Is parking easy in Winchester, IL?

As of early 2026, 100% of users say parking is easy

Are yards well-kept in Winchester, IL?

As of early 2026, 100% of users say yards are well-kept

Do kids play outside in Winchester, IL?

As of early 2026, 100% of users say kids play outside

Is Winchester, IL dog-friendly?

As of early 2026, 75% of users say it's dog friendly

Would people walk alone at night in Winchester, IL?

As of early 2026, 67% of users say people would walk alone at night

Does Winchester, IL show holiday spirit?

As of early 2026, 67% of users say there's holiday spirit

Is Winchester, IL walkable to restaurants?

As of early 2026, 50% of users say it's walkable to restaurants

Do residents of Winchester, IL plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Are neighbors friendly in Winchester, IL?

As of early 2026, 44% of users say neighbors are friendly

Are there community events in Winchester, IL?

As of early 2026, 33% of users say there are community events

Are the streets well-lit in Winchester, IL?

As of early 2026, 33% of users say streets are well-lit

OFF MARKET

$27,383

Tax assessed value

Studio
1,237 sqft

229 E Cherry St, Winchester, IL 62694

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
33 N Maple St, Winchester, IL	0.12	Single-Family Home	$35,000	04/08/26	3	1	1,392
250 E Pearl St, Winchester, IL	0.09	Single-Family Home	$180,000	10/20/26	3	1.5	1,654
27 N High St, Winchester, IL	0.06	Single-Family Home	$64,900	06/25/26	2	1	1,152
253 Overton Dr, Winchester, IL	0.12	Single-Family Home	$147,000	02/02/26	3	2	1,792
11 N Commercial St, Winchester, IL	0.53	Single-Family Home	$60,000	12/29/25	4	1	1,343
214 N Main St, Winchester, IL	0.33	Single-Family Home	$22,100	05/13/26	5	2	2,164
216 S Main St, Winchester, IL	0.43	Single-Family Home	$15,000	10/08/26	3	1	1,805
204 S Main St, Winchester, IL	0.41	Single-Family Home	$115,000	10/19/26	3	2	1,808
506 N Alsey Smith Rd, Winchester, IL	0.62	Single-Family Home	$95,000	09/21/26	3	1	1,376
120 N Commercial St, Winchester, IL	0.55	Single-Family Home	$85,000	06/22/26	3	1	1,440

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
221 E Cherry St, Winchester, IL 62694	0.02	$104,000	Studio	-	1,296	Off Market
15 N Broadway, Murrayville, IL 62668	0.03	-	Studio	-	-	Off Market
21 N Broadway St, Winchester, IL 62694	0.03	$75,000	Studio	-	965	Off Market
211 E Cherry St, Winchester, IL 62694	0.03	-	Studio	-	1,020	Off Market
11 S Broadway St, Winchester, IL 62694	0.04	-	-	-	-	Off Market
242 E Cherry St, Winchester, IL 62694	0.04	-	Studio	-	-	Off Market
212 E Cherry St, Winchester, IL 62694	0.04	-	Studio	-	1,009	Off Market
253 E Cherry St, Winchester, IL 62694	0.04	$62,900	Studio	-	1,149	Off Market
253 E Cherry St, Jacksonville, IL 62650	0.04	-	-	-	-	Off Market
27 N Broadway St, Winchester, IL 62694	0.04	-	Studio	-	-	Off Market
North Broadway, Winchester, IL 62694	0.04	-	-	-	-	Off Market
N Broadway St, Winchester, IL 62694	0.04	-	-	-	-	Off Market
15 N High St, Winchester, IL 62694	0.05	$81,200	Studio	-	-	Off Market
203 E Cherry St, Winchester, IL 62694	0.05	-	Studio	-	1,179	Off Market
22 N Broadway St, Winchester, IL 62694	0.05	-	Studio	-	1,097	Off Market
17 S Broadway St, Winchester, IL 62694	0.05	-	Studio	-	869	Off Market
252 E Cherry St, Winchester, IL 62694	0.05	$74,000	Studio	-	1,335	Off Market
202 E Cherry St, Winchester, IL 62694	0.05	-	Studio	-	874	Off Market
35 N Broadway St, Winchester, IL 62694	0.06	$62,000	Studio	-	-	Off Market
10 S Green St, Winchester, IL 62694	0.06	-	Studio	-	-	Off Market

Local Information

Map ViewExplore the area around 229 E Cherry St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1900

1,237 sqft

About this House

This single-family home is located at 229 E Cherry St, Winchester, IL. 229 E Cherry St is in Winchester, IL and in ZIP code 62694. This property has approximately 1,237 sqft of floor space. This property has a lot size of 9500 sqft and was built in 1900.

