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 4444 Oak Hill Rd estimated to be worth?

Trulia's estimated value for 4444 Oak Hill Rd in Oregon, WI is $1,144,100 .

What is the price history for 4444 Oak Hill Rd?

4444 Oak Hill Rd in Oregon, WI last sold for $592,000 in April 2012.

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.

How big is the lot at 4444 Oak Hill Rd?

The lot at 4444 Oak Hill Rd in Oregon, WI is about 4.3 acres .

OFF MARKET

$1,144,100

Trulia Estimate

4 Beds
4 Baths
4,500 sqft (on 4.34 acres)

4444 Oak Hill Rd, Oregon, WI 53575

Est. Refi. Payment $7,588/mo*

Refinance Your Home

Currently Off Market - Sold Apr 9, 2012 for $592,000

Home Value

Trulia Estimate

$1.14M

Since last month

$3K (-0.2%)

Since last year

$51K (+4.7%)

Since last sale

$552K (+93.3%)

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 +85% in the last 10 years

Month	Estimated value
2026
September 2026	$1.14M
August 2026	$1.15M
July 2026	$1.15M
June 2026	$1.17M
May 2026	$1.17M
April 2026	$1.15M
March 2026	$1.14M
February 2026	$1.1M
January 2026	$1.07M
2025
December 2025	$1.09M
November 2025	$1.07M
October 2025	$1.07M
September 2025	$1.09M
August 2025	$1.09M
July 2025	$1.09M
June 2025	$1.09M
May 2025	$1.11M
April 2025	$1.1M
March 2025	$1.09M
February 2025	$1.06M
January 2025	$1.04M
2024
December 2024	$1.04M
November 2024	$1.05M
October 2024	$1.06M
September 2024	$1.06M
August 2024	$1.08M
July 2024	$1.08M
June 2024	$1.07M
May 2024	$1.08M
April 2024	$1.07M
March 2024	$1.06M
February 2024	$1.03M
January 2024	$999K
2023
December 2023	$1.01M
November 2023	$991K
October 2023	$1.03M
September 2023	$1.02M
August 2023	$1.02M
July 2023	$1.05M
June 2023	$1.04M
May 2023	$1.07M
April 2023	$1.05M
March 2023	$1.02M
February 2023	$995K
January 2023	$985K
2022
December 2022	$981K
November 2022	$996K
October 2022	$1M
September 2022	$1.01M
August 2022	$1.01M
July 2022	$1.02M
June 2022	$1.04M
May 2022	$1.04M
April 2022	$1.02M
March 2022	$1.01M
February 2022	$974K
January 2022	$953K
2021
December 2021	$930K
November 2021	$923K
October 2021	$920K
September 2021	$918K
August 2021	$927K
July 2021	$955K
June 2021	$955K
May 2021	$966K
April 2021	$935K
March 2021	$892K
February 2021	$877K
January 2021	$867K
2020
December 2020	$838K
November 2020	$849K
October 2020	$850K
September 2020	$845K
August 2020	$827K
July 2020	$815K
June 2020	$812K
May 2020	$820K
April 2020	$831K
March 2020	$827K
February 2020	$839K
January 2020	$830K
2019
December 2019	$840K
November 2019	$841K
October 2019	$858K
September 2019	$819K
August 2019	$837K
July 2019	$827K
June 2019	$828K
May 2019	$832K
April 2019	$824K
March 2019	$834K
February 2019	$836K
January 2019	$775K
2018
December 2018	$762K
November 2018	$770K
October 2018	$766K
September 2018	$754K
August 2018	$759K
July 2018	$766K
June 2018	$760K
May 2018	$768K
April 2018	$759K
March 2018	$765K
February 2018	$762K
January 2018	$750K
2017
December 2017	$749K
November 2017	$598K
October 2017	$603K
September 2017	$589K
August 2017	$600K
July 2017	$591K
June 2017	$610K
May 2017	$622K
April 2017	$627K
March 2017	$617K
February 2017	$609K
January 2017	$610K
2016
December 2016	$609K
November 2016	$610K
October 2016	$613K
September 2016	$619K

