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

595 Cherry Wood Dr
Oregon, WI 53575

3 Beds
3.5 Baths
3,177 sqft (on 0.30 acres)

$577,400

Trulia Estimate

as of Jul 22, 2026

Est. Refi. Payment $3,743/mo*

Refinance Your Home

$577,400

Trulia Estimate

as of Jul 22, 2026

Est. Refi. Payment $3,743/mo*

Refinance Your Home

3 Beds

3.5 Baths

3,177 sqft

(on 0.30 acres)

Local Information

Map ViewExplore the area around 595 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

1993

Lot Size

0.3 acres

Living Area

3,177 sqft

Price/Sqft

$182

Parking

3 Car Garage

Description

Come home to this spacious 2 story home with a large finished lower level. The updated kitchen features quality cabinetry, newer stainless appliances, island, & granite counters. You’ll love the large living room with lots of windows, wood flrs, & gas fireplace with stone surround. The dinette patio doors leads to a fully fenced backyard & rear patio. The lovely vaulted foyer area & formal dining or flex room option rounds out the 1st floor. Upstairs, are 3 bedrooms, including a vaulted primary suite with a beautifully updated bath that boasts a double vanity, spa tub, sep. shower & a Lg walk-in closet. The LL offers a family room, flex room & utility area with 2nd set of stairs to the garage. The oversized insulated 3-car garage with heater completes this home! Close to parks & school.

595 Cherry Wood Dr, Oregon, WI 53575 is a 3 bedroom, 4 bathroom, 3,177 sqft single-family home built in 1993. It last sold for the $529,900 asking price on Jul 29, 2024. It is currently off market. The Trulia Estimate is $577,400, with a rent estimate of $3,481/month.

Home Details for 595 Cherry Wood Dr

Interior Features
Interior Details Basement: Full,Partially Finished,Sump PumpNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Dining Room, Kitchen, Living Room
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout Living Area: 3177 Square Feet
Appliances & Utilities Utilities: Cable AvailableAppliances: Washer, Dryer, Water Softener IncludedDryerLaundry: Main LevelWasher
Heating & Cooling Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 1Fireplace: 1 fireplace, Wood BurningHas a Fireplace
Levels, Entrance, & Accessibility Stories: 2Levels: Two

Exterior Features
Exterior Home Features Patio / Porch: PatioFencing: FencedFoundation: Poured concrete foundatn
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Additional Parking,Access to Basement,Attached,Garage Door Opener
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 2158 Square Feet

Property Information
Year Built Year Built: 1993
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building Construction Materials: Vinyl Siding
Property Information Not Included in Sale: Seller's personal property, 2nd floor bathroom mirror.Included in Sale: Refrigerator, Stove, Dishwasher, Microwave, Water Softener, Washer, Dryer, Some Window CoveringsParcel Number: 050911409452

Price & Status
Price List Price: $529,900
Status Change & Dates Off Market Date: Tue Jun 04 2024

Active Status
MLS Status: Sold

Location
Direction & Address City: OregonCommunity: Stone Ridge
School Information Elementary School: Prairie ViewElementary School District: OregonJr High / Middle School: OregonJr High / Middle School District: OregonHigh School: OregonHigh School District: Oregon

Building
Building Area Building Area: 3177 Square Feet

Lot Information
Lot Area: 0.30 acres

Offer
Listing Terms: Arms Length

Miscellaneous
BasementMls Number: 1975915Attribution Contact: Home: 608-219-9766Above Grade Unfinished Area: 2158

Last check for updates: about 12 hours ago

Listed by Ryan O Koch

Keller Williams Realty

Bought with: Joseph Pechauer, JMP Properties

Source: SCWMLS, MLS#1975915

Price History for 595 Cherry Wood Dr

Date	Price	Event	Source
07/29/2024	$530,000	Sold	N/A
Recording Date 07/29/2024 County Transfer Tax N/A Total Transfer Tax N/A
06/11/2024	$529,900	Pending	WIREX MLS #1975915

