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

248 N Main St
Oregon, WI 53575

3 Beds
2 Baths
1,677 sqft

$434,400

Trulia Estimate

as of Jul 31, 2026

Est. Refi. Payment $2,840/mo*

Refinance Your Home

$434,400

Trulia Estimate

as of Jul 31, 2026

Est. Refi. Payment $2,840/mo*

Refinance Your Home

3 Beds

2 Baths

1,677 sqft

Local Information

Map ViewExplore the area around 248 N Main St.
Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1900

Living Area

1,677 sqft

Price/Sqft

$259

Parking

Garage

About this House

Step into timeless charm with this beautifully updated home featuring hardwood floors, 9-ft ceilings, and stunning stained glass windows. Natural light fills the spacious interior, highlighted by a wood-burning fireplace and a large kitchen with two ovens. Enjoy modern updates, including smart switches, updated plumbing, and electric. The insulated garage offers a heated guest space. Recent updates include exterior paint (2024), Speed Queen washer/dryer (2023), furnace & AC (2021), and refreshed bathrooms (2025). Located in a vibrant, walkable neighborhood near coffee shops, restaurants, and more!

248 N Main St, Oregon, WI 53575 is a 3 bedroom, 2 bathroom, 1,677 sqft single-family home built in 1900. It last sold for $423,500 on May 5, 2025 (7% above the $395,000 asking price). It is currently off market. The Trulia Estimate is $434,400, with a rent estimate of $2,285/month.

Home Details for 248 N Main St

Interior Features
Interior Details Basement: PartialNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Dining Room, Kitchen, Living Room
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout Living Area: 1677 Square Feet
Appliances & Utilities Utilities: Cable AvailableAppliances: Washer, Dryer, Water Softener IncludedDryerLaundry: Main LevelWasher
Heating & Cooling Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 1Fireplace: 1 fireplace, Wood BurningHas a Fireplace
Levels, Entrance, & Accessibility Stories: 2Levels: Two

Exterior Features
Exterior Home Features Patio / Porch: DeckFencing: Fenced
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Additional Parking,Detached,Heated Garage,Garage Door Opener
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 1677 Square Feet

Property Information
Year Built Year Built: 1900
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Victorian
Building Construction Materials: Wood Siding
Property Information Not Included in Sale: seller's personal propertyIncluded in Sale: refrigerator, dishwasher, range/oven, microwave, water softenerParcel Number: 050901365322

Price & Status
Price List Price: $395,000
Status Change & Dates Off Market Date: Thu Mar 06 2025

Active Status
MLS Status: Sold

Location
Direction & Address City: Oregon
School Information Elementary School: Netherwood KnollElementary School District: OregonJr High / Middle School: OregonJr High / Middle School District: OregonHigh School: OregonHigh School District: Oregon

Building
Building Area Building Area: 1677 Square Feet

Lot Information
Lot Area: 8712 sqft

Offer
Listing Terms: Arms Length

Miscellaneous
BasementMls Number: 1994425Attribution Contact: info@mattwinz.comAbove Grade Unfinished Area: 1677

Last check for updates: about 17 hours ago

Listed by Matt Winzenried Real Estate Team

Realty Executives Cooper Spransy

Matthew Ecklund

Realty Executives Cooper Spransy

Bought with: Solveig Anne Schroerlucke, Compass Real Estate Wisconsin

Source: SCWMLS, MLS#1994425

Price History for 248 N Main St

Date	Price	Event	Source
05/05/2025	$423,500	Sold	N/A
Recording Date 05/05/2025 County Transfer Tax N/A Total Transfer Tax N/A
03/09/2025	$395,000	Pending	WIREX MLS #1994425

03/06/2025	$395,000	Listed For Sale	WIREX MLS #1994425

11/14/2023	$344,000	Sold	SCWMLS #1963569
Recording Date 11/14/2023 County Transfer Tax N/A Total Transfer Tax N/A
09/27/2023	$365,000	Pending	WIREX MLS #1963569

09/13/2023	$365,000	Listed For Sale	WIREX MLS #1963569

02/01/2016	$226,000	Sold	N/A
Recording Date 02/01/2016 Contract Date 01/29/2016 County Transfer Tax N/A Total Transfer Tax N/A
10/16/2015	$229,900	ListingRemoved	Agent Provided

07/08/2015	$229,900	PriceChange	Agent Provided
Price Change $9,100 (-4%)
04/23/2015	$239,000	PriceChange	Agent Provided
Price Change $4,000 (-2%)
02/17/2015	$243,000	PriceChange	Agent Provided
Price Change $6,900 (-3%)
01/22/2015	$249,900	Listed For Sale	Agent Provided

04/30/2007	$215,000	Sold	N/A
Recording Date 04/30/2007 Contract Date 04/20/2007 County Transfer Tax N/A Total Transfer Tax N/A
09/14/2005	$199,900	Sold	N/A
Recording Date 09/14/2005 Contract Date 09/09/2005 County Transfer Tax N/A Total Transfer Tax $600

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	$5,473
Assessment	$363,600

Home facts updated by county records

Comparable Sales for 248 N Main St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
247 Orchard Dr, Oregon, WI	0.31	Single-Family Home	$374,000	07/10/26	3	1.5	1,518
437 N Main St, Oregon, WI	0.25	Single-Family Home	$406,000	11/13/25	3	2	1,218
1017 Autumn Blaze Ct, Oregon, WI	0.30	Single-Family Home	$433,900	08/11/25	3	2.5	1,909
345 Veldor St, Oregon, WI	0.41	Single-Family Home	$440,000	06/15/26	3	2	1,932
404 N Main St, Oregon, WI	0.20	Single-Family Home	$411,000	08/04/25	4	2.5	1,960
403 E Lincoln St, Oregon, WI	0.42	Single-Family Home	$400,000	08/04/25	3	1.5	1,568
192 State St, Oregon, WI	0.46	Single-Family Home	$395,000	12/01/25	3	3	1,918
613 N Main St, Oregon, WI	0.42	Single-Family Home	$407,000	07/01/26	2	2	1,527

Nearby homes

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

Skip to last item

OFF MARKET
Est. $661,400
4 bd
2.5 ba
3,100 sqft
233 N Main St,
Oregon, WI 53575
OFF MARKET
Est. $344,500
4 bd
1.5 ba
1,673 sqft
120 Johnson St,
Oregon, WI 53575
SOLD
NOV 12, 2025
$180,000
3 bd
1 ba
1,209 sqft
163 Johnson St,
Oregon, WI 53575
OFF MARKET
Est. $365,700
3 bd
1 ba
1,165 sqft
126 W Lincoln 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. $380,800
3 bd
1 ba
1,746 sqft
223 Jefferson St,
Oregon, WI 53575
OFF MARKET
Est. $295,500
3 bd
1 ba
992 sqft
155 E Lincoln St,
Oregon, WI 53575
OFF MARKET
Est. $461,400
6 bd
2 ba
2,080 sqft
255-259 Park St,
Oregon, WI 53575
FOR SALE
348 ACRES
$799,000
7 bd
4 ba
4,560 sqft
270 Brook St,
Oregon, WI 53575
OFF MARKET
Est. $445,100
3 bd
2 ba
1,664 sqft
259 Jefferson St,
Oregon, WI 53575
SOLD
NOV 13, 2025
$406,000
3 bd
2 ba
1,218 sqft
437 N Main St,
Oregon, WI 53575

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 248 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. "
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