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Recently Sold Winchester, KY Homes

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  • /8

    $15,000

    Sold Dec 30, 2025

    61 Melbourne St, Winchester, KY 40391

    • Land
    • 4,356 Sq Ft
    • $150,000 per Acre

    Last Sold Summary

    • 40% Below List Price
    • 57 Days On Market

    Current Estimated Value $80,682

    Last Listing Agent Brian Lewis Guide Realty, Inc.

    61 Melbourne St, Winchester, KY 40391
  • /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
  • /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 $448,146

    Last Listing Agent Alyssa Ryan Marshall Lane Real Estate - Lexington

    1128 Lafayette Blvd, Winchester, KY 40391
  • /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 $288,526

    Last Listing Agent Terry Billiter Premier Property Consultants

    205 Beaumont Place, Winchester, KY 40391
  • /51

    $750,000

    Sold May 21, 2026

    1783 Gay Evans Rd, Winchester, KY 40391

    • 5 Beds
    • 3.5 Baths
    • 2,904 Sq Ft
    • Built 1998

    Last Sold Summary

    • 6% Below List Price
    • $258/SF
    • 135 Days On Market

    Current Estimated Value $758,759

    Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

    1783 Gay Evans Rd, Winchester, KY 40391
  • /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 $338,031

    Last Listing Agent Josh Wood Freedom Realty & Property Management

    408 Calmes Blvd, Winchester, KY 40391
  • /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 $306,425

    Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

    202 Dubuy Dr, Winchester, KY 40391
  • /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 $98,044

    Last Listing Agent Rony Jo Ballou Power House Realty

    15 Sycamore St, Winchester, KY 40391
  • /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 $199,524

    Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

    2721 Pretty Run Rd, Winchester, KY 40391
  • /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 $319,964

    Last Listing Agent Bradley Warford Century 21 Pinnacle

    329 Hanover Dr, Winchester, KY 40391
  • /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 $580,680

    Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

    2615 Crowe Ridge Rd, Winchester, KY 40391
  • /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 $291,429

    Last Listing Agent Bradley Morgan The Local Agents

    606 Laura Dr, Winchester, KY 40391
  • /62

    $431,000

    Sold May 12, 2026

    2 Stoney Brook Dr, Winchester, KY 40391

    • 3 Beds
    • 3.5 Baths
    • 3,633 Sq Ft
    • Built 1983

    Last Sold Summary

    • 1% Below List Price
    • $119/SF
    • 1 Day On Market

    Current Estimated Value $436,530

    Last Listing Agent Kelli Hunt Berkshire Hathaway HomeServices Foster Realtors

    2 Stoney Brook Dr, Winchester, KY 40391
  • /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 $182,660

    Last Listing Agent Garnett Davis Tom Goebel & Company

    612 Boone Ave, Winchester, KY 40391
  • /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 $287,231

    Last Listing Agent Holly Goeing The Agency

    10 Howard Dr, Winchester, KY 40391
  • /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 $348,495

    Last Listing Agent Holly Goeing The Agency

    3431 Colby Rd, Winchester, KY 40391
  • /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 $271,665

    Last Listing Agent Joyce Ratliff Tom Goebel & Company

    130 Village Ct, Winchester, KY 40391
  • /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 $245,286

    Last Listing Agent Kevin Bradley KB Realty Group

    619 Laura Dr, Winchester, KY 40391
  • /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 $863,879

    Last Listing Agent Michael Hilario The Agency

    1110 Craig Crossing, Winchester, KY 40391
  • /35

    $285,000

    Sold May 01, 2026

    192 Prescott Ln, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Built 2007

    Last Sold Summary

    • 4% Above List Price
    • $184/SF
    • 1 Day On Market

    Current Estimated Value $280,092

    Last Listing Agent Joy Murphy United Real Estate Bluegrass

    192 Prescott Ln, Winchester, KY 40391
  • /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 $289,121

    Last Listing Agent Brittany Beer eXp Realty, LLC

    729 Wayland Dr, Winchester, KY 40391
  • /14

    $125,000

    Sold Apr 01, 2026

    464 Ecton Rd, Winchester, KY 40391

    • Land
    • 1.03 Acres
    • $121,359 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 3 Days On Market

