744 S Main St, Oregon, WI 53575
SOLD
MAY 1, 2026

$248,600

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 900 sqft

744 S Main St, Oregon, WI 53575

Est. Refi. Payment $1,724/mo*
Refinance Your Home
Currently Off Market - Sold May 1, 2026 for $239,000

Home Value

Trulia Estimate
$249K
Since last month
Decreased$4K (-1.7%)
Since last year
Increased$5K (+1.9%)
Since last sale
Increased$10K (+4.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +75% in the last 10 years
MonthEstimated value
2026
September 2026$249K
August 2026$254K
July 2026$255K
June 2026$262K
May 2026$239K
April 2026$248K
March 2026$246K
February 2026$242K
January 2026$237K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
223 Thomson Ln, Oregon, WI
0.46
Condo
$245,000
09/29/25
2
1
1,276
498 Cledell St #2, Oregon, WI
0.38
Condo
$260,000
08/06/26
2
2
1,142
494 Cledell St #4, Oregon, WI
0.42
Condo
$236,900
09/01/26
2
2
1,142
1014 S Perry Pkwy, Oregon, WI
0.21
Condo
$349,000
05/22/26
3
2.5
1,842
965 Park St #101, Oregon, WI
0.79
Condo
$240,500
08/26/26
2
2
1,060
933 Park St #101, Oregon, WI
0.81
Condo
$228,000
08/06/26
2
2
1,046
941 Park St #101, Oregon, WI
0.81
Condo
$225,000
02/27/26
2
2
1,060
859 Park St #102, Oregon, WI
0.86
Condo
$243,000
05/01/26
2
2
1,007
883 Park St #201, Oregon, WI
0.85
Condo
$225,000
02/10/26
2
2
1,024

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
744 S Main St #1, Oregon, WI 53575
0.00
$239,000
2
1
900
Recently Sold
745 Scott St, Oregon, WI 53575
0.03
$391,400
3
2.5
1,770
Off Market
785 Scott St, Oregon, WI 53575
0.08
$430,100
3
2
1,854
Off Market
760 Scott St, Oregon, WI 53575
0.06
$430,000
3
2.5
1,880
Recently Sold
713 S Main St, Oregon, WI 53575
0.06
$731,700
8
4
4,200
Off Market
707 S Main St, Oregon, WI 53575
0.07
$716,300
8
4
4,200
Off Market
128 Village View Ct, Oregon, WI 53575
0.15
$434,600
3
3
2,454
Off Market
865 Miller Dr, Oregon, WI 53575
0.12
$400,000
3
2
1,800
Recently Sold
890 Clover Ln, Oregon, WI 53575
0.11
$401,900
3
1.5
1,562
Off Market
859 Pleasant Oak Dr, Oregon, WI 53575
0.14
$655,000
4
3.5
2,927
Recently Sold
695 S Main St, Oregon, WI 53575
0.10
$599,200
3
1.5
1,500
Off Market
1121-1123 Union Rd, Oregon, WI 53575
0.14
$525,000
6
3
2,808
Recently Sold

Local Information

  • Map ViewExplore the area around 744 S Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1986
900 sqft
$266/sqft

About this House

Beautifully maintained and updated ranch style 1/2 duplex condo located on quiet street, convenient location. This gem features 2 bedrooms, full bath and open, bright eat-in kitchen with new appliances. Full basement has potential for much additional living space. Large deck overlooks spacious fenced yard with mature trees. Don't miss out on this lovely home!
744 S Main St, Oregon, WI 53575 is a 2 bedroom, 1 bathroom, 900 sqft condo built in 1986. It last sold for $239,000 on May 1, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $248,600, with a rent estimate of $1,569/month.

Home Details for 744 S Main St

Interior Features

Levels, Entrance, & Accessibility
Stories: 1

Property Information

Year Built
Year Built: 1986
Property Type / Style
Property Type: Condo

Price & Status

Price
Price Per Sqft: $266/sqft

Community

Units in Building: 1

Price and Tax history

DateEventPrice
May 1, 2026
Source: N/A
Sold
$239,000
Jan 10, 2022
Source: N/A
Sold
$195,000
Sep 3, 2009
Source: N/A
Sold
$132,900
Jul 11, 2009
Source: Agent Provided
Listed For Sale
$137,900
Mar 31, 2006
Source: N/A
Sold
$134,900

Market trends in Oregon

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$535K
$4.17KMoM
Sale-to-List Price
—
Price per sq ft
$223
$18MoM
Available listings
43
8MoM

Around this home

What Locals Say about Oregon

At least 64 Trulia users voted on each feature.

  • 94 % Say parking is easy

  • 94 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say kids play outside

  • 86 % Say people would walk alone at night

  • 85 % Say yards are well-kept

  • 84 % Say car is needed

  • 80 % Say streets are well-lit

  • 80 % Say there's holiday spirit

  • 77 % Say it's quiet

  • 68 % Say it's walkable to restaurants

  • 68 % Say they plan to stay for at least 5 years

  • 68 % Say neighbors are friendly

  • 58 % Say there's wildlife

  • 48 % Say it's walkable to grocery stores

  • 43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Tanya Hoppe
    "Friendly and family orientated little Town with great school district. Our neighbors are great and watch out for each other. "
    0
    Flag
  • Khockett58
    "Village Oregon Great place to live. Great schools & sport Great food places to eat. Doctor clinics Gad stations Banks. Small town but close to drive in to Madison or Stoughton And other cities "
    0
    Flag
  • Lysagrant
    "15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
    0
    Flag
  • Tjrbackstroker
    "A quick drive up to Madison. The area is very drivable with not too much traffic. It is very easy to get on the highway."
    0
    Flag
  • Kelly J. P.
    "Love it here! Best move to call this home for our family to grow. Super nice community. We love our neighbors and enjoy to small town feel that Oregon has to offer & also super close to Madison for fun nights out!"
    2
    Flag
  • Ken D.
    "Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
    0
    Flag
  • Rachel
    "To always keep an eye on your kids no matter how safe a neighborhood is deemed to be. Oregon is a great place to live!"
    1
    Flag
  • miltydog
    "Wonderful schools and a strong sense of community"
    0
    Flag
  • Donna R. B.
    "Very private rural subdivision....may be a longer drive to madison but for the beautiful lot and privacy a huge bonus"
    0
    Flag
  • Stevie K.
    "If you like your privacy, multi level living, looking out the back you feel as if you are in the woods! Lots of updates and well cared for. Great neighbors, I used to be one but moved out West, so I have personally been inside and it's great! It is located on a private circle with little traffic! It's definitely a must see!"
    0
    Flag
  • Stefan
    "This area of Oregon is excellent. The schools are the best. The neighborhoods around Lincoln Road, County A and Hillcrest are nice, but, drivers have no regard for safety at all. Stay off these roads if you bike or run. Farm families are very nice, too. You will love bringing up children in this area. Oregon is the best community in the Madison area for kids and your families to live."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 744 S Main St

  • What is 744 S Main St estimated to be worth?
    Trulia's estimated value for 744 S Main St in Oregon, WI is $248,600.
  • What is the price history for 744 S Main St?
    744 S Main St in Oregon, WI last sold for $239,000 in May 2026.
  • Is Oregon a buyer's or seller's market?
    Oregon is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Oregon?
    The median sale price in Oregon is $535K. That is down $4.17K from the prior month.

Explore by feature - Pet Friendly

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