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 5520 Sheil Dr estimated to be worth?

Trulia's estimated value for 5520 Sheil Dr in Oregon, WI is $480,900 .

What is the price history for 5520 Sheil Dr?

5520 Sheil Dr in Oregon, WI last sold for $242,500 in March 2009.

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 5520 Sheil Dr?

The lot at 5520 Sheil Dr in Oregon, WI is about 0.79 acres (34,412 sq ft).

OFF MARKET

$480,900

Trulia Estimate

3 Beds
3 Baths
2,420 sqft (on 0.79 acres)

5520 Sheil Dr, Oregon, WI 53575

Est. Refi. Payment $3,264/mo*

Refinance Your Home

Currently Off Market - Sold Mar 11, 2009 for $242,500

Home Value

Trulia Estimate

$481K

Since last month

$3K (-0.7%)

Since last year

$5K (+1%)

Since last sale

$240K (+98.9%)

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 +68% in the last 10 years

Month	Estimated value
2026
September 2026	$482K
August 2026	$486K
July 2026	$498K
June 2026	$513K
May 2026	$514K
April 2026	$502K
March 2026	$491K
February 2026	$477K
January 2026	$461K
2025
December 2025	$468K
November 2025	$468K
October 2025	$468K
September 2025	$478K
August 2025	$476K
July 2025	$490K
June 2025	$485K
May 2025	$488K
April 2025	$483K
March 2025	$477K
February 2025	$461K
January 2025	$449K
2024
December 2024	$453K
November 2024	$457K
October 2024	$457K
September 2024	$460K
August 2024	$471K
July 2024	$472K
June 2024	$475K
May 2024	$475K
April 2024	$472K
March 2024	$468K
February 2024	$452K
January 2024	$434K
2023
December 2023	$430K
November 2023	$434K
October 2023	$440K
September 2023	$439K
August 2023	$444K
July 2023	$443K
June 2023	$444K
May 2023	$453K
April 2023	$441K
March 2023	$428K
February 2023	$416K
January 2023	$412K
2022
December 2022	$411K
November 2022	$416K
October 2022	$421K
September 2022	$424K
August 2022	$429K
July 2022	$442K
June 2022	$448K
May 2022	$445K
April 2022	$438K
March 2022	$427K
February 2022	$400K
January 2022	$392K
2021
December 2021	$386K
November 2021	$384K
October 2021	$383K
September 2021	$384K
August 2021	$386K
July 2021	$380K
June 2021	$390K
May 2021	$411K
April 2021	$391K
March 2021	$373K
February 2021	$364K
January 2021	$362K
2020
December 2020	$352K
November 2020	$349K
October 2020	$325K
September 2020	$323K
August 2020	$338K
July 2020	$338K
June 2020	$335K
May 2020	$326K
April 2020	$323K
March 2020	$326K
February 2020	$323K
January 2020	$322K
2019
December 2019	$322K
November 2019	$322K
October 2019	$322K
September 2019	$322K
August 2019	$319K
July 2019	$321K
June 2019	$319K
May 2019	$320K
April 2019	$311K
March 2019	$313K
February 2019	$310K
January 2019	$309K
2018
December 2018	$300K
November 2018	$299K
October 2018	$302K
September 2018	$308K
August 2018	$304K
July 2018	$297K
June 2018	$307K
May 2018	$295K
April 2018	$289K
March 2018	$303K
February 2018	$304K
January 2018	$292K
2017
December 2017	$289K
November 2017	$284K
October 2017	$285K
September 2017	$288K
August 2017	$295K
July 2017	$292K
June 2017	$293K
May 2017	$298K
April 2017	$298K
March 2017	$291K
February 2017	$283K
January 2017	$266K
2016
December 2016	$271K
November 2016	$290K
October 2016	$288K
September 2016	$287K

