Is Sunset Village, Madison, WI walkable to restaurants?

As of early 2026, 100% of users say it's walkable to restaurants

Does Sunset Village, Madison, WI have sidewalks?

As of early 2026, 100% of users say there are sidewalks

Is Sunset Village, Madison, WI dog-friendly?

As of early 2026, 96% of users say it's dog friendly

Do kids play outside in Sunset Village, Madison, WI?

As of early 2026, 92% of users say kids play outside

Is Sunset Village, Madison, WI walkable to grocery stores?

As of early 2026, 86% of users say it's walkable to grocery stores

Would people walk alone at night in Sunset Village, Madison, WI?

As of early 2026, 83% of users say people would walk alone at night

Is parking easy in Sunset Village, Madison, WI?

As of early 2026, 74% of users say parking is easy

Are yards well-kept in Sunset Village, Madison, WI?

As of early 2026, 74% of users say yards are well-kept

Is there wildlife in Sunset Village, Madison, WI?

As of early 2026, 74% of users say there's wildlife

Does Sunset Village, Madison, WI show holiday spirit?

As of early 2026, 73% of users say there's holiday spirit

Do residents of Sunset Village, Madison, WI plan to stay at least 5 years?

As of early 2026, 72% of users say they plan to stay for at least 5 years

Are the streets well-lit in Sunset Village, Madison, WI?

As of early 2026, 72% of users say streets are well-lit

Are neighbors friendly in Sunset Village, Madison, WI?

As of early 2026, 71% of users say neighbors are friendly

Is a car needed in Sunset Village, Madison, WI?

As of early 2026, 57% of users say car is needed

Is Sunset Village, Madison, WI quiet?

As of early 2026, 56% of users say it's quiet

Are there community events in Sunset Village, Madison, WI?

As of early 2026, 39% of users say there are community events

What is 4342 Upland Dr estimated to be worth?

Trulia's estimated value for 4342 Upland Dr in Madison, WI is $356,300 .

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.

What do residents say about the Sunset Village neighborhood?

Residents describe the Sunset Village neighborhood in Madison, WI as walkable to restaurants, pedestrian-friendly, and dog-friendly. See recently sold homes in Sunset Village, Madison .

How big is the lot at 4342 Upland Dr?

The lot at 4342 Upland Dr in Madison, WI is about 0.21 acres (9,362 sq ft).

Does 4342 Upland Dr have parking?

Yes, 4342 Upland Dr in Madison, WI has on-site parking.

OFF MARKET

$356,300

Trulia Estimate

3 Beds
1 Bath
864 sqft

4342 Upland Dr, Madison, WI 53705

Sunset Village

Refinance Your Home

Home Value

Trulia Estimate

$356K

Since last month

$3K (-0.7%)

Since last year

$7K (+1.9%)

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 +58% in the last 10 years

Month	Estimated value
2026
August 2026	$355K
July 2026	$358K
June 2026	$373K
May 2026	$370K
April 2026	$365K
March 2026	$355K
February 2026	$347K
January 2026	$343K
2025
December 2025	$336K
November 2025	$336K
October 2025	$338K
September 2025	$350K
August 2025	$348K
July 2025	$361K
June 2025	$355K
May 2025	$360K
April 2025	$366K
March 2025	$352K
February 2025	$338K
January 2025	$320K
2024
December 2024	$325K
November 2024	$325K
October 2024	$326K
September 2024	$329K
August 2024	$333K
July 2024	$341K
June 2024	$348K
May 2024	$345K
April 2024	$343K
March 2024	$333K
February 2024	$320K
January 2024	$304K
2023
December 2023	$306K
November 2023	$302K
October 2023	$310K
September 2023	$313K
August 2023	$315K
July 2023	$321K
June 2023	$322K
May 2023	$320K
April 2023	$306K
March 2023	$295K
February 2023	$288K
January 2023	$287K
2022
December 2022	$286K
November 2022	$290K
October 2022	$294K
September 2022	$296K
August 2022	$298K
July 2022	$310K
June 2022	$315K
May 2022	$315K
April 2022	$310K
March 2022	$301K
February 2022	$281K
January 2022	$275K
2021
December 2021	$273K
November 2021	$274K
October 2021	$276K
September 2021	$281K
August 2021	$287K
July 2021	$294K
June 2021	$313K
May 2021	$328K
April 2021	$320K
March 2021	$307K
February 2021	$302K
January 2021	$298K
2020
December 2020	$293K
November 2020	$288K
October 2020	$293K
September 2020	$296K
August 2020	$288K
July 2020	$296K
June 2020	$301K
May 2020	$301K
April 2020	$304K
March 2020	$308K
February 2020	$299K
January 2020	$300K
2019
December 2019	$290K
November 2019	$277K
October 2019	$256K
September 2019	$251K
August 2019	$254K
July 2019	$253K
June 2019	$252K
May 2019	$254K
April 2019	$249K
March 2019	$247K
February 2019	$249K
January 2019	$253K
2018
December 2018	$251K
November 2018	$244K
October 2018	$241K
September 2018	$246K
August 2018	$254K
July 2018	$255K
June 2018	$257K
May 2018	$262K
April 2018	$261K
March 2018	$256K
February 2018	$253K
January 2018	$258K
2017
December 2017	$260K
November 2017	$251K
October 2017	$255K
September 2017	$254K
August 2017	$250K
July 2017	$250K
June 2017	$249K
May 2017	$244K
April 2017	$239K
March 2017	$237K
February 2017	$232K
January 2017	$228K
2016
December 2016	$226K
November 2016	$229K
October 2016	$230K
September 2016	$227K
August 2016	$225K

