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

258 E Cherry St
Winchester, IL 62694

(on 0.25 acres)

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	Bath	Sqft
860 Worrell Ln, Winchester, IL	3.99	Lot/Land	$30,000	11/07/25	-	-
Winchester Glasgow Rd, Winchester, IL	5.07	Lot/Land	$847,500	05/08/26	-	-
Merritt Blacktop Rd, Jacksonville, IL	6.56	Lot/Land	$1,884,928	03/25/26	-	-

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
163 S Mechanic St, Winchester, IL 62694	0.08	$75,000	2	1	1,128	Recently Sold
158 S Mechanic St, Winchester, IL 62694	0.08	$104,500	3	1	1,455	Off Market
129 S Main St, Winchester, IL 62694	0.04	$94,100	2	2	1,386	Off Market
151 S Main St, Winchester, IL 62694	0.07	-	-	-	-	Off Market
111 W Cross St, Winchester, IL 62694	0.08	$55,000	2	1	650	Recently Sold
203 S Main St, Winchester, IL 62694	0.15	$70,700	3	2	1,659	Off Market
200 S Main St, Winchester, IL 62694	0.16	$134,900	4	2	2,080	For Sale
204 S Main St, Winchester, IL 62694	0.18	$129,900	3	2	1,808	For Sale
227 S Main St, Winchester, IL 62694	0.20	$21,400	3	1	1,592	Off Market
27 W Cherry St, Winchester, IL 62694	0.18	-	Studio	1.5	3,372	Off Market
12 N Mechanic St, Winchester, IL 62694	0.19	$65,800	3	1	1,561	Off Market
11 N Mechanic St, Winchester, IL 62694	0.20	$79,400	4	2	1,900	Off Market

Local Information

Map ViewExplore the area around 258 E Cherry St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Lot/Land

Year Built

1887

Lot Size

0.25 acres

About this House

This is a rare gemstone with a few rough edges waiting for you to polish it. This home features large rooms, 3-4 bedrooms, and 3 full baths. Lots of exposed wood and brick in the interior of the home. The back yard is large, fenced in, and has an outbuilding. Oak kitchen w/ breakfast bar. Large utility room, Huge Living room with beveled glass french doors. This is a must see home. Sq. ft. is approx. All offers subject to lender approval please give ample time for responses.

258 E Cherry St, Winchester, IL 62694 is a lot/land built in 1887. It is currently off market. The Trulia Estimate rent is $844/month.

Home Details for 258 E Cherry St

Interior Features
Levels, Entrance, & Accessibility Stories: 2

Property Information
Year Built Year Built: 1887
Property Type / Style Property Type: Lot Land

Lot Information
Lot Area: 0.25 acres

Price and Tax history

Year	Property tax	Tax assessment
2024	$91	$1,288

Home facts updated by county records

Additional Cost

Market trends in Winchester

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

—

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
6mo 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

Skip to last item

Results are loading

Skip to first item

Off Market Homes Near 258 E Cherry St

Skip to last item

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
SOLD
APR 8, 2026
$35,000
3 bd
1 ba
1,392 sqft
33 N Maple St,
Winchester, IL 62694
Darrell Moore, Worrell Land Services, LLC
SOLD
FEB 2, 2026
$147,000
3 bd
2 ba
1,792 sqft
253 Overton Dr,
Winchester, IL 62694
Stephanie L Do, Do Realty Services, Inc.
SOLD
DEC 29, 2025
$60,000
4 bd
1 ba
1,343 sqft
11 N Commercial St,
Winchester, IL 62694
Shawn Doerr, The Real Estate Group, Inc.
SOLD
DEC 19, 2025
$55,000
2 bd
1 ba
650 sqft
111 W Cross St,
Winchester, IL 62694
Marlee Schultz, Whitetail Properties Real Esta
SOLD
NOV 7, 2025
$30,000
860 Worrell Ln,
Winchester, IL 62694
Melanie Berry, Real Estate Center of Jacksonv
See more homes for sale in
Winchester
Take a look