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$437,500

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,242 Sq. Ft.
  • 2 Car Garage
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This darling piece of Oswego architectural history has been lovingly restored with exceptional care and timeless style. Ideally located just blocks from everything downtown Oswego has to offer, this home is a true community staple. Originally built in 1900, the residence now features a completely renovated interior paired with a spacious family room addition, blending historic charm with modern living. The open and airy main level flows seamlessly, while the second floor showcases a newly added primary suite, creating a comfortable and functional layout. Offering approximately 2,200 square feet of living space, the home includes four spacious bedrooms and three full bathrooms. Highlights include a beautifully renovated kitchen with stainless steel appliances, granite countertops, and a new dishwasher (2025), formal living and dining rooms, rich hardwood floors, and an unfinished basement for additional storage or future potential. Major recent updates provide peace of mind, including a new roof and siding (2024) and a new hot water heater (2024). Outside, enjoy an updated backyard oasis perfect for hosting, featuring an enormous yard ideal for entertaining, along with a detached two-car garage and a charming she-shed for hobbies or relaxation. This one-of-a-kind home delivers historic character, thoughtful updates, and an unbeatable location in the heart of Oswego.

Full Property Details for 371 S Madison St

General

  • Price: $437,500
  • Taxes: $7,054 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12537278
  • Updated: 1/2/2026
  • Added to Site: 20 day(s) ago

Rental Information

  • Complex Features: Street Paved

Interior

  • Basement: Unfinished
  • Interior Features: 1st-Floor Bedroom, 1st-Floor Bath, Open Floorplan
  • Appliances: Microwave, Dishwasher, Refrigerator, Disposal
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Bathroom Features: Double Sink

Bedrooms

  • Total Bedrooms: 4

Additional Information

  • Other Features: School Bus Service

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking Features: Yes, Garage Owned, Detached, Garage

Location

  • Area: Oswego
  • County: Kendall
  • Township: Oswego
  • Driving Directions: Route 25 to Madison (rte 34)

School Information

  • School District: 308
  • Elem School District: 308
  • Midd School District: 308
  • High School District: 308
  • Elementary School: Southbury Elementary School
  • Middle School: Traughber Junior High School
  • High School: Oswego High School
  • Private School: Oswego High School

Community

  • Assoc. Fees Include: None

Heating & Cooling

  • Cooling Type: Central Air Conditioning
  • Heating Type: Natural Gas, Electric, Steam

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Construction: Aluminum Siding, Cedar
  • Exterior Const.: Aluminum Siding, Cedar
  • Basement: Yes
  • Basement Desc.: Unfinished, Full
  • Foundation: Block
  • Roof: Asphalt
  • Sub-Flooring: Hardwood
  • Square Feet: 2,242
  • Sq. Ft. Source: Estimated
  • Year Built: 1900
  • Built Before 1978: Yes

Additional Structures

  • Other Structures: Shed(s)

Lot Features

  • Lot Size (Acres): 0.2729
  • Lot Size Range: .25 to .49 Acre
  • Lot Dimensions: 75 x 160

Financial Considerations

  • Assessment Year: 1900
  • Tax Amount: $7,054
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: Standard
  • Property ID: 320103004

Listed by Keller Williams ONEChicago

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— 371 S Madison St —

  • Keller Williams ONEChicago

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NMLS#: 1598647

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NMLS#: 1598647

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with our affiliated in-house agency

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Save up to an additional 20% by bundling your home and auto together!

Schools serving 371 S Madison St

School District:Oswego Community Unit School District 308
NameGradesDistance
Southbury Elementary School
820 Preston Lane, Oswego, IL 60543
K-51.6 mi
Traughber Jr High School
570 Colchester Drive, Oswego, IL 60543
6-81.4 mi
Oswego High School
4250 State Route 71, Oswego, IL 60543
9-120.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 371 S Madison St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/27/2025
Listed
$437,500
25%
MLS
11/16/2022
Sold
$350,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 371 S Madison St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,054
6%
$93,661
14%
2023
$6,670
100%
$82,159
10%
2022
-100%
$74,690
2%
2021
$4,951
2%
$73,226
2%
2020
$4,864
—
$71,790
1%
2019
$4,887
10%
$71,231
42%
2018
$4,423
7%
$50,246
9%
2017
$4,132
80%
$46,309
65%
2016
$2,291
-42%
$28,026
-34%
2015
$3,950
-1%
$42,206
4%
2014
$3,998
-3%
$40,582
-4%
2013
$4,142
1%
$42,273
-5%
2012
$4,090
—
$44,498
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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371 S Madison Street, Oswego, IL 60543 (MLS# 12537278) is a Single Family property with 4 bedrooms and 3 full bathrooms. 371 S Madison Street is currently listed for $437,500 and was received on December 27, 2025. Want to learn more about 371 S Madison Street? Do you have questions about finding other Single Family real estate for sale in Oswego? You can browse all Oswego real estate or contact a Coldwell Banker agent to request more information.

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