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
4334 Upland Dr, Madison, WI	0.02	Single-Family Home	$450,000	11/26/25	3	1	1,497
326 S Midvale Blvd, Madison, WI	0.14	Single-Family Home	$380,000	07/01/26	2	1	941
113 S Segoe Rd, Madison, WI	0.30	Single-Family Home	$385,200	09/26/25	3	1	1,067
4338 Upland Dr, Madison, WI	0.01	Single-Family Home	$630,000	05/01/26	3	1.5	1,735
4345 Hillcrest Dr, Madison, WI	0.04	Single-Family Home	$500,000	03/20/26	3	2	1,673
454 S Midvale Blvd, Madison, WI	0.36	Single-Family Home	$455,000	11/26/25	3	1	1,390
37 S Hillside Ter, Madison, WI	0.23	Single-Family Home	$480,000	02/09/26	2	1	1,344
2 S Owen Dr, Madison, WI	0.34	Single-Family Home	$353,000	08/13/26	2	1	768
114 S Segoe Rd, Madison, WI	0.33	Single-Family Home	$440,000	03/18/26	3	2	1,221
4329 Hillcrest Dr, Madison, WI	0.06	Single-Family Home	$690,000	04/01/26	3	1.5	1,703

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
4334 Upland Dr, Madison, WI 53705	0.02	$450,000	3	1	1,497	Recently Sold
4322 Upland Dr, Madison, WI 53705	0.06	$615,300	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	0.05	$456,800	4	2	1,428	Off Market
4329 Hillcrest Dr, Madison, WI 53705	0.06	$690,000	3	1.5	1,703	Recently Sold
313 S Midvale Blvd, Madison, WI 53705	0.09	$510,000	4	2	1,854	Recently Sold
4312 Upland Dr, Madison, WI 53705	0.10	$686,200	3	1.5	1,862	Off Market
4346 Hillcrest Dr, Madison, WI 53705	0.07	$541,800	3	2	2,010	Off Market
318 Falles Ct, Madison, WI 53705	0.11	$650,100	3	2	2,038	Off Market
306 S Midvale Blvd, Madison, WI 53705	0.10	$422,400	2	1	1,472	Off Market
322 Falles Ct, Madison, WI 53705	0.12	$612,700	3	2	1,894	Off Market

Local Information

Map ViewExplore the area around 4342 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

1951

Living Area

864 sqft

Price/Sqft

$412

About this House

4342 Upland Drive (Hilldale (Madison))
Address: 4342 Upland Drive, Madison WI 53705

Description: more than 900 sq feet with 3 bedroom, one story, park off street, large yard with trees and grass, on bus line to campus/downtown, property photos/inspection available, nice neighborhood,

4342 Upland Dr, Madison, WI 53705 is a 3 bedroom, 1 bathroom, 864 sqft single-family home in Sunset Village, built in 1951. More recently, it was listed as a rental in July 2013 with an asking price of $1,100 per month. That rental listing was removed on July 26, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $356,300, with a rent estimate of $2,302/month.

Home Details for 4342 Upland Dr

Interior Features
Interior Details BasementTypes of Rooms: Family Room, Master Bath
Heating & Cooling Heating: Forced Air, Stove, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1
Appliances & Utilities MicrowaveRefrigerator

Exterior Features
Exterior Home Features Roof: AsphaltDeckExterior: VinylLawn
Parking & Garage Parking: Off Street

Property Information
Year Built Year Built: 1951Year Updated: 1965
Property Type / Style Property Type: Single Family HomeArchitecture: Bungalow

Community
Units in Building: 1

Lot Information
Lot Area: 9362 sqft

Price and Tax history

Date	Event	Price
Mar 24, 2021 Source: N/A	ListingRemoved
Oct 7, 2018 Source: N/A	ListingRemoved	$285,000
Jul 9, 2018 Source: N/A	Listed For Sale	$285,000
Jul 12, 2017 Source: N/A	ListingRemoved	$265,000
Apr 18, 2017 Source: N/A	PriceChange	$265,000 Price increased by 6%
Feb 9, 2017 Source: N/A	PriceChange	$250,000 Price decreased by 9%
Jan 6, 2017 Source: N/A	PriceChange	$275,000 Price decreased by 8%
Sep 13, 2016 Source: N/A	Listed For Sale	$300,000
Jul 26, 2013 Source: N/A	ListingRemoved	$1,100
Jul 12, 2013 Source: N/A	Listed For Rent	$1,100

Year	Property tax	Tax assessment
2024	$6,583	$336,300

Additional Cost

Market trends in Madison

Last updated July 2026

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

2 Homes For You
Buy: $525k - $670k

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
Resident
1y ago
"Walk ability, access to public transportation, close to university and downtown . Access to shopping and restaurants "
0
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Mm
Resident
2y ago
"Walking or biking easy access to us and hospitals and anything else you might want to do. Extra schar"
0
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Kteelin g. c.
Resident
7y ago
"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
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ntn0301
14y ago
"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
14y ago
"Very nice, friendly, convenience and safe neighborhood"
0
Flag

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Frequently asked questions about 4342 Upland Dr

What is 4342 Upland Dr estimated to be worth?
Trulia's estimated value for 4342 Upland Dr in Madison, WI is $356,300.
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.
What do residents say about the Sunset Village neighborhood?
Residents describe the Sunset Village neighborhood in Madison, WI as walkable to restaurants, pedestrian-friendly, and dog-friendly. See recently sold homes in Sunset Village, Madison.
How big is the lot at 4342 Upland Dr?
The lot at 4342 Upland Dr in Madison, WI is about 0.21 acres (9,362 sq ft).
Does 4342 Upland Dr have parking?
Yes, 4342 Upland Dr in Madison, WI has on-site parking.