Recently Sold Winchester, KY Homes

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  /2

  $185,000 Sold Nov 28, 2025

  23 Hillcrest Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,557 Sq Ft
  • Built 1962

  Last Sold Summary

  • 12% Below List Price
  • $119/SF
  • 18 Days On Market

  Current Estimated Value $193,680

  Last Listing Agent Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
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  /22

  $216,000 Sold Feb 27, 2026

  521 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $158/SF
  • 17 Days On Market

  Current Estimated Value $222,469

  Last Listing Agent Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
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  /65

  $385,000 Sold Dec 11, 2025

  1731 Ford Hampton Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 27% Below List Price
  • $182/SF
  • 157 Days On Market

  Current Estimated Value $399,266

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
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  /62

  $325,000 Sold Apr 24, 2025

  138 Shanahan Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1996

  Last Sold Summary

  • 23% Below List Price
  • $172/SF
  • 88 Days On Market

  Current Estimated Value $330,309

  Last Listing Agent Christine McDonald FC Tucker Bluegrass

  138 Shanahan Ln, Winchester, KY 40391
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  /79

  $584,900 Sold Feb 17, 2026

  180 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $122/SF
  • 46 Days On Market

  Current Estimated Value $603,612

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
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  /15

  $110,000 Sold Sep 04, 2025

  706 Williamsburg Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 2024

  Last Sold Summary

  • 21% Below List Price
  • $119/SF

  Current Estimated Value $115,261

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan

  706 Williamsburg Dr, Winchester, KY 40391
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  /30

  $185,000 Sold Feb 06, 2026

  40 Garner St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft
  • Built 1950

  Last Sold Summary

  • 16% Below List Price
  • $137/SF
  • 217 Days On Market

  Current Estimated Value $195,036

  Last Listing Agent Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
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  /19

  $189,000 Sold Mar 03, 2026

  111 Quail Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft
  • Built 1994

  Last Sold Summary

  • $158/SF
  • 5 Days On Market

  Current Estimated Value $190,861

  Last Listing Agent Kim Dice EXP Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
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  /35

  $244,000 Sold Mar 09, 2026

  426 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,641 Sq Ft
  • Built 2004

  Last Sold Summary

  • $149/SF
  • 2 Days On Market

  Current Estimated Value $248,226

  Last Listing Agent Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
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  /2

  $160,000 Sold Sep 19, 2025

  8 Village Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $113/SF
  • 0 Days On Market

  Current Estimated Value $277,853

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  8 Village Dr, Winchester, KY 40391
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  /22

  $193,000 Sold Jun 06, 2025

  116 Linden Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Built 1945

  Last Sold Summary

  • 2% Below List Price
  • $166/SF
  • 3 Days On Market

  Current Estimated Value $199,117

  Last Listing Agent Jeremy Perryman United Real Estate Bluegrass

  116 Linden Ave, Winchester, KY 40391
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  /19

  $220,000 Sold Apr 23, 2025

  112 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $183/SF
  • 1 Day On Market

  Current Estimated Value $227,614

  Last Listing Agent Nena Honaker Tom Goebel & Company

  112 Central Ave, Winchester, KY 40391
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  /2

  $85,000 Sold Dec 12, 2025

  1385 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 6.43 Acres
  • $13,219 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 6 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1385 Sewell Shop Rd, Winchester, KY 40391
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  /53

  $867,500 Sold Aug 01, 2025

  511 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 4.5 Baths
  • 4,698 Sq Ft
  • Built 1885

  Last Sold Summary

  • 11% Below List Price
  • $185/SF
  • 318 Days On Market

  Current Estimated Value $908,797

  Last Listing Agent Greg Leveridge Block + Lot Real Estate

  511 Boone Ave, Winchester, KY 40391
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  /36

  $420,000 Sold Feb 25, 2026

  134 Fontaine Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft
  • Built 1994

  Last Sold Summary

  • 7% Below List Price
  • $153/SF
  • 126 Days On Market

  Current Estimated Value $421,734

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
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  /41

  $310,000 Sold Dec 29, 2025

  1996 White Conkwright Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,055 Sq Ft
  • Built 1966

  Last Sold Summary

  • 9% Below List Price
  • $294/SF
  • 45 Days On Market

  Current Estimated Value $320,605

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
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  /38

  $599,500 Sold Sep 08, 2025

  102 Bella Shae Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft
  • Built 2025

  Last Sold Summary

  • $272/SF
  • 72 Days On Market

  Current Estimated Value $584,967

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
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  /34

  $333,900 Sold Jul 28, 2025

  366 Hanover Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,162 Sq Ft
  • Built 2001

  Last Sold Summary

  • $154/SF
  • 2 Days On Market

  Current Estimated Value $337,463

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  366 Hanover Dr, Winchester, KY 40391
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  /10

  $100,000 Sold Feb 20, 2026

  17 Waveland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $94/SF
  • 4 Days On Market

  Current Estimated Value $144,535

  Last Listing Agent Darrell Lewis DIYFlatFee.Com

  17 Waveland Ave, Winchester, KY 40391
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  /37

  $220,000 Sold Sep 23, 2025

  213 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 4 Days On Market

  Current Estimated Value $218,554

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
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  /2

