Is parking easy in Oregon, WI?

As of early 2026, 94% of users say parking is easy

Is Oregon, WI dog-friendly?

As of early 2026, 94% of users say it's dog friendly

Does Oregon, WI have sidewalks?

As of early 2026, 92% of users say there are sidewalks

Do kids play outside in Oregon, WI?

As of early 2026, 87% of users say kids play outside

Would people walk alone at night in Oregon, WI?

As of early 2026, 86% of users say people would walk alone at night

Are yards well-kept in Oregon, WI?

As of early 2026, 85% of users say yards are well-kept

Is a car needed in Oregon, WI?

As of early 2026, 84% of users say car is needed

Are the streets well-lit in Oregon, WI?

As of early 2026, 80% of users say streets are well-lit

Does Oregon, WI show holiday spirit?

As of early 2026, 80% of users say there's holiday spirit

As of early 2026, 77% of users say it's quiet

Is Oregon, WI walkable to restaurants?

As of early 2026, 68% of users say it's walkable to restaurants

Do residents of Oregon, WI plan to stay at least 5 years?

As of early 2026, 68% of users say they plan to stay for at least 5 years

Are neighbors friendly in Oregon, WI?

As of early 2026, 68% of users say neighbors are friendly

Is there wildlife in Oregon, WI?

As of early 2026, 58% of users say there's wildlife

Is Oregon, WI walkable to grocery stores?

As of early 2026, 48% of users say it's walkable to grocery stores

Are there community events in Oregon, WI?

As of early 2026, 43% of users say there are community events

SOLD

MAY 1, 2026

744 S Main St
Oregon, WI 53575

2 Beds
1 Bath
900 sqft

$239,000

Last Sold: May 1, 2026

$266/sqft

Est. Refi. Payment $1,594/mo*

Refinance Your Home

$239,000

Last Sold: May 1, 2026

$266/sqft

Est. Refi. Payment $1,594/mo*

Refinance Your Home

2 Beds

1 Bath

900 sqft

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

Property Type

Condo

Year Built

1986

Living Area

900 sqft

Price/Sqft

$266/sqft

Description

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. It is currently off market. The Trulia Estimate is $256,300, with a rent estimate of $1,506/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 History for 744 S Main St

Date	Price	Event	Source
05/01/2026	$239,000	Sold	N/A
Recording Date 05/01/2026 Contract Date 04/29/2026 County Transfer Tax N/A Total Transfer Tax N/A
01/10/2022	$195,000	Sold	N/A
Recording Date 01/10/2022 County Transfer Tax N/A Total Transfer Tax N/A
09/03/2009	$132,900	Sold	N/A
Recording Date 09/03/2009 Contract Date 08/28/2009 County Transfer Tax N/A Total Transfer Tax N/A
07/11/2009	$137,900	Listed For Sale	Agent Provided

03/31/2006	$134,900	Sold	N/A
Recording Date 03/31/2006 Contract Date 03/24/2006 County Transfer Tax N/A Total Transfer Tax $405
04/08/2005	$125,000	Sold	N/A
Recording Date 04/08/2005 Contract Date 03/31/2005 County Transfer Tax N/A Total Transfer Tax $375

Market trends in Oregon

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Skip to last item

Results are loading

Skip to first item

Property Tax and Assessment

Year	2024
Tax	$2,991
Assessment	$208,900

Home facts updated by county records

Comparable Sales for 744 S Main St

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
492 Cledell St #1, Oregon, WI	0.42	Condo	$254,700	09/08/25	2	2	1,142
1014 S Perry Pkwy, Oregon, WI	0.21	Condo	$349,000	05/22/26	3	2.5	1,842
941 Park St #101, Oregon, WI	0.81	Condo	$225,000	02/27/26	2	2	1,060
917 Park St #202, Oregon, WI	0.83	Condo	$225,000	08/04/25	2	2	1,046
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
909 Park St #101, Oregon, WI	0.85	Condo	$231,000	02/05/26	2	2	1,060
859 Park St #101, Oregon, WI	0.86	Condo	$230,000	05/12/26	2	2	1,055

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

SOLD
APR 29, 2026
$239,000
2 bd
1 ba
900 sqft
744 S Main St #1,
Oregon, WI 53575
OFF MARKET
Est. $400,000
3 bd
2.5 ba
1,770 sqft
745 Scott St,
Oregon, WI 53575
OFF MARKET
Est. $435,100
3 bd
2 ba
1,854 sqft
785 Scott St,
Oregon, WI 53575
OFF MARKET
Est. $737,100
8 bd
4 ba
4,200 sqft
713 S Main St,
Oregon, WI 53575
OFF MARKET
Est. $717,700
8 bd
4 ba
4,200 sqft
707 S Main St,
Oregon, WI 53575
OFF MARKET
Est. $432,400
3 bd
3 ba
2,454 sqft
128 Village View Ct,
Oregon, WI 53575
SOLD
JUN 18, 2026
$400,000
3 bd
2 ba
1,800 sqft
865 Miller Dr,
Oregon, WI 53575
OFF MARKET
Est. $411,300
3 bd
1.5 ba
1,562 sqft
890 Clover Ln,
Oregon, WI 53575
SOLD
DEC 17, 2025
$655,000
4 bd
3.5 ba
2,927 sqft
859 Pleasant Oak Dr,
Oregon, WI 53575
OFF MARKET
Est. $571,500
3 bd
1.5 ba
1,500 sqft
695 S Main St,
Oregon, WI 53575
SOLD
MAR 16, 2026
$525,000
6 bd
3 ba
2,808 sqft
1121-1123 Union Rd,
Oregon, WI 53575
OFF MARKET
Est. $237,100
2 bd
1 ba
1,254 sqft
665 S Main St #4,
Oregon, WI 53575

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 744 S Main 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 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
Resident
2y ago
"Friendly and family orientated little Town with great school district. Our neighbors are great and watch out for each other. "
0
Flag
Khockett58
Resident
5y ago
"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
Resident
5y ago
"15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
0
Flag
Tjrbackstroker
Visitor
6y ago
"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.
Resident
6y ago
"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.
Resident
7y ago
"Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
0
Flag
Rachel
Resident
7y ago
"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
12y ago
"Wonderful schools and a strong sense of community"
0
Flag
Donna R. B.
12y ago
"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.
12y ago
"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
13y ago
"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