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

What is 446 Oakwood Dr estimated to be worth?

Trulia's estimated value for 446 Oakwood Dr in Oregon, WI is $529,100 .

What is the price history for 446 Oakwood Dr?

446 Oakwood Dr in Oregon, WI last sold for $385,000 in April 2021.

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.

Does 446 Oakwood Dr have air conditioning?

Yes, 446 Oakwood Dr in Oregon, WI has air conditioning.

Does 446 Oakwood Dr have laundry facilities?

Yes, 446 Oakwood Dr in Oregon, WI has in-unit laundry.

OFF MARKET

$529,100

Trulia Estimate

4 Beds
3.5 Baths
2,940 sqft

446 Oakwood Dr, Oregon, WI 53575

Est. Refi. Payment $3,479/mo*

Refinance Your Home

Currently Off Market - Sold Apr 30, 2021 for $385,000

Home Value

Trulia Estimate

$529K

Since last month

$8K (-1.6%)

Since last year

$7K (+1.4%)

Since last sale

$136K (+35.4%)

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 +66% in the last 10 years

Month	Estimated value
2026
September 2026	$521K
August 2026	$529K
July 2026	$529K
June 2026	$545K
May 2026	$544K
April 2026	$542K
March 2026	$532K
February 2026	$517K
January 2026	$509K
2025
December 2025	$502K
November 2025	$505K
October 2025	$507K
September 2025	$516K
August 2025	$514K
July 2025	$517K
June 2025	$520K
May 2025	$527K
April 2025	$525K
March 2025	$519K
February 2025	$505K
January 2025	$496K
2024
December 2024	$495K
November 2024	$496K
October 2024	$493K
September 2024	$494K
August 2024	$500K
July 2024	$504K
June 2024	$512K
May 2024	$514K
April 2024	$515K
March 2024	$509K
February 2024	$499K
January 2024	$479K
2023
December 2023	$473K
November 2023	$475K
October 2023	$477K
September 2023	$477K
August 2023	$477K
July 2023	$484K
June 2023	$485K
May 2023	$491K
April 2023	$481K
March 2023	$467K
February 2023	$454K
January 2023	$449K
2022
December 2022	$445K
November 2022	$449K
October 2022	$450K
September 2022	$448K
August 2022	$442K
July 2022	$447K
June 2022	$449K
May 2022	$446K
April 2022	$440K
March 2022	$436K
February 2022	$425K
January 2022	$417K
2021
December 2021	$412K
November 2021	$408K
October 2021	$403K
September 2021	$395K
August 2021	$401K
July 2021	$396K
June 2021	$393K
May 2021	$389K
April 2021	$405K
March 2021	$398K
February 2021	$389K
January 2021	$385K
2020
December 2020	$366K
November 2020	$364K
October 2020	$367K
September 2020	$362K
August 2020	$366K
July 2020	$363K
June 2020	$360K
May 2020	$358K
April 2020	$354K
March 2020	$351K
February 2020	$344K
January 2020	$344K
2019
December 2019	$344K
November 2019	$343K
October 2019	$343K
September 2019	$344K
August 2019	$347K
July 2019	$346K
June 2019	$346K
May 2019	$348K
April 2019	$346K
March 2019	$346K
February 2019	$344K
January 2019	$341K
2018
December 2018	$346K
November 2018	$346K
October 2018	$348K
September 2018	$361K
August 2018	$367K
July 2018	$368K
June 2018	$368K
May 2018	$359K
April 2018	$352K
March 2018	$356K
February 2018	$349K
January 2018	$347K
2017
December 2017	$336K
November 2017	$345K
October 2017	$344K
September 2017	$343K
August 2017	$343K
July 2017	$339K
June 2017	$339K
May 2017	$339K
April 2017	$332K
March 2017	$332K
February 2017	$322K
January 2017	$317K
2016
December 2016	$317K
November 2016	$318K
October 2016	$320K
September 2016	$315K

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
435 Ash St, Oregon, WI	0.04	Single-Family Home	$552,000	07/08/26	4	2.5	3,054
451 Oakwood Dr, Oregon, WI	0.04	Single-Family Home	$580,000	07/01/26	4	3	2,652
669 N Woods Edge Dr, Oregon, WI	0.38	Single-Family Home	$427,000	01/02/26	4	3	2,699
924 Brynhill Dr, Oregon, WI	0.07	Single-Family Home	$857,000	03/27/26	4	3.5	3,777
434 S Burr Oak Ave, Oregon, WI	0.33	Single-Family Home	$499,900	06/10/26	4	3	2,438
310 Ash St, Oregon, WI	0.28	Single-Family Home	$400,000	08/21/26	3	2.5	2,149
826 Sumac St, Oregon, WI	0.36	Single-Family Home	$610,000	12/22/25	4	3.5	2,943
963 Brynhill Dr, Oregon, WI	0.13	Single-Family Home	$784,800	11/13/25	5	3.5	3,366
1129 Lincoln Rd, Oregon, WI	0.38	Single-Family Home	$466,000	04/30/26	4	3	2,381
141 Amanda Ct, Oregon, WI	0.20	Single-Family Home	$480,000	02/05/26	4	3	2,132

