Recently Sold Winchester, KY Homes

/87
$250,000 Sold Apr 18, 2025

418 Jameson Way, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
- Built 1996
Last Sold Summary
- 4% Below List Price
- $149/SF
- 3 Days On Market
Current Estimated Value $256,760

Last Listing Agent Josh Wood Freedom Realty & Property Management

418 Jameson Way, Winchester, KY 40391
/36
$257,400 Sold Nov 21, 2025

103 Hampton Ave, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,715 Sq Ft
- Built 1958
Last Sold Summary
- 10% Below List Price
- $150/SF
- 4 Days On Market
Last Listing Agent Brett Bussell Turf Town Properties

103 Hampton Ave, Winchester, KY 40391
/58
$460,000 Sold Jul 11, 2025

150 Stone Crest Rd, Winchester, KY 40391
- 4 Beds
- 4 Baths
- 4,448 Sq Ft
- Built 1978
Last Sold Summary
- 6% Below List Price
- $103/SF
- 18 Days On Market
Last Listing Agent Brenda Murphy Murphy Realty Group

150 Stone Crest Rd, Winchester, KY 40391
/3
$219,000 Sold May 20, 2025

410 Paisley Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,628 Sq Ft
- Built 2005
Last Sold Summary
- $135/SF
- 18 Days On Market
Current Estimated Value $226,601

Last Listing Agent John Wilson Bluegrass Properties Group

410 Paisley Ct, Winchester, KY 40391
/27
$270,000 Sold Aug 25, 2025

9 Hillcrest Dr, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 1,813 Sq Ft
- Built 2005
Last Sold Summary
- 3% Below List Price
- $149/SF
- 13 Days On Market
Current Estimated Value $276,472

Last Listing Agent Melissa Brown Keller Williams Legacy Group

9 Hillcrest Dr, Winchester, KY 40391
/57
$170,000 Sold Dec 30, 2024

17 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,000 Sq Ft
- Built 1968
Last Sold Summary
- 10% Below List Price
- $170/SF
- 32 Days On Market
Current Estimated Value $180,277

Last Listing Agent Josh Wood Freedom Realty & Property Management

17 Hiawatha Trail, Winchester, KY 40391
/15
$249,900 Sold Jun 09, 2025

234 Prescott Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,463 Sq Ft
- Built 2005
Last Sold Summary
- $171/SF
- 17 Days On Market
Current Estimated Value $258,036

Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

234 Prescott Ln, Winchester, KY 40391
/98
$750,000 Sold Dec 10, 2025

3900 (Mt) Mount Sterling Rd, Winchester, KY 40391
- 6 Beds
- 5 Baths
- 4,843 Sq Ft
- Built 2004
Last Sold Summary
- 9% Below List Price
- $155/SF
- 42 Days On Market
Last Listing Agent Teresa Richmond Freedom Realty & Property Management

3900 (Mt) Mount Sterling Rd, Winchester, KY 40391
/2
$110,750 Sold Feb 07, 2025

Unlisted Address
- 2 Beds
- 1.5 Baths
- 1,008 Sq Ft
- Built 1979
Last Sold Summary
- $110/SF
Current Estimated Value $152,697

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

Unlisted Address
/24
$207,000 Sold May 12, 2025

411 Pueblo Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,040 Sq Ft
- Built 2023
Last Sold Summary
- 1% Above List Price
- $199/SF
- 3 Days On Market
Current Estimated Value $210,537

Last Listing Agent Zach Johnson The Brokerage

411 Pueblo Ct, Winchester, KY 40391
/14
$222,500 Sold Jul 15, 2025

313 Vanover Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,064 Sq Ft
- Built 1995
Last Sold Summary
- 5% Below List Price
- $209/SF
- 112 Days On Market
Current Estimated Value $227,541

Last Listing Agent Bob Sophiea eXp Realty, LLC

313 Vanover Way, Winchester, KY 40391
/24
$203,000 Sold Jun 23, 2025

502 Corley Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,289 Sq Ft
- Built 1990
Last Sold Summary
- 4% Above List Price
- $157/SF
- 4 Days On Market
Current Estimated Value $201,963

Last Listing Agent Peter doCouto Plum Tree Realty

502 Corley Ln, Winchester, KY 40391
/16
$168,500 Sold Feb 25, 2025

142 Spruce Ct, Winchester, KY 40391
- 4 Beds
- 1.5 Baths
- 1,215 Sq Ft
- Built 1970
Last Sold Summary
- 14% Below List Price
- $139/SF
- 406 Days On Market
Current Estimated Value $190,780

Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

142 Spruce Ct, Winchester, KY 40391
/17
$278,000 Sold Apr 15, 2025

218 Bracken Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,292 Sq Ft
- Built 2005
Last Sold Summary
- $215/SF
- 7 Days On Market
Current Estimated Value $286,247

Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

218 Bracken Ct, Winchester, KY 40391
/21
$525,000 Sold Aug 28, 2025

Unlisted Address
- 3 Beds
- 2 Baths
- 1,724 Sq Ft
- Built 2016
Last Sold Summary
- $305/SF
- 0 Days On Market
Current Estimated Value $532,788

Last Listing Agent Josh Wood Freedom Realty & Property Management

Unlisted Address
/12
$65,000 Sold Feb 18, 2025

123 Magnolia St, Winchester, KY 40391
- 1,386 Sq Ft
- Built 1950
Last Sold Summary
- 24% Below List Price
- $47/SF
- 102 Days On Market
Current Estimated Value $79,407

Last Listing Agent Shawna Wever Wever Realty LLC

123 Magnolia St, Winchester, KY 40391
/29
$385,000 Sold Apr 21, 2025

1623 Little Stoner Rd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,800 Sq Ft
- Built 1982
Last Sold Summary
- 9% Below List Price
- $138/SF
- 25 Days On Market
Current Estimated Value $403,089

Last Listing Agent Sharon Ben David Berkshire Hathaway de Movellan Properties

1623 Little Stoner Rd, Winchester, KY 40391
/19
$175,000 Sold Feb 13, 2025

7 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,215 Sq Ft
- Built 1968
Last Sold Summary
- 8% Below List Price
- $144/SF
- 54 Days On Market
Current Estimated Value $190,098

Last Listing Agent Josh Wood Freedom Realty & Property Management

7 Hiawatha Trail, Winchester, KY 40391
/45
$269,000 Sold Aug 22, 2025

402 Mcdowell Dr, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,136 Sq Ft
- Built 1986
Last Sold Summary
- 22% Below List Price
- $126/SF
- 2 Days On Market
Current Estimated Value $272,849

Last Listing Agent Christine McDonald FC Tucker Bluegrass

402 Mcdowell Dr, Winchester, KY 40391
/19
$219,000 Sold Sep 17, 2025

521 Hidden Hills Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,335 Sq Ft
- Built 2003
Last Sold Summary
- $164/SF
- 4 Days On Market
Current Estimated Value $221,753

Last Listing Agent Cathy Cornett-Wilson Rector Hayden Realtors

521 Hidden Hills Way, Winchester, KY 40391
/38
$250,000 Sold Jun 27, 2025

214 Southwind Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,768 Sq Ft
- Built 1975
Last Sold Summary
- 1% Below List Price
- $141/SF
- 3 Days On Market
Current Estimated Value $252,566

Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

214 Southwind Dr, Winchester, KY 40391
/35
$395,000 Sold Jan 23, 2025

22 Fontaine Blvd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
- Built 1990
Last Sold Summary
- $180/SF
- 2 Days On Market
Current Estimated Value $425,165

Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

22 Fontaine Blvd, Winchester, KY 40391
/31
$175,000 Sold Mar 26, 2025

224 3rd St, Winchester, KY 40391
- 2 Beds
- 1.5 Baths
- 962 Sq Ft
- Built 2024
Last Sold Summary
- $182/SF
- 60 Days On Market
Current Estimated Value $177,659

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

224 3rd St, Winchester, KY 40391
/22
$173,000 Sold May 09, 2025

160 Autumn Ct, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,287 Sq Ft
- Built 1960
Last Sold Summary
- 1% Below List Price
- $134/SF
- 1 Day On Market
Current Estimated Value $185,861

Last Listing Agent Phillip Neeley-Morrison Bluegrass Home Group

160 Autumn Ct, Winchester, KY 40391
/33
$379,900 Sold Apr 25, 2025

151 Hawthorne Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 2019
Last Sold Summary
- $211/SF
- 0 Days On Market
Current Estimated Value $386,962

Last Listing Agent Kymberly McCreary EXP Realty, LLC

151 Hawthorne Dr, Winchester, KY 40391
/40
$240,000 Sold Jul 29, 2025

400 Verna Dr, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 2,617 Sq Ft
- Built 1980
Last Sold Summary
- 14% Below List Price
- $92/SF
- 12 Days On Market
Current Estimated Value $265,037

Last Listing Agent Melodie Lincavage RE/MAX Elite Realty

400 Verna Dr, Winchester, KY 40391
/11
$185,000 Sold Jan 17, 2025

25 Hays St, Winchester, KY 40391
- 5 Beds
- 3.5 Baths
- 2,830 Sq Ft
- Built 1940
Last Sold Summary
- 7% Below List Price
- $65/SF
- 33 Days On Market
Current Estimated Value $232,966

