Chicago's best property management company, providing tenant screening, rent collection, property maintenance, property marketing, and more at reasonable cost.
Highland Park Property Management at its best!
Three Pentacles – Expert Property Management Company in Highland Park, IL
Looking for reliable property management in Highland Park, IL? Three Pentacles is a trusted property management company specializing in both residential property management and commercial property management throughout Highland Park and the surrounding areas. We deliver personalized, professional property management services tailored to meet the unique needs of property owners. Whether you’re managing a single-family home, apartment complex, retail space, or office building, Three Pentacles provides the hands-on support and local expertise you can count on.
We Manage All Types of Properties in Highland Park
About Highland Park
Highland Park, Illinois, founded in 1869, is a scenic Lake Michigan suburb with tree-lined ravines and a 100-ft bluff along its shoreline. Its early settlers came via the Chicago & Milwaukee Railroad, transforming the area from farmland into a refined residential enclave.
Today, Highland Park has about 30,200 residents living in roughly 11,700 households, with an average household size of 2.5. The demographic profile is predominately non-Hispanic white, with Asian and Hispanic communities contributing to its diversity. The local economy has long included professional services, boutique retail, and formerly the headquarters of large firms (e.g., Solo Cup), while its high median incomes reflect a stable and affluent community.
Culturally, the city shines through the Ravinia Festival, the nation’s oldest outdoor music festival and summer home to the Chicago Symphony Orchestra. Architecturally, landmarks like the historic Water Tower add character. Government in Highland Park operates under a council-manager system, with an elected mayor and city council.
Education is robust: Highland Park High School (District 113) serves the city with strong academics and community engagement. Public life also centers on the Highland Park Public Library, established in the 1880s. Transportation is well served by the Metra Union Pacific North Line, and major roadways connect residents to Chicago and beyond.
Notable residents include music icon Billy Corgan, singer Richard Marx, actress Rachel Brosnahan, and Olympic figure-skater Jason Brown.
On the global stage, Highland Park fosters cross-cultural ties through the Highland Park Sister Cities Foundation, which connects the city with Modena, Italy, Puerto Vallarta, Mexico, and Yerucham, Israel. The Foundation was honored by Sister Cities International for its outstanding programs.
For property owners seeking expert support, Three Pentacles, PLLC provides full-service management through its main Property Management Page. Highland Park is featured within the company’s Service Area, supported by comprehensive Management Services including leasing, inspections, and maintenance. Investors benefit from strong Guarantees and ongoing insights available on the Three Pentacles Blog. Additional resources include tailored Tenant Placement, streamlined Maintenance Coordination, and full Portfolio Support. Owners can explore more guidance across the Three Pentacles Website and access community-focused content designed to support long-term investment success.
WHY WE'RE DIFFERENT
Our guarantees give you peace of mind, knowing your property is in good hands and that we’re working hard to protect and enhance its value.
With Three Pentacles, PLLC, you’ll have a single point of contact—no more being passed from one representative to another just to get updates on your property. You’ll work directly with a dedicated Asset Manager who knows your property inside and out.
Since 2010, Arthur has served as an Illinois Receiver, managing properties in receivership in both Illinois state courts and the U.S. District Court for the Northern District of Illinois.
We have been closely working with attorneys, judges, and banks. Our managing broker has been an Associate Member of the Chicago Bar Association since 2012.
We are Real Experts in Real Estate™, experienced in property management, real estate investing, mortgages, title insurance, construction, and real estate law. Obtained the following real estate designations and certifications: CCIM, CAI, AARE, PRI, CNE, CIPS, CRB, CRS, GRI, ABR, RECS, SRES, ePRO.
Don’t settle for a typical 9-to-5, Monday-through-Friday property management company—Three Pentacles goes the extra mile, working for you 7 days a week to maximize the value of your property.
Our managing broker is a graduate of an Air Force Academy with a background in aviation engineering. This foundation brings a systems-oriented approach, strong discipline, and sharp analytical skills to our work—enabling us to efficiently help property owners improve and turn around their assets.
We perform tenant screening and background checks using a Private Detective Agency.
