321 Chicago St, Milton, WI 53563
OFF MARKET

321 Chicago St
Milton, WI 53563

  • 3 Beds
  • 2 Baths
  • 1,620 sqft (on 0.59 acres)

$363,000

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $2,260/mo*
Refinance Your Home

$363,000

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $2,260/mo*
Refinance Your Home
3 Beds
2 Baths
1,620 sqft
(on 0.59 acres)

Local Information

  • Map ViewExplore the area around 321 Chicago St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Spacious Home on Large Lot. Generously sized kitchen and livingroom with fireplace would make this a great home for entertaining. Some of the updates over the last 10 yrs are roof, central air, furnace and windows. Enjoy the screened in room off back of house and the large & private back yard. All you need to do here is bring your paint & paint brush and throw in some modern flooring and this place will become your Home!!!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 321 Chicago St

Interior Features

Levels, Entrance, & Accessibility
Stories: 1

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.59 acres

Price History for 321 Chicago St

DatePriceEventSource
01/03/2018$179,900Sold
N/A
07/18/2011$133,900ListingRemovedAgent Provided
06/27/2011$133,900Listed For SaleAgent Provided

Market trends in Milton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
50
4MoM
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Property Tax and Assessment

Year2024
Tax$4,576
Assessment$279,400
Home facts updated by county records

Comparable Sales for 321 Chicago St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
502 E Madison Ave, Milton, WI
0.40
Single-Family Home
$295,000
06/03/26
3
1.5
1,706
528 E Madison Ave, Milton, WI
0.35
Single-Family Home
$340,000
06/18/26
3
1.5
1,672
526 Greenman St, Milton, WI
0.33
Single-Family Home
$257,500
11/19/25
4
2
1,655
396 E Madison Ave, Milton, WI
0.49
Single-Family Home
$300,000
08/21/25
3
2
1,900
125 Parkview DRIVE, Milton, WI
0.26
Single-Family Home
$200,000
11/06/25
5
2
2,476
602 Parkview Dr, Milton, WI
0.29
Single-Family Home
$344,900
04/09/26
3
2
2,110
723 E High St, Milton, WI
0.20
Single-Family Home
$242,000
12/30/25
2
2
1,576
107 Parkview Dr, Milton, WI
0.27
Single-Family Home
$233,000
02/11/26
2
1
1,567
316 E High St, Milton, WI
0.58
Single-Family Home
$370,000
10/28/25
3
1.5
2,561
427 East Madison AVENUE, Milton, WI
0.41
Single-Family Home
$329,900
11/21/25
3
2.5
1,950

Nearby homes

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Assigned Schools

These are the assigned schools for 321 Chicago St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Milton

At least 36 Trulia users voted on each feature.

  • 100 % Say parking is easy

  • 91 % Say car is needed

  • 85 % Say yards are well-kept

  • 84 % Say kids play outside

  • 81 % Say people would walk alone at night

  • 76 % Say it's dog friendly

  • 75 % Say there's holiday spirit

  • 68 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 61 % Say there's wildlife

  • 58 % Say streets are well-lit

  • 53 % Say they plan to stay for at least 5 years

  • 52 % Say there are community events

  • 49 % Say there are sidewalks

  • 40 % Say it's walkable to restaurants

  • 37 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Sally J.
    "Neighbors are very friendly. Most homes are very neat and tidy. Annual chicken bbq in the park. Splash park for kids. New Veterans Memorial and playground. "
    0
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  • Stephanyjones25
    "Milton has a huge dog park with two different areas. Owners are always out walking their dogs. Dog are welcome in some but not all places. "
    0
    Flag
  • Shanteel
    "Small town good feel not much for entertainment or restaurants but Janesville is really close not any public transportation "
    0
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  • Lonisheldon
    "I've lived in this same house for over 20 years along with a few good neighbors. Walking distance to all schools, splash pad, lake, parks, grocery store, YMCA and other shops. "
    0
    Flag

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Apartments for Rent

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Homes for sale near 321 Chicago St

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Off Market Homes Near 321 Chicago St

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321 Chicago St, Milton, WI 53563 is a 3 bedroom, 2 bathroom, 1,620 sqft single-family home built in 1968. This property is not currently available for sale. 321 Chicago St was last sold on Jan 3, 2018 for $179,900. The current Trulia Estimate for 321 Chicago St is $363,000.