Near South Side Property Management

38 yrs +
What makes our company different is your competitive advantage
30 mil. +
Our syndicated marketing brings renters to your property
50 states
We use a private detective agency to screen tenants
Btm. line
Our expert leasing maximizes your rental income faster
Cash flow
Our consistent, hassle-free rent collection is money in your bank on-time
Stress free
We take care of your property maintenance, so you can rest easy

Partner with us for expert guidance

Leverage our consulting expertise to maximize returns and protect your assets!

Near South Side 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

  • Does your property manager have 38+ years of experience?
  • Has your property manager earned the following industry designations and certifications:
    CCIM, CAI, AARE, PRI, CNE, CIPS, CRB, CRS, GRI, ABR, RECS, SRES, ePRO?

  • Is your property manager a court-appointed receiver in state and federal courts?

  • Has your property manager argued cases before the State Court of Appeals?

  • Has your property manager argued cases before the Federal Court?

  • Was your property manager appointed by the FDIC to manage a failed townhome development?

  • Has your property manager built a real estate brokerage with 612 agents?

  • Has your property manager closed an average of 200 transactions per month?

  • Has your property manager closed $1 billion in sales annually?

  • Has your property manager developed and constructed condominium projects?

  • Has your property manager owned a mortgage banking company and understands the ins and outs of mortgage financing?

  • Has your property manager owned a title insurance agency and conducted title examinations?

  • Has your property manager served as President of the Illinois CCIM Chapter?

  • Has your property manager served on the Board of Directors of the Chicago Association of Realtors?

If your property manager has not done these things, your properties may be in the wrong hands, our complimentary consulting, included as part of our comprehensive services, helps clients make better-informed decisions, reduce risk, and maximize property performance and long-term returns.

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 better 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. 

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.

Complimentary consulting with a 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 Near South Side

The Near South Side is a vibrant and evolving neighborhood located just south of Chicago’s downtown Loop. Home to approximately 25,000 residents, it is known for its mix of historic architecture, modern residential developments, cultural institutions, and proximity to Lake Michigan. The neighborhood combines urban convenience, recreational opportunities, and a growing residential community, making it attractive to professionals, families, and students.

The Near South Side has a rich history that dates back to the 19th century. Originally a mix of industrial sites, rail yards, and working-class housing, the area gradually transformed into a residential and cultural hub. It includes historic districts such as Prairie Avenue, which was once home to some of Chicago’s wealthiest families. Over the past several decades, the neighborhood has seen significant redevelopment, including modern high-rise apartments, condominiums, and mixed-use developments along the lakefront and south of the Loop.

Housing in the Near South Side is diverse, ranging from historic mansions and greystones to modern high-rise condominiums and apartment buildings. The neighborhood offers both rental and ownership opportunities, appealing to young professionals, families, and long-term residents. Its proximity to the lake and downtown Chicago adds to its desirability, while newer developments have introduced contemporary amenities and luxury living options.

The neighborhood is culturally diverse, with residents representing various ethnic, professional, and socioeconomic backgrounds. Median household income is above the city average in many parts due to the influx of professionals and luxury housing. Community organizations, cultural institutions, and local businesses contribute to a dynamic social and cultural environment.

Education in the Near South Side includes access to public schools such as Phillips Academy High School and specialized programs in nearby schools. The neighborhood is also close to higher education institutions like DePaul University, Roosevelt University, and Columbia College Chicago, offering educational and cultural enrichment opportunities.

Economically, the Near South Side benefits from a mix of residential, commercial, and cultural activity. Major streets like Michigan Avenue, State Street, and South Dearborn host shops, restaurants, and entertainment venues. Many residents commute to the Loop or other parts of Chicago using CTA buses, the Red Line, or Metra, and the neighborhood’s proximity to major expressways makes commuting convenient.

Recreation and green space are key features of the Near South Side. The neighborhood borders Grant Park and the Museum Campus, offering walking paths, athletic fields, gardens, and access to Lake Michigan. Cultural attractions such as the Field Museum, Shedd Aquarium, and Soldier Field are located within or near the neighborhood, providing residents with world-class recreational and educational opportunities.

The Near South Side is recognized for its mix of historic charm and modern development, with active neighborhood associations and community organizations contributing to its sense of identity. Residents value the area’s proximity to downtown, cultural amenities, and recreational spaces, creating a lively and engaged community.

For those seeking a neighborhood with urban convenience, cultural richness, and lakefront access, the Near South Side offers a unique combination of historic architecture, modern housing, recreational opportunities, and vibrant community life. Its location just south of the Loop makes it a highly desirable area for Chicago residents.

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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