Living in Old Town, Chicago Old Town Real Estate for sale, Old Town condos, Old Town Apartments

Living In Old Town – Historic & Unique

When talking about making a life in Chicago’s urban center, you’d be unlikely to get very far before the topic of Old Town comes up.

A storied neighborhood and historic district, living in Old Town is a unique experience that practically encapsulates the entire city in a very small area.

The area itself traces its roots to Chicago’s earliest denizens, while today Old Town boasts trendy eateries that rub their big shoulders up against classic Victorian architecture.

Talk with us about Old Town

Chicago Old Town real estate is mostly vintage. However, there is also a nice mix of cottages, row houses, condos, and two-flats.

Not to be missed is the historic Old Town Triangle. It’s a section of row houses on cobblestone streets that gives people a flavor of old Chicago.

Want to rent? Here are the current Old Town rentals.

Explore Chicago Old Town real estate listings below or read more about living in Old Town.

Old Town Real Estate For Sale

New Listing - 9 hours online
$279,900
Condo For Sale
New
1
BED
1
TOTAL BATHS
1355 North Sandburg Terrace #1705
Chicago, IL 60610
 
New Listing - 10 hours online
$389,900
Condo For Sale
New
2
BED
2
TOTAL BATHS
1,015
SQFT
230 West Division Street #1308
Chicago, IL 60610
 
New Listing - 3 days online
$239,900
Condo For Sale
New
1
BED
1
TOTAL BATHS
800
SQFT
1360 North Sandburg Terrace #1808
Chicago, IL 60610
Cummings House Subdivision
New Listing - 3 days online
$359,900
Condo For Sale
New
2
BED
2
TOTAL BATHS
959
SQFT
230 West Division Street #707
Chicago, IL 60610
Venetian Subdivision
New Listing - 3 days online
$499,000
Condo For Sale
New
2
BED
2
TOTAL BATHS
1515 North Wells Street #3F
Chicago, IL 60610
 
New Listing - 3 days online
$924,000
Townhouse For Sale
New
3
BED
4
TOTAL BATHS
2,400
SQFT
220 West Scott Street #E
Chicago, IL 60610
Old Town Square Subdivision
New Listing - 3 days online
$349,500
Condo For Sale
New
2
BED
2
TOTAL BATHS
1,250
SQFT
1560 North Sandburg Terrace #615
Chicago, IL 60610
Sandburg Village Subdivision
New Listing - 5 days online
$949,500
Townhouse For Sale
New
4
BED
3
TOTAL BATHS
2,300
SQFT
1401 North Wieland Street #W
Chicago, IL 60610
Schiller Place Subdivision
New Listing - 5 days online
$420,000
Condo For Sale
New
2
BED
2
TOTAL BATHS
1444 North Orleans Street #7I
Chicago, IL 60610
 
New Listing - 6 days online
$436,500
Condo For Sale
Active
2
BED
2
TOTAL BATHS
1,100
SQFT
1309 North Wells Street #706
Chicago, IL 60610
Old Town Subdivision
New Listing - a week online
$1,899,000
Single Family Home For Sale
Active
4
BED
4
TOTAL BATHS
4,200
SQFT
1500 North North Park Avenue
Chicago, IL 60610
 
New Listing - a week online
$299,900
Condo For Sale
Active
1
BED
1
TOTAL BATHS
1460 North Sandburg Terrace #303
Chicago, IL 60610
 
Open House 07/05 at 11AM
Please verify times due to COVID-19
$2,749,000
Single Family Home For Sale
Active
5
BED
5
TOTAL BATHS
5,100
SQFT
1446 North Wieland Avenue
Chicago, IL 60610
 
New Listing - a week online
$799,900
Condo For Sale
Active
3
BED
3
TOTAL BATHS
2,899
SQFT
1522 North Cleveland Avenue #3
Chicago, IL 60610
 
New Listing - a week online
$455,000
Condo For Sale
Active
2
BED
2
TOTAL BATHS
1,250
SQFT
247 West Scott Street #309
Chicago, IL 60610
 
New Listing - a week online
$899,000
Townhouse For Sale
Active
4
BED
3
TOTAL BATHS
2,300
SQFT
1401 North Wieland Street #K
Chicago, IL 60610
 
New Listing - a week online
$200,000
Condo For Sale
Active
1
TOTAL BATHS
640
SQFT
1560 North Sandburg Terrace #3505J
Chicago, IL 60610
 
New Listing - a week online
$384,900
Condo For Sale
Active
2
BED
2
TOTAL BATHS
1,100
SQFT
1255 North Sandburg Terrace #402E
Chicago, IL 60610
 
New Listing - a week online
$589,900
Condo For Sale
Active
3
BED
2
TOTAL BATHS
1,940
SQFT
1520 North Sedgwick Street #4B
Chicago, IL 60610
 
New Listing - a week online
$290,000
Condo For Sale
Active
1
BED
1
TOTAL BATHS
1560 North Sandburg Terrace #2408
Chicago, IL 60610
James House Subdivision

More About Living In Old Town

Old Town is in 60610 and bordered by Armitage Avenue on the north, Division Street on the south, Clybourn Avenue on the southwest, Larrabee Street on the west and Clark Street on the east. Nearby neighborhoods include Chicago’s Gold Coast which sits just to the east.

