4334 Upland Dr, Madison, WI 53705
Property image
Property image
SOLD
NOV 26, 2025

$571,000

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,497 sqft

4334 Upland Dr, Madison, WI 53705

Sunset Village
Est. Refi. Payment $3,748/mo*
Refinance Your Home
Currently Off Market - Sold Nov 26, 2025 for $450,000

Home Value

Trulia Estimate
$571K
Since last month
Increased$3K (+0.5%)
Since last year
Increased$114K (+25%)
Since last sale
Increased$121K (+26.9%)
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 +110% in the last 10 years
MonthEstimated value
2026
August 2026$571K
August 2026$565K
July 2026$568K
June 2026$593K
May 2026$591K
April 2026$447K
March 2026$445K
February 2026$443K
January 2026$442K
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
0.04
Single-Family Home
$500,000
03/20/26
3
2
1,673
4338 Upland Dr, Madison, WI
0.01
Single-Family Home
$630,000
05/01/26
3
1.5
1,735
37 S Hillside Ter, Madison, WI
0.21
Single-Family Home
$480,000
02/09/26
2
1
1,344
454 S Midvale Blvd, Madison, WI
0.38
Single-Family Home
$455,000
11/26/25
3
1
1,390
4329 Hillcrest Dr, Madison, WI
0.04
Single-Family Home
$690,000
04/01/26
3
1.5
1,703
313 S Midvale Blvd, Madison, WI
0.11
Single-Family Home
$510,000
03/18/26
4
2
1,854
326 S Midvale Blvd, Madison, WI
0.16
Single-Family Home
$380,000
07/01/26
2
1
941

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
4338 Upland Dr, Madison, WI 53705
0.01
$630,000
3
1.5
1,735
Recently Sold
4322 Upland Dr, Madison, WI 53705
0.04
$618,800
3
1.5
1,646
Off Market
4345 Hillcrest Dr, Madison, WI 53705
0.04
$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
0.04
$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
0.08
$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
0.12
$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 4334 Upland Dr.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1956
1,497 sqft
$301/sqft
Garage

About this House

This Mid Century Modern home is very functional and made for simple living. It is located in the heart of the Midvale Area close to everything Madison has to offer. Home is in need of some love so bring all those ideas and make it your own. Only room that has been updated is the bath. Tiled shower and vanity. Lower-level family room is large and has walkout to back patio. Home has a deep, attached one car garage and sits on a wooded corner lot that has no home directly behind it. New Furnace installed 10/7/2025.
4334 Upland Dr, Madison, WI 53705 is a 3 bedroom, 1 bathroom, 1,497 sqft single-family home in Sunset Village, built in 1956. It last sold for the $450,000 asking price on Nov 26, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $571,000, with a rent estimate of $2,616/month.
Last check for updates: about 11 hours ago
Listed by Rich Roberts
Century 21 Affiliated Roessler
Bought with: The 608 Team, EXP Realty, LLC
Source: SCWMLS, MLS#2010171

Home Details for 4334 Upland Dr

Active Status

MLS Status: Sold

Interior Features

Interior Details
Basement: Full,Walk-Out AccessNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1497 Square Feet
Appliances & Utilities
Utilities: Internet - CableAppliances: Washer, Dryer, Water Softener IncludedDryerLaundry: Lower LevelWasher
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace
Levels, Entrance, & Accessibility
Stories: 1Levels: One

Exterior Features

Exterior Home Features
Patio / Porch: Deck, PatioFoundation: Poured concrete foundatn
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 1Parking: 1 car,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1008 Square Feet

Property Information

Year Built
Year Built: 1956
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Wood Siding
Property Information
Included in Sale: Refrigerator, Range/Oven, Dishwasher, Washer, Dryer, Water SoftenerParcel Number: 070920414251

Price & Status

Price
List Price: $450,000Price Per Sqft: $301/sqft
Status Change & Dates
Off Market Date: Thu Oct 09 2025

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

Agent Information

Buyer Agent
Buyer Company Name: The 608 Team

Building

Building Area
Building Area: 1497 Square Feet

Lot Information

Lot Area: 8712 sqft

Offer

Listing Terms: Arms Length

Miscellaneous

BasementMls Number: 2010171Attribution Contact: Off: 608-798-4000Above Grade Unfinished Area: 1008

Price and Tax history

DateEventPrice
Nov 26, 2025
Source: SCWMLS #2010171
Sold
$450,000
Oct 27, 2025
Source: WIREX MLS #2010171
Contingent
$450,000
Oct 9, 2025
Source: WIREX MLS #2010171
Listed For Sale
$450,000

Market trends in Madison

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$429K
$2.5KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$259
$7MoM
Available listings
551
5MoM

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 4334 Upland Dr

  • What is 4334 Upland Dr estimated to be worth?
    Trulia's estimated value for 4334 Upland Dr in Madison, WI is $571,000.
  • What is the price history for 4334 Upland Dr?
    4334 Upland Dr in Madison, WI last sold for $450,000 in November 2025.
  • 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 $429K. That is up $2.5K from the prior month.
  • Does 4334 Upland Dr have air conditioning?
    Yes, 4334 Upland Dr in Madison, WI has air conditioning.
  • Does 4334 Upland Dr have laundry facilities?
    Yes, 4334 Upland Dr in Madison, WI has in-unit laundry.

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