4338 Upland Drive, Madison, WI 53705
SOLD
APR 30, 2026

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

Map showing home location
© Google
-- mins to
Commute Destination

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
69 days ago

Home Details for 4338 Upland Drive

Active Status

MLS Status: Closed

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $575,000Price Per Sqft: $363/sqft

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

HOA

Association for this Listing: South Central Wisconsin MLS

Lot Information

Lot Area: 9583.2 sqft

Listing Info

Special Conditions: Arms Length

Miscellaneous

Mls Number: 2017988Living Area Range: 1501-1750Living Area Range Units: Square FeetMunicipality: MadisonAttribution Contact: Pref: 608-438-2130Above Grade Unfinished Area: 1735

Additional Information

Source Internet Entire Listing Display
Last check for updates: about 4 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

DatePriceEventSource
04/30/2026$630,000Sold
WIREX MLS #2017988
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
11/10/2022$250,000Sold
WIREX MLS #1946767
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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 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

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Assigned Schools

These are the assigned schools for 4338 Upland Drive.
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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Information is supplied by seller and other third parties and has not been verified. Copyright 2026 – WiREx – All Rights Reserved

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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.