Waukegan 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

Jacky R.

Can’t thankful enough Arthur for helping and walk me through all the way of Closing. If there’s a 10 out 10 Stars. 🌟I’ll give him 10 ⭐️ Stars. Thank you so much Three Pentacles, PLLC. More Power. All the best! ✅

Lou M.

“Art’s vision and brokerage system reflect the latest trends in the real estate business.”

Bill J.

“Arthur and staff have been very informative, insightful, and professional. My first impression was great! It’s nice to know and respect the amount of knowledge and wisdom that Arthur has accumulated.”

Mike E.

“Arthur first brings an extremely high level of integrity. Clearly, he is intelligent and creative, but none of that matters without integrity. Secondly, as a broker, Arthur learns each subject area he chooses for study thoroughly and deeply. Whether he is discussing RESPA, computers, or sales, it is clear that Arthur knows his areas of expertise well.”

Cynthia U.

“I have found Arthur and his support staff to be very approachable and more than willing to help with any question or concern that may arise. I know because I have a lot of them! I am also very impressed with how technologically advanced the company is ahead of any other firm in the industry.”

Nina T.

“I think Mr. van der Vant is very experienced, very responsible and very sharp. He has taken classes, he has written books, and people whom were once his partners in business, told me that he is one of the very few businessmen who has a big knowledge about the foreclosure market. It is always good to be surrounded by smart people. It is a pleasure to work with him. He is always on time and he always picks up the phone when you call him.”

Kevin S.

“I have NEVER been given, or seen, this level of support and attentiveness before from any broker. Arthur is super knowledgeable, attentive, and GENEROUS with his vast Real Estate experience and knowledge. He’s also a nice guy, and very easy to work with.”

Maria S.

“I love getting my big checks, and fast.”

Sherry Y.

“This is a very knowledgeable broker… I really enjoy having the opportunity to work with Arthur.”

Rumen T.

“It is a great company with very experienced broker, a company that provides everything for the client from real estate contract to closing. Thank you!”

Anita F.

“I left another real estate brokerage after 15 years and started working with this company, because this one is dedicated and actively moving our business into the future, it’s also accomplishing that at a conservative cost. Thank you.”

Tina S.

“I’m grateful that I don’t have to reinvent the wheel everyday, like I used to do. Looking forward to a good year!!!”

Todd P.

“This is a company that has a vision, a bright future and a focus that any real estate person should look into whether you are new to the business or an experienced veteran.”

Christian M.

“Art is nice and professional. He is very well informed on maintenances and care for units. Good at communicating, quick to respond to questions or requests.”

Navin N.

“Art is one of the best out there. Highly encourage folks to work with him.”

Aaron S.

” Art with Three Pentacles is easily one of the most knowledgeable property managers in Chicagoland. When I was looking for a new management company, I called a good 10 places. during the time I had a tenant I was in the middle of evicting. Without pitching me, Art asked thoughtful questions to learn more about the situation. He clearly has immense knowledge of the eviction process and housing court system. After our call, I engaged his services and he’s been prompt and supportive ever since. He has been navigating my difficult tenant situation with grace, using strategies that never crossed my mind. I feel secure knowing Art has my best interests forward, and is clearly able to manage my property within state and county compliance. He’s worth every penny, and if you’re looking for a property manager, he’s your guy.”

Jeff F.

“The owner of Three Pentacles is an outstanding property manager across the board. He has the technical understanding and experience with repairs to hire out for routine and major work in a methodical and cost-effective way, and he will go above and beyond to address emergency situations like the flooding of a basement apartment. By doing so, he not only serves the best interests of property owners but their tenants as well. Most impressive of all, he is extremely knowledgeable about everything related to leasing apartments, from obtaining a through background check of prospective tenants, to making sure leases comply with any local regulations, and taking the proper steps to evict a tenant when necessary. I would highly recommend Three Pentacles.”

Gena M.

“Experience was great love working with Three Pentacles, PLLC.”

Mercedes A.

“I highly recommend Three Pentacles PLLC. They have great attention to detail and go above and beyond to provide excellent service.”

AI optimized

We know what renter's are looking for and how your property compares

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

We know what renter's want to spend and how much money they make before they contact us

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

We screen applicants using a private detective agency

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

We are "Real Experts in Real Estate" ™

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

Our competitive advantage is perspective earned over decades

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

Our experience is measured not just in years, but in results

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!