229 E Cherry St, Winchester, IL 62694 is a studio, 1,237 sqft single-family home built in 1900. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $997/month.

Home Details for 229 E Cherry St

Interior Features
Levels, Entrance, & Accessibility Stories: 1

Property Information
Year Built Year Built: 1900
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 9500 sqft

Price and Tax history

Year	Property tax	Tax assessment
2024	$669	$27,383

Home facts updated by county records

Additional Cost

Market trends in Winchester

Last updated October 2026

Avg. sale price

—

Sale-to-List Price

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Price per sq ft

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Available listings

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Sourced by Trulia Market Trends

Around this home

Winchester Elementary School
PK-8
Public
399 Students
Winchester Community Unit School District 1
7/10
GreatSchools Rating
Parent Rating Average
School is bad at transitioning after family issues. The school is bad at transportation and communication as well. Special education is a class where the teacher does the homework for the student. Demanding they “give them their pencil” and then does their homework. This may also be why most graduates or upperclassmen at Winchester schools cannot write simple words and cannot read advanced words/sentences. I would absolutely not recommend this school to anyone. I plan to switch school districts to a better more education focused school district.
Parent Review
9mo ago
1 Reviews

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 Winchester

At least 1 Trulia users voted on each feature.

100 % Say parking is easy
100 % Say yards are well-kept
100 % Say kids play outside
75 % Say it's dog friendly
67 % Say people would walk alone at night
67 % Say there's holiday spirit
50 % Say it's walkable to restaurants
50 % Say they plan to stay for at least 5 years
44 % Say neighbors are friendly
33 % Say there are community events
33 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Off Market Homes Near 229 E Cherry St

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SOLD
OCT 20, 2026
$180,000
3 bd
1.5 ba
1,654 sqft
250 E Pearl St,
Winchester, IL 62694
Amy Lakamp, Brixx Properties
SOLD
OCT 19, 2026
$115,000
3 bd
2 ba
1,808 sqft
204 S Main St,
Winchester, IL 62694
Jess Spradlin, Spradlin Auction & Real Estate
SOLD
OCT 8, 2026
$15,000
3 bd
1 ba
1,805 sqft
216 S Main St,
Winchester, IL 62694
Darrell Moore, Worrell Land Services, LLC
SOLD
SEP 25, 2026
$70,000
4 bd
1.5 ba
1,586 sqft
37 E Lewis St,
Winchester, IL 62694
Darrell Moore, Worrell Land Services, LLC
SOLD
SEP 21, 2026
$95,000
3 bd
1 ba
1,376 sqft
506 N Alsey Smith Rd,
Winchester, IL 62694
Darrell Moore, Worrell Land Services, LLC
SOLD
JUN 25, 2026
$64,900
2 bd
1 ba
1,152 sqft
27 N High St,
Winchester, IL 62694
Melanie Berry, Real Estate Center of Jacksonv
SOLD
JUN 22, 2026
$85,000
3 bd
1 ba
1,440 sqft
120 N Commercial St,
Winchester, IL 62694
Jered Dennis, Swipe Home Property Group LLC
SOLD
JUN 15, 2026
$59,000
3 bd
1 ba
1,555 sqft
45 N Walnut St,
Winchester, IL 62694
Darrell Moore, Worrell Land Services, LLC
SOLD
MAY 21, 2026
$50,000
3 bd
1 ba
1,376 sqft
55 N Commercial St,
Winchester, IL 62694
Darrell Moore, Worrell Land Services, LLC
SOLD
MAY 13, 2026
$22,100
5 bd
2 ba
2,164 sqft
214 N Main St,
Winchester, IL 62694
Joseph E Tetzlaff, RE/MAX Professionals
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