Buyer's financing fell through. Here is your second chance! Rare mixed-use property now available in the heart of downtown Oswego! This versatile property offers the perfect blend of residential and commercial potential. Whether you're looking to run a thriving business on the main level with a spacious apartment above, or you're seeking a dual-income property with two separate apartments, this property has it all. The main floor office space is open and inviting, featuring a reception area, multiple workspace areas, a private office, an ADA-compliant bathroom, and an additional private bathroom. The second-floor apartment boasts a private entrance, ensuring privacy and convenience, and features 3 bedrooms along with a HUGE bonus loft space, providing ample room for living and storage. Additionally, the property includes a vast unfinished basement with high ceilings, offering endless possibilities for expansion or additional storage. Enjoy peace of mind with recent upgrades, including a brand-new roof, all-new siding, and newer windows throughout the property. The interiors feature extensive trim work and beautiful hardwood floors, adding a touch of elegance and charm to this already impressive property. The property includes a detached 2-car garage with a floored loft space, perfect for additional storage or potential conversion into a workspace. Utilities are metered separately for each unit, providing convenience and efficiency for both residential and commercial tenants. Situated in the heart of downtown Oswego, IL, this property benefits from over 10,000 traffic views per day, offering excellent visibility and making it a prime location for any business. 155 Chicago Road represents an incredible investment opportunity with its flexible use, prime location, and recent upgrades. Perfect for entrepreneurs, investors, or those seeking a multi-functional living space, this downtown Oswego gem is the perfect choice! Don't wait, this one won't be around long!
Multi-familyProperty Type
1925Year Built
2 garage spacesParking
Listed by Craig Caffarello• Your Place Realty Group
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
4
Baths
2
Stories
2
Lot width
—
Lot depth
—
Lot size
0.26 Acres
Year renovated
—
Sq. Ft.
2,209
Year built
1925
Style
Single Family Residential
County
Kendall County
APN
0317403001
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 22, 2026.
D-1
Downtown District
The D-1 Downtown District is established to accommodate pedestrianoriented development that serves the Village and surrounding communities. The D-1 District allows a wide range of commercial, residential, and institutional uses within Downtown Oswego.
Permitted uses
Include but are not limited to:
Bank
Garden center
General retail
Restaurant
Tavern / bar / nightclub / micro-Brewery
Mixed use building
Office
Public service
Park & open space
Property details
Parking
Parking Information
# of Garage Spaces: 2
# of Parking (Total): 8
Parking On-Site: Yes
Parking Features: Unassigned, Off Street
Parking: Garage,Space/s
Garage Ownership: Owned
Garage On-Site: Yes
Garage Type: Detached
Garage Details: Garage Door Opener(s),Transmitter(s)
Interior
Bathroom Information
# of Baths (Full): 2
# of Baths (1/2): 1
Bedroom Information
# of Bedrooms: 5
# of Bedrooms Possible: 5
Additional Rooms Information
Basement: Full
Basement Description: Unfinished
Interior Features
# of Rooms: 15
Exterior
Exterior Features
Exterior Features: Deck, Porch Screened
Building Information
# Of Units in Building: 2
Exterior Building Type: Vinyl Siding
Age: 91-100 Years
Built Before 1978 (Y/N): Yes
Roof: Asphalt
Property Information
Property Type: Two to Four Units
Conversion (Y/N): Y
Ownership: Fee Simple
Rebuilt (Y/N): No
Rehab (Y/N): No
General Information: School Bus Service
Parcel Number: 0317403001
Lot Information
Dimensions: 66.05X181.41X66X183.68
Lot Size: .25-.49 Acre
Zoning: COMMR
Financial
Tax Information
Tax Annual Amount: $6,882
Tax Year: 2023
Financial Information
Finance Code: Cash
Special Service Area: N
Utilities
Utility Information
Water Source: Public
Sewer: Public Sewer
Heating & Cooling
Heating: Natural Gas, Forced Air
Location
Multi-Unit Information
3 Br Unit(s) In Bldg: Yes
Unit Type 1 Information
Floor Number: 1
Sq. Ft.: 1,094
# of Rooms: 6
# of Bedrooms: 1
# of Bathrooms (Total): 2
# of Full Bathrooms: 1
# of Half Bathrooms: 1
Appliances and Features: Washer,Dryer,Accessible Entrance
Security Deposit: 0
Tenant Pays: Electric,Gas,Sewer,Water
Lease Expiration Date: Wednesday, May 1, 2024
Unit Type 2 Information
Floor Number: 2
Sq. Ft.: 1,556
# of Rooms: 8
# of Bedrooms: 3
# of Bathrooms (Total): 1
# of Full Bathrooms: 1
Appliances and Features: Stove,Refrigerator,Microwave
Tenant Pays: Electric,Gas,Sewer,Water
Lease Expiration Date: Wednesday, May 1, 2024
School Information
Elementary School District: 308
Middle Or Junior School District: 308
High School District: 308
Location Information
Township: Oswego
Corporate Limits: Oswego
Directions: Route 34 near Downtown Oswego.
Public facts
Beds: 4
Baths: 2.0
Sq. Ft.: 2,209
Stories: 2.0
Lot Size: 0.26 acres
Style: Single Family Residential
Year Built: 1925
Year Renovated: —
County: Kendall County
APN: 0317403001
Home facts updated by county records on Jul 22, 2026
Other
Listing Information
Holds Earnest Money: Yes
Possession: Closing
Some Photos Virtually Staged?: No
Around this home
Schools
Southbury Elementary School
Public K-5 • Assigned • 1.2mi
7/10
Traughber Junior High School
Public 6-8 • Assigned • 1.3mi
6/10
Oswego High School
Public 9-12 • Assigned • 0.4mi
8/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
3/10 Heat Factor
7 days above 103° expected this year, 15 days in 30 years
2/10 Wind Factor
1% chance of strong winds in next 30 years
3/10 Air Factor
3 unhealthy days expected this year, 4 days in 30 years
Provided by First Street
Historical weather
Oswego, IL • 60543
Average low and high temperatures (°F)
29
14
38
20
56
33
64
43
72
49
82
62
86
68
82
62
80
56
69
46
50
36
35
21
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 10.2 hours in
June and 3.5 hours in December, placing it below the
U.S. average for solar exposure.
10.2 hrs
3.5 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$413,000 – $499,000
Reach more buyers when you sell with Redfin. Save up to $4,337 in fees.3 minutes to get started.
Property information provided by MRED as Distributed by MLS Grid when last listed in 2025. This data may not match public records. Learn more.
Listing provided courtesy of: Advantage Realty Group
Listing agent: Ben Kastein (6306311296)
Based on information submitted to the MLS GRID as of Wed Sep 02 2026. 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.