4338 Upland Drive Madison, WI $ 575,000
4338 Upland Drive
$ 575,000
Recently Listed
Open House 3/28 11am - 1pm
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4338 Upland Drive

Madison, WI, 53705
$ 575,000
Bedrooms3 Baths1.1 Sq 1,735

Monthly Estimate*

$ 3,540

Listed by @properties-elleven Christie's
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Single Family Home for sale in Madison, WI

for $575,000 with 3 bedrooms and 1 full bath, 1 half bath. This 1,735 square foot home was built in 1954 on a lot size of 0.22.

The architecture does the work. 4338 Upland Drive is a period-correct mid-century modern in Madison's Sunset Village — original redwood paneling, terrazzo entry, sandstone brick fireplace, and windows that turn a wooded lot into a living painting. Floor-to-ceiling glass in the main living area. Corner windows in the primary bedroom that open to the canopy. Clerestory bands that catch the light and drag it across original redwood walls. The house was designed to dissolve the boundary between inside and out, and it still does. Three bedrooms, 1.5 baths, 1,700 square feet of split-level proportion that feels exactly as considered as it was when it was built. The kitchen has been refreshed with new appliances and built-in butcher-block without disturbing the bones. The powder room — dark walls, walnut vanity, globe pendants — is a quiet design statement. Nestled on a wooded lot just blocks from Hilldale, minutes from UW and University Hospital. Some homes are renovated this one was restore

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Open House

3/28/2026 11:00 AM - 1:00 PM
3/29/2026 12:00 PM - 2:30 PM
4338 Upland Drive Madison, WI
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 575,000

Bedrooms

3

Full Bath

1

Half Bath

1

Property Type

Single Family

Taxes

$ 9,741

Style

Bi-level,Contemporary

Lot Size

0.22

Year Built

1954

Town/City

Madison

County/Region

Dane

MLS | Web ID

2017988

Features
Exterior
Lot Description Wooded
Improvements 333100
Exterior Wood
Exterior Amenities Deck Patio
Driveway Paved
Lot Dimensions 81X115
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Interior
Interior Amenities Washer Dryer Water softener inc
Basement Crawl space None
Kitchen Dimensions 20x9
Kitchen Features Dishwasher Kitchen Island Range/Oven Refrigerator
Beds 3
Total Baths 1.5
Heating/Cooling Radiant Central air
Bedroom 2 Level M
Bedroom 3 Level M
Kitchen Level M
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General
Fireplaces Wood
Garage None
Zoning TR-C1
School District Madison
Full Baths 1
Half Baths 1
Subdivision Sunset Village
Style Bi-level Contemporary
County Dane
Class Single Family
Tax Year 2025
Fuel Electric Natural gas
Status Active
Status Detail 0
Year Built 1954
Directions Mineral Point to S Midvale Blvd R onto Felton Pl Left onto Falles Ct Falles Ct turns slightly right and becomes Upland Dr
High School West
City Madison
Elementary School Midvale/Lincoln
Middle School Hamilton
DOM 1
Price Per Sq Ft Total AG 331.41
County Qtr Section West Metro Madison
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* Excluded Features
List By
@Properties-Elleven Christie's

Broker

(608) 772-7462

Phone

brogan@ellevenre.com

Email

Affordability Calculator

$4,352
Per Month
81%
19%
0%
Monthly Principal & Interest
$3,540
Monthly Property Taxes
$812
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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.
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Nearby
1567983 Elementary School
1568270 Middle School
West High School High School
Pricing History
DatePricePrice ChangeDescription
3/24/2026$575,000 Listed Price

Map


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4338 Upland Drive, Madison, WI, 53705 is a Single Family Home for sale at $575,000 with 1,735 sqft and a lot size of 0.22. 4338 Upland Drive has 3 bedrooms, 1.1 baths, and was built in 1954. The property's zip code is 53705 which is in Madison, WI