  $110,000 Sold May 13, 2025

  140 Duclair Dr, Winchester, KY 40391

  • Land
  • 0.42 Acre
  • $261,905 per Acre

  Last Sold Summary

  • 900 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  140 Duclair Dr, Winchester, KY 40391
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  /44

  $515,000 Sold May 19, 2025

  31 Bonnie Brook Ln, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 4,091 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $126/SF
  • 294 Days On Market

  Current Estimated Value $545,180

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

  31 Bonnie Brook Ln, Winchester, KY 40391
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  /14

  $200,000 Sold Sep 19, 2025

  9711 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 11% Below List Price
  • 19 Days On Market

  Last Listing Agent Jessica Maloney Denniston Realty

  9711 Ironworks Rd, Winchester, KY 40391
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  /75

  $490,000 Sold Sep 26, 2025

  497 Goose Creek Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,972 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 2 Days On Market

  Current Estimated Value $464,023

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
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  /25

  $287,000 Sold Aug 20, 2025

  220 Mcdowell Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $205/SF
  • 36 Days On Market

  Current Estimated Value $298,976

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
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  /33

  $240,000 Sold Sep 10, 2025

  752 Wayland Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $97/SF
  • 18 Days On Market

  Current Estimated Value $255,668

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391
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  /24

  $275,000 Sold Mar 02, 2026

  434 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2012

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $237,019

  Last Listing Agent Joshua Davis The Agency

  434 Paisley Ct, Winchester, KY 40391
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  /27

  $185,000 Sold Mar 23, 2026

  616 Boone Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,223 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $151/SF
  • 16 Days On Market

  Current Estimated Value $197,049

  Last Listing Agent Garnett Davis Tom Goebel & Company

  616 Boone Ave, Winchester, KY 40391
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  /29

  $262,500 Sold Feb 18, 2026

  410 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 69 Days On Market

  Current Estimated Value $260,920

  Last Listing Agent Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
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  /27

  $245,000 Sold Jun 13, 2025

  8 Seneca Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $142/SF
  • 8 Days On Market

  Current Estimated Value $250,719

  Last Listing Agent Michael Hilario The Agency

  8 Seneca Dr, Winchester, KY 40391
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  /26

  $239,900 Sold Jun 23, 2025

  134 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Below List Price
  • $128/SF
  • 74 Days On Market

  Current Estimated Value $242,875

  Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

  134 Boone Ave, Winchester, KY 40391
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  /40

  $206,000 Sold Apr 29, 2025

  194 Spruce Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,053 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $196/SF
  • 25 Days On Market

  Current Estimated Value $212,967

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  194 Spruce Ct, Winchester, KY 40391
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  /31

  $240,200 Sold Oct 28, 2025

  203 Inverness Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,935 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $124/SF
  • 16 Days On Market

  Current Estimated Value $243,322

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  203 Inverness Ln, Winchester, KY 40391
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  /13

  $38,700 Sold May 20, 2025

  11 Spring St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1945

  Last Sold Summary

  • 3% Below List Price
  • $35/SF
  • 33 Days On Market

  Current Estimated Value $44,696

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  11 Spring St, Winchester, KY 40391
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  /36

  $345,000 Sold Jun 02, 2025

  1173 Lafayette Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $181/SF
  • 36 Days On Market

  Current Estimated Value $358,356

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  1173 Lafayette Blvd, Winchester, KY 40391
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  /43

  $339,000 Sold Feb 12, 2026

  106 Gibson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 2021

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $344,619

  Last Listing Agent Brittany Nester RO&CO Real Estate

  106 Gibson Way, Winchester, KY 40391
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  /36

  $472,500 Sold Sep 09, 2025

  208 Royal Oak Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,593 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Above List Price
  • $182/SF
  • 1 Day On Market

  Current Estimated Value $467,389

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  208 Royal Oak Dr, Winchester, KY 40391
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  /6

  $51,000 Sold May 14, 2025

  214 Ashton Oak Way, Winchester, KY 40391

  • Land
  • 0.25 Acre
  • $204,000 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 325 Days On Market

  Current Estimated Value $56,419

  Last Listing Agent Melia Hord Keller Williams Legacy Group

  214 Ashton Oak Way, Winchester, KY 40391
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  /23

  $135,000 Sold Jul 02, 2025

  2100 Old Log Lick Rd, Winchester, KY 40391

  • Land
  • 5 Acres
  • $27,000 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 69 Days On Market

  Current Estimated Value $140,632

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2100 Old Log Lick Rd, Winchester, KY 40391
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  /20

  $217,500 Sold Sep 30, 2025

  511 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $155/SF
  • 28 Days On Market

  Current Estimated Value $218,640

  Last Listing Agent Tyler I Back The Brokerage

  511 Acadia Way, Winchester, KY 40391

Showing Results 161 - 200, Page 5 of 12