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

532 Cherry Wood Dr
Oregon, WI 53575

4 Beds
2 Baths
1,740 sqft

$443,000

Trulia Estimate

as of Aug 6, 2026

Est. Refi. Payment $2,882/mo*

Refinance Your Home

$443,000

Trulia Estimate

as of Aug 6, 2026

Est. Refi. Payment $2,882/mo*

Refinance Your Home

4 Beds

2 Baths

1,740 sqft

Local Information

Map ViewExplore the area around 532 Cherry Wood Dr.
Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1992

Living Area

1,740 sqft

Price/Sqft

$255

About this House

This single-family home is located at 532 Cherry Wood Dr, Oregon, WI. 532 Cherry Wood Dr is in Oregon, WI and in ZIP code 53575. This property has 4 bedrooms, 2 bathrooms and approximately 1,740 sqft of floor space. This property has a lot size of 10454 sqft and was built in 1992.

532 Cherry Wood Dr, Oregon, WI 53575 is a 4 bedroom, 2 bathroom, 1,740 sqft single-family home built in 1992. It last sold for $352,000 on Sep 28, 2022. It is currently off market. The Trulia Estimate is $443,000, with a rent estimate of $2,799/month.

Home Details for 532 Cherry Wood Dr

Interior Features
Heating & Cooling Heating: Forced AirHeating Fuel: Forced Air
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace
Levels, Entrance, & Accessibility Floors: Hardwood

Property Information
Year Built Year Built: 1992
Property Type / Style Property Type: Single Family Home

Exterior Features
Exterior Home Features Exterior: Vinyl

Community
Units in Building: 1

Lot Information
Lot Area: 10454 sqft

Price History for 532 Cherry Wood Dr

Date	Price	Event	Source
09/28/2022	$352,000	Sold	N/A
Recording Date 09/28/2022 County Transfer Tax N/A Total Transfer Tax N/A
08/30/2022	$349,900	Pending	WIREX MLS #1940994

08/24/2022	$349,900	Listed For Sale	WIREX MLS #1940994

07/07/2020	$294,000	Sold	N/A
Recording Date 07/07/2020 Contract Date 06/29/2020 County Transfer Tax N/A Total Transfer Tax N/A
08/01/2017	$292,900	Sold	N/A
Recording Date 08/01/2017 Contract Date 07/31/2017 County Transfer Tax N/A Total Transfer Tax N/A
07/20/2017	$294,900	Pending	Agent Provided

06/14/2017	$294,900	PriceChange	Agent Provided
Price Change $4,100 (-1%)
05/10/2017	$299,000	Listed For Sale	Agent Provided

12/15/2014	$135,000	Sold	N/A
Recording Date 12/15/2014 Contract Date 12/10/2014 County Transfer Tax N/A Total Transfer Tax N/A

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	$5,690
Assessment	$377,100

Home facts updated by county records

Comparable Sales for 532 Cherry Wood Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
290 Ash St, Oregon, WI	0.25	Single-Family Home	$385,000	09/08/25	3	2	1,820
411 Butternut Dr, Oregon, WI	0.09	Single-Family Home	$480,000	03/04/26	3	2	2,130
434 S Burr Oak Ave, Oregon, WI	0.10	Single-Family Home	$499,900	06/10/26	4	3	2,438
168 Hickory Ct, Oregon, WI	0.20	Single-Family Home	$420,000	12/08/25	3	2	2,300
141 Amanda Ct, Oregon, WI	0.11	Single-Family Home	$480,000	02/05/26	4	3	2,132
218 Cedar Dr, Oregon, WI	0.19	Single-Family Home	$501,000	05/22/26	3	2.5	2,076
565 Oakwood Dr, Oregon, WI	0.35	Single-Family Home	$512,500	05/06/26	3	2	1,800
195 Ash St, Oregon, WI	0.40	Single-Family Home	$315,000	01/26/26	3	2	1,536
260 Ash St, Oregon, WI	0.29	Single-Family Home	$365,000	07/23/26	3	1.5	1,250
564 S Burr Oak Ave, Oregon, WI	0.21	Single-Family Home	$490,000	02/23/26	4	3	2,400

Nearby homes

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

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OFF MARKET
Est. $457,800
3 bd
2 ba
2,100 sqft
381 Cherry Wood Dr,
Oregon, WI 53575
OFF MARKET
Est. $458,000
4 bd
3 ba
2,064 sqft
431 Thomas Ct,
Oregon, WI 53575
SOLD
MAR 4, 2026
$480,000
3 bd
2 ba
2,130 sqft
411 Butternut Dr,
Oregon, WI 53575
SOLD
JUN 10, 2026
$499,900
4 bd
3 ba
2,438 sqft
434 S Burr Oak Ave,
Oregon, WI 53575
SOLD
FEB 5, 2026
$480,000
4 bd
3 ba
2,132 sqft
141 Amanda Ct,
Oregon, WI 53575
OFF MARKET
Est. $459,300
3 bd
2 ba
2,092 sqft
452 Lisa Ct,
Oregon, WI 53575
OFF MARKET
Est. $569,900
3 bd
3.5 ba
3,177 sqft
595 Cherry Wood Dr,
Oregon, WI 53575
SOLD
MAY 22, 2026
$501,000
3 bd
2.5 ba
2,076 sqft
218 Cedar Dr,
Oregon, WI 53575
OFF MARKET
Est. $514,000
3 bd
2 ba
1,970 sqft
182 Hickory Ct,
Oregon, WI 53575
SOLD
MAR 4, 2026
$475,000
5 bd
3.5 ba
2,763 sqft
163 Hickory Ct,
Oregon, WI 53575
OFF MARKET
Est. $557,400
4 bd
3 ba
2,849 sqft
399 Ash St,
Oregon, WI 53575
OFF MARKET
Est. $582,800
4 bd
3.5 ba
2,727 sqft
466 Lisa Ct,
Oregon, WI 53575

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Additional Cost

Assigned Schools

These are the assigned schools for 532 Cherry Wood 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!"
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"
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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
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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