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
451 Oakwood Dr, Oregon, WI 53575	0.04	$580,000	4	3	2,652	Recently Sold
505 Oakwood Dr, Oregon, WI 53575	0.07	$498,200	3	3	2,348	Off Market
422 Oakwood Dr, Oregon, WI 53575	0.03	$559,900	4	3.5	2,558	For Sale
924 Brynhill Dr, Oregon, WI 53575	0.07	$857,000	4	3.5	3,777	Recently Sold
535 Oakwood Dr, Oregon, WI 53575	0.10	$445,800	3	2	1,603	Off Market
956 Brynhill Dr, Oregon, WI 53575	0.10	$741,800	4	3	3,376	Off Market
435 Ash St, Oregon, WI 53575	0.04	$552,000	4	2.5	3,054	Recently Sold
970 Brynhill Dr, Oregon, WI 53575	0.13	$724,200	4	3.5	3,020	Off Market
963 Brynhill Dr, Oregon, WI 53575	0.13	$778,800	5	3.5	3,366	Off Market
570 Oakwood Dr, Oregon, WI 53575	0.14	$445,700	4	2	1,790	Off Market
395 Oakwood Dr, Oregon, WI 53575	0.09	$815,800	5	3.5	3,929	Off Market
565 Oakwood Dr, Oregon, WI 53575	0.15	$512,500	3	2	1,800	Recently Sold

Local Information

Map ViewExplore the area around 446 Oakwood Dr.
Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1996

2,940 sqft

$180/sqft

Garage

About this House

Location, location, location! Come for the top notch school district and proximity to the excitement of Madison, stay for the idyllic lifestyle that blends small town and city living in a safe, mature neighborhood. This large 4 bed, 3.5 bath home is situated on a quiet street with little traffic, great walkability, and easy access to conservation trails bordering the exclusivity of Bergamont without the exclusive price. The home has a new roof (2020), new W/D (2020), updated SS appliances, updated owners suite with fireplace and new paint throughout the main level. The LL has a spa-like bathroom, huge rec room, and 4th bedroom that is perfect for an office if working from home. Home features vaulted ceilings, two walk-outs, and a formal dining perfect for entertaining! Choice HW incl.

446 Oakwood Dr, Oregon, WI 53575 is a 4 bedroom, 4 bathroom, 2,940 sqft single-family home built in 1996. It last sold for $385,000 on Apr 30, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $529,100, with a rent estimate of $3,670/month.

Home Details for 446 Oakwood Dr

Interior Features
Interior Details BasementTypes of Rooms: Walk In Closet, Dining Room
Heating & Cooling Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features
Exterior Home Features Roof: OtherExterior: Vinyl
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached

Property Information
Year Built Year Built: 1996
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial

Community
Units in Building: 1

Lot Information
Lot Area: 10018 sqft

Price and Tax history

Date	Event	Price
May 4, 2021 Source: RE/MAX International	ListingRemoved
May 3, 2021 Source: RE/MAX International #1903270	Pending	$389,900
Apr 30, 2021 Source: SCWMLS #1903270	Sold	$385,000
Mar 24, 2021 Source: SCWMLS #1903270	PriceChange	$389,900 Price decreased by 3%
Mar 11, 2021 Source: SCWMLS #1903270	Listed For Sale	$399,900
Sep 6, 2013 Source: N/A	Sold	$275,000
Jul 19, 2013 Source: Agent Provided	Listed For Sale	$275,000
Jul 18, 2007 Source: N/A	Sold	$268,000

Year	Property tax	Tax assessment
2024	$6,954	$455,900

Additional Cost

Market trends in Oregon

Last updated August 2026

Avg. sale price

$535K

$4.17KMoM

Sale-to-List Price

—

Price per sq ft

$223

$18MoM

Available listings

8MoM

Around this home

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 "
0
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Lysagrant
Resident
6y ago
"15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
0
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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!"
2
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Ken D.
Resident
7y ago
"Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
0
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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"
0
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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"
0
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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
14y 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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LGBTQ Local Legal Protections

Frequently asked questions about 446 Oakwood Dr

What is 446 Oakwood Dr estimated to be worth?
Trulia's estimated value for 446 Oakwood Dr in Oregon, WI is $529,100.
What is the price history for 446 Oakwood Dr?
446 Oakwood Dr in Oregon, WI last sold for $385,000 in April 2021.
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.
Does 446 Oakwood Dr have air conditioning?
Yes, 446 Oakwood Dr in Oregon, WI has air conditioning.
Does 446 Oakwood Dr have laundry facilities?
Yes, 446 Oakwood Dr in Oregon, WI has in-unit laundry.