A Little History

Long before Chicago was Chicago, or even before European immigrants stumbled onto the area, Old Town real estate was essentially made up of a loose collection of Native American tribes who used the area as a trade post and home.

St Michael - Chicago Old Town Real Estate

St Michael’s Survived The Great Chicago Fire.

A precursor to Chicago’s role as a hub of trade and commerce, multiple tribes were recorded to have been living in Old Town under a mutually beneficial arrangement. These included the Potawatomi, Miami, and Illinois. Shortly after the turn of the 19th century, these tribes would not be living in Old Town much longer. Because the Treaty of Chicago forcibly removed them and Old Town real estate was then settled by German immigrants.

Likely one of Old Town real estate’s most prolific landmarks, St. Michael’s church stands as a monument to early European colonizers. And is a testament to lauded German engineering. Originally built by Bavarian immigrants, St. Michael’s was one of only a handful of structures to survive the Great Chicago Fire.

Living in Old Town means walking streets that predate Chicago city planning

You’ll need to become accustomed to its unique pattern. Old Town’s streets are among the few in the city that do not adhere to Chicago’s famous grid pattern. Old Town residents often wonder why Clark Street follows a somewhat irregular line. It’s because it stands along one of the area’s earliest roads that followed a ridge running alongside Lake Michigan.

Old Town’s history continues unabated through the 20th Century

Today this history is most visible in its only El stop, servicing the Brown & Purple Lines, on North Sedgwick. Located in the heart of Old Town, this El stop is among the oldest in the city and one of the few original stops still standing. It was built in 1900.

Commerce and history are wonderful, but Old Town carries the flag for civil progress as well

Living in Old Town means being a neighbor to the Henry Gerber house. Named in honor of its owner, this piece of Old Town real estate was the home of the Society for Human Rights: the first gay rights organization in American history. This fabulous bit of trivia is all the more incredible when one understand it was founded in 1924. The Henry Gerber House was named a Chicago Landmark in June 2001, a National Historic Landmark 14 years later, and still stands today at 1701 N Crilly Ct.

The middle of the 20th century saw a dramatic change in those living in Old Town

Following the white flight of the 1950s, many of Old Town real estate’s gorgeous Victorian homes and storefronts were left vacant and available, often for cheap. Consequently the area became home to three unique groups searching for a place in the Second City. First, Old Town became the unofficial basecamp for hippie culture in the Midwest. Next, a sizable community of Puerto Ricans put down roots along the north and west corners of the neighborhood. Finally, Old Town’s real estate was the chosen home of the newly out homosexual culture.

You don’t get that kind of diversity without a resultant cultural explosion

So when such a variety of people who called Old Town real estate home came together, many of Chicago’s most famous institutions came into existence. Ubiquitous city names like The Second City, Old Town Ale House, and the Up Down Tobacco Shop all came to be living in Old Town during this period. Most of these icons still call Old Town home today, even if they’re not exactly in the same spot where they started. (But then again, who among us still is?)

Similarly, the Old Town School of Folk Music first opened its doors during Chicagos revival of the genre. It saw singer-songwriters such as Bonnie Koloc, Bob Gibson, John Prine, and more grace its halls and the surrounding venues.

From the Old Town School of Folk Music came other venues for artists to ply their trades. Notably, the now-famous Mother Blues club. It boasted greats ranging from Brazil ’66 and Jefferson Airplane, to legendary comedian George Carlin standing on their little slice of Old Town real estate.

An “always exciting place to live”

Perhaps the best way to conclude a write up of Old Town real estate is with a description of living in Old Town from 1967. Penned by Richard Atcheson for a write-up in Holiday Magazine, the colorful biography still rings true today:

“There is a little piece of Chicago Real Estate, west of Lincoln Park, that is the pride of urban conservationists and the despair of bulldozers. It is a community widely known as Old Town… full of conflict, full of life; a sometimes maddening but always exciting place to live.”

Just let us know if you’re interested in living in Old Town, or have questions about buying or renting Old Town real estate.

Talk With Us

It’s never too early to get started!