Vintage homes for sale & real estate in Heart of Chicago, IL

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ABOUT THIS HOME
Vintage Home for sale in Heart of Chicago, IL:
Live in the vibrant Restaurant Row of the iconic Pilsen neighborhood located just 2 blocks from the Pink Line. ! This stunning unit combines historic charm with modern luxury. Step into an open-concept layout with split bedrooms, hardwood floors throughout, and soaring 10-foot ceilings. Enjoy incredible natural light from the massive east-facing bay windows that flood the space with morning sun. The kitchen features 42" European flat-panel cabinetry and white granite countertops. Conveniences include in-unit washer/dryer, private storage room, bike storage, carport parking.

$295,000

2 beds2 baths1,300 sq ft

2354 S Oakley Ave Unit B2, Chicago, IL 60608

10-foot ceilings • Hardwood floors • Open-concept layout

ABOUT THIS HOME
Vintage Home for sale in Heart of Chicago, IL:
Remarkable Investment Opportunity in the Heart of Pilsen! This is a fantastic, fully-gutted mixed-use building, ready for immediate development. The blueprints and permits are already in place, making it a seamless transition for you to bring your business to the first floor, while enjoying two spacious, two-bedroom apartments on the second floor. Whether you're looking to start a business, expand your current one, or simply invest in a prime location, this property offers endless possibilities. Located in the vibrant and ever-growing Pilsen neighborhood, you'll be surrounded by a dynamic arts scene, unique local businesses, and an incredible sense of community. This is your chance to own

$399,900

— beds— baths— sq ft

1702 S Paulina St, Chicago, IL 60608

Mixed-use building • First floor • Pilsen neighborhood

ABOUT THIS HOME
Vintage Home for sale in Heart of Chicago, IL:
Frame 2-unit building in the HEART OF CHICAGO Pilsen!. 1st floor has 2 bedrooms, 1 bath, spacious living room, updated kitchen with newer cabinets and counter top. ceramic tile floor, newer furnace with a/c, newer windows. 2nd floor has 2 bedrooms, 1 bath, updated kitchen with newer cabinets and counter top. Separate utilities, unfinished basement, 2 car garage. Close to public transportation, Pink line, stores, schools, expressway. Pre-approved buyers please.

$430,000

4 beds2 baths— sq ft

1934 W 21st Pl, Chicago, IL 60608

Close to schools • Newer cabinets • Newer windows

ABOUT THIS HOME
Vintage Home for sale in Heart of Chicago, IL:
Attention savvy buyers/investors-this is your chance to own a piece of Chicago's vibrant history in the heart of Pilsen/heart of Chicago neighborhood. This Victorian 2-unit with a coach house offers space, character, and endless potential. Imagine transforming this property into a multi-unit haven-both buildings offer duplex possibilities. Parking for 4 plus vechiles and a location that's walkable to restaurants, shops, and transit, this is a rare chance to invest in a community that celebrates diversity and growth. Sold in As-Is condition. Seller makes no legal representation to the 4th coach house unit. Renovation needed. Cash or strong conventional buyers preferred. FHA 203k may be consi

$369,900

6 beds4 baths— sq ft

1817 W 21st St, Chicago, IL 60608

Duplex possibilities • Walkable to transit • Victorian 2-unit

ABOUT THIS HOME
Vintage Home for sale in Heart of Chicago, IL:
Pilsen brick single family home in excellent location. Property features 1st floor Bedroom, kitchen, living room, dining room and full bath duplexed to finished attic for an additional bedroom. Remodeled lower level with updated kitchen and bath, 2 bedrooms, large living area, canned lighting and full walk in laundry room. Back yard features new cement work, patio, fully secured and large gated parking pad. Newer roof and AC. All room sizes estimated.

