381 Cherry Wood Drive

Oregon, WI
$ 449,900 Beds 3 Baths 2 Sq 2,100
Monthly Estimate* How much can I afford?

Showings Begin 10-15-2026 - Welcome home to this beautiful 3-bedroom, 2-bath property in the desirable Hickory Estates neighborhood. The spacious kitchen and dinette area offer plenty of room for everyday living and feature a walkout to the deck, perfect for outdoor dining and entertaining. Enjoy the large fenced backyard with ample space for recreation, gardening, or relaxing. The inviting living room provides plenty of natural light and easy access to outdoor living areas, while the cozy family room features a wood-burning fireplace, creating the perfect gathering space for family and friends. The spacious primary bedroom offers a comfortable retreat at the end of the day. Ideally located directly across from a park and just minutes from downtown Oregon, this home also provides convenient access to the community's extensive paved walking trails. Combining comfort, space, and a fantastic location, this home is ready for its next owner to enjoy. New Roof & Siding 2025, New A/C 2026

Single Family

  • Price
  • $ 449,900
  • City
  • Oregon
  • Bedrooms
  • 3
  • Full Bathrooms
  • 2
  • County
  • DANE
  • Half Bathrooms
  • 0
  • Area
  • OREGON - V
  • Lot Size
  • 0.32 Acres
  • Zip
  • 53575
  • Sqr Footage
  • 2,100
  • Year Built
  • 1990
  • Taxes
  • $ 5931
  • Style
  • Tri-level
  • MLS#
  • 2033003
Listed By: Bunbury & Assoc, REALTORS;
Data Source: South Central Wisconsin MLS (SCWMLS)

Features

General

Fireplaces Wood
Garage 2 car,Opener
Zoning G1
School District Oregon
Full Baths 2
Subdivision Hickory Estates
Style Tri-level
County Dane
Class Single Family
Accessibility Features Level lot
Tax Year 2025
Fuel Natural gas
Status Active
Items Included Refrigerator,Range/Oven,Microwave,Dishwasher,Water Softener,Washer,Dryer,Small Shed in Yard
Year Built 1990
Directions Jefferson St. to Burr Oak to Cherry Wood
High School Oregon
City Oregon
Elementary School Call School District
Middle School Oregon
DOM 2
Price Per Sq Ft Total AG 214.24
County Qtr Section Dane SW

Interior Features

Interior Amenities Vaulted ceiling,Washer,Dryer,Water softener inc,Cable available,At Least 1 tub,Internet - Cable
Basement Full,Partially finished
Family Room Dimensions 20x11
Kitchen Dimensions 17x12
Kitchen Features Range/Oven,Refrigerator,Dishwasher,Microwave,Disposal
Beds 3
Total Baths 2
Heating/Cooling Forced air,Central air
Other Room 2 Dim 22x12
Other Room 2 Rec Room
Finished SqFt 2100
Bedroom 2 Dim 13x9
Bedroom 3 Dim 10x9
Other Room Dim 12x11
Laundry Level L
Other Room Den/Office
Bedroom 2 Level U
Bedroom 3 Level U
Family Room Level L
Kitchen Level M
Other Room 2 Lvl L
Other Room Lvl L
SqFt Source Assessor
Full Baths Lower 1
Full Baths Upper 1

Exterior Features

Lot Description Corner,Sidewalk
Improvements 352400
Exterior Aluminum/Steel
Exterior Amenities Deck,Fenced Yard,Storage building
Driveway Paved,Extra paving
Water/Waste Municipal water,Municipal sewer

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Baraboo, WI office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Call School District Elementary School
Middle School Oregon Middle School
High School Oregon High School

Price History

9/23/2026 Listed $449,900

Property vs Zip Code Average in 53575

Price
AVG $600K
$450K
Taxes
AVG $5,509
$5,931
Year Built
AVG 1994
1990

Areas That We Cover

381 Cherry Wood Drive Oregon, WI is a Single Family Home for sale at $449900 with 2100 sqft and a lot size of 0.32 Acres Acre(s). 381 Cherry Wood Drive Oregon has 3 bedrooms, 2 baths and was built in 1990. The property's zip code is 53575 which is in Oregon, WI

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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