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Recently Sold Winchester, IL Homes

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  • /26

    $55,000

    Sold Dec 19, 2025

    111 W Cross St, Winchester, IL 62694

    • 2 Beds
    • 1 Bath
    • 650 Sq Ft

    Last Sold Summary

    • 8% Below List Price
    • $85/SF
    • 11 Days On Market

    Current Estimated Value $59,662

    Last Listing Agent Marlee Schultz Whitetail Properties Real Esta

    111 W Cross St, Winchester, IL 62694
  • /38

    $390,000

    Sold Jan 30, 2026

    759 Big Swan Rd, Winchester, IL 62694

    • 3 Beds
    • 2.5 Baths
    • 1,771 Sq Ft
    • Built 1998

    Last Sold Summary

    • 11% Below List Price
    • $220/SF
    • 78 Days On Market

    Current Estimated Value $307,241

    Last Listing Agent Kolton Johner Freedom Realty

    759 Big Swan Rd, Winchester, IL 62694
  • /2

    $82,000

    Sold Oct 30, 2025

    240 E Cross St, Winchester, IL 62694

    • 3 Beds
    • 1 Bath
    • 1,433 Sq Ft
    • Built 1940

    Last Sold Summary

    • $57/SF
    • 20 Days On Market

    Current Estimated Value $82,438

    Last Listing Agent Clayton Yates The Real Estate Group, Inc.

    240 E Cross St, Winchester, IL 62694
  • /19

    $147,000

    Sold Feb 02, 2026

    253 Overton Dr, Winchester, IL 62694

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2017

    Last Sold Summary

    • 2% Below List Price
    • $82/SF
    • 12 Days On Market

    Current Estimated Value $145,509

    Last Listing Agent Stephanie Do Do Realty Services, Inc.

    253 Overton Dr, Winchester, IL 62694
  • /38

    $61,100

    Sold Jul 10, 2025

    701 Alsey Smith Rd, Winchester, IL 62694

    • 4 Beds
    • 2 Baths
    • 2,318 Sq Ft
    • Built 1915

    Last Sold Summary

    • 28% Below List Price
    • $26/SF
    • 99 Days On Market

    Last Listing Agent Lisa Webb Third Street Realty

    701 Alsey Smith Rd, Winchester, IL 62694
  • /31

    $34,900

    Sold Aug 29, 2025

    115 Jackson St, Winchester, IL 62694

    • 2 Beds
    • 2 Baths
    • 2,259 Sq Ft

    Last Sold Summary

    • 9% Below List Price
    • $15/SF
    • 164 Days On Market

    Last Listing Agent Emily Odle MCR Realty Professionals, Inc

    115 Jackson St, Winchester, IL 62694
  • /21

    $100,000

    Sold Oct 02, 2025

    158 S Mechanic St, Winchester, IL 62694

    • 3 Beds
    • 1 Bath
    • 1,455 Sq Ft
    • Built 1900

    Last Sold Summary

    • 13% Below List Price
    • $69/SF
    • 2 Days On Market

    Current Estimated Value $94,486

    Last Listing Agent Darrell Moore Worrell Land Services, LLC

    158 S Mechanic St, Winchester, IL 62694
  • /19

    $60,000

    Sold Dec 29, 2025

    11 N Commercial St, Winchester, IL 62694

    • 4 Beds
    • 1 Bath
    • 1,343 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Below List Price
    • $45/SF
    • 9 Days On Market

    Current Estimated Value $71,194

    Last Listing Agent SHAWN DOERR The Real Estate Group, Inc.

    11 N Commercial St, Winchester, IL 62694
  • /21

    $22,100

    Sold May 13, 2026

    214 N Main St, Winchester, IL 62694

    • 5 Beds
    • 2 Baths
    • 2,164 Sq Ft
    • Built 1887

    Last Sold Summary

    • 60% Below List Price
    • $10/SF
    • 64 Days On Market

    Current Estimated Value $143,853

    Last Listing Agent Joe Tetzlaff RE/MAX Professionals

    214 N Main St, Winchester, IL 62694
  • /66

    $410,000

    Sold Aug 19, 2025

    638 N Main St, Winchester, IL 62694

    • 4 Beds
    • 3.5 Baths
    • 3,735 Sq Ft
    • Built 2000

    Last Sold Summary

    • 7% Below List Price
    • $110/SF
    • 33 Days On Market

    Current Estimated Value $408,819

    Last Listing Agent Dominic Casey Apex Realty of Illinois, LLC

    638 N Main St, Winchester, IL 62694
  • /57

    $847,500

    Sold May 08, 2026

    00 Winchester Glasgow, Winchester, IL 62694

    • Land
    • 113.47 Acres
    • $7,469 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 10 Days On Market

