4338 Upland Dr
Madison, WI 53705
Sunset Village- 3 Beds
- 1.5 Baths
- 1,735 sqft
$630,000
Last Sold: May 1, 2026
10% over list $575K
$363/sqft
Est. Refi. Payment $4,078/mo*
$630,000
Last Sold: May 1, 2026
10% over list $575K
$363/sqft
Est. Refi. Payment $4,078/mo*
3 Beds
1.5 Baths
1,735 sqft
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1954
Living Area
1,735 sqft
Price/Sqft
$363/sqft
Parking
Open Parking
About this House
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
4338 Upland Dr, Madison, WI 53705 is a 3 bedroom, 2 bathroom, 1,735 sqft single-family home in Sunset Village, built in 1954. It last sold for $630,000 on May 1, 2026 (10% above the $575,000 asking price). More recently, it was listed as a rental in February 2026 with an asking price of $3,200 per month. That rental listing was removed on March 6, 2026. It is currently off market. The Trulia Estimate is $631,500, with a rent estimate of $3,123/month.
Home Details for 4338 Upland Dr
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Interior Details Basement: Crawl Space,NoneNumber of Rooms: 5Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1Number of Bathrooms (main level): 1 |
Dimensions and Layout Living Area: 1735 Square Feet |
Appliances & Utilities Appliances: Washer, Dryer, Water Softener IncludedDryerWasher |
Heating & Cooling Heating: RadiantHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Radiant |
Fireplace & Spa Fireplace: Wood BurningHas a Fireplace |
Levels, Entrance, & Accessibility Stories: 2Levels: Two, Bi-level |
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Exterior Home Features Patio / Porch: Deck, PatioVegetation: Wooded |
Parking & Garage No CarportNo GarageNo Attached GarageHas Open ParkingParking: No Garage |
Frontage Not on Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (above surface): 1735 Square Feet |
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Year Built Year Built: 1954 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary |
Building Construction Materials: Wood Siding |
Property Information Not Included in Sale: Sellers personal propertyIncluded in Sale: Dishwasher, range/oven, Refrigerator, Washer/DryerParcel Number: 070920414243 |
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Price List Price: $575,000Price Per Sqft: $363/sqft |
Status Change & Dates Off Market Date: Tue Mar 24 2026 |
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MLS Status: Sold |
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Direction & Address City: MadisonCommunity: Sunset Village |
School Information Elementary School: Midvale/LincolnElementary School District: MadisonJr High / Middle School: HamiltonJr High / Middle School District: MadisonHigh School: WestHigh School District: Madison |
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Building Area Building Area: 1735 Square Feet |
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Lot Area: 9583.2 sqft |
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Listing Terms: Arms Length |
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BasementMls Number: 2017988Attribution Contact: Pref: 608-438-2130Above Grade Unfinished Area: 1735 |
Last check for updates: about 4 hours ago
Listed by Melissa LeGrand
@properties-elleven Christie's International
Bought with: Brogan Brunker, @properties-elleven Christie's International
Source: SCWMLS, MLS#2017988
Price History for 4338 Upland Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 05/01/2026 | $630,000 | Sold | N/A |
| 03/30/2026 | $575,000 | Pending | WIREX MLS #2017988 |
| 03/24/2026 | $575,000 | Listed For Sale | WIREX MLS #2017988 |
| 03/06/2026 | $3,400 | ListingRemoved | Zillow Rentals |
| 02/16/2026 | $3,400 | PriceChange | Zillow Rentals |
| 02/15/2026 | $3,200 | Listed For Rent | Zillow Rentals |
| 11/14/2022 | $250,000 | Sold | N/A |
Market trends in Madison
Last updated June 2026
Avg. sale price
$423K
$7.67KMoM
Sale-to-List Price
102.8%
1.0%MoM
Price per sq ft
$260
$10MoM
Available listings
704
43MoM
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $9,588 |
| Assessment | $489,800 |
Home facts updated by county records
Comparable Sales for 4338 Upland Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.03 | Single-Family Home | $500,000 | 03/20/26 | 3 | 2 | 1,673 | |
0.05 | Single-Family Home | $690,000 | 04/01/26 | 3 | 1.5 | 1,703 | |
0.01 | Single-Family Home | $450,000 | 11/26/25 | 3 | 1 | 1,497 | |
0.11 | Single-Family Home | $510,000 | 03/18/26 | 4 | 2 | 1,854 | |
0.24 | Single-Family Home | $625,000 | 12/10/25 | 3 | 1.5 | 1,944 | |
0.26 | Single-Family Home | $670,000 | 05/22/26 | 3 | 2 | 1,708 | |
0.30 | Single-Family Home | $532,500 | 06/18/26 | 3 | 2 | 1,793 | |
0.19 | Single-Family Home | $630,000 | 04/17/26 | 2 | 1.5 | 1,706 | |
0.29 | Single-Family Home | $550,000 | 06/26/26 | 3 | 2 | 2,007 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 4338 Upland Dr.
What Locals Say about Sunset Village
At least 22 Trulia users voted on each feature.
100 % Say it's walkable to restaurants
100 % Say there are sidewalks
96 % Say it's dog friendly
92 % Say kids play outside
86 % Say it's walkable to grocery stores
83 % Say people would walk alone at night
74 % Say parking is easy
74 % Say yards are well-kept
74 % Say there's wildlife
73 % Say there's holiday spirit
72 % Say they plan to stay for at least 5 years
72 % Say streets are well-lit
71 % Say neighbors are friendly
57 % Say car is needed
56 % Say it's quiet
39 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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