Recently Sold Winchester, KY Homes

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  /20

  $189,900 Sold Jul 14, 2025

  2342 Ironworks Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1970

  Last Sold Summary

  • $180/SF
  • 2 Days On Market

  Current Estimated Value $192,970

  Last Listing Agent Dylan Justice GSP Homes

  2342 Ironworks Rd, Winchester, KY 40391
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  /2

  $363,000 Sold Oct 30, 2025

  614 S Maple St Unit B3, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,734 Sq Ft
  • Built 1985

  Last Sold Summary

  • $209/SF
  • 0 Days On Market

  Current Estimated Value $329,780

  Last Listing Agent Holly Goeing The Agency

  614 S Maple St Unit B3, Winchester, KY 40391
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  /13

  $75,000 Sold Jul 01, 2025

  2431 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,113 Sq Ft
  • Built 1920

  Last Sold Summary

  • 25% Below List Price
  • $67/SF
  • 74 Days On Market

  Current Estimated Value $79,432

  Last Listing Agent A. Rebecca Woods Woods Realty Group

  2431 Pine Ridge Rd, Winchester, KY 40391
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  /34

  $305,000 Sold Nov 04, 2025

  123 Strawberry Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $170/SF
  • 1 Day On Market

  Current Estimated Value $303,968

  Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

  123 Strawberry Ln, Winchester, KY 40391
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  /31

  $222,500 Sold Dec 19, 2025

  359 Silverton Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $148/SF
  • 18 Days On Market

  Last Listing Agent Christal Browning Four Seasons Realty

  359 Silverton Way, Winchester, KY 40391
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  /27

  $275,000 Sold Jun 13, 2025

  216 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,726 Sq Ft
  • Built 2008

  Last Sold Summary

  • 6% Below List Price
  • $159/SF
  • 129 Days On Market

  Current Estimated Value $280,977

  Last Listing Agent Brittany Lewis National Real Estate

  216 Prescott Ln, Winchester, KY 40391
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  /32

  $249,900 Sold Apr 30, 2025

  102 Churchill Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,887 Sq Ft
  • Built 1980

  Last Sold Summary

  • $132/SF
  • 3 Days On Market

  Current Estimated Value $259,177

  Last Listing Agent Brian Webb Redfin

  102 Churchill Dr, Winchester, KY 40391
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  /28

  $244,000 Sold Sep 12, 2025

  252 S Highland St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1935

  Last Sold Summary

  • 2% Below List Price
  • $126/SF
  • 17 Days On Market

  Current Estimated Value $240,755

  Last Listing Agent Austina Bruton Re/Max Elite Realty - Hamburg

  252 S Highland St, Winchester, KY 40391
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  /31

  $194,000 Sold May 22, 2025

  429 Paisley Ct, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,352 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Below List Price
  • $143/SF
  • 3 Days On Market

  Current Estimated Value $204,359

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  429 Paisley Ct, Winchester, KY 40391
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  /70

  $260,000 Sold Feb 10, 2025

  705 Oil Springs Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1979

  Last Sold Summary

  • 13% Below List Price
  • $165/SF
  • 35 Days On Market

  Current Estimated Value $284,914

  Last Listing Agent Victoria Byrd HomeFirst Real Estate

  705 Oil Springs Rd, Winchester, KY 40391
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  /33

  $450,000 Sold Jun 06, 2025

  210 Candlewood Dr, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,046 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $148/SF
  • 49 Days On Market

  Current Estimated Value $448,649

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  210 Candlewood Dr, Winchester, KY 40391
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  /16

  $65,000 Sold Feb 19, 2025

  233 E Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 873 Sq Ft
  • Built 1940

  Last Sold Summary

  • $74/SF
  • 71 Days On Market

  Current Estimated Value $103,692

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  233 E Washington St, Winchester, KY 40391
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  /38

  $335,000 Sold Apr 29, 2025

  204 Abbeywood Dr, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • Built 2004

  Last Sold Summary

  • $124/SF
  • 6 Days On Market

  Current Estimated Value $333,671

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  204 Abbeywood Dr, Winchester, KY 40391
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  /37

