Recently Sold Winchester, KY Homes

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  /8

  $15,000 Sold Dec 30, 2025

  61 Melbourne St, Winchester, KY 40391

  • Land
  • 0.1 Acre
  • $150,000 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 57 Days On Market

  Current Estimated Value $52,699

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
• Explore Winchester

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  /20

  $189,500 Sold Dec 18, 2025

  13015 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 17% Below List Price
  • 134 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13015 Irvine Rd, Winchester, KY 40391
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  /43

  $430,000 Sold Jun 16, 2025

  1128 Lafayette Blvd, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,465 Sq Ft
  • Built 1995

  Last Sold Summary

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

  Current Estimated Value $454,295

  Last Listing Agent Alyssa Ryan Marshall Lane Real Estate - Lexington

  1128 Lafayette Blvd, Winchester, KY 40391
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  /41

  $272,000 Sold Jun 26, 2025

  205 Beaumont Place, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1995

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 4 Days On Market

  Current Estimated Value $286,307

  Last Listing Agent Terry Billiter Premier Property Consultants

  205 Beaumont Place, Winchester, KY 40391
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  /75

  $315,000 Sold Jun 27, 2025

  408 Calmes Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $170/SF
  • 46 Days On Market

  Current Estimated Value $329,049

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  408 Calmes Blvd, Winchester, KY 40391
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  /41

  $302,500 Sold Jan 05, 2026

  202 Dubuy Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Below List Price
  • $168/SF
  • 5 Days On Market

  Current Estimated Value $303,140

  Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

  202 Dubuy Dr, Winchester, KY 40391
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  /31

  $88,500 Sold Aug 08, 2025

  15 Sycamore St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1945

  Last Sold Summary

  • 12% Below List Price
  • $77/SF
  • 28 Days On Market

  Current Estimated Value $105,431

  Last Listing Agent Rony Jo Ballou Power House Realty

  15 Sycamore St, Winchester, KY 40391
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  /30

  $190,000 Sold Mar 06, 2026

  2721 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2000

  Last Sold Summary

  • 37% Below List Price
  • $130/SF
  • 12 Days On Market

  Current Estimated Value $268,900

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
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  /35

  $308,000 Sold Oct 03, 2025

  329 Hanover Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 5 Days On Market

  Current Estimated Value $309,837

  Last Listing Agent Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
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  /70

  $424,900 Sold Jun 02, 2025

  4353 Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,952 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Below List Price
  • $144/SF
  • 5 Days On Market

  Last Listing Agent M Gail Cleaver United Real Estate Bluegrass

  4353 Boonesboro Rd, Winchester, KY 40391
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  /81

  $599,500 Sold Aug 18, 2025

  2615 Crowe Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,222 Sq Ft
  • Built 2018

  Last Sold Summary

  • $270/SF
  • 1 Day On Market

  Current Estimated Value $577,764

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  2615 Crowe Ridge Rd, Winchester, KY 40391
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  /35

  $265,000 Sold Jun 18, 2025

  606 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $118/SF
  • 82 Days On Market

  Current Estimated Value $273,424

  Last Listing Agent Bradley Morgan The Local Agents

  606 Laura Dr, Winchester, KY 40391
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  /21

  $175,000 Sold Nov 18, 2025

  612 Boone Ave, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,262 Sq Ft
  • Built 1958

  Last Sold Summary

  • 12% Below List Price
  • $139/SF
  • 13 Days On Market

  Current Estimated Value $199,365

  Last Listing Agent Garnett Davis Tom Goebel & Company

  612 Boone Ave, Winchester, KY 40391
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  /24

  $277,500 Sold Aug 21, 2025

  10 Howard Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1961

  Last Sold Summary

  • 3% Below List Price
  • $175/SF
  • 0 Days On Market

  Current Estimated Value $283,681

  Last Listing Agent Holly Goeing The Agency

  10 Howard Dr, Winchester, KY 40391
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  /19

  $170,000 Sold Apr 28, 2025

  223 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  Last Sold Summary

  • 8% Below List Price
  • $166/SF
  • 82 Days On Market

  Current Estimated Value $179,997

  Last Listing Agent Jordan James Lifstyl Real Estate

  223 Blair Ave, Winchester, KY 40391
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  /14

  $320,000 Sold Oct 17, 2025

  3431 Colby Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 5,237 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $61/SF
  • 7 Days On Market

  Current Estimated Value $324,708

  Last Listing Agent Holly Goeing The Agency

  3431 Colby Rd, Winchester, KY 40391
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  /41

  $265,000 Sold Nov 12, 2025

  130 Village Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $133/SF
  • 4 Days On Market

  Current Estimated Value $267,281

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  130 Village Ct, Winchester, KY 40391
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  /37

  $207,000 Sold May 23, 2025

  632 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1974

  Last Sold Summary

  • $185/SF
  • 41 Days On Market

  Current Estimated Value $206,824

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  632 Laura Dr, Winchester, KY 40391
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  /31

  $231,000 Sold Jun 30, 2025

  619 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • Built 1980

  Last Sold Summary

  • $165/SF
  • 17 Days On Market

  Current Estimated Value $240,315

  Last Listing Agent Kevin Bradley KB Realty Group

  619 Laura Dr, Winchester, KY 40391
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  /64

  $929,000 Sold Sep 05, 2025

  1110 Craig Crossing, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,670 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $348/SF
  • 23 Days On Market

