Winchester, IL homes for sale & real estate

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FOR SALE BY OWNER

23 W Pleasant St, Winchester, IL 62694
23 W Pleasant St, Winchester, IL 62694
23 W Pleasant St, Winchester, IL 62694
ABOUT THIS HOME
Winchester, IL Homes for Sale
2300 sq. ft. Great neighborhood and great school district. 3 bedroom 1-1/2 bath, but two additional rooms could easily be turned into bedrooms. Attached garage with additional storage in the garage. Message for additional information and pics.

$134,900

4 beds1.5 baths2,300 sq ft

23 W Pleasant St, Winchester, IL 62694

8,712 sq ft lot • Garage • Car-dependent

$449,000

4 beds3.5 baths3,741 sq ft

638 N Main St, Winchester, IL 62694

1.32 acre lot • 3 garage spots • Pool

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Nearby homes that match your criteria

Within 2 miles

$42,500

3 beds2 baths924 sq ft

102 W Smithland St, Murrayville, IL 62668

0.25 acre lot • 2 garage spots • Car-dependent

COMING SOON

29 Greenbriar Dr, Jacksonville, IL 62650
29 Greenbriar Dr, Jacksonville, IL 62650
29 Greenbriar Dr, Jacksonville, IL 62650
ABOUT THIS HOME
Winchester, IL Homes for Sale
Coming Soon! Like New Tri Level in Great West Side Location! This 4-bedroom 3 full bath is full updates. All New Kitchen, Flooring, Baths, Roof, Light fixtures, Doors, Garage Door. Come and take a look. Home is still under construction. Updated HVAC. Patio and Pergola out back. Fenced backyard. Eisenhower Elementary District.

$229,000

4 beds3 baths1,884 sq ft

29 Greenbriar Dr, Jacksonville, IL 62650

9,600 sq ft lot • 2 garage spots • Car-dependent

$230,000

2 beds2.5 baths1,614 sq ft

5 Southvale Dr, Jacksonville, IL 62650

8,910 sq ft lot • 2 garage spots • Somewhat walkable

$375,000

4 beds3.5 baths4,188 sq ft

29 Elizabeth Pl, Jacksonville, IL 62650

0.33 acre lot • 2 garage spots • Car-dependent

OPEN SUN, 12PM TO 1:30PM

$340,000

4 beds3.5 baths3,369 sq ft

65 Alice Dr, Jacksonville, IL 62650

0.78 acre lot • 2 garage spots • Car-dependent

8 Westfair Dr, Jacksonville, IL 62650
8 Westfair Dr, Jacksonville, IL 62650
8 Westfair Dr, Jacksonville, IL 62650
ABOUT THIS HOME
Winchester, IL Homes for Sale
All Brick Duplex with 3.5 car detached garage. Excellent west side location. One side is 3 bedrooms and 1 bath. The other side is 2-bedroom 1 bath. Front of Garage roof was replaced April 2025.

$189,000

5 beds2 baths2,064 sq ft

8 Westfair Dr, Jacksonville, IL 62650

0.31 acre lot • Car-dependent

Property at 701 Alsey Smith Rd, Alsey, IL 62610, 4 beds, 2 baths

$74,900

4 beds2 baths2,318 sq ft

701 Alsey Smith Rd, Alsey, IL 62610

Property at 7 Greenbriar Dr, Jacksonville, IL 62650, 3 beds, 2 baths

$227,900

3 beds2 baths1,842 sq ft

7 Greenbriar Dr, Jacksonville, IL 62650

Property at 115 Jackson St, Winchester, IL 62694, 2 beds, 1 bath

$38,500

2 beds1 bath2,259 sq ft

115 Jackson St, Winchester, IL 62694

Property at 20 Briarwyck Dr, Jacksonville, IL 62650, 3 beds, 3 baths

$219,900

3 beds3 baths2,330 sq ft

20 Briarwyck Dr, Jacksonville, IL 62650

Property at 18 Jacobs Ln, Jacksonville, IL 62650, 4 beds, 4.5 baths

$489,900

4 beds4.5 baths8,140 sq ft

18 Jacobs Ln, Jacksonville, IL 62650

Property at 102 W Lorton St, Roodhouse, IL 62082, 3 beds, 1.5 baths

$105,000

3 beds1.5 baths2,027 sq ft

102 W Lorton St, Roodhouse, IL 62082

Property at 455 N Plum St, Pearl, IL 62361-2053, 3 beds, 2 baths

$150,000

3 beds2 baths1,292 sq ft

455 N Plum St, Pearl, IL 62361-2053

Property at 801 NW 1200 St, Hillview, IL 62650

$2,022,600

— beds— baths— sq ft

801 NW 1200 St, Hillview, IL 62650

Property at 238 E Prairie St, Roodhouse, IL 62082, 4 beds, 2 baths

$142,500

4 beds2 baths3,160 sq ft

238 E Prairie St, Roodhouse, IL 62082

Property at 60 Alice Dr, Jacksonville, IL 62650, 4 beds, 3.5 baths

$439,900

4 beds3.5 baths4,400 sq ft

60 Alice Dr, Jacksonville, IL 62650

Property at 1112 W Hall St, Jacksonville, IL 62650, 3 beds, 2 baths

$169,900

3 beds2 baths1,804 sq ft

1112 W Hall St, Jacksonville, IL 62650

Property at 330 S Florence Rd, Pittsfield, IL 62363, 3 beds, 1 bath

$149,900

3 beds1 bath1,400 sq ft

330 S Florence Rd, Pittsfield, IL 62363

Property at County HWY 10 0, Pearl, IL 62361

$1,818,000

— beds— baths— sq ft

County HWY 10 0, Pearl, IL 62361

Property at 53 Applebee Farms Dr, Jacksonville, IL 62650

$39,900

— beds— baths— sq ft

53 Applebee Farms Dr, Jacksonville, IL 62650

Based on information submitted to the MLS GRID as of Sun Apr 27 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Winchester, IL

Cities

Zip Codes

62694 homes for sale
$74,900

Winchester, IL real estate trends

$140K

Sale price

$39

Sale $/sq ft

Under list price

3.4%

Days on market

Down payment

—

Total homes sold

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