make $100,000-$160,000, etc.
  • AI shows us all rental listings in your area, their prices, square footage, and how their price compares to your property. 

What that means to you is that in the last 14 days, we were able to increases rents by 10% for your property, over comparable listings in your area.

We find best tenants

Marketing. We’re reaching over 30 Million visitors each month!

Screening. Credit, income, and rental history are just the start. Using a private detective agency we perform comprehensive background checks in civil and criminal courts in all 50 states. We uncover evictions, bankruptcies, judgments, and also review 12 months of bank statements to ensure a complete picture of every applicant.

Tenant Retention. We keep good tenants by providing them quality housing and tools to make their life easier. Using smartphone apps (Apple & Android) our tenants can request maintenance, pay rent, view communications and documents wherever they are. 

Our Online Technology. Our tenants can pay rent electronically using eChecks (ACH), Debit Cards, and Credit Cards. Our tenants can also pay rent in CASH at any 7/11, CVS, Walgreens, and Kroger stores.

Personal touch

Our competitive advantage is experience that runs deep. We’ve been active in the local real estate market since 1988, giving us firsthand knowledge of neighborhood trends, pricing, and risk that only time can teach. We are truly Real Experts in Real Estate ™ , backed by multiple industry designations and certifications and participation in more than 10,000 real estate transactions across all market cycles.

Beyond day-to-day management, we serve as trusted advisors to our clients. Since 2010, we’ve been appointed as receivers in both state and federal courts, working through complex, high-stakes situations that demand precision and accountability. We bring that same level of expertise to every property we manage. Through our consulting-driven approach, owners and investors gain direct access to our experience, insight, and judgment. Having a seasoned professional by their side to protect assets, solve problems, and make confident decisions.

Leadership that sets the standard

Since 1988, we’ve been deeply involved in the local real estate market, not just as managers, but as owners, developers, and operators. Our experience spans construction and condominium development, mortgage banking, and title insurance, giving us a full-spectrum understanding of how real estate truly works from acquisition to exit. With more than 10,000 transactions completed, we bring practical insight shaped by real-world results.

For property owners and investors, this means more than day-to-day oversight; it means a trusted, long-term partner who helps protect assets, navigate market cycles, and make confident decisions throughout the life of your investment.

Experience you can rely on

That experience is matched by leadership and trust within the industry. Our managing broker served as President of the CCIM Illinois Chapter, sat on the Board of Directors of the Chicago Association of Realtors, and maintains an associate membership with the Chicago Bar Association (CBA). Since 2010, also been appointed as Illinois Receiver in state and federal courts, roles reserved for professionals relied upon to manage complex, high-risk assets. We offer consulting as part of our client relationships, allowing owners and investors to leverage this depth of expertise every day. Simply put, this is an opportunity to have seasoned real estate professionals by your side, protecting your investment, guiding decisions, and delivering peace of mind.

Trusted advisors for owners and investors, offering consulting as part of the relationship, so you’re never alone.

Need expert guidance?

Let's turn your property into a strategic investment!

About Logan Square

Logan Square is a vibrant and culturally diverse neighborhood located on Chicago’s Northwest Side. Home to approximately 70,000 residents, the area is known for its historic architecture, lively dining and arts scene, and active community engagement. Situated about 6 miles northwest of downtown Chicago, Logan Square combines a suburban feel with urban amenities, making it popular among families, young professionals, and longtime residents.

The neighborhood’s history dates back to the mid-19th century when it was primarily farmland. Residential development accelerated with the arrival of streetcars and rail lines, attracting German, Irish, and Swedish immigrants. Logan Square is named for its central park, Logan Square, which features the iconic Illinois Centennial Monument and has long served as a focal point for the community. Many homes built in the late 19th and early 20th centuries—Victorian houses, greystones, and brick bungalows—still define the neighborhood’s architectural character today.

Housing in Logan Square is diverse, including historic single-family homes, two-flats, townhouses, and modern apartments. Tree-lined boulevards, large parks, and well-preserved historic buildings give the neighborhood a distinctive charm. While homeownership is common, gentrification in recent decades has brought an influx of higher-income residents, resulting in rising property values and a mix of longtime and new residents.

Logan Square is culturally rich and diverse, with residents from a variety of ethnic backgrounds. Historically home to European immigrants, the neighborhood now includes Latino, Asian, and other communities, creating a vibrant cultural tapestry. Median household income is slightly above the city average, reflecting a mix of working- and middle-class households alongside newer, higher-income residents. Local restaurants, cafes, galleries, and shops reflect this diversity and contribute to the neighborhood’s dynamic character.

Education is a key part of Logan Square’s community life. The neighborhood is served by Chicago Public Schools including Chase Elementary and Madero High School, as well as private and charter schools. Schools often engage with local arts and cultural programs, adding to the neighborhood’s creative atmosphere and family-friendly appeal.

Economically, Logan Square thrives on a combination of small businesses, retail, and restaurants along major corridors such as Milwaukee Avenue, Logan Boulevard, and Western Avenue. The neighborhood also features breweries, cafes, and local markets that attract visitors and support the local economy. Many residents commute to downtown Chicago via the Blue Line, CTA buses, or bike-friendly streets.

Recreation and culture are central to Logan Square life. Logan Square park and boulevards offer green space, walking paths, and athletic fields. Nearby Humboldt Park and the 606 Trail provide additional outdoor recreation opportunities. Community events, farmers markets, and arts festivals foster engagement and strengthen neighborhood identity.

Logan Square is known for its strong community involvement, cultural vibrancy, and historic preservation efforts. Residents take pride in maintaining the neighborhood’s character while embracing new cultural influences and amenities.

For those seeking a lively, diverse, and accessible neighborhood in Chicago, Logan Square offers a unique combination of historic charm, active community life, quality schools, and urban convenience. Its tree-lined streets, cultural richness, and neighborhood pride make Logan Square a desirable place to live on the city’s Northwest Side.

Protecting your property and maximizing returns

Our syndicated property marketing service can work wonders for you! Even the best property owners struggle to find qualified tenants without effective rental property marketing strategies and the ability to screen applicants.

We help prevent evictions and property damage. We perform comprehensive tenant screening using a private detective agency to protect your real estate investments.

Our goal is to maximize your Net Operating Income (NOI). We attract high-quality tenants through targeted marketing strategies and thorough screening processes.

Property owners can rely on us for timely rent collection and smooth bank transactions. Tenants can appreciate our Online Portal to securely pay rent, submit maintenance requests, access documents, and more…

How often have you struggled to find a contractor for a repair job at a reasonable price? One of our most valued value-added services is our ability to perform small and large repairs at reasonable rates and on short notice.

Whether you’re a seasoned investor, a first-time buyer, or seeking to expand, our consulting services are designed to provide you with the insights and strategies you need to succeed.

Ready to get more than management?

Gain a trusted partner for the life of your investment!

Our expertise

At Three Pentacles, PLLC, we provide comprehensive real estate services, combining expert brokerage and property management to meet all your needs. From acquisitions and sales to leasing, rent collection, and maintenance, our team ensures your property thrives. With experience across all property types, we deliver tailored strategies and hands-on support for long-term success.

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