Old Town Real Estate For Sale

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Old Town Condos For Sale, Chicago IL Within its iconic iron gates, Old Town and Old Town real estate stand as a hub of Chicago's cultural history. In fact, many of the city's oldest real estate can be found within the Old Town Triangle Historic District. This is where Chicago's famous improv scene all started with The Second City and a string of other comedy clubs. Modern full amenity condo buildings rise up in and around the Old Town neighborhood, providing excellent views of the city life below.

For those seeking quiet real estate options that exemplify Old Town's rich history, plenty of brick walk-ups may be found all throughout the area's peaceful tree-lined streets. And homebuyers looking to combine contemporary luxury with vintage charm can have the best of both worlds with a fully updated condo inside one of Old Town's many historical residential buildings.

Besides its many comedy clubs, Old Town offers plenty in the way of premier dining and nightlife. Restaurants, lounges and clubs line Wells Street, while cafes, bakeries and coffee shops supply your daytime fix. For those who prefer eating in, a variety of specialty ingredient shops like the Spice House or Old Town Oil will keep gourmet kitchens well-stocked.  For more information on Old Town real estate for sale and other downtown Chicago neighborhoods, contact Leo Clark, Chicago's luxury real estate expert.  

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New
1726 N Orchard Street 1c, Chicago

$2,100

1726 N Orchard Street 1c, Chicago

1 Bed 1 Bath 0 SqFt Residential Lease MLS® # 12779288

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New
1636 N Wells Street 612, Chicago

$2,100

1636 N Wells Street 612, Chicago

0 Beds 1 Bath 0 SqFt Residential Lease MLS® # 12777937

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1636 N Wells Street 2214, Chicago

$2,150

1636 N Wells Street 2214, Chicago

0 Beds 1 Bath 550 SqFt Residential Lease MLS® # 12729824

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New
1211 N Lasalle Street 704, Chicago

$2,250

1211 N Lasalle Street 704, Chicago

1 Bed 1 Bath 714 SqFt Residential Lease MLS® # 12748362

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1660 N Lasalle Street 3503, Chicago

$2,400

1660 N Lasalle Street 3503, Chicago

0 Beds 1 Bath 550 SqFt Residential Lease MLS® # 12771556

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1560 N Sandburg Terrace 3407, Chicago

$2,400

1560 N Sandburg Terrace 3407, Chicago

1 Bed 1 Bath 640 SqFt Residential Lease MLS® # 12754872

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1255 N Sandburg Terrace 2403, Chicago

$2,400

1255 N Sandburg Terrace 2403, Chicago

1 Bed 1 Bath 748 SqFt Residential Lease MLS® # 12759032

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New
1211 N Lasalle Street 901, Chicago

$2,616

1211 N Lasalle Street 901, Chicago

1 Bed 1 Bath 650 SqFt Residential Lease MLS® # 12737281

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1636 N Wells Street 1108, Chicago

$2,650

1636 N Wells Street 1108, Chicago

1 Bed 1 Bath 750 SqFt Residential Lease MLS® # 12748843

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New
1360 N Sandburg Terrace 410, Chicago

$2,650

1360 N Sandburg Terrace 410, Chicago

1 Bed 1 Bath 750 SqFt Residential Lease MLS® # 12770385

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1212 N Lasalle Street 2505, Chicago

$2,800

1212 N Lasalle Street 2505, Chicago

1 Bed 1 Bath 0 SqFt Residential Lease MLS® # 12770543

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New
1537 N Orleans Avenue 4g, Chicago

$2,970

1537 N Orleans Avenue 4g, Chicago

1 Bed 1 Bath 700 SqFt Residential Lease MLS® # 12767161

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New
1560 N Sandburg Terrace 2104, Chicago

$3,000

1560 N Sandburg Terrace 2104, Chicago

1 Bed 1 Bath 860 SqFt Residential Lease MLS® # 12768441

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1355 N Sandburg Terrace 1801d, Chicago

$3,000

1355 N Sandburg Terrace 1801d, Chicago

2 Beds 1 Bath 0 SqFt Residential Lease MLS® # 12726251

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New
1225 N Orleans Street 502, Chicago

$3,300

1225 N Orleans Street 502, Chicago

2 Beds 2 Baths 1,200 SqFt Residential Lease MLS® # 12760410

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343 W Old Town Court 205, Chicago

$3,500

343 W Old Town Court 205, Chicago

1 Bed 1 Bath 1,000 SqFt Residential Lease MLS® # 12766226

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1246 N Wells Street 2, Chicago