  $379,000 Sold Dec 22, 2025

  122 Le Ann Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,587 Sq Ft
  • Built 1978

  Last Sold Summary

  • $147/SF
  • 7 Days On Market

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  122 Le Ann Ln, Winchester, KY 40391
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  /21

  $173,000 Sold Aug 15, 2025

  222 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 964 Sq Ft
  • Built 1998

  Last Sold Summary

  • $179/SF
  • 2 Days On Market

  Current Estimated Value $177,356

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

  222 Buffalo Trace, Winchester, KY 40391
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  /2

  $247,000 Sold Jul 31, 2025

  724 Terry Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $110/SF
  • 6 Days On Market

  Current Estimated Value $274,892

  Last Listing Agent Samantha Gray National Real Estate

  724 Terry Dr, Winchester, KY 40391
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  /2

  $88,000 Sold Mar 19, 2025

  226 Athens Boonesboro Rd, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 2,482 Sq Ft

  Last Sold Summary

  • 30% Below List Price
  • $35/SF
  • 26 Days On Market

  Current Estimated Value $112,283

  Last Listing Agent Damon Ballinger C Roger Lewis Agency

  226 Athens Boonesboro Rd, Winchester, KY 40391
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  /33

  $270,000 Sold Mar 07, 2025

  137 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $210/SF
  • 6 Days On Market

  Current Estimated Value $293,155

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  137 Summerhill Way, Winchester, KY 40391
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  /26

  $195,000 Sold Nov 06, 2025

  388 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,224 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Below List Price
  • $159/SF
  • 31 Days On Market

  Current Estimated Value $198,674

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  388 Colby Ridge Blvd, Winchester, KY 40391
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  /46

  $365,000 Sold Oct 27, 2025

  7875 Bybee Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 2021

  Last Sold Summary

  • 9% Below List Price
  • $226/SF
  • 79 Days On Market

  Current Estimated Value $369,239

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  7875 Bybee Rd, Winchester, KY 40391
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  /34

  $205,000 Sold Jun 30, 2025

  42 Wheeler Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,013 Sq Ft
  • Built 1950

  Last Sold Summary

  • 16% Below List Price
  • $202/SF
  • 13 Days On Market

  Current Estimated Value $210,219

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  42 Wheeler Ave, Winchester, KY 40391
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  /67

  $470,000 Sold Dec 02, 2025

  415 David Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,989 Sq Ft
  • Built 1999

  Last Sold Summary

  • 19% Below List Price
  • $118/SF
  • 58 Days On Market

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  415 David Ln, Winchester, KY 40391
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  /23

  $196,400 Sold Mar 21, 2025

  112 Quail Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $135/SF
  • 114 Days On Market

  Current Estimated Value $223,847

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  112 Quail Ridge Rd, Winchester, KY 40391
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  /11

  $205,000 Sold Oct 10, 2025

  322 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,110 Sq Ft
  • Built 2001

  Last Sold Summary

  • 5% Above List Price
  • $185/SF
  • 1 Day On Market

  Current Estimated Value $203,910

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC

  322 Buffalo Trace, Winchester, KY 40391
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  /33

  $333,500 Sold Aug 20, 2025

  543 S Maple St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft
  • Built 1946

  Last Sold Summary

  • 5% Below List Price
  • $218/SF
  • 38 Days On Market

  Current Estimated Value $333,142

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  543 S Maple St, Winchester, KY 40391
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  /82

  $475,000 Sold Oct 23, 2025

  102 Camelot Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,679 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Above List Price
  • $129/SF
  • 3 Days On Market

  Current Estimated Value $476,712

  Last Listing Agent Scott Fryar Keller Williams Bluegrass Realty

  102 Camelot Dr, Winchester, KY 40391
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  /68

  $460,000 Sold Oct 10, 2025

  946 Pine Ridge Rd, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 3,523 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $131/SF
  • 8 Days On Market

