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

38 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	0.09	Single-Family Home	$35,000	04/08/26	3	1	1,392
45 N Walnut St, Winchester, IL	0.09	Single-Family Home	$59,000	06/15/26	3	1	1,555
111 W Cross St, Winchester, IL	0.21	Single-Family Home	$55,000	12/19/25	2	1	650
27 N High St, Winchester, IL	0.22	Single-Family Home	$64,900	06/25/26	2	1	1,152
250 E Pearl St, Winchester, IL	0.22	Single-Family Home	$180,000	10/20/26	3	1.5	1,654
253 Overton Dr, Winchester, IL	0.23	Single-Family Home	$147,000	02/02/26	3	2	1,792
37 E Lewis St, Winchester, IL	0.26	Single-Family Home	$70,000	09/25/26	4	1.5	1,586
214 N Main St, Winchester, IL	0.28	Single-Family Home	$22,100	05/13/26	5	2	2,164
204 S Main St, Winchester, IL	0.33	Single-Family Home	$115,000	10/19/26	3	2	1,808
216 S Main St, Winchester, IL	0.35	Single-Family Home	$15,000	10/08/26	3	1	1,805

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
24 N Walnut St, Winchester, IL 62694	0.03	$78,100	Studio	-	1,176	Off Market
15 N Walnut St, Winchester, IL 62694	0.04	-	Studio	-	-	Off Market
E Cherry St, Winchester, IL 62694	0.05	-	-	-	-	Off Market
23 N Walnut St, Winchester, IL 62694	0.06	$71,900	Studio	-	545	Off Market
28 S Walnut St, Winchester, IL 62694	0.06	$83,800	Studio	-	954	Off Market
21 N Maple St, Winchester, IL 62694	0.06	-	Studio	-	1,018	Off Market
33 N Hill St, Winchester, IL 62694	0.06	$119,300	Studio	-	1,648	Off Market
155 E Market St, Alsey, IL 62694	0.07	-	Studio	-	-	Off Market
27 N Maple St, Winchester, IL 62694	0.07	-	Studio	-	1,004	Off Market
34 S Walnut St, Winchester, IL 62694	0.07	$90,700	3	2	965	Off Market
31 N Walnut St, Winchester, IL 62694	0.07	-	Studio	-	1,114	Off Market
24 N Walnut St, Winchester, IL 62694	0.07	-	3	1	1,521	Off Market
35 S Maple St, Winchester, IL 62694	0.08	$97,300	Studio	-	1,137	Off Market
465 W Cherry St, Winchester, IL 62694	0.08	-	Studio	-	-	Off Market
20 N Walnut St, Winchester, IL 62694	0.08	-	Studio	-	-	Off Market
35 N Walnut St, Winchester, IL 62694	0.08	-	Studio	-	554	Off Market
34 N Hill St, Winchester, IL 62694	0.08	-	-	-	-	Off Market
126 E Cherry St, Winchester, IL 62694	0.08	$129,800	Studio	-	1,349	Off Market
3 S Broadway St, Winchester, IL 62694	0.08	-	Studio	-	844	Off Market
34 N Walnut St, Winchester, IL 62694	0.08	$45,300	Studio	-	-	Off Market

Homes for rent near 38 E Cherry St

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Local Information

Map ViewExplore the area around 38 E Cherry St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

About this House

What's unique:Great curb appeal

38 E Cherry St is in Winchester, IL and in ZIP code 62694.

38 E Cherry St, Winchester, IL 62694 is a unknown. More recently, it was listed as a rental in January 2026 with an asking price of $50,000 per month. That rental listing was removed on April 9, 2026. This property is not currently displayed as for sale or rent on Trulia.

Home Details for 38 E Cherry St

Property Information
Property Type / Style Property Type: Unknown

Price and Tax history

Date	Event	Price
Apr 9, 2026 Source: My State MLS #11622745	ListingRemoved	$39,900
Mar 3, 2026 Source: My State MLS #11622745	PriceChange	$39,900 Price decreased by 20%
Jan 23, 2026 Source: My State MLS #11622745	Listed For Rent	$50,000

Additional Cost

Market trends in Winchester

Last updated September 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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 38 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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