Last Listing Agent Chase Pennington Team Pannell Real Estate

25 Hays St, Winchester, KY 40391
/8
$195,000 Sold Dec 08, 2025

222 Holiday Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,100 Sq Ft
- Built 1985
Last Sold Summary
- 7% Below List Price
- $177/SF
- 349 Days On Market
Last Listing Agent Sophia Herald Herald Real Estate

222 Holiday Rd, Winchester, KY 40391
/43
$249,000 Sold Dec 31, 2024

704 Byrd Ave, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,566 Sq Ft
- Built 1950
Last Sold Summary
- $159/SF
- 10 Days On Market
Current Estimated Value $251,236

Last Listing Agent Sherry Stephens Murphy Realty Group

704 Byrd Ave, Winchester, KY 40391
/41
$270,000 Sold Oct 14, 2025

321 S Maple St, Winchester, KY 40391
- 6 Beds
- 4 Baths
- 4,490 Sq Ft
- Built 1900
Last Sold Summary
- 3% Below List Price
- $60/SF
- 9 Days On Market
Last Listing Agent Josh Wood Freedom Realty & Property Management

321 S Maple St, Winchester, KY 40391
/88
$740,000 Sold Apr 25, 2025

865 Sugar Ridge Rd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,146 Sq Ft
- Built 1997
Last Sold Summary
- 25% Below List Price
- $345/SF
- 88 Days On Market
Current Estimated Value $762,547

Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

865 Sugar Ridge Rd, Winchester, KY 40391
/39
$155,000 Sold Apr 24, 2025

10 Sylvania Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 953 Sq Ft
- Built 1961
Last Sold Summary
- 11% Below List Price
- $163/SF
- 207 Days On Market
Current Estimated Value $161,265

Last Listing Agent Christa Joynt Keller Williams Commonwealth

10 Sylvania Ave, Winchester, KY 40391
/16
$201,000 Sold Sep 05, 2025

128 Alabama St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,526 Sq Ft
- Built 1930
Last Sold Summary
- 7% Below List Price
- $132/SF
- 66 Days On Market
Current Estimated Value $201,964

Last Listing Agent Paul Eads Woods Realty Group

128 Alabama St, Winchester, KY 40391
/33
$180,000 Sold Sep 02, 2025

307 Blair Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- Built 1977
Last Sold Summary
- $180/SF
- 22 Days On Market
Current Estimated Value $179,976

Last Listing Agent Brooke Otis Mullins RO&CO Real Estate

307 Blair Ave, Winchester, KY 40391
/9
$190,000 Sold Jul 15, 2025

507 Hidden Hills Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 2001
Last Sold Summary
- 2% Below List Price
- $170/SF
- 5 Days On Market
Current Estimated Value $193,738

Last Listing Agent Sondra Clark Taylor Real Estate, LLC

507 Hidden Hills Way, Winchester, KY 40391
/37
$392,500 Sold Sep 08, 2025

576 Marseille Blvd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,991 Sq Ft
- Built 1991
Last Sold Summary
- 2% Below List Price
- $131/SF
- 24 Days On Market
Current Estimated Value $389,240

Last Listing Agent James Turek Bluegrass Sotheby's International Realty

576 Marseille Blvd, Winchester, KY 40391
/54
$350,000 Sold Apr 04, 2025

308 W Hickman St, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 2,681 Sq Ft
Last Sold Summary
- 9% Below List Price
- $131/SF
- 136 Days On Market
Current Estimated Value $353,032

Last Listing Agent Dalis Alvarez The Agency

308 W Hickman St, Winchester, KY 40391
/8
$80,000 Sold Feb 26, 2025

120 E Lexington Ave, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,332 Sq Ft
- Built 1934
Last Sold Summary
- 24% Below List Price
- $60/SF
- 80 Days On Market
Last Listing Agent Sondra Clark Taylor Real Estate, LLC

120 E Lexington Ave, Winchester, KY 40391
/41
$60,000 Sold Oct 24, 2025

145 Riverbend Ln, Winchester, KY 40391
- 1 Bed
- 1 Bath
- 740 Sq Ft
- Built 1984
Last Sold Summary
- 20% Below List Price
- $81/SF
- 6 Days On Market
Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

145 Riverbend Ln, Winchester, KY 40391
/2
$366,363 Sold May 22, 2025

140 Gibson Way, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,269 Sq Ft
- Built 2024
Last Sold Summary
- $161/SF
- 162 Days On Market
Current Estimated Value $369,613

Last Listing Agent Neshia Gaines Christies International Real Estate Bluegrass

140 Gibson Way, Winchester, KY 40391

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