Would people walk alone at night in Windsor, WI?

As of early 2026, 97% of users say people would walk alone at night

Is parking easy in Windsor, WI?

As of early 2026, 91% of users say parking is easy

Is a car needed in Windsor, WI?

As of early 2026, 91% of users say car is needed

Is Windsor, WI dog-friendly?

As of early 2026, 90% of users say it's dog friendly

Are yards well-kept in Windsor, WI?

As of early 2026, 82% of users say yards are well-kept

Do kids play outside in Windsor, WI?

As of early 2026, 82% of users say kids play outside

Is Windsor, WI quiet?

As of early 2026, 76% of users say it's quiet

Does Windsor, WI show holiday spirit?

As of early 2026, 70% of users say there's holiday spirit

Are neighbors friendly in Windsor, WI?

As of early 2026, 67% of users say neighbors are friendly

Are the streets well-lit in Windsor, WI?

As of early 2026, 61% of users say streets are well-lit

Does Windsor, WI have sidewalks?

As of early 2026, 58% of users say there are sidewalks

Are there community events in Windsor, WI?

As of early 2026, 48% of users say there are community events

Is there wildlife in Windsor, WI?

As of early 2026, 47% of users say there's wildlife

Do residents of Windsor, WI plan to stay at least 5 years?

As of early 2026, 37% of users say they plan to stay for at least 5 years

Is Windsor, WI walkable to restaurants?

As of early 2026, 28% of users say it's walkable to restaurants

Is Windsor, WI walkable to grocery stores?

As of early 2026, 15% of users say it's walkable to grocery stores

What is 4375 Van Winkle Way estimated to be worth?

Trulia's estimated value for 4375 Van Winkle Way in Deforest, WI is $385,400 .

What is the price history for 4375 Van Winkle Way?

4375 Van Winkle Way in Deforest, WI last sold for $255,000 in June 2019.

Is Deforest a buyer's or seller's market?

Deforest is currently a seller's market, based on recent for-sale activity.

What do residents say about Deforest?

Residents describe Deforest, WI as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Deforest, WI .

Does 4375 Van Winkle Way have air conditioning?

Yes, 4375 Van Winkle Way in Deforest, WI has air conditioning.

Does 4375 Van Winkle Way have laundry facilities?

Yes, 4375 Van Winkle Way in Deforest, WI has in-unit laundry.

OFF MARKET

4375 Van Winkle Way
Deforest, WI 53532

3 Beds
2 Baths
2,371 sqft

$385,400

Trulia Estimate

as of Aug 24, 2026

$385,400

Trulia Estimate

as of Aug 24, 2026

3 Beds

2 Baths

2,371 sqft

Home Value

Trulia Estimate

$385K

Since last month

$400 (-0.1%)

Since last year

$16K (+4.2%)

Since last sale

$131K (+51.4%)

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 +120% in the last 10 years

Month	Estimated value
2026
August 2026	$386K
July 2026	$387K
June 2026	$394K
May 2026	$391K
April 2026	$394K
March 2026	$387K
February 2026	$374K
January 2026	$368K
2025
December 2025	$369K
November 2025	$366K
October 2025	$365K
September 2025	$376K
August 2025	$371K
July 2025	$378K
June 2025	$378K
May 2025	$384K
April 2025	$385K
March 2025	$375K
February 2025	$365K
January 2025	$357K
2024
December 2024	$361K
November 2024	$363K
October 2024	$355K
September 2024	$358K
August 2024	$364K
July 2024	$367K
June 2024	$371K
May 2024	$374K
April 2024	$372K
March 2024	$367K
February 2024	$356K
January 2024	$345K
2023
December 2023	$340K
November 2023	$340K
October 2023	$345K
September 2023	$345K
August 2023	$342K
July 2023	$346K
June 2023	$347K
May 2023	$313K
April 2023	$307K
March 2023	$300K
February 2023	$291K
January 2023	$288K
2022
December 2022	$287K
November 2022	$290K
October 2022	$291K
September 2022	$293K
August 2022	$293K
July 2022	$296K
June 2022	$299K
May 2022	$296K
April 2022	$294K
March 2022	$293K
February 2022	$283K
January 2022	$279K
2021
December 2021	$276K
November 2021	$275K
October 2021	$275K
September 2021	$276K
August 2021	$278K
July 2021	$283K
June 2021	$291K
May 2021	$299K
April 2021	$293K
March 2021	$289K
February 2021	$286K
January 2021	$282K
2020
December 2020	$282K
November 2020	$281K
October 2020	$275K
September 2020	$276K
August 2020	$273K
July 2020	$271K
June 2020	$270K
May 2020	$268K
April 2020	$268K
March 2020	$266K
February 2020	$263K
January 2020	$260K
2019
December 2019	$259K
November 2019	$257K
October 2019	$258K
September 2019	$256K
August 2019	$257K
July 2019	$256K
June 2019	$255K
May 2019	$272K
April 2019	$246K
March 2019	$235K
February 2019	$229K
January 2019	$239K
2018
December 2018	$239K
November 2018	$238K
October 2018	$231K
September 2018	$232K
August 2018	$232K
July 2018	$229K
June 2018	$223K
May 2018	$225K
April 2018	$217K
March 2018	$217K
February 2018	$207K
January 2018	$207K
2017
December 2017	$206K
November 2017	$184K
October 2017	$182K
September 2017	$183K
August 2017	$180K
July 2017	$185K
June 2017	$185K
May 2017	$182K
April 2017	$181K
March 2017	$183K
February 2017	$183K
January 2017	$184K
2016
December 2016	$186K
November 2016	$183K
October 2016	$180K
September 2016	$175K
August 2016	$176K