  Current Estimated Value $797,299

  Last Listing Agent Michael Hilario The Agency

  1110 Craig Crossing, Winchester, KY 40391
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  /6

  $225,000 Sold Apr 22, 2025

  845 Gay Evans Rd, Winchester, KY 40391

  • Land
  • 8.59 Acres
  • $26,193 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 35 Days On Market

  Last Listing Agent Holly Goeing The Agency

  845 Gay Evans Rd, Winchester, KY 40391
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  /2

  $299,900 Sold Aug 08, 2025

  Unlisted Address

  • 3 Beds
  • 3 Baths
  • 2,054 Sq Ft
  • Built 1970

  Last Sold Summary

  • $146/SF

  Current Estimated Value $298,513

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  Unlisted Address
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  /21

  $207,000 Sold May 12, 2025

  513 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2001

  Last Sold Summary

  • 4% Below List Price
  • $154/SF
  • 35 Days On Market

  Current Estimated Value $218,150

  Last Listing Agent Tyler I Back The Brokerage

  513 Acadia Way, Winchester, KY 40391
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  /19

  $288,500 Sold Feb 24, 2026

  729 Wayland Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $147/SF
  • 92 Days On Market

  Current Estimated Value $279,281

  Last Listing Agent Brittany Beer EXP Realty, LLC

  729 Wayland Dr, Winchester, KY 40391
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  /33

  $332,000 Sold Oct 14, 2025

  1831 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $189/SF
  • 82 Days On Market

  Current Estimated Value $327,026

  Last Listing Agent Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
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  /32

  $283,000 Sold Apr 03, 2025

  193 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft
  • Built 2004

  Last Sold Summary

  • $172/SF
  • 3 Days On Market

  Current Estimated Value $284,264

  Last Listing Agent Justin Satterwhite SimpliHOM

  193 Prescott Ln, Winchester, KY 40391
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  /25

  $223,000 Sold Nov 04, 2025

  204 Crawford Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,636 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 1 Day On Market

  Current Estimated Value $221,780

  Last Listing Agent Tisha Monte Bluegrass Properties Group

  204 Crawford Ct, Winchester, KY 40391
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  /29

  $227,500 Sold Sep 11, 2025

  301 Cabin Creek Heights, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,220 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Above List Price
  • $186/SF
  • 0 Days On Market

  Current Estimated Value $225,702

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  301 Cabin Creek Heights, Winchester, KY 40391
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  /2

  $125,000 Sold May 23, 2025

  265 Duclair Dr, Winchester, KY 40391

  • Land
  • 1.01 Acres
  • $123,762 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  265 Duclair Dr, Winchester, KY 40391
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  /41

  $279,900 Sold Aug 12, 2025

  225 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft
  • Built 2006

  Last Sold Summary

  • $155/SF
  • 8 Days On Market

  Current Estimated Value $286,653

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  225 Prescott Ln, Winchester, KY 40391
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  /49

  $442,500 Sold Apr 18, 2025

  321 Frontier Way, Winchester, KY 40391

  • 6 Beds
  • 3.5 Baths
  • 3,882 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Below List Price
  • $114/SF
  • 134 Days On Market

  Current Estimated Value $452,947

  Last Listing Agent Olivia White Deborah Ball Realty

  321 Frontier Way, Winchester, KY 40391
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  /24

  $185,000 Sold Jun 23, 2025

  605 Dixiana Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 23 Days On Market

  Current Estimated Value $193,527

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  605 Dixiana Dr, Winchester, KY 40391
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  /58

  $850,000 Sold Jun 27, 2025

  2158 Venable Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1988

  Last Sold Summary

  • $285/SF
  • 1 Day On Market

  Current Estimated Value $851,707

  Last Listing Agent Emily Miller Bluegrass Sotheby's International Realty

  2158 Venable Rd, Winchester, KY 40391
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  /39

  $340,000 Sold Oct 10, 2025

  219 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,929 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $116/SF
  • 48 Days On Market

  Current Estimated Value $348,458

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  219 Hampton Ave, Winchester, KY 40391
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  /69

  $282,500 Sold Sep 30, 2025

  227 Cross Brook Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $187/SF
  • 9 Days On Market

  Current Estimated Value $281,135

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  227 Cross Brook Ln, Winchester, KY 40391
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  /75

  $289,900 Sold Aug 11, 2025

  126 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft
  • Built 1992

  Last Sold Summary

  • $203/SF
  • 0 Days On Market

  Current Estimated Value $290,576

  Last Listing Agent Jennifer Guyton White Realty, LLC

  126 Ashley Dr, Winchester, KY 40391
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  /58

  $345,000 Sold Nov 14, 2025

  205 Chardonnay Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,179 Sq Ft
  • Built 1991

  Last Sold Summary

  • 8% Below List Price
  • $158/SF
  • 59 Days On Market

  Current Estimated Value $352,950

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  205 Chardonnay Ct, Winchester, KY 40391
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  /27

  $210,000 Sold Sep 04, 2025

  305 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $183/SF
  • 1 Day On Market

  Current Estimated Value $212,312

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  305 Geronimo Ct, Winchester, KY 40391
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  /44

  $320,000 Sold Nov 21, 2025

  104 Teakwood Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 24 Days On Market

  Current Estimated Value $319,295

  Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

  104 Teakwood Ct, Winchester, KY 40391
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  /2

  $195,000 Sold May 15, 2025

  Unlisted Address

  • 4 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • Built 1980

  Last Sold Summary

  • $107/SF

  Current Estimated Value $214,647

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address

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