2395 White Oak Trail

Oregon, WI
$ 1,599,999 Beds 4 Baths 4.5 Sq 5,263
Monthly Estimate* How much can I afford?

This one-of-a-kind home sits on nearly three wooded acres in an old growth neighborhood, tucked on a quiet street, with downtown Madison around 15 minutes away. The 5,263 sq ft Contemporary carries a finished walkout lower level, 2 family rooms with custom gas fireplaces, and two screened porches: one opens directly off the office with a hot tub built in for four-season use. Beyond the attached garage, two detached garages complete the property, including a custom toy garage built for the collector: car lift, epoxy floors, and a finished upper level where you can host a guest for the night or just hang out. The kitchen holds a breakfast bar, island, and full appliance suite, and the primary suite includes a walk-in shower with marble countertops. Wet bar, whole-home water softener, natural gas heat, and private well and septic with a full sprinkler system with fire protection, and alarm system to help lower you insurance cost. Come tour the house today!

Single Family

  • Price
  • $ 1,599,999
  • City
  • Oregon
  • Bedrooms
  • 4
  • Full Bathrooms
  • 4
  • County
  • DANE
  • Half Bathrooms
  • 1
  • Area
  • DUNN - T
  • Lot Size
  • 2.94 Acres
  • Zip
  • 53575
  • Sqr Footage
  • 5,263
  • Year Built
  • 1990
  • Taxes
  • $ 14098
  • Style
  • Contemporary
  • MLS#
  • 2028815
Listed By: EXIT Realty HGM;
Data Source: South Central Wisconsin MLS (SCWMLS)

Features

General

Fireplaces 3+ fireplaces,Gas
Garage 2 car,3 car,Attached,Detached,Heated,Opener,4+ car,Garage door > 8 ft high,Garage stall > 26 ft deep
Zoning R
School District Oregon
Full Baths 4
Half Baths 1
Style Contemporary
County Dane
Class Single Family
Accessibility Features Open floor plan,First floor bedroom,First floor full bath,Level drive,Low pile or no carpeting
Tax Year 2025
Fuel Natural gas
Status Active
Items Included Range/oven,refrigerator,dishwasher,microwave,water softener,all window coverings,washer,dryer,outbuildings,hot tub,car lift
Year Built 1990
Directions Hwy 14 to Cty MM to Cty B,left on White Oak,left on White Oak Ct.
High School Oregon
City Dunn
Elementary School Forest Edge
Middle School Oregon
DOM 58
Price Per Sq Ft Total AG 304.01
County Qtr Section Dane SE

Interior Features

Interior Amenities Walk-in closet(s),Great room,Vaulted ceiling,Skylight(s),Washer,Dryer,Water softener inc,Jetted bathtub,Wet bar,Cable available,At Least 1 tub,Split bedrooms,Hot tub,Internet - Cable
Basement Full,Full Size Windows/Exposed,Walkout to yard,Finished,Poured concrete foundatn
Family Room Dimensions 24x23
Laundry Dimensions 8x6
Kitchen Dimensions 22x14
Kitchen Features Breakfast bar,Kitchen Island,Range/Oven,Refrigerator,Dishwasher,Microwave,Disposal
Dining Room Dimensions 17x11
Beds 4
Total Baths 4.5
Heating/Cooling Forced air,Central air
Other Room 4 Dim 27x14
Other Room 3 Screened Porch
Other Room 3 Dim 29x13
Other Room 2 Dim 19x10
Other Room 2 Den/Office
Other Room 4 Rec Room
Finished SqFt 5263
Bedroom 2 Dim 20x16
Bedroom 3 Dim 16x20
Bedroom 4 Dim 19x9
Other Room Dim 12x11
Laundry Level M
Other Room Sun Room
Bedroom 2 Level U
Bedroom 3 Level M
Bedroom 4 Level L
Dining Room Level M
Family Room Level M
Kitchen Level M
Other Room 2 Lvl M
Other Room 3 Lvl M
Other Room Lvl M
SqFt Source Assessor
Full Baths Lower 1
Full Baths Main 1
Full Baths Upper 2

Exterior Features

Lot Description Wooded,Rural-in subdivision
Improvements 603600
Exterior Wood
Exterior Amenities Patio,Storage building,Accessory Dwelling Unit
Driveway Paved
Water/Waste Non-Municipal/Prvt dispos,Well

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
Adjust Payment Options
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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 Forest Edge Elementary School
Middle School Oregon Middle School
High School Oregon High School

Price History

7/24/2026 Listed $1,599,999

Property vs Zip Code Average in 53575

Price
AVG $630K
$1.6M
Taxes
AVG $5,071
$14,098
Year Built
AVG 1996
1990
Visits
AVG 65
17
Data Provided by Inside Real Estate®

Areas That We Cover

2395 White Oak Trail Oregon, WI is a Single Family Home for sale at $1599999 with 5263 sqft and a lot size of 2.94 Acres Acre(s). 2395 White Oak Trail Oregon has 4 bedrooms, 4 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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