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 4414 Van Winkle Way estimated to be worth?

Trulia's estimated value for 4414 Van Winkle Way in Deforest, WI is $492,900 .

What is the price history for 4414 Van Winkle Way?

4414 Van Winkle Way in Deforest, WI last sold for $278,000 in December 2016.

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 4414 Van Winkle Way?

The lot at 4414 Van Winkle Way in Deforest, WI is about 0.33 acres (14,375 sq ft).

OFF MARKET

$492,900

Trulia Estimate

4 Beds
2.5 Baths
1,920 sqft (on 0.33 acres)

4414 Van Winkle Way, Deforest, WI 53532

Est. Refi. Payment $3,344/mo*

Refinance Your Home

Currently Off Market - Sold Dec 12, 2016 for $278,000

Home Value

Trulia Estimate

$493K

Since last month

$3K (-0.6%)

Since last year

$8K (+1.7%)

Since last sale

$218K (+78.2%)

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 +74% in the last 10 years

Month	Estimated value
2026
September 2026	$496K
August 2026	$499K
July 2026	$504K
June 2026	$511K
May 2026	$509K
April 2026	$515K
March 2026	$505K
February 2026	$490K
January 2026	$473K
2025
December 2025	$476K
November 2025	$473K
October 2025	$476K
September 2025	$487K
August 2025	$485K
July 2025	$488K
June 2025	$488K
May 2025	$489K
April 2025	$486K
March 2025	$482K
February 2025	$468K
January 2025	$458K
2024
December 2024	$461K
November 2024	$461K
October 2024	$462K
September 2024	$461K
August 2024	$470K
July 2024	$469K
June 2024	$474K
May 2024	$476K
April 2024	$474K
March 2024	$471K
February 2024	$456K
January 2024	$439K
2023
December 2023	$436K
November 2023	$435K
October 2023	$443K
September 2023	$442K
August 2023	$441K
July 2023	$450K
June 2023	$443K
May 2023	$448K
April 2023	$437K
March 2023	$425K
February 2023	$415K
January 2023	$409K
2022
December 2022	$407K
November 2022	$410K
October 2022	$413K
September 2022	$415K
August 2022	$416K
July 2022	$429K
June 2022	$436K
May 2022	$437K
April 2022	$432K
March 2022	$425K
February 2022	$401K
January 2022	$393K
2021
December 2021	$386K
November 2021	$383K
October 2021	$381K
September 2021	$381K
August 2021	$384K
July 2021	$390K
June 2021	$385K
May 2021	$371K
April 2021	$358K
March 2021	$346K
February 2021	$343K
January 2021	$340K
2020
December 2020	$338K
November 2020	$337K
October 2020	$337K
September 2020	$336K
August 2020	$321K
July 2020	$322K
June 2020	$321K
May 2020	$320K
April 2020	$321K
March 2020	$322K
February 2020	$318K
January 2020	$321K
2019
December 2019	$324K
November 2019	$324K
October 2019	$325K
September 2019	$320K
August 2019	$324K
July 2019	$321K
June 2019	$323K
May 2019	$321K
April 2019	$320K
March 2019	$319K
February 2019	$318K
January 2019	$313K
2018
December 2018	$311K
November 2018	$311K
October 2018	$309K
September 2018	$309K
August 2018	$308K
July 2018	$307K
June 2018	$308K
May 2018	$306K
April 2018	$303K
March 2018	$299K
February 2018	$297K
January 2018	$297K
2017
December 2017	$292K
November 2017	$294K
October 2017	$292K
September 2017	$293K
August 2017	$289K
July 2017	$290K
June 2017	$291K
May 2017	$290K
April 2017	$289K
March 2017	$285K
February 2017	$281K
January 2017	$280K
2016
December 2016	$279K
November 2016	$283K
October 2016	$284K
September 2016	$285K

