Highwood, IL Real Estate
A vibrant, diverse village known for its renowned dining scene and small-town charm just north of Highland Park.
Overview
Highwood is a small, vibrant village of about 5,000 residents located just north of Highland Park. Despite its compact size, Highwood has built a reputation as one of the North Shore's premier dining destinations, with a concentration of acclaimed restaurants that draw visitors from across the region.
The village offers a diverse, close-knit community with a walkable downtown and a mix of housing styles, from historic cottages to newer townhomes. Its location on the Metra Union Pacific North line makes commuting to Chicago easy.
Lifestyle
Highwood's lifestyle is lively and community-centered. The village is famous for its restaurant scene, seasonal festivals, and a strong sense of local pride. Events like the Highwood Pumpkin Fest and weekly summer concerts bring residents together throughout the year.
The community is diverse and welcoming, with a small-town feel that is rare so close to Chicago. Many residents walk to dinner, shops, and the train, making it one of the more walkable villages on the North Shore.
Schools
Highwood is served by North Shore School District 112 for elementary and middle school, and Township High School District 113, with students attending Highland Park High School. Both districts are highly rated and offer strong academic and extracurricular programs.
Historic Downtown
Downtown Highwood is the heart of the village and the center of its renowned dining scene. The walkable downtown features a high concentration of restaurants, cafes, and small shops, creating a lively atmosphere, especially on weekends and evenings.
The Highwood Metra station is located downtown, providing convenient access to Chicago.
Outdoor Recreation
While Highwood is small, residents enjoy access to nearby parks and the Lake Michigan beaches of neighboring Highland Park. The village has its own community parks and is close to the Green Bay Trail for biking and walking.
Dining
Dining is Highwood's signature attraction. The village is home to a remarkable concentration of acclaimed restaurants spanning Italian, Mexican, American, and contemporary cuisines. It is widely considered one of the best dining destinations on the North Shore.
Housing & Market Overview
The Highwood real estate market is compact and distinctive, with a mix of historic homes, cottages, and newer townhome developments. Its relatively accessible price points and walkable location make it attractive to first-time buyers and those seeking a low-maintenance North Shore lifestyle.
Mark's construction background helps buyers evaluate the condition of older homes and the value of newer construction in this unique market.
Renovate or Rebuild?
Highwood's housing stock includes historic cottages and smaller homes alongside newer townhome developments. Buyers considering renovation should weigh the village's zoning, which governs setbacks and lot coverage for the smaller lots common here. From a contractor's perspective, the key is whether an older home's structure supports a cost-effective renovation or whether the lot is better suited for new construction.
Because many Highwood lots are compact, expansion rather than teardown is often the more practical path. Mark's contracting background lets him assess the structural condition and give you a realistic read on what the village will permit.
Moving & Relocation Information
Relocating to Highwood offers an easy entry into North Shore living with a short commute. The Highwood Metra station on the Union Pacific North line provides direct service to downtown Chicago. The village is also convenient to US-41 and I-94.
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Frequently Asked Questions
Expert answers about living in Highwood.
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