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
1089 US Highway 14, Oregon, WI	0.66	Single-Family Home	$1,100,000	10/23/25	4	3.5	4,352
581 Concord Dr, Oregon, WI	1.21	Single-Family Home	$850,000	12/17/25	5	3.5	4,059
491 Concord Dr, Oregon, WI	1.29	Single-Family Home	$730,000	06/10/26	4	3	4,284
4795 Eisenhower St, Oregon, WI	1.36	Single-Family Home	$730,000	10/31/25	5	3.5	3,650
1349 Sunrise Rd, Oregon, WI	1.36	Single-Family Home	$1,800,000	10/10/25	4	4.5	5,803
901 County Road Mm, Oregon, WI	1.58	Single-Family Home	$832,000	04/22/26	3	3	3,068
938 Johnson Ave, Oregon, WI	1.19	Single-Family Home	$530,000	03/26/26	3	2.5	1,932
663 Oak Ridge Rd, Oregon, WI	1.93	Single-Family Home	$865,000	06/30/26	4	3.5	3,725
994 Autumn Blaze Way, Oregon, WI	1.37	Single-Family Home	$617,000	10/17/25	4	3	2,722
445 Foxfield Ct, Oregon, WI	1.33	Single-Family Home	$759,900	06/15/26	4	2.5	3,006

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
991 Highway 14, Oregon, WI 53575	0.34	$335,000	2	1	864	For Sale
4323 Oak Hill Rd, Oregon, WI 53575	0.46	-	-	-	-	Off Market
4287 Oak Hill Rd, Oregon, WI 53575	0.68	-	2	1.5	1,770	Off Market
1089 US Highway 14, Oregon, WI 53575	0.66	$1,142,900	4	3.5	4,352	Off Market
1185 Highway 14, Oregon, WI 53575	0.68	-	-	-	-	Off Market
4488 Hill Rd, Oregon, WI 53575	0.79	$1,949,900	5	4	5,764	Off Market
948 Mesa Dr, Oregon, WI 53575	0.85	$440,000	3	2	2,000	Off Market
1157 Sunrise Rd, Oregon, WI 53575	0.88	$526,500	3	1	1,600	Off Market
929 Mesa Dr, Oregon, WI 53575	0.92	$349,500	3	1	1,464	Off Market
Sunrise Rd, Oregon, WI 53575	0.97	-	-	-	-	Off Market
4217 County Road A, Oregon, WI 53575	1.04	$420,700	3	1	1,628	Off Market
4718 Hoover St, Oregon, WI 53575	1.09	$419,600	3	1	1,528	Off Market

Local Information

Map ViewExplore the area around 4444 Oak Hill Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 2002

4.34 acre lot

4,500 sqft

$254/sqft

About this House

Executive ranch home on 4+ acres w/Oregon schools. Custom Dream Kitchen has granite counters, cherry cabinets & walk-in pantry. Vaulted great room w/open living/dining room & gas fireplace. Main level master suite w/private full bath, gas fireplace, jetted tub & dbl vanities. Main level office & sun room w/wood burning fireplace. Finished walkout LL has in-floor radiant heat, game room, family room w/wet bar and 2 bdrms. Also birch floors, 6-panel doors, central vac and intercom. Too many features to list!

4444 Oak Hill Rd, Oregon, WI 53575 is a 4 bedroom, 4 bathroom, 4,500 sqft single-family home built in 2002. It last sold for $592,000 on Apr 9, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,144,100, with a rent estimate of $4,371/month.

Home Details for 4444 Oak Hill Rd

Property Information
Year Built Year Built: 2002
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 4.34 acres

Price and Tax history

Date	Event	Price
Apr 9, 2012 Source: N/A	Sold	$592,000
Aug 19, 2011 Source: Agent Provided	Listed For Sale	$629,900

Year	Property tax	Tax assessment
2024	$11,366	$863,500

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

Brooklyn Elementary School
PK-4
Public
363 Students
Oregon School District
9/10
GreatSchools Rating
Parent Rating Average
Love this school and the people that work there. A+
Other Review
6y ago
2 Reviews

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
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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."
0
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Kelly J. P.
Resident
7y 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
8y 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 4444 Oak Hill Rd

What is 4444 Oak Hill Rd estimated to be worth?
Trulia's estimated value for 4444 Oak Hill Rd in Oregon, WI is $1,144,100.
What is the price history for 4444 Oak Hill Rd?
4444 Oak Hill Rd in Oregon, WI last sold for $592,000 in April 2012.
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.
How big is the lot at 4444 Oak Hill Rd?
The lot at 4444 Oak Hill Rd in Oregon, WI is about 4.3 acres.