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

SOLD

MAY 6, 2026

565 Oakwood Dr
Oregon, WI 53575

3 Beds
2 Baths
1,800 sqft (on 0.25 acres)

$512,500

Last Sold: May 6, 2026

8% over list $475K

$285/sqft

Est. Refi. Payment $3,323/mo*

Refinance Your Home

$512,500

Last Sold: May 6, 2026

8% over list $475K

$285/sqft

Est. Refi. Payment $3,323/mo*

Refinance Your Home

3 Beds

2 Baths

1,800 sqft

(on 0.25 acres)

Local Information

Map ViewExplore the area around 565 Oakwood 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

1999

Lot Size

0.25 acres

Living Area

1,800 sqft

Price/Sqft

$285/sqft

Parking

Garage

About this House

This beautifully kept home offers peace and an abundance of natural sunlight. This home boasts natural hardwood floors throughout first floor, vaulted ceilings, open kitchen, spacious primary and more. Bring your ideas for the large unfinished basement; already stubbed for a bathroom. Walking distance to parks and trails, short distance to downtown Oregon and 20 min drive to downtown Madison. Don’t miss out on calling this classic beauty your home!

565 Oakwood Dr, Oregon, WI 53575 is a 3 bedroom, 2 bathroom, 1,800 sqft single-family home built in 1999. It last sold for $512,500 on May 6, 2026 (8% above the $474,900 asking price). It is currently off market. The Trulia Estimate is $509,700, with a rent estimate of $2,695/month.

Home Details for 565 Oakwood Dr

Interior Features
Interior Details Basement: FullNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 2
Dimensions and Layout Living Area: 1800 Square Feet
Appliances & Utilities Appliances: 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, GasHas a Fireplace
Levels, Entrance, & Accessibility Stories: 1Levels: One

Exterior Features
Exterior Home Features Patio / Porch: Patio
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: 2 car,Garage Door Opener
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 1800 Square Feet

Property Information
Year Built Year Built: 1999
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building Construction Materials: Brick, Stone, Vinyl Siding
Property Information Not Included in Sale: Sellers' Personal PropertyIncluded in Sale: Refrigerator, microwave, oven, dishwasher, washer/dryer, April Aire Humidity System, Water SoftenerParcel Number: 050911441113

Price & Status
Price List Price: $474,900Price Per Sqft: $285/sqft
Status Change & Dates Off Market Date: Thu Apr 09 2026

Active Status
MLS Status: Sold

Media
Virtual TourSee Virtual Tour

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: 1800 Square Feet

Lot Information
Lot Area: 10890 sqft

Listing Info
Special Conditions: Restrictions/Covenants

Offer
Listing Terms: Arms Length

Miscellaneous
BasementMls Number: 2020132Above Grade Unfinished Area: 1800

Last check for updates: about 4 hours ago

Listed by Elizabeth Joy Barthen

Relish Realty

Bought with: Laura Lahti, Y Realty Wisconsin

Source: SCWMLS, MLS#2020132

Price History for 565 Oakwood Dr

Date	Price	Event	Source
05/06/2026	$512,500	Sold	N/A
Recording Date 05/06/2026 County Transfer Tax N/A Total Transfer Tax N/A
04/15/2026	$474,900	Pending	WIREX MLS #2020132

04/09/2026	$474,900	Listed For Sale	WIREX MLS #2020132

06/23/2014	$263,000	Sold	N/A
Recording Date 06/23/2014 Contract Date 06/10/2014 County Transfer Tax N/A Total Transfer Tax N/A
04/03/2014	$264,900	Listed For Sale	Agent Provided

Market trends in Oregon

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

2MoM

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Property Tax and Assessment

Year	2024
Tax	$6,658
Assessment	$437,400

Home facts updated by county records

Comparable Sales for 565 Oakwood Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
411 Butternut Dr, Oregon, WI	0.41	Single-Family Home	$480,000	03/04/26	3	2	2,130
290 Ash St, Oregon, WI	0.46	Single-Family Home	$385,000	09/08/25	3	2	1,820
451 Oakwood Dr, Oregon, WI	0.13	Single-Family Home	$580,000	07/01/26	4	3	2,652
435 Ash St, Oregon, WI	0.19	Single-Family Home	$552,000	07/08/26	4	2.5	3,054
168 Hickory Ct, Oregon, WI	0.43	Single-Family Home	$420,000	12/08/25	3	2	2,300
970 Brynhill Dr, Oregon, WI	0.04	Single-Family Home	$700,000	08/21/25	4	3.5	3,020
1129 Lincoln Rd, Oregon, WI	0.30	Single-Family Home	$466,000	04/30/26	4	3	2,381
156 Hickory Ct, Oregon, WI	0.44	Single-Family Home	$576,000	04/23/26	3	2.5	2,194
218 Cedar Dr, Oregon, WI	0.48	Single-Family Home	$501,000	05/22/26	3	2.5	2,076

Nearby homes

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

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OFF MARKET
L121 Alpine Pkwy,
Oregon, WI 53575
OFF MARKET
Est. $441,400
4 bd
2 ba
1,790 sqft
570 Oakwood Dr,
Oregon, WI 53575
OFF MARKET
Est. $866,700
4 bd
2.5 ba
3,596 sqft
1008 Brynhill DRIVE,
Oregon, WI 53575
Closed
OFF MARKET
Est. $940,200
4 bd
3.5 ba
3,539 sqft
1078 Brynhill Dr,
Oregon, WI 53575
OFF MARKET
Est. $721,300
4 bd
3.5 ba
3,020 sqft
970 Brynhill Dr,
Oregon, WI 53575
OFF MARKET
Est. $911,700
5 bd
3.5 ba
3,581 sqft
1048 Brynhill Dr,
Oregon, WI 53575
OFF MARKET
Est. $887,400
5 bd
3 ba
3,918 sqft
1028 Brynhill Dr,
Oregon, WI 53575
OFF MARKET
Est. $812,200
5 bd
3.5 ba
3,186 sqft
1038 Brynhill Dr,
Oregon, WI 53575
OFF MARKET
L169 Alpine Pkwy,
Oregon, WI 53575
OFF MARKET
Est. $445,700
3 bd
2 ba
1,603 sqft
535 Oakwood Dr,
Oregon, WI 53575
OFF MARKET
Lot 136 Brynhill Dr,
Oregon, WI 53575

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Additional Cost

Assigned Schools

These are the assigned schools for 565 Oakwood 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."
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."
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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
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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