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 4402 Van Winkle Way estimated to be worth?

Trulia's estimated value for 4402 Van Winkle Way in Deforest, WI is $464,600 .

What is the price history for 4402 Van Winkle Way?

4402 Van Winkle Way in Deforest, WI last sold for $214,500 in February 2012.

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 .

How big is the lot at 4402 Van Winkle Way?

The lot at 4402 Van Winkle Way in Deforest, WI is about 0.28 acres (12,197 sq ft).

OFF MARKET

$464,600

Trulia Estimate

4 Beds
3 Baths
2,023 sqft (on 0.28 acres)

4402 Van Winkle Way, Deforest, WI 53532

Refinance Your Home

Currently Off Market - Sold Feb 24, 2012 for $214,500

Home Value

Trulia Estimate

$465K

Since last month

$3K (-0.7%)

Since last year

$13K (+2.9%)

Since last sale

$251K (+116.8%)

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 +82% in the last 10 years

Month	Estimated value
2026
August 2026	$465K
August 2026	$465K
July 2026	$469K
June 2026	$477K
May 2026	$474K
April 2026	$479K
March 2026	$470K
February 2026	$457K
January 2026	$445K
2025
December 2025	$445K
November 2025	$446K
October 2025	$443K
September 2025	$456K
August 2025	$452K
July 2025	$456K
June 2025	$459K
May 2025	$461K
April 2025	$459K
March 2025	$454K
February 2025	$442K
January 2025	$434K
2024
December 2024	$437K
November 2024	$438K
October 2024	$437K
September 2024	$438K
August 2024	$450K
July 2024	$451K
June 2024	$453K
May 2024	$457K
April 2024	$451K
March 2024	$447K
February 2024	$435K
January 2024	$417K
2023
December 2023	$415K
November 2023	$415K
October 2023	$423K
September 2023	$424K
August 2023	$424K
July 2023	$431K
June 2023	$429K
May 2023	$428K
April 2023	$417K
March 2023	$407K
February 2023	$398K
January 2023	$394K
2022
December 2022	$392K
November 2022	$397K
October 2022	$400K
September 2022	$401K
August 2022	$402K
July 2022	$416K
June 2022	$424K
May 2022	$423K
April 2022	$419K
March 2022	$414K
February 2022	$393K
January 2022	$386K
2021
December 2021	$380K
November 2021	$378K
October 2021	$376K
September 2021	$377K
August 2021	$380K
July 2021	$385K
June 2021	$381K
May 2021	$370K
April 2021	$368K
March 2021	$347K
February 2021	$350K
January 2021	$340K
2020
December 2020	$330K
November 2020	$335K
October 2020	$345K
September 2020	$342K
August 2020	$317K
July 2020	$316K
June 2020	$312K
May 2020	$312K
April 2020	$313K
March 2020	$315K
February 2020	$305K
January 2020	$304K
2019
December 2019	$303K
November 2019	$303K
October 2019	$301K
September 2019	$298K
August 2019	$298K
July 2019	$297K
June 2019	$299K
May 2019	$307K
April 2019	$310K
March 2019	$306K
February 2019	$311K
January 2019	$304K
2018
December 2018	$303K
November 2018	$300K
October 2018	$295K
September 2018	$294K
August 2018	$296K
July 2018	$298K
June 2018	$298K
May 2018	$298K
April 2018	$287K
March 2018	$285K
February 2018	$280K
January 2018	$282K
2017
December 2017	$282K
November 2017	$274K
October 2017	$273K
September 2017	$271K
August 2017	$271K
July 2017	$272K
June 2017	$279K
May 2017	$273K
April 2017	$278K
March 2017	$271K
February 2017	$266K
January 2017	$268K
2016
December 2016	$266K
November 2016	$261K
October 2016	$258K
September 2016	$255K

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
4396 Low Countries Rd, Deforest, WI	0.06	Single-Family Home	$499,000	03/02/26	4	2.5	2,011
4383 Van Winkle Way, Deforest, WI	0.04	Single-Family Home	$503,000	08/03/26	3	2	2,146
4398 Van Winkle Way, Deforest, WI	0.02	Single-Family Home	$480,000	01/20/26	3	2	2,492
6926 Old Amsterdam Way, Deforest, WI	0.10	Single-Family Home	$496,500	03/30/26	3	2.5	2,350
4380 Van Winkle Way, Deforest, WI	0.06	Single-Family Home	$545,000	06/09/26	4	3.5	2,821
4401 Cradle Hill Dr, Deforest, WI	0.33	Single-Family Home	$450,000	05/01/26	3	2.5	1,848
4400 Singel Way, Deforest, WI	0.23	Single-Family Home	$469,900	11/13/25	3	3.5	1,997
4040 Whistle Rock, Deforest, WI	0.45	Single-Family Home	$567,000	07/29/26	4	3	2,536
4414 Gray Rd, Deforest, WI	0.08	Single-Family Home	$210,000	08/17/26	4	2	1,782
6776 Dawn Dr, Windsor, WI	0.45	Single-Family Home	$420,000	06/16/26	3	2	1,972