    Current Estimated Value $143,008

    Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

    464 Ecton Rd, Winchester, KY 40391
  • /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 $328,075

    Last Listing Agent Joshua Davis The Agency

    1831 Kiddville Rd, Winchester, KY 40391
  • /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 $227,856

    Last Listing Agent Tisha Monte Bluegrass Properties Group

    204 Crawford Ct, Winchester, KY 40391
  • /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 $233,397

    Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

    301 Cabin Creek Heights, Winchester, KY 40391
  • /16

    $165,000

    Sold Apr 30, 2026

    47 Buckner St, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft
    • Built 1930

    Last Sold Summary

    • 8% Below List Price
    • $101/SF
    • 24 Days On Market

    Current Estimated Value $177,975

    Last Listing Agent Michael Hilario The Agency

    47 Buckner St, Winchester, KY 40391
  • /56

    $320,000

    Sold Jun 03, 2026

    215 Old Log Lick Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 2002

    Last Sold Summary

    • 9% Below List Price
    • $221/SF
    • 53 Days On Market

    Current Estimated Value $330,695

    Last Listing Agent Kerry Ball Local First Realty, LLC

    215 Old Log Lick Rd, Winchester, KY 40391
  • /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 $286,532

    Last Listing Agent Teresa Richmond Freedom Realty & Property Management

    225 Prescott Ln, Winchester, KY 40391
  • /20

    $217,500

    Sold May 22, 2026

    7 Hiawatha Trail, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,190 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $183/SF
    • 10 Days On Market

    Current Estimated Value $218,710

    Last Listing Agent Serena Cassidy Coldwell Banker McMahan

    7 Hiawatha Trail, Winchester, KY 40391
  • /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 $198,347

    Last Listing Agent Dale Hatton Dream Maker Realty, LLC

    605 Dixiana Dr, Winchester, KY 40391
  • /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 $866,775

    Last Listing Agent Emily Miller Bluegrass Sotheby's International Realty

    2158 Venable Rd, Winchester, KY 40391
  • /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 $356,139

    Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

    219 Hampton Ave, Winchester, KY 40391
  • /28

    $83,000

    Sold May 08, 2026

    32 Hays St, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • Built 1950

    Last Sold Summary

    • 8% Below List Price
    • $54/SF
    • 5 Days On Market

    Current Estimated Value $95,129

    Last Listing Agent Christa Joynt Keller Williams Commonwealth

    32 Hays St, Winchester, KY 40391
  • /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 $282,813

    Last Listing Agent Josh Wood Freedom Realty & Property Management

    227 Cross Brook Ln, Winchester, KY 40391
  • /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 $293,814

    Last Listing Agent Jennifer Guyton White Realty, LLC

    126 Ashley Dr, Winchester, KY 40391
  • /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 $356,978

    Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

    205 Chardonnay Ct, Winchester, KY 40391
  • /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 $218,245

    Last Listing Agent Aaron Kendall Lifstyl Real Estate

    305 Geronimo Ct, Winchester, KY 40391
  • /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 $326,533

    Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

    104 Teakwood Ct, Winchester, KY 40391
  • /33

    $219,900

    Sold May 28, 2026

    21 Kentucky St, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • Built 1920

    Last Sold Summary

    • $164/SF
    • 2 Days On Market

    Current Estimated Value $216,772

    Last Listing Agent Jenny Mateyoke Keller Williams Legacy Group

    21 Kentucky St, Winchester, KY 40391
  • /39

    $549,000

    Sold Jul 30, 2025

    154 Hawthorne Dr, Winchester, KY 40391

    • 5 Beds
    • 3.5 Baths
    • 3,478 Sq Ft
    • Built 2020

    Last Sold Summary

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

    Current Estimated Value $593,991

    Last Listing Agent Jarran Thomas The Agency

    154 Hawthorne Dr, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 12

Frequently Asked Questions

What is the average home price in Winchester, KY?
Homes for sale in Winchester, KY have an average home price of $341,824.
What is the average time to sell a house in Winchester, KY?
The houses for sale in Winchester, KY spend an average of 35 days on the market.
What is the number of active homes for sale in Winchester, KY?
There are 87 active homes for sale in Winchester, KY.
How many homes have sold over the last 12 months in Winchester, KY?
321 homes have sold in Winchester, KY over the last 12 months.

Home Prices in Winchester, KY

Home Price Trends

Median Sale Price
$260,000
Median Single Family Sale Price
$268,000
Median Townhouse Sale Price
$185,000
Median 2 Bedroom Sale Price
$172,450
Median 1 Bedroom Sale Price
$169,900
Average Price Per Sq Ft
$162
Number of Homes for Sale
87
Last 12 months Home Sales
321
Months of Supply
3.30
Median List Price
$270,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
9%
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