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	0.08	Single-Family Home	$503,000	08/03/26	3	2	2,146
4398 Van Winkle Way, Deforest, WI	0.07	Single-Family Home	$480,000	01/20/26	3	2	2,492
4380 Van Winkle Way, Deforest, WI	0.11	Single-Family Home	$545,000	06/09/26	4	3.5	2,821
6926 Old Amsterdam Way, Deforest, WI	0.12	Single-Family Home	$496,500	03/30/26	3	2.5	2,350
4401 Cradle Hill Dr, Deforest, WI	0.32	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
6776 Dawn Dr, Windsor, WI	0.47	Single-Family Home	$420,000	06/16/26	3	2	1,972
4414 Gray Rd, Deforest, WI	0.08	Single-Family Home	$210,000	08/17/26	4	2	1,782
4040 Whistle Rock, Deforest, WI	0.46	Single-Family Home	$567,000	07/29/26	4	3	2,536

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
4387 Van Winkle Way, Deforest, WI 53532	0.07	$568,900	4	3	2,459	Off Market
4398 Van Winkle Way, Deforest, WI 53532	0.07	$480,000	3	2	2,492	Recently Sold
4396 Low Countries Rd, Deforest, WI 53532	0.06	$499,000	4	2.5	2,011	Recently Sold
4383 Van Winkle Way, Deforest, WI 53532	0.08	$503,000	3	2	2,146	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	0.09	$498,300	4	2.5	3,017	Off Market
4380 Van Winkle Way, Deforest, WI 53532	0.11	$545,000	4	3.5	2,821	Recently Sold
6875 & 6879 Rembrandt Rd, Windsor, WI 53598	0.13	$691,400	8	5	4,050	Off Market
4426 Gray Rd, Deforest, WI 53532	0.11	$289,300	2	1.5	1,368	Off Market
4428 Gray Rd, Deforest, WI 53532	0.11	$277,900	2	1.5	1,368	Off Market
6926 Old Amsterdam Way, Deforest, WI 53532	0.12	$496,500	3	2.5	2,350	Recently Sold
4440 Gray Rd, Deforest, WI 53532	0.13	$299,000	2	1.5	1,368	Off Market

Local Information

Map ViewExplore the area around 4414 Van Winkle Way.
Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

0.33 acre lot

1,920 sqft

$257/sqft

About this House

You'll love this Prairie-style home with its beautiful wood floors & relaxing decor located in popular Holland Fields just steps away from a school bus stop. This 1920 sq. ft. home features an open floor plan with red birch wood floors throughout first level, 4 bedrooms, 2.5 baths, 1st floor laundry with California Closets & a master suite with WIC (also California Closets) & full bath with soaking tub. Home has solid 3-panel doors, wood blinds, painted trim & gas fireplace.

4414 Van Winkle Way, Deforest, WI 53532 is a 4 bedroom, 3 bathroom, 1,920 sqft single-family home. It last sold for $278,000 on Dec 12, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $492,900, with a rent estimate of $2,901/month.

Home Details for 4414 Van Winkle Way

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 0.33 acres

Price and Tax history

Date	Event	Price
Dec 12, 2016 Source: N/A	Sold	$278,000
Sep 23, 2016 Source: Agent Provided	Listed For Sale	$284,900

Year	Property tax	Tax assessment
2024	$6,514	$470,100

Additional Cost

Market trends in Windsor

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

8MoM

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
2mo 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
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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
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Matthew
14y ago
"I have visited family in the area numerous times and we love it!!!"
0
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LGBTQ Local Legal Protections

Frequently asked questions about 4414 Van Winkle Way

What is 4414 Van Winkle Way estimated to be worth?
Trulia's estimated value for 4414 Van Winkle Way in Deforest, WI is $492,900.
What is the price history for 4414 Van Winkle Way?
4414 Van Winkle Way in Deforest, WI last sold for $278,000 in December 2016.
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 4414 Van Winkle Way?
The lot at 4414 Van Winkle Way in Deforest, WI is about 0.33 acres (14,375 sq ft).