4338 Upland Dr, Madison, WI 53705
SOLD
MAY 1, 2026

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

  • Map ViewExplore the area around 4338 Upland Dr.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

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

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $575,000Price Per Sqft: $363/sqft
Status Change & Dates
Off Market Date: Tue Mar 24 2026

Active Status

MLS Status: Sold

Location

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

Building

Building Area
Building Area: 1735 Square Feet

Lot Information

Lot Area: 9583.2 sqft

Offer

Listing Terms: Arms Length

Miscellaneous

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

DatePriceEventSource
05/01/2026$630,000Sold
N/A
03/30/2026$575,000PendingWIREX MLS #2017988
03/24/2026$575,000Listed For SaleWIREX MLS #2017988
03/06/2026$3,400ListingRemovedZillow Rentals
02/16/2026$3,400PriceChange
Zillow Rentals
02/15/2026$3,200Listed For RentZillow Rentals
11/14/2022$250,000Sold
N/A

Market trends in Madison

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$423K
$7.67K
MoM
Sale-to-List Price
102.8%
1.0%
MoM
Price per sq ft
$260
$10
MoM
Available listings
704
43
MoM
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Property Tax and Assessment

Year2024
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

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Assigned Schools

These are the assigned schools for 4338 Upland Dr.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

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.
  • Msgt621
    "Walk ability, access to public transportation, close to university and downtown . Access to shopping and restaurants "
  • Mm
    "Walking or biking easy access to us and hospitals and anything else you might want to do. Extra schar"
  • Kteelin g. c.
    "The side streets have low levels of traffic and people do not drive fast. The Sequoya library is within walking distance and there are many parks throughout."
  • ntn0301
    "It's a quiet, clean, nice, safe and convenience neighborhood. Close to many interesting places, downtown, hospital, Hilldale, shopping malls, etc. Good schools, friendly and warm neighbors... Love this place when I lived there."
  • ntn0301
    "Very nice, friendly, convenience and safe neighborhood"

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Homes for sale near 4338 Upland Dr

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Off Market Homes Near 4338 Upland Dr

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