$3,600

1246 N Wells Street 2, Chicago

2 Beds 1 Bath 900 SqFt Residential Lease MLS® # 12741786

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New
1344 N North Park Avenue 1, Chicago

$3,600

1344 N North Park Avenue 1, Chicago

2 Beds 1 Bath 0 SqFt Residential Lease MLS® # 12779006

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1552 N North Park Avenue 704, Chicago

$3,797

1552 N North Park Avenue 704, Chicago

2 Beds 2 Baths 923 SqFt Residential Lease MLS® # 12741792

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New
230 W Division Street 1404, Chicago

$3,800

230 W Division Street 1404, Chicago

2 Beds 2 Baths 1,292 SqFt Residential Lease MLS® # 12730211

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1255 N Sandburg Terrace 1202, Chicago

$3,800

1255 N Sandburg Terrace 1202, Chicago

2 Beds 2 Baths 1,100 SqFt Residential Lease MLS® # 12763601

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1212 N Lasalle Street 601, Chicago

$3,800

1212 N Lasalle Street 601, Chicago

2 Beds 2 Baths 1,100 SqFt Residential Lease MLS® # 12769622

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New
1360 N Sandburg Terrace 2002c, Chicago

$3,900

1360 N Sandburg Terrace 2002c, Chicago

2 Beds 2 Baths 1,200 SqFt Residential Lease MLS® # 12776316

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1660 N La Salle Drive 3502, Chicago

$4,200

1660 N La Salle Drive 3502, Chicago

2 Beds 2 Baths 1,019 SqFt Residential Lease MLS® # 12749991

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Open House
1850 N Clark Street 2803, Chicago

$4,300

1850 N Clark Street 2803, Chicago

2 Beds 2 Baths 1,100 SqFt Residential Lease
Sun, Oct 11th, 2026 @ 11am - 1pm
MLS® # 12738708

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1309 N Wells Street 706, Chicago

$4,300

1309 N Wells Street 706, Chicago

2 Beds 2 Baths 1,100 SqFt Residential Lease MLS® # 12767020

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New
159 W North Avenue 406, Chicago

$4,595

159 W North Avenue 406, Chicago

2 Beds 2 Baths 992 SqFt Residential Lease MLS® # 12774432

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New
1555 N Sandburg Terrace 305k, Chicago

$4,695

1555 N Sandburg Terrace 305k, Chicago

2 Beds 2 Baths 0 SqFt Residential Lease MLS® # 12774844

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1539 N Wells Street 8, Chicago

$6,500

1539 N Wells Street 8, Chicago

4 Beds 2 Baths 1,212 SqFt Residential Lease MLS® # 12739440

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1444 N Orleans Street 9phk, Chicago

$8,750

1444 N Orleans Street 9phk, Chicago

3 Beds 4 Baths 3,300 SqFt Residential Lease MLS® # 12714945

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1201 N Lasalle Street 3301, Chicago

$8,896

1201 N Lasalle Street 3301, Chicago

3 Beds 2 Baths 1,713 SqFt Residential Lease MLS® # 12741401

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1201 N Lasalle Street 3303, Chicago

$8,977

1201 N Lasalle Street 3303, Chicago

3 Beds 3 Baths 1,628 SqFt Residential Lease MLS® # 12741629

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1201 N Lasalle Street 3404, Chicago

$9,143

1201 N Lasalle Street 3404, Chicago

3 Beds 2 Baths 1,458 SqFt Residential Lease MLS® # 12743134

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1841 N Orleans Street, Chicago

$25,000

1841 N Orleans Street, Chicago

5 Beds 4.5 Baths 0 SqFt Residential Lease MLS® # 12748871

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New
1850 N Clark Street 810, Chicago

$225,000

1850 N Clark Street 810, Chicago

0 Beds 1 Bath 0 SqFt Residential MLS® # 12756637

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Open House
1850 N Clark Street 2104, Chicago

$225,000

1850 N Clark Street 2104, Chicago

0 Beds 1 Bath 0 SqFt Residential
Sun, Oct 11th, 2026 @ 11am - 1pm
MLS® # 12766673

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Open House
1555 N Sandburg Terrace 209k, Chicago

$235,000

1555 N Sandburg Terrace 209k, Chicago

1 Bed 1 Bath 830 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 1:30pm
MLS® # 12761332

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1455 N Sandburg Terrace 803, Chicago

$235,000

1455 N Sandburg Terrace 803, Chicago

1 Bed 1 Bath 644 SqFt Residential MLS® # 12720770

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1660 N Lasalle Drive 3403, Chicago