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
4398 Van Winkle Way, Deforest, WI	0.05	Single-Family Home	$480,000	01/20/26	3	2	2,492
4383 Van Winkle Way, Deforest, WI	0.04	Single-Family Home	$503,000	08/03/26	3	2	2,146
6926 Old Amsterdam Way, Deforest, WI	0.13	Single-Family Home	$496,500	03/30/26	3	2.5	2,350
4400 Singel Way, Deforest, WI	0.26	Single-Family Home	$469,900	11/13/25	3	3.5	1,997
4396 Low Countries Rd, Deforest, WI	0.11	Single-Family Home	$499,000	03/02/26	4	2.5	2,011
6776 Dawn Dr, Windsor, WI	0.41	Single-Family Home	$420,000	06/16/26	3	2	1,972
4380 Van Winkle Way, Deforest, WI	0.03	Single-Family Home	$545,000	06/09/26	4	3.5	2,821
4401 Cradle Hill Dr, Deforest, WI	0.37	Single-Family Home	$450,000	05/01/26	3	2.5	1,848
4414 Gray Rd, Deforest, WI	0.10	Single-Family Home	$210,000	08/07/26	4	2	1,782
4389 Curry Ln, Windsor, WI	0.52	Single-Family Home	$367,500	06/04/26	3	1.5	1,484

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
4380 Van Winkle Way, Deforest, WI 53532	0.03	$545,000	4	3.5	2,821	Recently Sold
6875 & 6879 Rembrandt Rd, Windsor, WI 53598	0.02	$708,200	8	5	4,050	Off Market
4398 Van Winkle Way, Deforest, WI 53532	0.05	$480,000	3	2	2,492	Recently Sold
4383 Van Winkle Way, Deforest, WI 53532	0.04	$503,000	3	2	2,146	Recently Sold
4387 Van Winkle Way, Deforest, WI 53532	0.06	$570,700	4	3	2,459	Off Market
4358 Gray Rd, Deforest, WI 53532	0.09	$421,400	3	1.5	2,150	Off Market
4396 Low Countries Rd, Deforest, WI 53532	0.11	$499,000	4	2.5	2,011	Recently Sold
4414 Gray Rd, Deforest, WI 53532	0.10	$210,000	4	2	1,782	Recently Sold
6906 Rembrandt Rd, Deforest, WI 53532	0.13	$439,200	3	2.5	1,602	Off Market
6914 Old Amsterdam Way, Deforest, WI 53532	0.13	$506,200	4	2.5	3,017	Off Market
6906 Rembrandt Rd, Windsor, WI 53598	0.13	$447,400	3	2.5	1,716	Off Market
6926 Old Amsterdam Way, Deforest, WI 53532	0.13	$496,500	3	2.5	2,350	Recently Sold

Local Information

Map ViewExplore the area around 4375 Van Winkle Way.
Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

2002

Living Area

2,371 sqft

Price/Sqft

$163

Parking

Garage

About this House

This single-family home is located at 4375 Van Winkle Way, Deforest, WI. 4375 Van Winkle Way is in Deforest, WI and in ZIP code 53532. This property has 3 bedrooms, 2 bathrooms and approximately 2,371 sqft of floor space. This property has a lot size of 8276 sqft and was built in 2002.