Request a call-back

About Waukegan

Waukegan, Illinois is a historic and diverse city located in Lake County, approximately 35 miles north of downtown Chicago along the western shore of Lake Michigan. Known for its waterfront access, cultural diversity, historic architecture, and revitalized downtown, Waukegan offers a unique mix of urban and suburban living. With a population of roughly 87,000 residents, it is one of the largest cities in Lake County, attracting families, professionals, artists, and retirees seeking a dynamic and culturally rich community.

The history of Waukegan dates back to the early nineteenth century. Founded in 1829, the city’s name is derived from a Native American term believed to mean “fort” or “fortified place.” Waukegan grew rapidly as an industrial and manufacturing hub, benefiting from its location on Lake Michigan and proximity to railroads. Throughout the twentieth century, the city became a center for shipping, manufacturing, and commerce, shaping its diverse economy and culturally rich population. Many historic buildings, neighborhoods, and landmarks reflect Waukegan’s long and varied history.

Waukegan covers approximately 24 square miles, with neighborhoods ranging from historic districts near downtown to suburban residential areas and lakefront communities. Housing options are diverse, including single family homes, condominiums, townhouses, and apartment complexes. The city’s historic neighborhoods feature early twentieth century architecture, while newer developments provide modern conveniences and family friendly layouts. Waukegan offers a mix of affordability, location, and lifestyle options suitable for a wide range of residents.

Education in Waukegan is provided by Waukegan Community Unit School District 60, which serves students from kindergarten through high school. Local schools offer academic programs, athletics, arts education, and extracurricular activities. Waukegan also hosts several private and parochial schools, as well as nearby colleges such as College of Lake County, providing higher education opportunities for residents and fostering lifelong learning.

The local economy in Waukegan is diverse and evolving. Historically centered on manufacturing and shipping, the city has expanded into healthcare, retail, services, and government employment. Waukegan is home to regional offices, local businesses, and the Waukegan Port District, which supports commercial and recreational activity on Lake Michigan. Recent revitalization efforts downtown have introduced cultural centers, restaurants, and entertainment venues, enhancing both the economy and quality of life.

Recreation and cultural amenities in Waukegan are abundant. The Lake Michigan shoreline provides residents with boating, fishing, beaches, and scenic walking paths. The Waukegan Park District manages parks, sports fields, playgrounds, trails, and community programs for residents of all ages. The city also features cultural institutions such as the Genesee Theatre, art galleries, and community events celebrating music, film, and local history. Forest preserves and nature areas nearby offer additional opportunities for hiking, biking, and outdoor exploration.

Cultural and civic life in Waukegan is vibrant, reflecting its diverse population. Residents actively participate in community organizations, volunteer programs, and neighborhood associations. City leadership focuses on public safety, infrastructure, and economic development, ensuring Waukegan remains a secure and attractive city for families, professionals, and retirees. Community events, festivals, and local initiatives foster civic engagement and pride.

Transportation access in Waukegan is excellent for both commuting and regional travel. The city is served by Metra’s Union Pacific North Line, providing direct rail access to downtown Chicago. Major highways, including Interstate 94 and U.S. Route 41, allow convenient travel throughout Lake County and northern Illinois. Waukegan is also within driving distance of Chicago O’Hare International Airport and General Mitchell International Airport in Milwaukee, supporting both domestic and international travel.

Demographically, Waukegan is a diverse community with a wide range of household incomes and cultural backgrounds. Median household income is slightly below the national average, reflecting the city’s mix of working families, young professionals, and retirees. A combination of owner occupied and rental housing provides options for various lifestyles. The city’s diversity, historic neighborhoods, and revitalized cultural districts make Waukegan appealing for individuals and families seeking an urban environment with access to suburban amenities.

For prospective residents, Waukegan offers a blend of historic character, lakefront living, cultural diversity, and convenient access to Chicago and northern Illinois. Its combination of residential neighborhoods, economic opportunities, educational resources, and recreational amenities makes it attractive to families, professionals, and retirees seeking a vibrant yet approachable city. With ongoing investment in infrastructure, community development, and cultural programming, Waukegan continues to be one of Lake County’s most dynamic and evolving communities.

Protecting your property and maximizing returns

Ready to get more than management?

Gain a trusted partner for the life of your investment!

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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.