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

OFF MARKET

442 N Main St
Oregon, WI 53575

3 Beds
2 Baths
1,475 sqft (on 0.56 acres)

$426,900

Trulia Estimate

as of Jul 19, 2026

$426,900

Trulia Estimate

as of Jul 19, 2026

3 Beds

2 Baths

1,475 sqft

(on 0.56 acres)

Local Information

Map ViewExplore the area around 442 N Main St.
Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This beautifully built & maintained Craftsmen style home with its new kitchen, formal dining & superb 3-season porch is set on a lovely half acre fenced yard right in the center of Oregon. Vintage features include a great master bedroom suite, pillared room divider, antique hardware, stenciling & lots of built-ins, some with leaded glass doors. The heated 3-car garage has additional workshop space, high doors & attic storage. All the appliances are included. Area rugs in dining & living rms are negotiable.

442 N Main St, Oregon, WI 53575 is a 3 bedroom, 2 bathroom, 1,475 sqft single-family home built in 1920. It last sold for $178,000 on Sep 7, 2012. It is currently off market. The Trulia Estimate is $426,900, with a rent estimate of $2,252/month.

Home Highlights

Parking

No Info

Outdoor

No Info

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 442 N Main St

Interior Features
Levels, Entrance, & Accessibility Stories: 1
Interior Details Types of Rooms: Family Room

Property Information
Year Built Year Built: 1920
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 0.56 acres

Price History for 442 N Main St

Date	Price	Event	Source
09/07/2012	$178,000	Sold	N/A
Recording Date 09/07/2012 Contract Date 09/05/2012 County Transfer Tax N/A Total Transfer Tax N/A
06/16/2012	$175,000	Listed For Sale	Agent Provided

Market trends in Oregon

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

2MoM

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Property Tax and Assessment

Year	2024
Tax	$5,147
Assessment	$343,300

Home facts updated by county records

Comparable Sales for 442 N Main St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
437 N Main St, Oregon, WI	0.05	Single-Family Home	$406,000	11/13/25	3	2	1,218
247 Orchard Dr, Oregon, WI	0.13	Single-Family Home	$374,000	07/09/26	3	1.5	1,518
326 Prairie View Ct, Oregon, WI	0.28	Single-Family Home	$225,000	11/12/25	4	2	1,440
277 N Main St, Oregon, WI	0.23	Single-Family Home	$329,300	04/30/26	3	2	1,555
403 E Lincoln St, Oregon, WI	0.36	Single-Family Home	$400,000	08/04/25	3	1.5	1,568
613 N Main St, Oregon, WI	0.17	Single-Family Home	$407,000	07/01/26	2	2	1,527
404 N Main St, Oregon, WI	0.05	Single-Family Home	$411,000	08/04/25	4	2.5	1,960
448 E Lincoln St, Oregon, WI	0.43	Single-Family Home	$397,000	08/13/25	3	2	1,440
163 Johnson St, Oregon, WI	0.20	Single-Family Home	$180,000	11/12/25	3	1	1,209
105 Dale Dr, Oregon, WI	0.50	Single-Family Home	$415,000	08/26/25	3	2	1,590

Nearby homes

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

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OFF MARKET
Est. $431,100
5 bd
3 ba
2,324 sqft
500 N Main St,
Oregon, WI 53575
SOLD
NOV 13, 2025
$406,000
3 bd
2 ba
1,218 sqft
437 N Main St,
Oregon, WI 53575
OFF MARKET
Est. $423,600
4 bd
2.5 ba
1,960 sqft
404 N Main St,
Oregon, WI 53575
OFF MARKET
Est. $329,200
3 bd
2 ba
980 sqft
115 Monroe St,
Oregon, WI 53575
OFF MARKET
Est. $293,900
3 bd
1 ba
992 sqft
155 E Lincoln St,
Oregon, WI 53575
COMING SOON
0.28 ACRES
$435,000
4 bd
2 ba
2,410 sqft
145 Dewey St,
Oregon, WI 53575
OFF MARKET
Est. $348,200
2 bd
1.5 ba
1,032 sqft
546 N Main St,
Oregon, WI 53575
OFF MARKET
Est. $369,400
3 bd
1 ba
1,165 sqft
126 W Lincoln St,
Oregon, WI 53575
OFF MARKET
Est. $543,700
5 bd
3 ba
2,952 sqft
561 N Main St,
Oregon, WI 53575
OFF MARKET
Est. $476,100
3 bd
2 ba
2,017 sqft
156 Monroe St,
Oregon, WI 53575
SOLD
JUL 9, 2026
$374,000
3 bd
1.5 ba
1,518 sqft
247 Orchard Dr,
Oregon, WI 53575
SOLD
JUL 1, 2026
$407,000
2 bd
2 ba
1,527 sqft
613 N Main St,
Oregon, WI 53575

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Additional Cost

Assigned Schools

These are the assigned schools for 442 N 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. "
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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 "
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Lysagrant
Resident
5y ago
"15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
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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."
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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!"
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Ken D.
Resident
7y ago
"Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
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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
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miltydog
12y ago
"Wonderful schools and a strong sense of community"
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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"
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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!"
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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."
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