    Last Listing Agent Jesse Stay LandGuys, LLC of Illinois

    00 Winchester Glasgow, Winchester, IL 62694
  • /27

    $74,900

    Sold Jun 24, 2025

    11 N Mechanic St, Winchester, IL 62694

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 1900

    Last Sold Summary

    • $39/SF
    • 3 Days On Market

    Current Estimated Value $77,418

    Last Listing Agent Allison Worrell Worrell Land Services, LLC

    11 N Mechanic St, Winchester, IL 62694
  • /14

    $195,000

    Sold Jul 31, 2025

    223 E Jefferson St, Winchester, IL 62694

    • 3 Beds
    • 3 Baths
    • 3,200 Sq Ft
    • Built 1887

    Last Sold Summary

    • $61/SF
    • 6 Days On Market

    Current Estimated Value $165,861

    Last Listing Agent Stephanie Do Do Realty Services, Inc.

    223 E Jefferson St, Winchester, IL 62694
  • /48

    $365,000

    Sold Jun 16, 2025

    759 400 N, Winchester, IL 62694

    • 3 Beds
    • 2.5 Baths
    • 1,627 Sq Ft
    • Built 1998

    Last Sold Summary

    • 8% Below List Price
    • $224/SF
    • 59 Days On Market

    Current Estimated Value $307,241

    Last Listing Agent Joe Cebuhar Whitetail Properties Real Esta

    759 400 N, Winchester, IL 62694
  • /8

    $127,500

    Sold Jan 26, 2026

    1050 McGlaughlin Rd, Winchester, IL 62694

    • 2 Beds
    • 1 Bath
    • 1,744 Sq Ft
    • Built 2016

    Last Sold Summary

    • 15% Below List Price
    • $73/SF
    • 65 Days On Market

    Last Listing Agent Melanie Berry Real Estate Center of Jacksonv

    1050 McGlaughlin Rd, Winchester, IL 62694
  • /14

    $35,000

    Sold Apr 08, 2026

    33 N Maple St, Winchester, IL 62694

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft
    • Built 1900

    Last Sold Summary

    • 41% Below List Price
    • $25/SF
    • 127 Days On Market

    Current Estimated Value $56,496

    Last Listing Agent Darrell Moore Worrell Land Services, LLC

    33 N Maple St, Winchester, IL 62694
  • /47

    $72,000

    Sold Sep 24, 2025

    419 Dolen Rd, Winchester, IL 62694

    • 3 Beds
    • 1.5 Baths
    • 1,711 Sq Ft
    • Built 1950

    Last Sold Summary

    • 15% Below List Price
    • $42/SF
    • 28 Days On Market

    Current Estimated Value $88,776

    Last Listing Agent Carolyn Hymes The Real Estate Group, Inc.

    419 Dolen Rd, Winchester, IL 62694
  • /18

    $75,000

    Sold Oct 29, 2025

    163 S Mechanic St, Winchester, IL 62694

    • 2 Beds
    • 1 Bath
    • 1,128 Sq Ft

    Last Sold Summary

    • 17% Below List Price
    • $66/SF
    • 5 Days On Market

    Current Estimated Value $76,762

    Last Listing Agent Darrell Moore Worrell Land Services, LLC

    163 S Mechanic St, Winchester, IL 62694
  • /11

    $130,000

    Sold Jul 18, 2025

    205 N High St, Winchester, IL 62694

    • 2 Beds
    • 1 Bath
    • 1,598 Sq Ft
    • Built 1969

    Last Sold Summary

    • $81/SF
    • 1 Day On Market

    Current Estimated Value $129,336

    Last Listing Agent Darrell Moore Worrell Land Services, LLC

    205 N High St, Winchester, IL 62694
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