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
4398 Van Winkle Way, Deforest, WI 53532	0.02	$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	0.04	$570,700	4	3	2,459	Off Market
4380 Van Winkle Way, Deforest, WI 53532	0.06	$545,000	4	3.5	2,821	Recently Sold
6875 & 6879 Rembrandt Rd, Windsor, WI 53598	0.08	$707,500	8	5	4,050	Off Market
4396 Low Countries Rd, Deforest, WI 53532	0.06	$499,000	4	2.5	2,011	Recently Sold
4414 Gray Rd, Deforest, WI 53532	0.08	$210,000	4	2	1,782	Recently Sold
6914 Old Amsterdam Way, Deforest, WI 53532	0.08	$507,000	4	2.5	3,017	Off Market
6926 Old Amsterdam Way, Deforest, WI 53532	0.10	$496,500	3	2.5	2,350	Recently Sold
4358 Gray Rd, Deforest, WI 53532	0.15	$421,200	3	1.5	2,150	Off Market
6906 Rembrandt Rd, Deforest, WI 53532	0.15	$437,700	3	2.5	1,602	Off Market
6906 Rembrandt Rd, Windsor, WI 53598	0.15	$447,500	3	2.5	1,716	Off Market

Local Information

Map ViewExplore the area around 4402 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

Lot Size

0.28 acres

Living Area

2,023 sqft

Price/Sqft

$230

About this House

ALL YOU HAVE TO DO IS MOVE IN AND MOW THE LAWN!! THIS WONDERFULLY CARED FOR HOME OFFERS YOU THE VERSATILITY OF 4 BEDRMS, 3 BATHS, GAS FIREPLACE, HARDWOOD FLRS, HUGE WRAP-AROUND DECK, WALKOUT FROM FAMILY ROOM, LARGE FLAT YARD, 1ST FLR LAUNDRY,ALL APPLIANCES AND AN AMAZING PARK JUST BLOCKS AWAY!! ALL THIS IN GORGEOUS HOLLAND FIELDS, JUST MINUTES TO SCHOOLS, SHOPPING AND HWY ACCESS! THIS GEM OF A HOME WON'T LAST LONG. CALL NOW!!

4402 Van Winkle Way, Deforest, WI 53532 is a 4 bedroom, 3 bathroom, 2,023 sqft single-family home built in 2002. It last sold for $214,500 on Feb 24, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $464,600, with a rent estimate of $2,835/month.

Home Details for 4402 Van Winkle Way

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

Community
Units in Building: 1

Lot Information
Lot Area: 0.28 acres

Price and Tax history

Date	Event	Price
Feb 24, 2012 Source: N/A	Sold	$214,500
Feb 2, 2012 Source: Agent Provided	PriceChange	$214,500 Price decreased by 3%
Oct 29, 2011 Source: Agent Provided	PriceChange	$220,000 Price decreased by 3%
Oct 1, 2011 Source: Agent Provided	PriceChange	$225,900 Price decreased by 1%
Aug 7, 2011 Source: Agent Provided	PriceChange	$228,500 Price decreased by 3%
Jul 3, 2011 Source: Agent Provided	Listed For Sale	$234,900
Jun 4, 2008 Source: N/A	Sold	$244,900
Apr 22, 2008 Source: Agent Provided	Listed For Sale	$249,900

Year	Property tax	Tax assessment
2024	$5,878	$425,100

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
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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 4402 Van Winkle Way

What is 4402 Van Winkle Way estimated to be worth?
Trulia's estimated value for 4402 Van Winkle Way in Deforest, WI is $464,600.
What is the price history for 4402 Van Winkle Way?
4402 Van Winkle Way in Deforest, WI last sold for $214,500 in February 2012.
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.
How big is the lot at 4402 Van Winkle Way?
The lot at 4402 Van Winkle Way in Deforest, WI is about 0.28 acres (12,197 sq ft).