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
5498 Windridge Rd, Oregon, WI	0.25	Single-Family Home	$524,900	04/06/26	3	3	2,388
5570 Sheil Dr, Oregon, WI	0.19	Single-Family Home	$450,000	11/26/25	3	2	2,164
5533 Windridge Rd, Oregon, WI	0.20	Single-Family Home	$620,000	10/14/25	3	3.5	3,000
1055 Glenway Rd, Oregon, WI	0.68	Single-Family Home	$465,000	08/21/26	4	2	1,714
5438 Marie Rd, Oregon, WI	0.38	Single-Family Home	$765,500	05/05/26	4	2	2,776
5556 County Road A, Brooklyn, WI	0.83	Single-Family Home	$522,800	06/15/26	4	2.5	2,288
655 Cypress Way, Oregon, WI	1.39	Single-Family Home	$199,900	05/12/26	4	3.5	3,340
659 Rinpoche Ln, Oregon, WI	1.07	Single-Family Home	$1,275,000	05/29/26	4	4	4,087
656 Rinpoche Ln, Oregon, WI	1.10	Single-Family Home	$850,000	06/29/26	4	3.5	3,745
667 Cypress Way, Oregon, WI	1.43	Single-Family Home	$636,000	10/27/25	3	2	1,817

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
5512 Sheil Dr, Oregon, WI 53575	0.02	$493,500	3	2.5	1,875	Off Market
5456 Sundrift Ct, Oregon, WI 53575	0.17	$583,900	3	3.5	2,800	Off Market
5563 Sheil DRIVE, Oregon, WI 53575	0.18	$380,100	4	1.5	1,382	Off Market
5570 Sheil Dr, Oregon, WI 53575	0.19	$450,000	3	2	2,164	Recently Sold
5533 Windridge Rd, Oregon, WI 53575	0.20	$643,900	3	3.5	3,000	Off Market
Lot 23 Ralph Rd, Oregon, WI 53575	0.22	$94,000	-	-	-	Recently Sold
920 S Azure Ct, Oregon, WI 53575	0.23	$580,400	3	3.5	2,683	Off Market
5498 Windridge Rd, Oregon, WI 53575	0.25	$524,900	3	3	2,388	Recently Sold
5462 Windridge Rd, Oregon, WI 53575	0.29	$481,700	3	2.5	2,336	Off Market
5592 Ralph Rd, Oregon, WI 53575	0.28	$360,700	3	2	2,114	Off Market
5438 Marie Rd, Oregon, WI 53575	0.38	$765,500	4	2	2,776	Recently Sold
872 Hillcrest Ln, Oregon, WI 53575	0.36	$515,500	3	2.5	2,752	Off Market

Local Information

Map ViewExplore the area around 5520 Sheil Dr.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1979

0.79 acre lot

2,420 sqft

$199/sqft

About this House

A fantastic value in a great neighborhood! That's what you'll say after viewing this immaculate ranch home in the quaint neighborhood of Hillcrest Heights. Situated on a manicured 3/4 acre lot wtih hundreds of perennials, an abundance of fruit trees and raspberries galore, you'll find the tranquility you've been looking for. Recent updates include remodeled kitchen w/granite and new appliances, windows, roof, siding & hot tub room. There's even a new 14X30 detached gar. for toys or possible shop.

5520 Sheil Dr, Oregon, WI 53575 is a 3 bedroom, 3 bathroom, 2,420 sqft single-family home built in 1979. It last sold for $242,500 on Mar 11, 2009. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $480,900, with a rent estimate of $3,175/month.

Home Details for 5520 Sheil Dr

Property Information
Year Built Year Built: 1979
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 0.79 acres

Price and Tax history

Date	Event	Price
Mar 11, 2009 Source: N/A	Sold	$242,500
Jan 12, 2009 Source: Agent Provided	Listed For Sale	$269,900
Dec 11, 2008 Source: Agent Provided	ListingRemoved	$269,900
Jun 10, 2008 Source: Agent Provided	Listed For Sale	$269,900

Year	Property tax	Tax assessment
2024	$5,467	$432,900

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

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
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
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 5520 Sheil Dr

What is 5520 Sheil Dr estimated to be worth?
Trulia's estimated value for 5520 Sheil Dr in Oregon, WI is $480,900.
What is the price history for 5520 Sheil Dr?
5520 Sheil Dr in Oregon, WI last sold for $242,500 in March 2009.
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 5520 Sheil Dr?
The lot at 5520 Sheil Dr in Oregon, WI is about 0.79 acres (34,412 sq ft).