Highwood Property Management

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

Highwood 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

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 best 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.

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

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.

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About Highwood

Highwood, Illinois is a compact and vibrant suburb located in Lake County, just north of Highland Park and approximately 25 miles north of downtown Chicago. Known for its historic charm, cultural diversity, and active community life, Highwood offers residents a unique blend of small-town character with urban accessibility. With a population of roughly 5,500 residents, the city attracts families, professionals, and individuals who value community engagement, walkable neighborhoods, and proximity to Lake Michigan.

The history of Highwood dates back to the mid-19th century, when the area was originally farmland and forests along the western shore of Lake Michigan. The village developed as a hub for Swedish and Norwegian immigrants, later attracting a diverse population including Italian and Latin American communities. Highwood was incorporated in 1887, and its growth was closely tied to the railroad and industrial development in the region. Many historic buildings and homes remain, reflecting the city’s rich architectural and cultural heritage.

Highwood covers roughly 0.6 square miles, making it one of the smaller suburbs in Lake County. The city is predominantly residential, with a mix of single-family homes, townhouses, and multi-family dwellings. Streets are compact and walkable, often lined with mature trees and historic architecture. Housing styles include classic early 20th-century bungalows, Colonial Revival, and contemporary designs. The city’s size and layout foster a strong sense of community and neighborhood connectivity.

Education is a key consideration for families in Highwood. The city is served by Highwood School District 77, which provides elementary and middle school education, while students typically attend North Shore School District 112 or nearby high schools in Highland Park and Deerfield for secondary education. Schools are known for their academic programs, extracurricular opportunities, and emphasis on student success. Families also have access to private and parochial schools in neighboring communities, offering additional educational choices.

Highwood’s local economy is anchored by small businesses, restaurants, and retail establishments that reflect the city’s cultural diversity. Downtown Highwood, often called the “Small Town with a Big Heart”, features an eclectic mix of dining, boutique shops, and community spaces that serve both residents and visitors. The city’s vibrant cultural scene and walkable commercial district create a lively environment while maintaining a friendly, small-town atmosphere.

Recreation and outdoor amenities are integral to life in Highwood. Residents have access to nearby Lake Michigan beaches, forest preserves, and parks, providing opportunities for walking, biking, boating, and seasonal outdoor activities. The city also hosts community events, festivals, and cultural celebrations that foster engagement and pride among residents. Highwood’s emphasis on walkability, open spaces, and recreational programming enhances the quality of life for people of all ages.

Cultural and civic life in Highwood is strong and community-centered. The city hosts annual events such as parades, festivals, and arts programs that bring residents together and celebrate local heritage. Civic organizations and volunteer initiatives promote neighborhood involvement, public safety, and community improvement projects. The city’s rich history, diversity, and cultural offerings contribute to a welcoming and dynamic environment for residents.

Transportation is convenient in Highwood, despite its compact size. Major roadways and proximity to Interstate 94 provide access to Chicago and other suburbs. Public transportation options, including nearby Metra rail stations in Highland Park and Deerfield, support commuter travel to downtown Chicago. The city’s location allows residents to enjoy a small-town atmosphere while maintaining easy connectivity to urban employment, entertainment, and cultural destinations.

Demographically, Highwood is composed of families, professionals, and retirees who value cultural diversity, walkable neighborhoods, and active community life. Median household income is slightly above the national average, reflecting the city’s economic stability. Housing is a mix of owner-occupied and rental properties, accommodating a range of residents while preserving the city’s historic charm.

For prospective residents, Highwood offers a blend of historic character, cultural diversity, walkable neighborhoods, and community engagement. Its combination of small-town charm, convenient location, and access to Lake Michigan makes it an attractive place to live for families, professionals, and retirees alike. With its strong civic life, vibrant downtown, and natural amenities, Highwood remains one of the most desirable communities in Lake County for those seeking a unique, connected, and high-quality suburban lifestyle.

Protecting your property and maximizing returns

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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.