  Current Estimated Value $481,117

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  946 Pine Ridge Rd, Winchester, KY 40391
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  /34

  $252,000 Sold Jul 30, 2025

  216 Connie Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2017

  Last Sold Summary

  • $202/SF
  • 2 Days On Market

  Current Estimated Value $250,811

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  216 Connie Ln, Winchester, KY 40391
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  /21

  $259,900 Sold Jul 10, 2025

  302 April Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,321 Sq Ft
  • Built 2002

  Last Sold Summary

  • $197/SF
  • 12 Days On Market

  Current Estimated Value $262,601

  Last Listing Agent Michael Hilario The Agency

  302 April Way, Winchester, KY 40391
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  /30

  $185,000 Sold Jun 18, 2025

  308 Essex Ct, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,188 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $156/SF
  • 3 Days On Market

  Current Estimated Value $194,899

  Last Listing Agent Lisa Sosa Keller Williams Commonwealth

  308 Essex Ct, Winchester, KY 40391
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  /22

  $600,000 Sold Aug 19, 2025

  1203 Irvine Rd, Winchester, KY 40391

  • Land
  • 12.38 Acres
  • $48,465 per Acre

  Last Sold Summary

  • 37% Below List Price
  • 125 Days On Market

  Current Estimated Value $930,902

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1203 Irvine Rd, Winchester, KY 40391
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  /17

  $228,500 Sold Feb 06, 2026

  394 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft
  • Built 1900

  Last Sold Summary

  • $123/SF
  • 9 Days On Market

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  394 S Main St, Winchester, KY 40391
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  /2

  $75,000 Sold Dec 16, 2025

  1477 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 4.82 Acres
  • $15,560 per Acre

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1477 Sewell Shop Rd, Winchester, KY 40391
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  /48

  $255,000 Sold Apr 30, 2025

  305 Skylark Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,358 Sq Ft
  • Built 1965

  Last Sold Summary

  • $108/SF
  • 45 Days On Market

  Current Estimated Value $274,432

  Last Listing Agent Melodie Lincavage RE/MAX Elite Realty

  305 Skylark Dr, Winchester, KY 40391
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  /47

  $350,000 Sold May 01, 2025

  206 Honeysuckle Ln, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,117 Sq Ft
  • Built 1999

  Last Sold Summary

  • $165/SF
  • 3 Days On Market

  Current Estimated Value $358,456

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  206 Honeysuckle Ln, Winchester, KY 40391
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  /76

  $690,000 Sold Feb 24, 2025

  775 Sugar Ridge Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Below List Price
  • $241/SF
  • 2 Days On Market

  Current Estimated Value $561,253

  Last Listing Agent Cassie Foley CENTURY 21 Advantage Realty

  775 Sugar Ridge Rd, Winchester, KY 40391
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  /23

  $197,000 Sold Mar 31, 2025

  42 Park Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,129 Sq Ft

  Last Sold Summary

  • 14% Below List Price
  • $174/SF
  • 54 Days On Market

  Current Estimated Value $196,843

  Last Listing Agent Jonathan McMahan Coldwell Banker McMahan

  42 Park Ave, Winchester, KY 40391
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  /42

  $249,000 Sold Oct 22, 2025

  9 Apache Trail, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $142/SF
  • 117 Days On Market

  Current Estimated Value $254,034

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  9 Apache Trail, Winchester, KY 40391
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  /92

  $364,900 Sold Jul 31, 2025

  31 Mockingbird Valley Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $145/SF
  • 209 Days On Market

  Current Estimated Value $374,758

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  31 Mockingbird Valley Rd, Winchester, KY 40391
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  /2

  $216,450 Sold Apr 30, 2025

  408 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,628 Sq Ft
  • Built 2005

  Last Sold Summary

  • $133/SF
  • 0 Days On Market

  Current Estimated Value $221,746

  Last Listing Agent John Wilson Bluegrass Properties Group

  408 Paisley Ct, Winchester, KY 40391

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