Chicago's best property management company, providing tenant screening, rent collection, property marketing, and more at reasonable cost.
Winnetka Property Management at its best!
Three Pentacles – Expert Property Management Company in Winnetka, IL
Looking for reliable property management in Winnetka, IL? Three Pentacles is a trusted property management company specializing in both residential property management and commercial property management throughout Winnetka 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 Winnetka
About Winnetka
Winnetka is a village in Cook County, Illinois, United States, located 16 miles (26 km) north of downtown Chicago. The population was 12,316 as of 2019. The village is one of the wealthiest places in the nation in terms of household income. It was the second-ranked Illinois community on Bloomberg’s 2019 Richest Places Annual Index. In 2020, 24/7 Wall Street ranked Winnetka as the second-best small town to live in the United States. In 1836 the Erastus Patterson family arrived in Winnetka via ox-drawn wagon after a journey from Woodstock, Vermont. Near the Green Bay Trail on a bluff overlooking Lake Michigan, somewhat east of the present Christ Church on Sheridan Road, the Pattersons built a log tavern to provide food and shelter to travelers.
In 1847, John and Susannah Garland and their eight children bought the tavern, which they enlarged. They also built a sawmill, a red brick house for themselves and eventually, Winnetka’s first church-on the Christ Church site in 1869. About 100 people lived in the area when New Trier Township, named after Trier, Germany (the original home of many of the area’s settlers), was organized in 1850. Shortly after and anticipating the construction of the railroad, Chicago pioneer Charles Peck and his friend Walter Gurnee, president of the newly formed Chicago and Milwaukee Railroad’s train service in 1854 assured Winnetka’s suburban future, as the railroad became the major force in the development of the North Shore.
Often called the “founders of Winnetka,” Charles and Sarah Peck built a large house northwest of Elm and Maple Streets. Sarah Peck, who named Winnetka after a Native American phrase thought to mean “beautiful land,” organized the Village’s first school, a private one, in 1856. Charles Peck encouraged the planting of donated elms along Elm Street. In 1869, the Pecks donated the Village Green (also known as the Village Common) to the community. Reflecting the public spirit of its donors, the Village Green remains something of a spiritual center for Winnetka, as well as a meeting place for residents and host to many Village celebrations.
Although it may have looked like a farming community, mid-1850s Winnetka lay only five miles north of Evanston’s Northwestern University-one of the few seats of higher learning in Illinois. Winnetka’s early residents, many from New England, were well-educated, highly religious, and reform minded. Reflecting the values of the time, the Village’s charter, granted by the state in 1869, banned the public consumption and sale of alcohol, while enforcing the planting and protection of shade trees.
Relative to other North Shore communities, Winnetka’s growth was slow prior to 1900. The 1880 population was 584 and grew to 1,883 by 1900. After 1900, the Village started to grow more rapidly, and by 1920, the population had more than tripled to 6,694. Within the next ten years, the Village population doubled to today’s level – 12,187 (2010 Census).
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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