Redwood Walls Meet Terrazzo Floors in This $575K Wisconsin Midcentury
The split-level 1954 home still has many of its original finishes—plus an updated kitchen, bathroom, and powder room.
Location: 4338 Upland Drive, Madison, Wisconsin
Price: $575,000
Year Built: 1954
Renovation Date: 2026
Renovation Designer: Anthony Fenning, Fenning Construction
Footprint: 1,735 square feet (3 bedrooms, 1.5 baths)
Lot Size: 0.22 Acres
From the Agent: "4338 Upland Drive is a period-correct, midcentury-modern home in Madison’s Sunset Village. Clerestory bands catch the light and drag it across original redwood walls. The house has three bedrooms, 1.5 baths, and a 1,700-square-foot, split-level plan that feels exactly as considered as it was when it was built. The home has been thoughtfully updated—new hardwood floors, a redesigned powder room, a refreshed kitchen with period-appropriate proportions—without compromising what makes it significant. It’s nestled on a wooded lot just blocks from Hilldale, and minutes from UW and University Hospital. Some homes are renovated; this one was restored."
The terrazzo flooring at the home’s entry is original.
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
The double-height living room has west- and south-facing floor-to-ceiling windows.
Photo by Shanna Wolf of S. Photography
The home’s fireplace is made from sandstone brick.
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
Original redwood paneling clads the walls throughout the home.
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
In the primary bedroom, glass sliders open to a balcony.
Photo by Shanna Wolf of S. Photography
Photo by Shanna Wolf of S. Photography
The new powder room features a vanity made of walnut and granite.
Photo by Shanna Wolf of S. Photography
The backyard is home to bur oaks, Japanese maples, and more.
Photo by Shanna Wolf of S. Photography
4338 Upland Drive in Madison, Wisconsin, is currently listed for $575,000 by Brogan Brunker and Melissa LeGrand of Christie’s International Real Estate.
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