Winchester, IL Homes

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  /14

  $57,500

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  33 N Maple St, Winchester, IL 62694

  This home has tons of potential! It offers two official bedrooms, but functionally is being used as a three bedroom with the former family room being used as a bedroom. Home also includes a large living room with hardwood floors, eat-in kitchen, full bath and enclosed back entry. An unattached 22×20 garage all on a corner lot measuring approximately 80’x90'. Selling As-Is, inspections welcome.

  Darrell Moore Worrell Land Services, LLC

  

  33 N Maple St, Winchester, IL 62694
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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

  Last Listing Agent Marlee Schultz Whitetail Properties Real Esta

  

  111 W Cross St, Winchester, IL 62694
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  /17

  Est $164,262 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,572 Sq Ft

  601 N Main St, Winchester, IL 62694

  

  601 N Main St, Winchester, IL 62694
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  /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

  Last Listing Agent Kolton Johner Freedom Realty

  

  759 Big Swan Rd, Winchester, IL 62694
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  /13

  Est $93,463 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,386 Sq Ft

  129 S Main St, Winchester, IL 62694

  

  129 S Main St, Winchester, IL 62694
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  /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 $79,369

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

  

  240 E Cross St, Winchester, IL 62694
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  /16

  Est $83,266 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,368 Sq Ft

  129 S Mechanic St, Winchester, IL 62694

  

  129 S Mechanic St, Winchester, IL 62694
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  /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

  Last Listing Agent Stephanie Do Do Realty Services, Inc.

  

  253 Overton Dr, Winchester, IL 62694
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  /16

  Est $72,277 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,956 Sq Ft

  134 S Mechanic St, Winchester, IL 62694

  

  134 S Mechanic St, Winchester, IL 62694
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  /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
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  /12

  Est $81,860 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,141 Sq Ft

  14 S Arch St, Winchester, IL 62694

  

  14 S Arch St, Winchester, IL 62694
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  /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
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  /7

  Est $49,335 Not Listed For Sale

  151 S Main St, Winchester, IL 62694

  

  151 S Main St, Winchester, IL 62694
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  /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 $94,627

  Last Listing Agent Darrell Moore Worrell Land Services, LLC

  

  158 S Mechanic St, Winchester, IL 62694
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  /91

  Est $203,431 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  136 E Pearl St, Winchester, IL 62694

  136 E Pearl St, Winchester, IL 62694
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  /80

  $140,000 Sold Mar 13, 2025

  14 N Maple St, Winchester, IL 62694

  • 4 Beds
  • 4 Baths
  • 3,550 Sq Ft
  • Built 1897

  Last Sold Summary

  • 3% Below List Price
  • $39/SF
  • 111 Days On Market

  Current Estimated Value $161,801

  Last Listing Agent Judy Eoff RE/MAX Results Plus

  

  14 N Maple St, Winchester, IL 62694
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  /19

  Est $71,145 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 938 Sq Ft

  136 N Walnut St, Winchester, IL 62694

  

  136 N Walnut St, Winchester, IL 62694
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  /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

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

  

  11 N Commercial St, Winchester, IL 62694
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  /33

  Est $110,542 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,207 Sq Ft

  115 E Pearl St, Winchester, IL 62694

  

  115 E Pearl St, Winchester, IL 62694
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  /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 $400,390

  Last Listing Agent Dominic Casey Apex Realty of Illinois, LLC

  

  638 N Main St, Winchester, IL 62694
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  /12

  Est $71,217 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,659 Sq Ft

  203 S Main St, Winchester, IL 62694

  

  203 S Main St, Winchester, IL 62694
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  /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 $77,008

  Last Listing Agent Allison Worrell Worrell Land Services, LLC

  

  11 N Mechanic St, Winchester, IL 62694
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  /25

  Est $162,277 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,247 Sq Ft

  346 E Jefferson St, Winchester, IL 62694

  

  346 E Jefferson St, Winchester, IL 62694
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  /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 $167,857

  Last Listing Agent Stephanie Do Do Realty Services, Inc.

  

  223 E Jefferson St, Winchester, IL 62694
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  /21

  Est $137,375 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,550 Sq Ft

  124 E Hardin St, Winchester, IL 62694

  

  124 E Hardin St, Winchester, IL 62694
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  /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 $391,902

  Last Listing Agent Joe Cebuhar Whitetail Properties Real Esta

  

  759 400 N, Winchester, IL 62694
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  /22

  Est $162,663 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  49 Lashmet Dr, Winchester, IL 62694

  

  49 Lashmet Dr, Winchester, IL 62694
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  /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
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  /10

  Est $67,364 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 910 Sq Ft

  31 N Commercial St, Winchester, IL 62694

  

  31 N Commercial St, Winchester, IL 62694
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  /39

  $78,000 Sold Apr 06, 2025

  361 N Elm St, Winchester, IL 62694

  • 3 Beds
  • 1 Bath
  • 1,830 Sq Ft
  • Built 1850

  Last Sold Summary

  • 8% Below List Price
  • $43/SF
  • 50 Days On Market

  Current Estimated Value $90,177

  Last Listing Agent Judy Eoff RE/MAX Results Plus

  

  361 N Elm St, Winchester, IL 62694
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  /23

  Est $97,513 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,276 Sq Ft

  17 N Commercial St, Winchester, IL 62694

  

  17 N Commercial St, Winchester, IL 62694
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  $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 $89,589

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

  

  419 Dolen Rd, Winchester, IL 62694
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  /14

  Est $115,016 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,074 Sq Ft

  131 Railroad St, Winchester, IL 62694

  

  131 Railroad St, Winchester, IL 62694
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  /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 $76,577

  Last Listing Agent Darrell Moore Worrell Land Services, LLC

  

  163 S Mechanic St, Winchester, IL 62694
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  /2

  Est $259,734 Not Listed For Sale

  • Studio
  • 1,008 Sq Ft

  764 Old Route 36, Winchester, IL 62694

  764 Old Route 36, Winchester, IL 62694
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  /28

  $20,000 Sold Apr 29, 2025

  227 S Main St, Winchester, IL 62694

  • 3 Beds
  • 1 Bath
  • 1,592 Sq Ft
  • Built 1900

  Last Sold Summary

  • 43% Below List Price
  • $13/SF
  • 22 Days On Market

  Current Estimated Value $45,509

  Last Listing Agent Allison Worrell Worrell Land Services, LLC

  

  227 S Main St, Winchester, IL 62694
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  /29

  Est $158,146 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  609 N Main St, Winchester, IL 62694

  

  609 N Main St, Winchester, IL 62694
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  /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 $131,271

  Last Listing Agent Darrell Moore Worrell Land Services, LLC

  

  205 N High St, Winchester, IL 62694
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  /77

  Est $274,226 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,200 Sq Ft

  992 Blackburn Rd, Winchester, IL 62694

  

  992 Blackburn Rd, Winchester, IL 62694
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  /60

  Est $121,141 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  757 Witwer Rd, Winchester, IL 62694

  

  757 Witwer Rd, Winchester, IL 62694

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