Highland Park 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 Highland Park

Highland Park, Illinois is an affluent and picturesque suburb located in Lake County, approximately 25 miles north of downtown Chicago along the scenic western shore of Lake Michigan. Known for its tree-lined streets, historic architecture, cultural richness, and top-tier schools, Highland Park offers residents a blend of suburban luxury, natural beauty, and urban convenience. With a population of roughly 30,000 residents, the city appeals to families, professionals, and retirees seeking a vibrant yet tranquil community.

The history of Highland Park dates back to the mid-19th century. The area was originally inhabited by Native American tribes before European settlers arrived in the 1830s. Highland Park was officially incorporated in 1869, becoming one of the earliest suburban communities in Lake County. The city grew rapidly due to its attractive location along Lake Michigan, access to transportation, and development of residential neighborhoods. Many historic homes and landmarks still stand today, reflecting the city’s rich architectural heritage and long-standing commitment to community planning.

Highland Park covers approximately 15 square miles and is characterized by a mix of residential neighborhoods, commercial areas, and parks. Housing options range from historic estates and Craftsman-style homes to modern single-family houses and condominiums. Streets are lined with mature trees, landscaped yards, and scenic vistas, particularly near the lakefront and forest preserves. The city offers a high quality of life with neighborhoods that balance privacy, aesthetics, and community accessibility.

Education is a cornerstone of Highland Park. The city is served by Highland Park High School District 113 for secondary education and Elementary School District 112 for elementary and middle school education. Schools are widely recognized for academic excellence, extracurricular programs, and strong community engagement. Additionally, several private and parochial schools in the area provide alternative educational options, making Highland Park attractive to families seeking high-quality education.

Highland Park’s economy is diverse, with local businesses, professional services, retail, and hospitality supporting the community. The downtown area features boutique shops, restaurants, coffeehouses, and cultural venues, providing residents with convenient amenities and vibrant social hubs. The city’s location along Lake Michigan and proximity to major highways such as Interstate 94 make it accessible for commuters and regional travelers, supporting both local businesses and professional residents.

Recreation and outdoor amenities are abundant in Highland Park. The city is home to numerous parks, trails, and natural areas maintained by the Highland Park Park District. Residents enjoy hiking, biking, golf, tennis, swimming, and other recreational activities. Proximity to Lake Michigan offers opportunities for boating, fishing, and water-based recreation, while nearby forest preserves provide additional outdoor experiences. Highland Park also hosts cultural events, festivals, and farmers markets that encourage community engagement and active lifestyles.

Cultural and civic life in Highland Park is vibrant and community-centered. The city supports arts organizations, theaters, galleries, and performance venues, including the well-regarded North Shore Center for the Performing Arts. Civic programs and volunteer opportunities foster a sense of community pride and involvement. Highland Park’s cultural richness, combined with its historic charm, makes it a hub for both local residents and visitors seeking arts, education, and recreational experiences.

Transportation is a significant advantage for Highland Park residents. The city is served by Metra’s Union Pacific North Line, providing direct commuter rail access to downtown Chicago. Major roadways, including Interstate 94, ensure efficient travel to Chicago and surrounding suburbs. This connectivity allows residents to enjoy a suburban lifestyle while maintaining access to urban employment, cultural, and entertainment opportunities.

Demographically, Highland Park is composed primarily of families, professionals, and retirees who value education, safety, and high-quality amenities. Median household income is well above the national average, reflecting the city’s affluence and economic stability. Housing ranges from historic estates and luxury properties to more modest single-family homes, accommodating a variety of residents while maintaining the community’s upscale character.

For prospective residents, Highland Park offers a blend of historic charm, scenic neighborhoods, excellent schools, cultural richness, and recreational opportunities. Its combination of suburban luxury, lakefront access, and convenient commuting options makes it an attractive place to live for families, professionals, and retirees alike. With its strong sense of community, abundant amenities, and natural beauty, Highland Park remains one of the most desirable communities in Lake County for those seeking a high-quality suburban lifestyle.

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.