4375 Van Winkle Way, Deforest, WI 53532 is a 3 bedroom, 2 bathroom, 2,371 sqft single-family home built in 2002. It last sold for $255,000 on Jun 28, 2019. It is currently off market. The Trulia Estimate is $385,400, with a rent estimate of $2,668/month.

Home Details for 4375 Van Winkle Way

Interior Features
Heating & Cooling Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details Types of Rooms: Walk In Closet
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher

Property Information
Year Built Year Built: 2002
Property Type / Style Property Type: Single Family Home

Exterior Features
Exterior Home Features DeckExterior: Stone, Vinyl, BrickPatio
Parking & Garage GarageParking: Garage Attached

Lot Information
Lot Area: 8276 sqft

Price and Tax history

Date	Event	Price
Jun 28, 2019 Source: N/A	Sold	$255,000
May 16, 2019 Source: Agent Provided	PriceChange	$269,900 Price decreased by 3%
May 14, 2019 Source: Agent Provided	Listed For Sale	$278,000
Nov 7, 2012 Source: Agent Provided	ListingRemoved	$174,900
Nov 6, 2012 Source: Agent Provided	Listed For Sale	$174,900
Nov 27, 2006 Source: N/A	Sold	$177,000

Year	Property tax	Tax assessment
2024	$4,112	$300,000

Additional Cost

Market trends in Windsor

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

18MoM

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.

What Locals Say about Windsor

At least 30 Trulia users voted on each feature.

97 % Say people would walk alone at night
91 % Say parking is easy
91 % Say car is needed
90 % Say it's dog friendly
82 % Say yards are well-kept
82 % Say kids play outside
76 % Say it's quiet
70 % Say there's holiday spirit
67 % Say neighbors are friendly
61 % Say streets are well-lit
58 % Say there are sidewalks
48 % Say there are community events
47 % Say there's wildlife
37 % Say they plan to stay for at least 5 years
28 % Say it's walkable to restaurants
15 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Trulia User
Resident
1mo ago
"Commuters use personal vehicles 100% of the time."
0
Flag
Ayang1127
Prev. Resident
7y ago
"Large yards, quiet neighbors, and minimal traffic streets. Dog park and trails near by too within walking distance "
0
Flag
Jmclain
Resident
7y ago
"Great place to raise a family. Safe at night. Good schools and friendly neighbors are a plus. Roads well maintained and a nice pArk nearby. "
2
Flag
Lmickeymouse1
Resident
7y ago
"this neighborhood isn't special, we live across from Windsor Breads. They like to park at the end of people's driveways, and it's hard to see around cars,alot of times customers block driveways. Windsor Breads, dont clear front for parking in the winter ,for there customers to park, it's very dangerous. "
0
Flag
Erv135xx
Resident
8y ago
"I lived here 40 plus year and.they have a nice 3 mile walking path along a check and woods very nice used a lot"
0
Flag
Kristen M.
13y ago
"Beautiful secluded quiet neighborhood close enough to highway 19 to get anywhere quickly but far enough off the beaten path to have only local traffic in the neighborhood."
0
Flag
Matthew
13y ago
"I have visited family in the area numerous times and we love it!!!"
0
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 4375 Van Winkle Way

What is 4375 Van Winkle Way estimated to be worth?
Trulia's estimated value for 4375 Van Winkle Way in Deforest, WI is $385,400.
What is the price history for 4375 Van Winkle Way?
4375 Van Winkle Way in Deforest, WI last sold for $255,000 in June 2019.
Is Deforest a buyer's or seller's market?
Deforest is currently a seller's market, based on recent for-sale activity.
What do residents say about Deforest?
Residents describe Deforest, WI as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Deforest, WI.
Does 4375 Van Winkle Way have air conditioning?
Yes, 4375 Van Winkle Way in Deforest, WI has air conditioning.
Does 4375 Van Winkle Way have laundry facilities?
Yes, 4375 Van Winkle Way in Deforest, WI has in-unit laundry.