$369,900

4 beds2 baths1,800 sq ft

2213 S Oakley Ave, Chicago, IL 60608

Finished attic • New cement work • Updated kitchen

Property at 2338 W 18th Pl, Chicago, IL 60608, 7 beds, 3 baths

$736,900

7 beds3 baths— sq ft

2338 W 18th Pl, Chicago, IL 60608

Property at 2109 W 18th Pl, Chicago, IL 60608, 6 beds, 5 baths

$799,000

6 beds5 baths— sq ft

2109 W 18th Pl, Chicago, IL 60608

Property at 2228 W Cermak Rd, Chicago, IL 60608, 9 beds, 2 baths

$899,000

9 beds2 baths— sq ft

2228 W Cermak Rd, Chicago, IL 60608

Property at 2012 W Coulter St, Chicago, IL 60608, 3 beds, 3.5 baths

$669,900

3 beds3.5 baths3,000 sq ft

2012 W Coulter St, Chicago, IL 60608

Property at 2440 S Oakley Ave, Chicago, IL 60608, 7 beds, 4 baths

$699,000

7 beds4 baths— sq ft

2440 S Oakley Ave, Chicago, IL 60608

Property at 2222 W 21st St, Chicago, IL 60608, 11 beds, 8 baths

$825,000

11 beds8 baths7,500 sq ft

2222 W 21st St, Chicago, IL 60608

Property at 2300 W 19th St, Chicago, IL 60608, 4 beds, 2 baths

$425,000

4 beds2 baths1,495 sq ft

2300 W 19th St, Chicago, IL 60608

Property at 2140 W Cermak Rd, Chicago, IL 60608

$900,000

— beds— baths4,320 sq ft

2140 W Cermak Rd, Chicago, IL 60608

Property at 1616 W 18th Pl, Chicago, IL 60608

$1,549,000

— beds— baths6,250 sq ft

1616 W 18th Pl, Chicago, IL 60608

Property at 1718 S Ashland Ave, Chicago, IL 60608

$575,000

— beds— baths— sq ft

1718 S Ashland Ave, Chicago, IL 60608

Property at 2335 W 21 St, Chicago, IL 60608, 10 beds, 5 baths

$699,900

10 beds5 baths— sq ft

2335 W 21 St, Chicago, IL 60608

Property at 2410 S Blue Island Ave, Chicago, IL 60608

$699,900

— beds— baths— sq ft

2410 S Blue Island Ave, Chicago, IL 60608

Property at 1714 S Ashland Ave, Chicago, IL 60608

$1,190,000

— beds— baths— sq ft

1714 S Ashland Ave, Chicago, IL 60608

Property at 2128 W Cermak Rd, Chicago, IL 60608

$699,000

— beds— baths— sq ft

2128 W Cermak Rd, Chicago, IL 60608

Property at 2334 W 21st St, Chicago, IL 60608

$159,999

— beds— baths— sq ft

2334 W 21st St, Chicago, IL 60608

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ABOUT THIS HOME
Vintage Home for sale in Heart of Chicago, IL:
This fully renovated multifamily property presents a turn-key investment opportunity with full occupancy and strong in-place cash flow. The attractive brick building features modernized layouts with open floor plans, newly updated kitchens, and contemporary bathrooms, appealing to today's renters seeking both style and functionality. The renovations enhance the property's long-term durability while reducing near-term capital needs, offering investors peace of mind and stable operations from day one. Adding to the upside, the property includes a vacant coach house located above the rear garage. This space is primed for renovation and conversion into an additional rental unit, providing a cle

$1,200,000

— beds— baths5,904 sq ft

1813 S Ashland Ave, Chicago, IL 60608

Turn-key investment • Fully renovated • Modernized layouts

ABOUT THIS HOME
Vintage Home for sale in Heart of Chicago, IL:
A 4-unit building, brick 2-story apartment building is for sale via auction. Situated in a desirable Pilsen location within the business shopping district at 18th and Ashland Avenue, this building is currently gutted with plans to develop as four, 2 bedroom and 2 bath units with central air conditioning and in-unit washer/dryer set ups. Minutes from Medical District, 18th Street entertainment district, UIC and more. Pilsen is a neighborhood on the lower west side of Chicago. Commercial space is clustered along 18th St. as well as Ashland in this largely residential neighborhood. The 18th St. CTA Pink Line stop is a short distance away.

$400,000

8 beds8 baths— sq ft

1817 S Ashland Ave, Chicago, IL 60608

Medical district • Cta pink line stop • In-unit washer dryer

Based on information submitted to the MLS GRID as of Fri Dec 26 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Heart of Chicago

There are currently 20 vintage homes for sale in Heart of Chicago at a median listing price of $497K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Heart of Chicago stay on the market for 63 days and receive 4 offers. Popular neighborhoods include West Town, Bronzeville, South Loop, West Loop, and Bridgeport. This map is refreshed with the newest listings in Heart of Chicago every 15 minutes.

In the past month, 5 homes have been sold in Heart of Chicago. In addition to houses in Heart of Chicago, there were also 7 condos, 1 townhouse, and 17 multi-family units for sale in Heart of Chicago last month. Find your dream home in Heart of Chicago using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Heart of Chicago are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Heart of Chicago. If you're looking to sell your home in the Heart of Chicago area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Heart of Chicago with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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