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

$631,600

Trulia Estimate
  • 3 Beds
  • 1.5 Baths
  • 1,735 sqft

4338 Upland Dr, Madison, WI 53705

Sunset Village
Refinance Your Home
Currently Off Market - Sold May 1, 2026 for $630,000 (10% above list price)

Home Value

Trulia Estimate
$632K
Since last month
Decreased$2K (-0.3%)
Since last year
Increased$76K (+13.7%)
Since last sale
$200 (0%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +101% in the last 10 years
MonthEstimated value
2026
August 2026$630K
August 2026$630K
July 2026$632K
June 2026$634K
May 2026$632K
April 2026$618K
March 2026$611K
February 2026$572K
January 2026$557K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4345 Hillcrest Dr, Madison, WI
0.03
Single-Family Home
$500,000
03/20/26
3
2
1,673
4329 Hillcrest Dr, Madison, WI
0.05
Single-Family Home
$690,000
04/01/26
3
1.5
1,703
4334 Upland Dr, Madison, WI
0.01
Single-Family Home
$450,000
11/26/25
3
1
1,497
313 S Midvale Blvd, Madison, WI
0.11
Single-Family Home
$510,000
03/18/26
4
2
1,854
4129 Hillcrest Dr, Madison, WI
0.24
Single-Family Home
$625,000
12/10/25
3
1.5
1,944
4206 Bagley Pkwy, Madison, WI
0.26
Single-Family Home
$670,000
05/22/26
3
2
1,708
122 S Segoe Rd, Madison, WI
0.30
Single-Family Home
$532,500
06/18/26
3
2
1,793
321 S Owen Dr, Madison, WI
0.19
Single-Family Home
$630,000
04/17/26
2
1.5
1,706
429 S Midvale Blvd, Madison, WI
0.29
Single-Family Home
$550,000
06/26/26
3
2
2,007

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
4334 Upland Dr, Madison, WI 53705
0.01
$450,000
3
1
1,497
Recently Sold
4322 Upland Dr, Madison, WI 53705
0.06
$618,800
3
1.5
1,646
Off Market
4345 Hillcrest Dr, Madison, WI 53705
0.03
$500,000
3
2
1,673
Recently Sold
201 S Midvale Blvd, Madison, WI 53705
0.04
$455,400
4
2
1,428
Off Market
4329 Hillcrest Dr, Madison, WI 53705
0.05
$690,000
3
1.5
1,703
Recently Sold
313 S Midvale Blvd, Madison, WI 53705
0.11
$510,000
4
2
1,854
Recently Sold
4312 Upland Dr, Madison, WI 53705
0.09
$686,200
3
1.5
1,862
Off Market
4346 Hillcrest Dr, Madison, WI 53705
0.06
$544,500
3
2
2,010
Off Market
318 Falles Ct, Madison, WI 53705
0.12
$650,100
3
2
2,038
Off Market
306 S Midvale Blvd, Madison, WI 53705
0.11
$421,100
2
1
1,472
Off Market
322 Falles Ct, Madison, WI 53705
0.13
$615,800
3
2
1,894
Off Market

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

Single-Family Home
Built in 1954
1,735 sqft
$363/sqft
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $631,600, with a rent estimate of $2,984/month.
Last check for updates: about 17 hours ago
Listed by Melissa LeGrand
@properties-elleven Christie's International
Bought with: Melissa LeGrand, @properties-elleven Christie's International
Source: SCWMLS, MLS#2017988

Home Details for 4338 Upland Dr

Active Status

MLS Status: Sold

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

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

Price and Tax history

DateEventPrice
May 1, 2026
Source: N/A
Sold
$630,000
Mar 30, 2026
Source: WIREX MLS #2017988
Pending
$575,000
Mar 24, 2026
Source: WIREX MLS #2017988
Listed For Sale
$575,000
Mar 6, 2026
Source: Zillow Rentals
ListingRemoved
$3,400
Feb 16, 2026
Source: Zillow Rentals
PriceChange
$3,400
Price increased by 6%

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$427K
$3.33KMoM
Sale-to-List Price
102.4%
0.3%MoM
Price per sq ft
$266
$5MoM
Available listings
555
149MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Sunset Village
See Local Highlights
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 "
    0
    Flag
  • Mm
    "Walking or biking easy access to us and hospitals and anything else you might want to do. Extra schar"
    0
    Flag
  • 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."
    0
    Flag
  • 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."
    0
    Flag
  • ntn0301
    "Very nice, friendly, convenience and safe neighborhood"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 4338 Upland Dr

  • What is 4338 Upland Dr estimated to be worth?
    Trulia's estimated value for 4338 Upland Dr in Madison, WI is $631,600.
  • What is the price history for 4338 Upland Dr?
    4338 Upland Dr in Madison, WI last sold for $630,000 in May 2026.
  • Is Madison a buyer's or seller's market?
    Madison is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $427K. That is up $3.33K from the prior month.
  • Does 4338 Upland Dr have air conditioning?
    Yes, 4338 Upland Dr in Madison, WI has air conditioning.
  • Does 4338 Upland Dr have laundry facilities?
    Yes, 4338 Upland Dr in Madison, WI has in-unit laundry.

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