06/04/2024	$529,900	Listed For Sale	WIREX MLS #1975915

05/19/2020	$388,500	Sold	N/A
Recording Date 05/19/2020 Contract Date 05/15/2020 County Transfer Tax N/A Total Transfer Tax N/A
05/06/2020	$397,999	Pending	Agent Provided

03/23/2020	$397,999	PriceChange	Agent Provided
Price Change $11,901 (-3%)
03/06/2020	$409,900	Listed For Sale	Agent Provided

12/18/2019	$419,900	ListingRemoved	Agent Provided

10/16/2019	$419,900	Listed For Sale	Agent Provided

08/13/2008	$227,000	Sold	N/A
Recording Date 08/13/2008 Contract Date 07/23/2008 County Transfer Tax N/A Total Transfer Tax N/A
05/08/2008	$239,900	Listed For Sale	Agent Provided

03/19/2008	$276,359	Sold	N/A
Recording Date 03/19/2008 Contract Date 03/10/2008 County Transfer Tax N/A Total Transfer Tax N/A
03/09/2008	$249,900	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	$7,869
Assessment	$512,900

Home facts updated by county records

Comparable Sales for 595 Cherry Wood Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
435 Ash St, Oregon, WI	0.09	Single-Family Home	$552,000	07/01/26	4	2.5	3,054
466 Lisa Ct, Oregon, WI	0.15	Single-Family Home	$570,000	08/11/25	4	3.5	2,727
156 Hickory Ct, Oregon, WI	0.18	Single-Family Home	$576,000	04/23/26	3	2.5	2,194
334 Lynne Trl, Oregon, WI	0.15	Single-Family Home	$560,000	08/13/25	4	3.5	2,860
451 Oakwood Dr, Oregon, WI	0.17	Single-Family Home	$580,000	07/01/26	4	3	2,652
141 Amanda Ct, Oregon, WI	0.07	Single-Family Home	$480,000	02/05/26	4	3	2,132
411 Butternut Dr, Oregon, WI	0.15	Single-Family Home	$480,000	03/04/26	3	2	2,130
218 Cedar Dr, Oregon, WI	0.21	Single-Family Home	$501,000	05/22/26	3	2.5	2,076
163 Hickory Ct, Oregon, WI	0.19	Single-Family Home	$475,000	03/04/26	5	3.5	2,763
970 Brynhill Dr, Oregon, WI	0.25	Single-Family Home	$700,000	08/21/25	4	3.5	3,020

Nearby homes

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

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OFF MARKET
Est. $565,300
4 bd
3 ba
2,849 sqft
399 Ash St,
Oregon, WI 53575
SOLD
FEB 5, 2026
$480,000
4 bd
3 ba
2,132 sqft
141 Amanda Ct,
Oregon, WI 53575
SOLD
JUL 1, 2026
$552,000
4 bd
2.5 ba
3,054 sqft
435 Ash St,
Oregon, WI 53575
FOR SALE
3D VIEW
0.29 ACRES
$575,000
4 bd
3.5 ba
2,558 sqft
422 Oakwood Dr,
Oregon, WI 53575
OFF MARKET
Est. $577,100
4 bd
3.5 ba
2,860 sqft
334 Lynne Trl,
Oregon, WI 53575
OFF MARKET
Est. $521,700
3 bd
2 ba
1,970 sqft
182 Hickory Ct,
Oregon, WI 53575
SOLD
MAR 4, 2026
$480,000
3 bd
2 ba
2,130 sqft
411 Butternut Dr,
Oregon, WI 53575
SOLD
DEC 8, 2025
$420,000
3 bd
2 ba
2,300 sqft
168 Hickory Ct,
Oregon, WI 53575
FOR SALE
0.25 ACRES
$424,999
3 bd
2.5 ba
2,149 sqft
310 Ash St,
Oregon, WI 53575
OFF MARKET
Est. $463,000
4 bd
3 ba
2,064 sqft
431 Thomas Ct,
Oregon, WI 53575
SOLD
APR 23, 2026
$576,000
3 bd
2.5 ba
2,194 sqft
156 Hickory Ct,
Oregon, WI 53575

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Additional Cost

Assigned Schools

These are the assigned schools for 595 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 "
0
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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"
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"
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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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