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$3,300,000

  • For Sale
  • Active
  • Single Family
  • 7 Beds
  • 5 Full Baths
  • 3 Partial Baths
  • 12,178 Sq. Ft.
  • 4 Car Garage
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Executive home situated on 1.5 acres w/expansive views, offering luxury & craftsmanship. The main level showcases an impressive great room w/floor to ceiling stone fireplace. Gourmet chef?s kitchen with adjacent screen porch. Family room features a brick surround fireplace. Mud room, laundry & butler pantry on main level. Private owner?s suite featuring a spa-inspired bath, soaking tub, & custom closet. 4 additional bdrms, 2nd laundry & hidden paneled office complete the upper level. The spacious walk-out lower level is designed for recreation & entertaining. Complete w/a wet bar, theater rm, game area, indoor sport court, & gym. Outdoors, a private resort awaits with a sparkling pool, oversized patio, stunning pool house with fireplace, outdoor kitchen & grill. 4 car heated garage. Located in the highly desirable Middleton School District. This exceptional estate offers a rare combination of sophisticated living, superior craftsmanship, & resort-inspired amenities.

Full Property Details for 4908 Winners Cir

General

  • Price: $3,300,000
  • Taxes: $32,099 (2025)
  • Status: Active
  • Type: Single Family
  • Source: Wirex_South_Central_Wisconsin_MLS_Corporation_SCW
  • MLS ID: 2032111
  • Updated: 9/9/2026
  • Added to Site: 31 day(s) ago

Interior

  • Appliances: Range/Oven, Refrigerator, Dishwasher, Microwave, Disposal

Rooms

Bathrooms

  • Total Bathrooms: 8
  • Full Bathrooms: 5
  • Half Bathrooms: 3
  • Bathroom: Master Bedroom Bath: Full, Master Bedroom Bath, Master Bedroom Bath: Walk-In Shower, Master Bedroom Bath: Tub/No Shower

Bedrooms

  • Total Bedrooms: 7
  • Primary Bedroom: 21 x 21, Main
  • Bedroom 2: 14 x 21, Upper
  • Bedroom 3: 20 x 19, Upper
  • Bedroom 4: 19 x 18, Upper
  • Bedroom 5: 17 x 13, Upper

Other Rooms

  • Living Room: 22 x 23, Main
  • Family Room: 20 x 16, Main
  • Kitchen: 15 x 23, Main
  • Dining Room: 17 x 16, Main
  • Exercise Room: 16 x 13, Lower

Exterior

  • Exterior Features: Deck, Patio, Fenced Yard, In-Ground Pool, Sprinkler System, Screened Porch

Parking

  • Garage: Yes
  • Garage Spaces: 4
  • Garage Description: Attached, 4 Car

Location

  • Municipality: Springfield
  • County: Dane
  • Subdivision: Bridle Ridge
  • Driving Directions: West on Airport, R- Bonner, R- Vosen Rd, L- Bridle Ridge Pass, R- on Winners Circle

School Information

  • School District: Middleton-Cross Plains
  • Elementary School: Sunset Ridge
  • Middle School: Glacier Creek
  • High School: Middleton

Heating & Cooling

  • Heating Fuel: Natural Gas
  • Heating/Cooling: Forced Air, Central Air Conditioning

Utilities

  • Water/Sewer: Well, Private Septic System

Structural Information

  • Architectural Style: Colonial
  • Description/Design: 2 Stories
  • Exterior Const.: Masonite/Pressboard, Stone
  • Basement Desc.: Full, Exposed, Full-Size Windows, Walk-Out/Outer Door, Partially Finished, High Ceiling (8 Feet or Higher), Poured Concrete
  • Square Feet: 12,178
  • Square Feet Range: 5001 or More
  • Sq. Ft. Source: Blueprint
  • Year Built: 2017

Additional Structures

  • Other Structures: Storage Building

Lot Features

  • Lot Size Source: Assessor/Public Record
  • Zoning: Res

Financial Considerations

  • Tax Amount: $32,099
  • Tax Year: 2025

Disclosures and Reports

  • Exclusions: Sellers personal property
  • Inclusions: All appliances, All window treatments, 2- Washers, 2- Dryers, Water softener, Outdoor grill.

Listed by Collective Real Estate Group

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Listing agents

— 4908 Winners Cir —

  • Collective Real Estate Group

  • Collective Real Estate Group

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NMLS#: 1598647

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NMLS#: 1598647

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Save up to an additional 20% by bundling your home and auto together!

Schools serving 4908 Winners Cir

School District:Middleton-Cross Plains School District
NameGradesDistance
Sunset Ridge Elementary School, Middleton, WI
8686 Airport Road, Middleton, WI 53562
K-40.8 mi
Glacier Creek Middle School
2800 Military Road, Cross Plains, WI 53528
5-82.8 mi
Middleton High School
2100 Bristol Street, Middleton, WI 53562
9-124.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 4908 Winners Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/05/2026
Listed
$3,300,000
9.09%
MLS
1/20/2026
Sold
$3,025,000
—
Public Record
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Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 4908 Winners Cir

Year
Property Taxes
Change
Tax Assessment
Change
2025
$32,183
11%
$2,620,500
78%
2024
$29,106
5%
$1,471,000
—
2022
$27,778
6%
$1,471,000
—
2022
$26,252
1%
$1,471,000
—
2021
$26,048
—
$1,471,000
—
2020
$26,020
12%
$1,471,000
—
2019
$23,326
479%
$1,471,000
463%
2018
$4,026
89%
$261,300
90%
2017
$2,130
-3%
$137,500
—
2016
$2,186
-2%
$137,500
—
2015
$2,230
—
$137,500
—
2014
$2,241
-3%
$137,500
—
2013
$2,308
—
$137,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Collective Real Estate Group

4908 Winners Circle, Middleton, WI 53562 (MLS# 2032111) is a Single Family property with 7 bedrooms, 5 full bathrooms and 3 partial bathrooms. 4908 Winners Circle is currently listed for $3,300,000 and was received on September 05, 2026. Want to learn more about 4908 Winners Circle? Do you have questions about finding other Single Family real estate for sale in Middleton? You can browse all Middleton real estate or contact a Coldwell Banker agent to request more information.

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