Old Town Homes For Sale - Chicago

The Old Town real estate market is filled with both prestigious and practical homes. Explore the market with Chicago Real Estate Mall.

As its name would suggest, Old Town is one of Chicago's most historic neighborhoods, with elegant Victorian-era buildings and brick alleys on many of the streets. Located in Chicago's North Side, just west of Gold Coast and south of Lincoln Park, Old Town has a charming business district, highlighted by a thriving arts and live theater scene. Those living here do so for many reasons, mainly because of the neighborhood's central location and walkability to most of the city's top attractions, but also because of the attractive home for sale in Old Town. The celebrated brick homes are part of the reason why the community is known for its affluence, but that doesn't mean there aren't affordable homes in Old Town. A variety of single- and multi-family options gives buyers and renters plenty of choice, so browse our listings to find your ideal home!

Learn additional benefits of living in Old Town below the listings. There's more info on the home styles and the amenities within the neighborhood.

Search Old Town Real Estate Listings

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
Refine your search to less than 500 properties to save.
Click on the map to draw your polygon search.
Click on the map to draw your radius search.
Search only mappable listings within the map's bounds.
$19,500,000
 

915 North Dearborn Street, Chicago

6 Beds, 6½ Baths, 13.4k SqFt
Built for attorney John H. Thompson based on one of Cobb and Frost's last designs, Thompson House remains one of the most visually stunning landmark homes in Chicago's Gold Coast. This grand private residence on Dearborn Street is located in a residential / business planned development area, which offers many use possibilities. Impeccably detailed woodwork and gorgeous stained-glass windows speak to the affluence and grandeur of a bygone era.
$10,500,000
 

1336 North State Parkway, Chicago

5 Beds, 7 Baths, 9,000 SqFt
Historic elegance melds perfectly with modern sophistication throughout this meticulously updated and immaculately maintained 9000 square foot home. Perfectly sited in the heart of the Gold Coast, this landmark residence is uniquely positioned and flooded with sunlight. The epitome of grandeur and perfectly crafted for world class entertaining, this grand home also offers very comfortable moments for everyday living throughout. Tremendous
$7,999,000
 

1325 North Astor Street #13, Chicago

6 Beds, 6 Baths, 7,900 SqFt
Absolutely stunning, David Adler designed duplex penthouse set atop one of the finest, vintage condominium buildings on Astor Street. Available for the first time in nearly 50 years, this 6 bedroom home boasts nearly 8000 square feet and features 3 separate private terraces with amazing city and lake views. The expansive living room, with parquet floors and original paneled walls is perfect for entertaining. The elegant, light-filled and
$6,999,000
 

1432 North State Parkway, Chicago

8 Beds, 6½ Baths, 10.4k SqFt
Located on an extraordinary double lot in the heart of Chicago's Gold Coast, this 9,100 sqft mansion offers the best of all worlds! Original handcrafted architectural details have been preserved while it was transformed by LG Development into a comfortable 21st century home with state-of-the-art infrastructure and a modern floorplan designed for entertaining and family living. There are 7 bedrooms (including a luxurious full floor master with
$6,999,000
 

1300 North State Parkway #1202, Chicago

5 Beds, 5½ Baths, 5,913 SqFt
One of the most sophisticated homes to come to market, PH 1202 at the Ambassador is in a league of its own. Warm modern details grace this 5913 Sqft PH in the Heart of Chicagos most sought after neighborhood. Purchased as raw space and reimagined by the team at Wheeler Kearns, This incredibly bright home boasts a gracious entry,13ft ceilings, A stunning Venetian plaster wrapped circular staircase,5 bedrooms (4 en suite), Formal lvng/dining rms,
$6,494,999
 

1246 North Astor Street, Chicago

5 Beds, 7 Baths,
GOLD COAST! JUST COMPLETED LUXURIOUS MANSION LOCATED ON PRESTIGIOUS ASTOR STREET. HOME RENOVATED DOWN TO THE STUDS IN 2019 BY AWARD WINNING NOAH PROPERTIES AND DESIGNED BY LISEK INTERIORS. THIS APROX 10,000 SQUARE FEET, EXTRA WIDE, HISTORIC CORNER HOME FEATURES 5 SUN DRENCHED BEDS PLUS DEN ON SECOND AND THIRD FLOOR, 6 BATHS, 2 POWDER ROOMS, 3 WET BARS, BUTLER'S PANTRY, GREAT SIZE REC ROM IN LOWER LEVEL, ELEVATOR TO ALL FLOORS, PHENOMENAL OUTDOOR
New
$6,000,000
 