$245,000

1660 N Lasalle Drive 3403, Chicago

0 Beds 1 Bath 550 SqFt Residential MLS® # 12771289

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New
1560 N Sandburg Terrace 507j, Chicago

$248,000

1560 N Sandburg Terrace 507j, Chicago

1 Bed 1 Bath 700 SqFt Residential MLS® # 12754730

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1360 N Sandburg Terrace 2104c, Chicago

$250,000

1360 N Sandburg Terrace 2104c, Chicago

1 Bed 1 Bath 600 SqFt Residential MLS® # 12754021

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1212 N La Salle Drive 1409, Chicago

$251,000

1212 N La Salle Drive 1409, Chicago

1 Bed 1 Bath 750 SqFt Residential MLS® # 12645252

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1212 N Lasalle Street 2505, Chicago

$259,000

1212 N Lasalle Street 2505, Chicago

1 Bed 1 Bath 0 SqFt Residential MLS® # 12763500

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Open House
1660 N La Salle Drive 3310, Chicago

$270,000

1660 N La Salle Drive 3310, Chicago

1 Bed 1 Bath 0 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 1pm
MLS® # 12757886

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New
1355 N Sandburg Terrace 2206d, Chicago

$275,000

1355 N Sandburg Terrace 2206d, Chicago

1 Bed 1 Bath 780 SqFt Residential MLS® # 12728949

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1455 N Sandburg Terrace 808b, Chicago

$279,000

1455 N Sandburg Terrace 808b, Chicago

1 Bed 1 Bath 827 SqFt Residential MLS® # 12727241

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1850 N Clark Street 307, Chicago

$280,000

1850 N Clark Street 307, Chicago

1 Bed 1 Bath 800 SqFt Residential MLS® # 12698625

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New
1360 N Sandburg Terrace 1106c, Chicago

$295,000

1360 N Sandburg Terrace 1106c, Chicago

1 Bed 1 Bath 0 SqFt Residential MLS® # 12736182

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Contact Our Old Town REALTORS®

Let our team of expert Old Town real estate agents help!

If you're ready to buy or sell a home in Chicago's Old Town neighborhood, call or text us right now to see how we can help. Our team of Old Town real estate agents knows the neighborhood housing market better than anybody in the business. And if you're specifically looking to sell, also be sure to reach out and we'll be happy to send you a free, no-obligation market analysis so you can get a better idea of what your Old Town home or condo is worth in today's market. 

Thinking of Selling Your Old Town Home or Condo?

If you're looking to sell your Old Town home or condo in today's ultra-competitive market, contact Gold Coast Realty to learn more about how we can get your property sold fast, and for the price you need!

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The Location: Chicago's Old Town Neighborhood at a Glance

Bounded by the Gold Coast to the east, Lincoln Park to the north, and parts of River North to the south, it’s hard to dislike where living in Old Town puts you, as you’ll basically be surrounded by three of Chicago’s hottest and most sought after neighborhoods. For anyone working in downtown Chicago, Old Town also provide a pretty easy and quick commute to just about any part of the downtown area, especially the Gold Coast, Streeterville, the Loop, or the South Loop via the CTA Red Line. Old Town real estate for sale also features a pretty close proximity to the lakefront as well, which certainly has its perks during the spring and summer. Generally speaking, Old Town’s officialy boundaries are defined by Division Street to the south, Clybourn Avenue and Halsted Street to the west, Armitage Avenue to the north, and Clark Street to the east (but that’s if you include the Old Town Triangle sub-neighborhood as well).

As alluded to above, real estate for sale in Chicago’s Old Town neighborhood is quite diverse, ranging from historic old townhomes and vintage condo buildings to all kinds of newer construction condo and single-family home developments. Potential home buyers browsing the Old Town real estate market will also find a fairly nice mix of high-rise condos in the neighborhood as well, most notably along LaSalle or Clark Street. Depending on needs and wants, a great place to begin your Old Town home search in Chicago is somewhere near or along the Wells Street Corridor, as there’s nothing quite like living living near all the restaurants, bars, and entertainment that makes this neighborhood really come alive in the evenings. But be warned, real estate along Wells Street is definitely among the most highly sought after when it comes to Old Town real estate, so options may be limited!

Contact Us For More Information About Old Town Real Estate

For obvious reasons, Old Town continues to be a favorite among downtown Chicago home buyers, which is exactly why you should get all the help you can when looking for a new place to live somewhere in the neighborhood. So, for more information about Old Town real estate or to perhaps schedule a private showing for a home or condo listing you’d like to see in person, don’t delay any longer and contact Gold Coast Realty at (312) 280-9600 and discuss all your home buying goals with one of our downtown Chicago real estate experts today!