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

5520 Sheil Dr
Oregon, WI 53575

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

$507,100

Trulia Estimate

as of Jul 22, 2026

Est. Refi. Payment $3,296/mo*

Refinance Your Home

$507,100

Trulia Estimate

as of Jul 22, 2026

Est. Refi. Payment $3,296/mo*

Refinance Your Home

3 Beds

3 Baths

2,420 sqft

(on 0.79 acres)

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

Property Type

Single-Family Home

Year Built

1979

Lot Size

0.79 acres

Living Area

2,420 sqft

Price/Sqft

$210

Description

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. It is currently off market. The Trulia Estimate is $507,100, with a rent estimate of $2,844/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 History for 5520 Sheil Dr

Date	Price	Event	Source
03/11/2009	$242,500	Sold	N/A
Recording Date 03/11/2009 Contract Date 03/02/2009 County Transfer Tax N/A Total Transfer Tax N/A
01/12/2009	$269,900	Listed For Sale	Agent Provided

12/11/2008	$269,900	ListingRemoved	Agent Provided

06/10/2008	$269,900	Listed For Sale	Agent Provided

Market trends in Oregon

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

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Property Tax and Assessment

Year	2024
Tax	$5,467
Assessment	$432,900

Home facts updated by county records

Comparable Sales for 5520 Sheil Dr

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
5592 Ralph Rd, Oregon, WI	0.28	Single-Family Home	$349,900	08/14/25	3	2	2,114
5533 Windridge Rd, Oregon, WI	0.20	Single-Family Home	$620,000	10/14/25	3	3.5	3,000
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
624 Rinpoche Ln, Oregon, WI	1.19	Single-Family Home	$1,110,000	08/05/25	5	3.5	4,608

Nearby homes

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

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OFF MARKET
Est. $503,700
3 bd
2.5 ba
1,875 sqft
5512 Sheil Dr,
Oregon, WI 53575
OFF MARKET
Est. $596,300
3 bd
3.5 ba
2,800 sqft
5456 Sundrift Ct,
Oregon, WI 53575
OFF MARKET
Est. $389,600
4 bd
1.5 ba
1,382 sqft
5563 Sheil DRIVE,
Oregon, WI 53575
Closed
SOLD
NOV 26, 2025
$450,000
3 bd
2 ba
2,164 sqft
5570 Sheil Dr,
Oregon, WI 53575
SOLD
OCT 14, 2025
$620,000
3 bd
3.5 ba
3,000 sqft
5533 Windridge Rd,
Oregon, WI 53575
SOLD
DEC 16, 2025
$94,000
Lot 23 Ralph Rd,
Oregon, WI 53575
OFF MARKET
Est. $602,300
3 bd
3.5 ba
2,683 sqft
920 S Azure Ct,
Oregon, WI 53575
SOLD
APR 6, 2026
$524,900
3 bd
3 ba
2,388 sqft
5498 Windridge Rd,
Oregon, WI 53575
OFF MARKET
Est. $494,600
3 bd
2.5 ba
2,336 sqft
5462 Windridge Rd,
Oregon, WI 53575
OFF MARKET
Est. $360,600
3 bd
2 ba
2,114 sqft
5592 Ralph Rd,
Oregon, WI 53575
SOLD
MAY 5, 2026
$765,500
4 bd
2 ba
2,776 sqft
5438 Marie Rd,
Oregon, WI 53575
OFF MARKET
Est. $531,800
3 bd
2.5 ba
2,752 sqft
872 Hillcrest Ln,
Oregon, WI 53575

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Additional Cost

Assigned Schools

These are the assigned schools for 5520 Sheil Dr.

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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