Listed by Denise Holmes • Collective Real Estate Group.

For sale

$3,300,000

Est. $21,579/mo —

•

12,178

sq ft

4908 Winners Cir, Middleton, WI 53562

About this home

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.

Single-familyProperty Type

2017Year Built

1.5 acresLot Size

$271Price/Sq.Ft.

$65/moHOA Dues

4 car garageParking

Listed by Denise Holmes • Collective Real Estate Group

Listed by Lindsay Koth • Collective Real Estate Group

Listing updated: Oct 20, 2026 at 05:00pm

Redfin checked: 2 minutes ago

•Source:SCWMLS as distributed by WIREX #2032111

Payment calculator

$21,579 per month

Principal and interest$18,234

Property taxes

HOA dues

Home insurance

Utilities

5 minutes to get started. No credit impact.

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Open houses

No upcoming open houses.

Nearby open houses (10)

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Karla Downing • First Weber Inc
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$512,000
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$499,900
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5030 S Valley Rd, Black Earth, WI 53515
Peggy Acker-Farber • RE/MAX Preferred
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3 beds1 bath912 sq ft
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Joe Copeland • Realty Executives Cooper Spransy
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5 beds2.5 baths2,548 sq ft
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Denise Holmes • Collective Real Estate Group
OPEN TODAY, 12PM TO 2PMVIDEO TOUR
$469,900
3 beds2 baths1,968 sq ft
3218 Davidson St, Cross Plains, WI 53528
Jean Armendariz-Kerr • Mode Realty Network
OPEN TODAY, 12PM TO 2PM3D WALKTHROUGH
$525,000
4 beds2 baths2,394 sq ft
5801 Old Sauk Rd, Madison, WI 53705
Marine Yoo • Real Broker LLC
OPEN TODAY, 12PM TO 2PM
$445,000
3 beds2.5 baths1,820 sq ft
7801 Twinflower Dr, Madison, WI 53719
Natalie Aneskavich • Lakeland Real Estate LLC
OPEN TODAY, 2PM TO 4PM
$575,000
4 beds3 baths2,393 sq ft
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Living In Madison Real Estate Group • Keller Williams Realty

Around this home

Schools

K - 12
Preschool & daycare

Sunset Ridge Elementary School

Public PreK-4 • Assigned • 0.8mi

7/10

Glacier Creek Middle School

Public 5-8 • Assigned • 2.8mi

9/10

Middleton High School

Public 9-12 • Assigned • 4.1mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

4908 Winners Cir · $3,300,000

DAYS ON MARKET

The average home goes pending in 55 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

LIST PRICE

Median list price in this area is $479,984. (85% lower than this home)

PRICE DROP

19% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Full, exposed basement with full-size windows, walk-out/outer door, partial finish, 8'+ ceilings and poured concrete
Breakfast bar, pantry and kitchen island

Bedrooms
Main-level master bedroom (21 x 21)
Upper-level bedroom 2 (14 x 21)
Upper-level bedroom 3 (20 x 19)
Upper-level bedroom 4 (19 x 18)
Upper-level bedroom 5 (17 x 13)

Bathrooms
Five full bathrooms
Three half bathrooms
Master bath with tub (no shower) and separate walk-in shower

Kitchen
Range/oven
Refrigerator
Dishwasher
Microwave
Garbage disposal

Laundry & utility
Includes two washers and two dryers
Water softener

Heating & cooling
Forced air heating
Central air conditioning
Natural gas fuel

Sale and tax history for 4908 Winners Cir

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2025

$32,183 (+10.6%)

$233,300 + $2,387,200

$2,620,500

2024

$29,106 (+4.8%)

$137,500 + $1,333,500

$1,471,000

2023

$27,778 (+5.8%)

$137,500 + $1,333,500

$1,471,000

2022

$26,252 (+0.8%)

$137,500 + $1,333,500

$1,471,000

2021

$26,048 (+0.1%)

$137,500 + $1,333,500

$1,471,000

2020

$26,020 (+11.6%)

$137,500 + $1,333,500

$1,471,000

2019

$23,326 (+479.4%)

$137,500 + $1,333,500

$1,471,000

2018

$4,026 (+89.0%)

$137,500 + $123,800

$261,300

2017

$2,130 (−2.5%)

$137,500

2016

$2,185 (−2.5%)

$137,500

2014

$2,241 (−2.9%)

$137,500

2013

$2,307

$137,500

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

1.5 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Other

County

Dane County

APN

080831401000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 7, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

2/10 Heat Factor

7 days above 98° expected this year, 14 days in 30 years

2/10 Wind Factor

Minor risk of severe winds over next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Middleton, WI • 53562

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

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Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Redfin Estimate for 4908 Winners Cir

$3,172,232

$128K under list price of $3.30M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.1M to $3.5M.

SOLD SEP 15, 2026
$1,420,000 Last sold price
5 beds4.5 baths5,354 sq ft
4498 Nina Ln, Middleton, WI 53562
$6/sq ft
smaller lot
5 years older
SOLD SEP 30, 2026
$1,600,000 Last sold price
5 beds4.5 baths6,034 sq ft
9913 Shadow Ridge Trl, Middleton, WI 53562
$6/sq ft
smaller lot
7 years older
SOLD JUL 15, 2026
$3,500,000 Last sold price
4 beds6.5 baths9,019 sq ft
4743 Delmara Rd, Middleton, WI 53562
$117/sq ft
larger lot
13 years older
SOLD JUL 17, 2026
$1,100,000 Last sold price
5 beds3.5 baths3,513 sq ft
4664 Stonewood Dr, Middleton, WI 53562
$42/sq ft
larger lot
Local rules require you to be signed in
4528 Coneflower Ct, Middleton, WI 53562
$1,420,900 Last sold price
— beds— baths— sq ft
4528 Coneflower Ct, Middleton, WI 53562
Source: Public Records
larger lot
no basement
SOLD JUL 28, 2026
$1,050,000 Last sold price
5 beds4.5 baths5,000 sq ft
4479 Shooting Star Ave, Middleton, WI 53562
$61/sq ft
smaller lot
11 years older

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Details provided by SCWMLS as distributed by WIREX and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Market insights

Property details

Sale and tax history for 4908 Winners Cir

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 4908 Winners Cir

Early Access listings

Nearby similar homes

New listings for sale in 53562

More real estate resources