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$339,900

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 2 Full Baths
  • 1,987 Sq. Ft.
  • 2 Car Garage
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Historic Charm Meets Modern Versatility ? 20 Minutes from Madison! Step into timeless elegance with this spacious 3-story, 5-bedroom, 2-bath gem?perfectly suited for full-time residence or short-term rental. Currently operating as a successful Airbnb on the second floor, the lower two levels serve as a comfortable owner?s retreat. The third floor offers exciting potential for additional living space. Original hardwood floors & stunning trim throughout, original woodwork & doors, including a charming butler?s pantry off the kitchen, new concrete driveway w/French drain for worry-free maintenance, newer windows & a high-efficiency natural gas boiler system?keeping heating bills incredibly low. Nestled near the historic downtown district w/easy access to local parks & sits right on the bike trail?ideal for outdoor enthusiasts. Dreaming of a character-filled family home, a profitable rental property, or beautiful permanent home. This versatile beauty delivers!

Full Property Details for 355 W Madison St

General

  • Price: $339,900
  • Taxes: $4,248 (2024)
  • Status: Active
  • Type: Single Family
  • Source: Wirex_Realtors_Association_of_North_Western_Wisconsin_NWW
  • MLS ID: 1594321
  • Updated: 12/11/2025
  • Added to Site: 158 day(s) ago

Interior

  • Interior Features: Circuit Breakers
  • Appliances: Dishwasher, Dryer, Disposal, Microwave, Range/Oven, Refrigerator, Washer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: 13 x 11, Main
  • Bedroom 2: 13 x 9, Main
  • Bedroom 3: 13 x 13, Upper
  • Bedroom 4: 13 x 12, Upper

Other Rooms

  • Living Room: 20 x 14, Main
  • Kitchen: 12 x 12, Main
  • Dining Room: 14 x 8, Main

Exterior

  • Exterior Features: 3 Season Porch, Patio, Brick Patio, Enclosed Porch, Porch, Fenced Yard

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Garage Description: 2 Car, Detached, Opener Included

Location

  • Municipality: Waterloo
  • County: Jefferson
  • Driving Directions: Take Hwy 19 East from Madison or Highway 19 West from Milwaukee to Waterloo. Highway 19 turns into West Madison Street. Home is in the historic district.

Heating & Cooling

  • Heating Fuel: Natural Gas
  • Heating/Cooling: Wall Air Conditioning, Other, Radiant

Utilities

  • Water/Sewer: Municipal Sewer, Municipal Water

Structural Information

  • Description/Design: 2 Stories
  • Exterior Const.: Brick, Steel, Vinyl
  • Basement Desc.: Full, Block, Stone
  • Square Feet: 1,987
  • Square Feet Range: 1751 to 2000
  • Year Built: 1900

Lot Features

  • Lot Size (Acres): 0.33
  • Lot Size Range: Less than .5 Acres
  • Lot Dimensions: 0 x 0 x
  • Zoning: Commercial, Residential

Financial Considerations

  • Tax Amount: $4,248
  • Tax Year: 2024

Disclosures and Reports

  • Exclusions: Excluded:Sellers Personal
  • Inclusions: Included:Dishwasher, Included:Dryer, Included:Fenced Yard, Included:Garage Opener, Included:Garbage Disposal, Included:Microwave, Included:Oven/Range, Included:Refrigerator, Included:Washer

Listed by eXp Realty LLC

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— 355 W Madison St —

  • eXp Realty LLC

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NMLS#: 1598647

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NMLS#: 1598647

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

Schools serving 355 W Madison St

School District:Waterloo School District
NameGradesDistance
Waterloo Elementary School
785 North Monroe Street, Waterloo, WI 53594
PK-40.6 mi
Waterloo Middle School
865 North Monroe Street, Waterloo, WI 53594
7-80.5 mi
Waterloo High School, Waterloo, WI
865 North Monroe Street, Waterloo, WI 53594
9-120.5 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 355 W Madison St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/25/2025
Price Reduced
$339,900
-1.45%
MLS
11/10/2025
Price Reduced
$344,900
-1.43%
MLS
10/13/2025
Price Reduced
$349,900
-4.11%
MLS
8/23/2025
Price Reduced
$364,900
-2.67%
MLS
8/13/2025
Price Reduced
$374,900
-5.06%
MLS
8/11/2025
Listed
$394,900
43.6%
MLS
8/01/2023
Sold
$275,000
—
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 355 W Madison St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$4,464
25%
$277,400
56%
2023
$3,560
6%
$177,700
—
2022
$3,359
-2%
$177,700
—
2021
$3,420
-6%
$177,700
22%
2020
$3,632
5%
$145,600
—
2019
$3,452
1%
$145,600
—
2018
$3,412
2%
$145,600
—
2017
$3,332
—
$145,600
—
2016
$3,321
-2%
$145,600
—
2015
$3,405
3%
$145,600
—
2014
$3,320
1%
$145,600
—
2013
$3,290
—
$145,600
—
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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Listed by eXp Realty LLC

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355 W Madison Street, Waterloo, WI 53594 (MLS# 1594321) is a Single Family property with 5 bedrooms and 2 full bathrooms. 355 W Madison Street is currently listed for $339,900 and was received on August 11, 2025. Want to learn more about 355 W Madison Street? Do you have questions about finding other Single Family real estate for sale in Waterloo? You can browse all Waterloo real estate or contact a Coldwell Banker agent to request more information.

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