4338 Upland Dr Madison, WI 53705
Sunset Village NeighborhoodEstimated payment $3,860/month
Highlights
- Deck
- Contemporary Architecture
- Patio
- Hamilton Middle School Rated A
- Wooded Lot
- Kitchen Island
About This Home
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
Listing Agent
@properties-elleven Christie's International Brokerage Phone: 608-438-2130 License #57439-90 Listed on: 03/07/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $9,741
Year Built
- Built in 1954
Lot Details
- 9,583 Sq Ft Lot
- Lot Dimensions are 81x115
- Wooded Lot
- Property is zoned TR-C1
Parking
- Paved Parking
Home Design
- Contemporary Architecture
- 2-Story Property
- Wood Siding
Interior Spaces
- 1,735 Sq Ft Home
- Wood Burning Fireplace
- Crawl Space
Kitchen
- Oven or Range
- Dishwasher
- Kitchen Island
Bedrooms and Bathrooms
- 3 Bedrooms
- Walk-in Shower
Laundry
- Dryer
- Washer
Outdoor Features
- Deck
- Patio
Schools
- Midvale/Lincoln Elementary School
- Hamilton Middle School
- West High School
Utilities
- Central Air
- Radiant Heating System
- Water Softener
Community Details
- Sunset Village Subdivision
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $9,741 | $541,700 | $208,600 | $333,100 |
| 2023 | $7,577 | $437,300 | $189,600 | $247,700 |
| 2022 | $14,346 | $380,300 | $164,900 | $215,400 |
| 2021 | $7,325 | $358,800 | $155,600 | $203,200 |
| 2020 | $7,404 | $341,700 | $148,200 | $193,500 |
| 2019 | $7,042 | $325,400 | $141,100 | $184,300 |
| 2018 | $6,713 | $309,900 | $128,300 | $181,600 |
| 2017 | $6,735 | $298,000 | $122,200 | $175,800 |
| 2016 | $6,508 | $281,100 | $115,300 | $165,800 |
| 2015 | $6,216 | $260,000 | $106,700 | $153,300 |
| 2014 | $6,090 | $260,000 | $106,700 | $153,300 |
| 2013 | $5,394 | $234,500 | $93,000 | $141,500 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 03/30/2026 03/30/26 | Pending | -- | -- | -- | |
| 03/24/2026 03/24/26 | For Sale | $575,000 | 0.0% | $331 / Sq Ft | |
| 03/07/2026 03/07/26 | Off Market | $575,000 | -- | -- | |
| 11/10/2022 11/10/22 | Sold | $250,000 | 0.0% | $144 / Sq Ft | View Prior Sale |
| 10/30/2022 10/30/22 | Pending | -- | -- | -- | |
| 10/30/2022 10/30/22 | For Sale | $250,000 | -- | $144 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $250,000 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $200,000 | New Conventional |
Source: South Central Wisconsin Multiple Listing Service
MLS Number: 2017988
APN: 0709-204-1424-3
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Ask me questions while you tour the home.