4338 Upland Drive
Madison, WI 53705
Sunset Village- 3 Beds
- 1.5 Baths
- 1,735 sqft
$630,000
Last Sold: Apr 30, 2026
10% over list $575K
$363/sqft
Est. Refi. Payment $3,988/mo*
$630,000
Last Sold: Apr 30, 2026
10% over list $575K
$363/sqft
Est. Refi. Payment $3,988/mo*
3 Beds
1.5 Baths
1,735 sqft
Local Information
© Google
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Description
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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from April 30, 2026
Home Highlights
Parking
No Info
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
$363/sqft
Listed
68 days ago
Home Details for 4338 Upland Drive
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MLS Status: Closed |
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Interior Details Basement: Crawl Space,None / SlabNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bathroom, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 3Main Level Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 1735 Square Feet |
Appliances & Utilities Appliances: Range/Oven, Refrigerator, Dishwasher, Washer, Dryer, Water SoftenerDishwasherDryerRefrigeratorWasher |
Heating & Cooling Heating: Natural Gas,Electric,RadiantHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas |
Levels, Entrance, & Accessibility Stories: 2Levels: Bi-Level, Two |
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Exterior Home Features Patio / Porch: Deck, Patio |
Parking & Garage No CarportNo GarageNo Attached GarageParking: 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 SidingNot a New Construction |
Property Information Condition: 21+ YearsNot 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 |
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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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Association for this Listing: South Central Wisconsin MLS |
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Lot Area: 9583.2 sqft |
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Special Conditions: Arms Length |
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Mls Number: 2017988Living Area Range: 1501-1750Living Area Range Units: Square FeetMunicipality: MadisonAttribution Contact: Pref: 608-438-2130Above Grade Unfinished Area: 1735 |
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Source Internet Entire Listing Display |
Last check for updates: about 8 hours ago
Listed by Melissa LeGrand, (608) 438-2130
@properties-elleven Christie's International
Brogan Brunker, (608) 772-7462
@properties-elleven Christie's International
Bought with: Brogan Brunker
Originating MLS: South Central Wisconsin MLS
Source: WIREX MLS, MLS#2017988

Price History for 4338 Upland Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 04/30/2026 | $630,000 | Sold | WIREX MLS #2017988 |
| 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 |
| 11/10/2022 | $250,000 | Sold | WIREX MLS #1946767 |
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $9,588 |
| Assessment | $489,800 |
Home facts updated by county records
Comparable Sales for 4338 Upland Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.03 | Single-Family Home | $500,000 | 03/18/26 | 3 | 2 | 1,673 | |
0.05 | Single-Family Home | $690,000 | 03/31/26 | 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 | 03/13/26 | 4 | 2 | 1,854 | |
0.24 | Single-Family Home | $625,000 | 12/08/25 | 3 | 1.5 | 1,944 | |
0.26 | Single-Family Home | $670,000 | 05/19/26 | 3 | 2 | 1,708 | |
0.26 | Single-Family Home | $750,000 | 06/20/25 | 3 | 2 | 1,843 | |
0.19 | Single-Family Home | $630,000 | 04/17/26 | 2 | 1.5 | 1,706 | |
0.24 | Single-Family Home | $660,000 | 12/10/25 | 3 | 1.5 | 1,600 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 4338 Upland Drive.
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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Homes for sale near 4338 Upland Drive
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Information is supplied by seller and other third parties and has not been verified. Copyright 2026 – WiREx – All Rights Reserved
Homes for rent near 4338 Upland Drive
4338 Upland Drive, Madison, WI 53705 is a 3 bedroom, 2 bathroom, 1,735 sqft single-family home built in 1954. 4338 Upland Drive is located in Sunset Village, Madison. This property is not currently available for sale. 4338 Upland Drive was last sold on Apr 30, 2026 for $630,000 (10% higher than the asking price of $575,000). The current Trulia Estimate for 4338 Upland Drive is $630,600.