Highwood

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Professional Property Management in

Highwood

Three Pentacles, PLLC provides reliable, full-service property management, real estate brokerage, and construction/remodeling 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.

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.

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

Our syndicated property marketing service can work wonders for you! Even the best property owners struggle to find qualified tenants without effective rental property marketing strategies and the ability to screen applicants.

We help prevent evictions and property damage. We perform comprehensive tenant screening using a private detective agency to protect your real estate investments.

Our goal is to maximize your Net Operating Income (NOI). We attract high-quality tenants through targeted marketing strategies and thorough screening processes.

Property owners can rely on us for timely rent collection and smooth bank transactions. Tenants can appreciate our Online Portal to securely pay rent, submit maintenance requests, access documents, and more…

How often have you struggled to find a contractor for a repair job at a reasonable price? One of our most valued value-added services is our ability to perform small and large repairs at reasonable rates and on short notice.

Whether you’re a seasoned investor, a first-time buyer, or seeking to expand, our consulting services are designed to provide you with the insights and strategies you need to succeed.

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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.

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