Overview
Listings
Map
Lifestyle
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Demographics
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LUXESQUIRE

Highland Park
Arts, ravines, and a lake to the east.

THE NEIGHBORHOOD STORY

Highland Park occupies a distinctive position on the North Shore — it is larger and more urban-feeling than Glencoe or Winnetka, with a genuine downtown commercial district, a diverse and engaged arts community, and a topography shaped by ravines and Lake Michigan bluffs that makes its residential setting among the most dramatic on the entire shore. Ravinia Festival calls Highland Park home, and the festival's summer presence infuses the community with a cultural energy that is genuinely transformative. The city has invested heavily in its lakefront parks and downtown, and the result is a community that delivers on its considerable promise.

WHY RESIDENTS LOVE IT

•   Ravinia Festival — thelegendary outdoor music venue anchors Highland Park's cultural identity everysummer.

•   Ravine and blufftopography — the natural landscape creates home settings that are unlikeanything else on the North Shore.

•   Vibrant downtown — agenuine commercial district with independent restaurants, boutiques, andcultural venues.

•   Metra Union PacificNorth Line — direct downtown service in approximately 45 minutes.

•   New Trier and HighlandPark High School — access to two of Illinois's top-performing public highschools.

•   Active arts community —Highland Park Arts Center, galleries, and a year-round cultural calendar.

HOMES & ARCHITECTURE

Highland Park's architectural range reflects its history as an early planned resort community. Bluff and ravine-adjacent properties feature dramatic siting with lake or ravine views and represent the market's most distinctive offerings. The downtown area and surrounding neighborhoods contain craftsman, colonial, and Prairie School homes from the early 20th century. Larger estate homes concentrate in the neighborhoods north of downtown and along the lake bluffs. The overall market is diverse in both price and style.

PROPERTY TYPES AT A GLANCE

Property Type Description
Bluff & Ravine Properties Dramatically sited homes above the lake bluffs or ravine system — the market's most distinctive segment.
Prairie School & Craftsman Homes Early 20th-century architecture defining the historic residential neighborhoods near downtown.
Colonial & Traditional Estates The North Shore standard — formal architecture with full amenity packages on larger lots.
Downtown Condominiums Urban-style living in the heart of Highland Park's commercial district for buyers seeking walkability.

POCKETS & DISTRICTS

Pocket / District Character & Vibe
East Highland Park/Lakefront Maximum prestige, lake access, bluff views, most competitive market
Ravinia District Walking distance to the festival, charming residential streets, strong community identity
Downtown Core Walkable, vibrant, mixed-use, ideal for buyers who want urban energy in a suburban setting

HOW TO MOVE AROUND

Metra's Union Pacific North Line serves Highland Park and Ravinia stations. Metra North Central Line also serves the western portions. Driving accesses US-41 and I-94. Local Tip: Highland Park has invested significantly in its downtown streetscape, and the walkability within the downtown district rivals many urban neighborhoods.

DINING & NIGHTLIFE

Fine Dining

•   Ravinia Festivaldining — The festival's hospitalityprogram offers excellent dining experiences through the summer season

•   Betise Bistro — French-inspired bistro with consistent quality anda warm neighborhood following

Casual & Neighborhood Favorites

•   Half Day Brewing — Community gathering place with craft beer and arelaxed, welcoming atmosphere

•   Port Edward — Beloved seafood institution with a North Shorefollowing that spans generations

Late Night

•   Downtown HighlandPark bar scene — A modest but genuinelate-night dining and bar scene centered on the commercial district

GREEN SPACE & OUTDOORS

•   Ravinia Park — The legendary outdoor venue set in a wooded park —Highland Park's most beloved institution

•   Rosewood Beach — Community lakefront park with beach access,pavilion, and bluff views

•   Lake County ForestPreserves — Extensive preserve systemwith hiking, cycling, and natural habitat adjacent to the community

Highland Park Signature Listings

For Sele

$2,500,000

654 Ocean Dr, Miami, FL 33101

4 BA
5 BD
MLS# 345678
Explore All Lincoln Park Homes
Active Under Contract

$950,000

321 Trendy Blvd, Chicago, IL 60601

1 BA
1 BD
MLS# 210987
Explore All Lincoln Park Homes
Active Under Contract

$450,000

789 Rustic Rd, Austin, TX 73301

1 BA
2 BD
MLS# 789012
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Active Under Contract

$850,000

456 Elegant Ave, Los Angeles, CA 90001

3 BA
4 BD
MLS# 654321
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For Sale

$1,200,000

123 Luxury St, New York, NY 10001

2 BA
3 BD
MLS# 123456
Explore All Lincoln Park Homes

Lifestyle & Points of Interest

01
Dining
02
Coffee
03
Grocery
04
Bars / Nightlife
05
Fitness
06
Parks
08
Schools
07
Dog Parks
09
Hospitals
10
Transit
Dining
Coffee
Grocery
Bars / Nightlife
Fitness
Parks
Schools
Dog Parks
Hospitals
Transit

EDUCATION LANDSCAPE

School Type Grades Notes
Highland Park Elementary Schools District 112 Public K-5 Well-regarded district with multiple elementary schools
Edgewood Middle School District 112 Public 6-8 Strong middle school program
Highland Park Elementary Schools District 113 Public 9-12 Highly regarded comprehensive high school with excellent arts and academic programs
North Shore Country Day Private PK-12 One of the North Shore's most respected private school options
High School
Mixed Schools
type
Name
Category
Grades
School rating
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
Private
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
type
Name
Category
Grades
School rating
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5

WHO LIVES HERE

Population Median Age Avg. Household Income
29,700 44 $172,000
Population Density Gender Split Education
Medium 47% Male / 53% Female 72% Bachelor's or higher
High School
Mixed Schools
type
Name
Category
Grades
School rating
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
Private
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
type
Name
Category
Grades
School rating
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5
Intrinsic 2 Charter High School
79 W Monroe St Ste 400, Chicago, IL, 60603
PUBLIC
9th - 12th
1/5

WALKABILITY & ACCESS SCORES

58
Walk
Walk Score
52
Bike
Bike Score
38
Transit
Transit Score

THE LUXESQUIRE INSIDER TAKE

Highland Park is the North Shore community that consistently surprises buyers who come in with fixed assumptions. The bluff properties are among the most dramatically beautiful in the entire region. Ravinia is a 90-night cultural program in your backyard. And the pricing, while premium, is measurably more accessible than Winnetka or Kenilworth. It checks every box.

Get in Touch

Have questions or want to book a tour? Contact us today and our team will guide you every step of the way.

Contact Us

A Chicago luxury real estate brokerage guided by Realtor-Lawyers.

Strategic. Discreet. White-Glove.

Contact

122 S Michigan Ave, Suite 1390
Chicago, IL 60603

Phone:

312.912.7262

Fax:

312.912.7255

Email:

info@luxesquire.com
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