Highland Park vs Deerfield: How to Choose Your Ideal Community

Torn between Highland Park and Deerfield for your North Shore move? You are not alone. Both communities offer strong schools, beautiful neighborhoods, and easy access to Chicago, yet they feel different day to day. This guide walks you through the tradeoffs so you can match each town’s character, commute, and costs to your goals. Let’s dive in.

Quick snapshot: Highland Park vs Deerfield

Highland Park at a glance

• Strong lakefront presence with beaches and scenic neighborhoods.
• A larger downtown with more arts and cultural programming, including a well-known summer music venue.
• A wider mix of housing styles, including older homes, estate lots, and architecturally distinct properties.
• Walkable retail and dining clusters that support an active street life.

Deerfield at a glance

• Classic suburban feel with many post‑war and newer subdivisions.
• Family‑oriented park district amenities and neighborhood‑scale downtown.
• Proximity to corporate offices and business parks that support local employment.
• Convenient highway access and planned neighborhoods with mid‑sized lots.

Common tradeoffs to consider

• Highland Park often offers stronger lake access and a bigger cultural footprint, with more historic homes that may require more maintenance.
• Deerfield typically delivers easier‑to‑maintain housing stock and planned subdivisions, with slightly more suburban quiet and convenient access to office corridors.
• Pricing can vary by block in both towns. Expect older or lake‑proximate homes in Highland Park to carry premiums, while Deerfield can offer competitive price per square foot for similar space.

Housing and neighborhoods

If you love character and variety, Highland Park gives you a broad spectrum of homes, from early 20th‑century architecture to newer infill and renovated classics. You will also find pockets of larger lots, historic districts, and neighborhoods close to the lake. Condos and townhomes exist, though single‑family homes dominate.

If you want a low‑maintenance lifestyle, Deerfield’s many mid‑century and late‑20th‑century homes can be appealing. Planned subdivisions, cul‑de‑sacs, and mid‑sized yards are common. You will also see some newer construction and occasional infill options, plus smaller clusters of townhomes and condos.

Across both towns, market pace and inventory vary by neighborhood and season. Before you bid, compare recent sales on your target blocks and study price per square foot trends for the past year.

What to check for your address

• Age of the home, recent updates, and the condition of major systems.
• Lot size, setbacks, and whether the area lies in a historic district or near the lake.
• Recent comparable sales for the block and current inventory competition.
• Any homeowners association or village code rules that affect exterior changes.

Schools and education

Both communities connect to well‑regarded public high schools through Township High School District 113. Elementary and middle school boundaries can vary street by street, and several K‑8 districts serve different parts of each municipality. Private and parochial options are available throughout the North Shore corridor.

Focus on the schools that align with your needs, then confirm the assignment for your specific address. Academic performance indicators, program offerings, and extracurriculars can differ across campuses.

When comparing, review official report cards and district sites for up‑to‑date information. Boundaries and programs change, so always verify.

What to check for your address

• The exact elementary, middle, and high schools that serve the property.
• The latest state report cards, program offerings, and graduation or college‑readiness indicators.
• Transportation options, including bus eligibility and walkability to school.
• Any special programs you may want, such as gifted, dual‑language, IB, AP, music, theater, or athletics.

Commute and transportation

Both Highland Park and Deerfield sit on the Metra Milwaukee District North line, which offers trains to downtown Chicago. Each municipality has stations with parking options that may require permits. Schedules, travel times, and ridership can vary by time of day, so check the current timetable.

If you drive, you will appreciate quick access to the Edens and I‑94 corridor, along with major arterials like Lake Cook Road and Deerfield Road. Many residents also commute to nearby suburban employers, which shapes local traffic patterns during peak hours.

Plan your commute by testing both rail and driving at your typical departure times. If you will rely on station parking, ask about permit availability and waitlists before you commit to a home.

What to check for your address

• The nearest Metra station, schedule, and parking permit status.
• Typical drive times to your workplace during peak and off‑peak hours.
• Alternate routes for winter weather or construction.
• Access to local buses and park‑and‑ride options if you prefer transit.

Amenities, culture, and open space

Highland Park stands out for its lakefront beaches, extensive parkland, and a larger cultural footprint anchored by a major summer music venue. Its downtown offers more continuous retail and dining, plus specialty shops that support an active street scene. The city also maintains a full calendar of community events and arts programming.

Deerfield leans into family‑oriented recreation with a strong park district, ball fields, pools, and community programming year‑round. With corporate campuses and shopping centers nearby, you benefit from a steady daytime population and convenient daily services. Downtown Deerfield is smaller and neighborhood‑focused, which many find calm and easy to navigate.