We combine modern technology, online-systems, and decades of real estate experience with old fashion values. We run this company the way our grandparents taught us: “Anything worth doing, is worth doing right.” TM
Our team has helped landlords throughout Chicagoland and across Illinois maximize the value of their real estate investments. Let us put our expertise and dedication to work for you, too!
Arthur holds the equivalent of two doctorates in real estate through advanced professional designations:
CCIM Designation (2000): In 2000, Arthur earned the prestigious Certified Commercial Investment Member (CCIM) designation from the CCIM Institute. This designation is awarded upon completion of a rigorous graduate-level curriculum and demonstration of extensive qualifying experience. Recognized globally, CCIM professionals are regarded as experts in commercial and investment real estate.
CAI Designation (2010): In 2010, Arthur completed the Certified Auctioneers Institute (CAI) program at Indiana University. This graduate-level program focuses on asset liquidation and auction strategies, and is the highest professional designation in the auction industry.
Since earning his CAI designation, Arthur has served as a court-appointed Receiver in Illinois, managing distressed and litigated properties under the jurisdiction of both state and federal courts.
We understand the ins and outs of local real estate
Cook County
Three Pentacles, PLLC provides property management services across North and Northwest areas of Cook County, Illinois. Our experienced team understands the unique needs of property owners and tenants in North and Northwest areas of Cook County, offering tailored solutions that ensure success:
DuPage County
Three Pentacles, PLLC provides property management services in DuPage County, Illinois. Three Pentacles manages residential properties and commercial properties in DuPage County, IL. For more information see communities listed below:
- Addison
- Bloomingdale
- Darien
- Glen Ellyn
- Lisle
- Roselle
- Wayne
- Winfield
- Aurora
- Bolingbrook
- Downers Grove
- Hanover Park
- Lombard
- Schaumburg
- West Chicago
- Wood Dale
- Bartlett
- Burr Ridge
- Elk Grove Village
- Hinsdale
- Naperville
- St. Charles
- Westmont
- Woodridge
- Batavia
- Carol Stream
- Elmhurst
- Itasca
- Oak Brook
- Villa Park
- Wheaton
- Bensenville
- Clarendon Hills
- Glendale Heights
- Lemont
- Oakbrook Terrace
- Warrenville
- Willowbrook
Lake County
Three Pentacles, PLLC provides property management services to property owners in Lake County, Illinois. Three Pentacles manages residential properties and commercial properties in Lake County, IL. For details see communities listed below:
- Antioch
- Buffalo Grove
- Grayslake
- Highland Park
- Lake Barrington
- Lakemoor
- Mettawa
- Port Barrington
- Round Lake Park
- Wadsworth
- Bannockburn
- Deer Park
- Green Oaks
- Highwood
- Lake Bluff
- Libertyville
- Mundelein
- Riverwoods
- Third Lake
- Wauconda
- Barrington
- Deerfield
- Gurnee
- Indian Creek
- Lake Forest
- Lincolnshire
- North Barrington
- Round Lake
- Tower Lakes
- Waukegan
- Barrington Hills
- Fox Lake
- Hainesville
- Island Lake
- Lake Villa
- Lindenhurst
- Old Mill Creek
- Round Lake Beach
- Vernon Hills
- Wheeling
- Beach Park
- Fox River Grove
- Hawthorn Woods
- Kildeer
- Lake Zurich
- Long Grove
- Park City
- Round Lake Heights
- Volo
- Winthrop Harbor
McHenry County
Three Pentacles, PLLC provides property management services in McHenry County, Illinois. Three Pentacles manages residential properties and commercial properties in McHenry County, IL. For more information see communities listed below:
- Algonquin
- Huntley
- Barrington Hills
- Island Lake
- Cary
- Lake in the Hills
- Crystal Lake
- Lakemoor
- Fox River Grove
Kane County
Three Pentacles, PLLC provides property management services in Kane County, Illinois. Three Pentacles manages residential properties and commercial properties in Kane County, IL. For more information see communities listed below:
- Batavia
- North Aurora
- Carpentersville
- Sleepy Hollow
- East Dundee
- South Elgin
- Elgin
- St. Charles
- Geneva
- West Dundee
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