Overview
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Map
Lifestyle
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Demographics
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LUXESQUIRE

Old Town
Comedy, jazz, and Chicago's most charming blocks.

THE NEIGHBORHOOD STORY

Old Town is one of Chicago's most historically layered neighborhoods — it has been, at various points, a German-American immigrant community, the city's bohemian counterculture hub (the Second City was born here), a folk music mecca, and today, one of the North Side's most desirable family neighborhoods. This evolution has left an extraordinarily rich cultural and physical landscape: Victorian row houses and cottages from the 1870s, the Second City comedy theater, Kingston Mines blues club, Wells Street's independent restaurants, and some of Chicago's most intimate and architecturally distinctive residential blocks.

WHY RESIDENTS LOVE IT

•   Second City — thelegendary comedy institution that launched careers from John Belushi to TinaFey calls Old Town home.

•   Wells Street commercialcorridor — one of Chicago's most charming and walkable retail and diningstreets.

•   Victorian cottagedistrict — the Old Town Triangle contains some of Chicago's oldest survivingresidential architecture.

•   Kingston Mines — thelegendary blues club is a neighborhood institution and a Chicago culturallandmark.

•   Proximity to LincolnPark — the 1,200-acre park is immediately north, extending the neighborhood'srecreational assets enormously.

•   Gold Coast adjacency —Old Town's southern border connects directly to Chicago's most prestigiousresidential address.

HOMES & ARCHITECTURE

Old Town's most distinctive residential architecture is the Old Town Triangle Historic District — a collection of Victorian cottages, row houses, and worker's homes from the 1870s and 1880s, many rebuilt after the Chicago Fire. These small-scale, intimate buildings create a streetscape unlike anything else in Chicago. The neighborhood also contains greystone two-flats and three-flats, larger Victorian single-family homes on the premier blocks, and modern infill construction.

PROPERTY TYPES AT A GLANCE

Property Type Description
Old Town Triangle Historic Cottages & Row Houses Post-Fire Victorian construction — Chicago's oldest surviving residential neighborhood fabric.
Greystone Single-Family Homes Limestone and greystone construction on the premium residential blocks — the neighborhood's luxury tier.
Two-Flats & Three-Flats Classic Chicago investment and owner-occupant options throughout the neighborhood.
New Construction Condominiums Modern boutique buildings responding to sustained demand in this highly desirable neighborhood.

POCKETS & DISTRICTS

Pocket / District Character & Vibe
Old Town Triangle Historic District Most intimate, most historically significant, most architecturally irreplaceable
Wells Street Corridor Commercial heart, most walkable, dining and entertainment density
Lincoln Park Border Park adjacency, more modern residential, highest demand for family buyers

HOW TO MOVE AROUND

Brown Line at Sedgwick station. Multiple bus routes on Wells, North, and Clybourn. Walking distance to Red Line at Clark/Division. Lakefront Trail via Lincoln Park immediately accessible. Local Tip: Old Town's position between the Gold Coast and Lincoln Park means that residents can walk to two of Chicago's most important neighborhoods.

DINING & NIGHTLIFE

Fine Dining

•   Boka (Lincoln Parkadjacent) — One of Chicago's mostcelebrated dining rooms within easy reach

Casual & Neighborhood Favorites

•   Old Jerusalem — Long-running Middle Eastern restaurant beloved forits authentic simplicity and consistent quality

•   Twin Anchors — Chicago's most famous ribs joint — Frank Sinatraate here, and residents still debate whether it is better than ever

Late Night

•   Kingston Mines — Live Chicago blues until 4 a.m. — a nationaltreasure operating in the neighborhood's backyard

GREEN SPACE & OUTDOORS

•   Lincoln Park — The 1,200-acre park is immediately north — Old Townresidents have effectively unlimited parkland at their doorstep

•   Oz Park — A beloved neighborhood park with Wizard ofOz-themed sculptures and active family programming

•   North Avenue Beach(via Lincoln Park) — One of Chicago'smost popular lakefront beaches, accessible by a short walk through the park

Old Town 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
Explore All Lincoln Park Homes
Active Under Contract

$850,000

456 Elegant Ave, Los Angeles, CA 90001

3 BA
4 BD
MLS# 654321
Explore All Lincoln Park Homes
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
Lincoln Elementary CPS Public K-8 The neighborhood's well-regarded public elementary option
LaSalle Language Academy CPS Magnet PK-8 Bilingual magnet school with strong academic outcomes
Latin School of Chicago Private PK-12 One of Chicago's most prestigious private schools, nearby in the Gold Coast
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
21,400 35 $118,000
Population Density Gender Split Education
High 50% Male / 50% 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

94
Walk
Walk Score
84
Bike
Bike Score
76
Transit
Transit Score

THE LUXESQUIRE INSIDER TAKE

Old Town is Chicago's most charmed neighborhood — small enough to feel intimate, connected enough to access everything. The Triangle's Victorian cottages are genuinely irreplaceable. Second City, Kingston Mines, Twin Anchors — the cultural density per block here is extraordinary. Buyers who discover Old Town typically never seriously consider anywhere else again.

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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