Regional favorites like the Chicago Botanic Garden are a quick drive from both communities and can be part of your weekend routine. Compare the event calendars, library offerings, and park amenities to see which fits how you spend your free time.

What to explore

• Park district facilities, pools, and seasonal programs.
• Downtown walkability, restaurant variety, and local shops.
• Community events, arts programming, and library services.
• Proximity to beaches, trails, and regional attractions.

Taxes, utilities, and cost of ownership

Property taxes vary by address based on school districts and other taxing bodies. Lakefront proximity, lot size, and home value can all influence the bill. Because assessments and levies change, review the last two years of tax bills for any home you are considering.

Insurance needs can differ as well. Older homes and lake‑adjacent properties may require specific coverage for structures or flood risk. Utility costs and services can vary by village, including water, sewer, trash, and leaf removal.

Get a complete picture before you write an offer so you understand the full monthly and annual cost of ownership.

What to request up front

• Last two years of property tax bills and any reassessment notices.
• A homeowners insurance quote that accounts for age, location, and coverage needs.
• A utility cost snapshot for water, sewer, trash, and any special services.
• Notes on special assessments, bond referenda, or special service areas.

Safety, services, and community

Both villages publish public safety updates and annual reports you can review. Look at recent trends for property and violent crime to understand neighborhood context. For peace of mind, pull recent incident logs for the blocks you are considering.

Consider proximity to hospitals, urgent care, and fire or EMS services when you map your weekly routine. Community health resources and civic groups, like neighborhood or business associations, can also signal a connected community.

Use official sources to compare trends rather than relying on anecdotes. Context matters block by block, so aim for address‑specific data.

What to review

• Police department annual reports and recent incident maps.
• Distance to hospitals, urgent care, and response times when available.
• Local volunteer groups, business associations, and community calendars.

Resale and long‑term value

Long‑term value depends on demand drivers like school reputation, access to Metra, and neighborhood character. Highland Park’s architectural variety and lake proximity can command premiums, though older inventory may require ongoing investment. Deerfield’s newer housing stock can lower near‑term maintenance, which appeals to many buyers.

Study 5‑ to 10‑year appreciation trends for each community using multiple sources. Look for patterns in inventory cycles, list‑to‑sale dynamics, and days on market for your target neighborhood. The right choice balances lifestyle fit today with healthy resale prospects tomorrow.

Due diligence checklist

• Historical price trends for your target neighborhood, not just the town.
• Inventory patterns, days on market, and seasonal list‑to‑sale trends.
• Typical renovation costs for homes similar to the one you want.
• Features that support resale, like walkability, transit access, or unique architecture.

Decision checklist

Use these questions to clarify your best fit:

• Do you want lakefront access and a larger arts scene or a quieter, more suburban subdivision feel?
• Which specific schools do you need, and does a particular elementary or middle school drive your choice?
• Is vintage architecture and character a must, or do you prefer newer, easier‑to‑maintain construction?
• Will you prioritize a rail commute to downtown, highway access to suburban job centers, or both?
• How long do you plan to stay, and how important are appreciation trends for resale?
• What is your tolerance for maintenance, and do you need a large yard for kids or pets?

Next steps

Your next move is to compare actual addresses, not just towns. Pull school assignments and the latest report cards, review the last two years of tax bills, line up insurance quotes, and test your commute by train and by car. Walk each downtown, visit parks and libraries, and tour homes on the exact blocks you like.

If you want a guided, local process with address‑specific data and on‑the‑ground neighborhood insights, reach out to Kim Kelley Residential. With 25+ years in Highland Park and the surrounding North Shore, you will get seasoned, founder‑led advice tailored to how your family lives.

FAQs

How do Highland Park and Deerfield differ in daily lifestyle?

• Highland Park offers lakefront access and a larger arts and dining scene, while Deerfield delivers a quieter suburban feel with strong park district amenities.

Which town is better for a Chicago commute by train?

• Both are served by the Metra Milwaukee District North line; compare stations, schedules, and parking permit availability based on your home’s location.

How do schools compare between the two communities?

• Both feed into well‑regarded public high schools through District 113, but elementary and middle school boundaries vary; confirm assignments and review official report cards.

Where will I likely find newer, lower‑maintenance homes?

• Deerfield has a larger share of mid‑century and late‑20th‑century homes and planned subdivisions, which many buyers find easier to maintain.

Is Highland Park more walkable than Deerfield?

• Highland Park’s downtown is larger and more continuous, which can offer more walkable retail and dining; walkability still varies block by block in both towns.

What should I verify before buying near the lake or in a historic area?

• Check floodplain maps, historic district status, insurance requirements, and local code or design guidelines that may affect renovations.