1516 North Lake Shore Drive, Chicago

10 Beds, 6 Baths, 12k SqFt
A luxury residence like this is not viewed it's experienced. Originally built for Edward Tyler Blair, a Chicago investment banking magnate, the home was designated as a Chicago Landmark in 1989 and is listed on both the National Register and Illinois Register of Historic Places. Every once in a while an exceptional opportunity presents itself. This is one of those times. 1516 Lake Shore Drive is a jewel in the crown of the Gold Coast of
$5,999,000
 

1241 North State Parkway, Chicago

6 Beds, 7 Baths, 7,430 SqFt
Bloomfield Development presents an ultra-rare, new construction, 7,400-square-foot single-family home in the heart of the famed Gold Coast. Located on an oversized 150' deep parcel on one of Chicago's most prestigious streets, this classic home features a French limestone facade, 6 bedrooms, 6 full baths, 2 half baths, a 5-stop elevator, & a garage for up to 4 cars (with optional lift & breezeway attachment). Enter through the elegant
$5,989,000
 

65 East Goethe Street #m102, Chicago

4 Beds, 5½ Baths, 5,800 SqFt
This magnificent residence lives like a single family with approx. 5800 square feet on 2 floors and a private street entrance, yet offers the 24-hr.security, maintenance and management services of an 18-unit luxury, boutique condominium building...the best of both worlds! It showcases the finest designer finishes, creating a timeless oasis in Chicago's Gold Coast neighborhood. The space flows easily from a formal living room, dining room,
$5,900,000
 

1316 North Astor Street, Chicago

6 Beds, 7½ Baths, 10.6k SqFt
First time on the market since this renovation was first offered! Behind this classic Potter Palmer mansion sits an architectural vision with grand room sizes, gracious ceiling heights and cool modern lines throughout. Elevator access to all levels as well as an architecturally significant scissor staircase to all levels. The main level of the home offers great spaces for living and dining and tremendous light pours in through a two story
$4,995,000
 

1441 North State Parkway, Chicago

6 Beds, 9½ Baths, 9,750 SqFt
Set on a 35' wide lot in the heart of Chicago's Gold Coast, this 9,750 sqft graystone has been fully renovated offering a masterful combination of old-world grandeur and modern amenities. The extra wide, extra deep interior allows for beautifully proportioned rooms with high ceilings and abundant light. Each above grade level has more than 2,600 sqft of refined living space with elegant formal rooms and 6 spacious bedrooms. The master suite
$4,950,000
 

1520 North Dearborn Parkway, CHICAGO

5 Beds, 4½ Baths, 7,623 SqFt
New style. New look. Move right in! Freshly painted white in this total restoration of fabulous Gold Coast 1898 row house. No detail was overlooked. Luxury in every single inch of the home including moldings, marquetry, fabulous original staircase, stain glass, 3 gas fireplaces, lovely built-ins, quality finishes, and stunning murals. Totally modern floorplan with amazing cook's kitchen and adjacent family room that leads to charming landscaped

 

For custom search tools, as well as the ability to save your favorite properties and receive email notifications about new listings that meet your specified requirements, register with Chicago Real Estate Mall today!

 

Discover Old Town Real Estate

The red brick exteriors of many Old Town homes for sale are perfect representations of classic residential Chicago architecture. As you make your way down these lovely tree-lined family-friendly streets, you'll likely find it to be a refreshing change from the high rises downtown. Townhomes, historic condos, and single-family homes blend together nicely, creating a plethora of options for a wide range of residents. In addition to homes built in the Victorian style, the Old Town real estate market also includes Queen Anne and Italianate-style homes.

However, if you like the neighborhood, but still prefer to live in a more modern high rise, you're still in luck. Several towering condo buildings are located along busier streets such as LaSalle Drive and Clark Street. Mid-rise condo buildings are also available, with many of the units providing modern interior features, much like the high rises. For those looking to living near Old Town's restaurant and bar district, there are many condos for sale and rent along Wells Street, which will put you at the heart of the action.

Old Town Amenities

Old Town's location puts you at a close proximity to almost all of the top areas of Chicago if you're looking for something to do. In fact, the entire city is easily accessible via public transit from everywhere in Old Town.

For amenities within the neighborhood, there are plenty of restaurants and live entertainment venues to keep you busy at night in this thriving community. Among the top places to eat are Sauce, Dinotto Ristorante, and Salpicon, along with plenty of ethnic chain restaurants. For a laugh after your meal, try The Second City Theater and Zanies Comedy Club. There are also several bars and night clubs to get your dance on.

Finally, one of the best perks of Old Town is that it's located right beside the western edge of Lincoln Park. This 1,200-acre section of green space, trails, and museums is perhaps the most renowned park in all of Chicago and brings joy to hundreds, if not thousands, of residents and tourists daily.

If you're interested in Old Town real estate, contact the experts at Chicago Real Estate Mall.

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Ann M Mall INC are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed.

Listing information last updated on April 9th, 2020 at 2:20am CDT.