Recently Sold Winchester, KY Homes

/33
$159,200 Sold Oct 09, 2025

646 Laura Dr, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,534 Sq Ft
- Built 1980
Last Sold Summary
- 6% Below List Price
- $104/SF
- 16 Days On Market
Last Listing Agent Kimberly Brunson Hunter Real Estate

646 Laura Dr, Winchester, KY 40391
/32
$183,000 Sold Jul 30, 2025

517 Hidden Hills Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 2001
Last Sold Summary
- $163/SF
- 78 Days On Market
Current Estimated Value $189,703

Last Listing Agent Brenda Sipes Bridgewater Real Estate

517 Hidden Hills Way, Winchester, KY 40391
/17
$175,000 Sold May 07, 2025

220 Jackson St, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,228 Sq Ft
- Built 1940
Last Sold Summary
- $143/SF
- 1 Day On Market
Current Estimated Value $171,938

Last Listing Agent Joanna Howell Bluegrass Properties Group

220 Jackson St, Winchester, KY 40391
/35
$189,900 Sold Jan 16, 2025

24 Hughes Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
- Built 2024
Last Sold Summary
- $158/SF
- 24 Days On Market
Current Estimated Value $208,752

Last Listing Agent Nena Honaker Tom Goebel & Company

24 Hughes Ave, Winchester, KY 40391
/61
$220,000 Sold Nov 10, 2025

313 Snowden Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,232 Sq Ft
- Built 1960
Last Sold Summary
- 12% Below List Price
- $179/SF
- 51 Days On Market
Last Listing Agent Josh Wood Freedom Realty & Property Management

313 Snowden Dr, Winchester, KY 40391
/53
$80,000 Sold Apr 30, 2025

307 Jackson St, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,629 Sq Ft
- Built 1950
Last Sold Summary
- 33% Below List Price
- $49/SF
- 67 Days On Market
Current Estimated Value $91,237

Last Listing Agent Josh Wood Freedom Realty & Property Management

307 Jackson St, Winchester, KY 40391
/32
$285,000 Sold Jul 03, 2025

602 Laura Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,690 Sq Ft
- Built 1976
Last Sold Summary
- 11% Below List Price
- $169/SF
- 168 Days On Market
Current Estimated Value $286,213

Last Listing Agent Ryan O'Gara Real Broker, LLC

602 Laura Dr, Winchester, KY 40391
/2
$401,500 Sold May 15, 2025

Unlisted Address
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
- Built 1998
Last Sold Summary
- $201/SF
Current Estimated Value $402,221

Last Listing Agent Null Non-Member Non-Member Office

Unlisted Address
/17
$595,000 Sold Nov 17, 2025

304 Winterberry Dr, Winchester, KY 40391
- 7 Beds
- 4 Baths
- 4,386 Sq Ft
- Built 1999
Last Sold Summary
- 1% Below List Price
- $136/SF
- 10 Days On Market
Last Listing Agent Beckie Moore Bluegrass Properties Group

304 Winterberry Dr, Winchester, KY 40391
/18
$246,500 Sold May 16, 2025

6278 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,176 Sq Ft
- Built 1978
Last Sold Summary
- 7% Below List Price
- $210/SF
- 35 Days On Market
Current Estimated Value $262,122

Last Listing Agent Angela Yonts EXP Realty, LLC

6278 Irvine Rd, Winchester, KY 40391
/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
Last Listing Agent Samantha Gray National Real Estate

23 Hillcrest Dr, Winchester, KY 40391
/32
$230,000 Sold Mar 21, 2025

200 Bracken Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,252 Sq Ft
- Built 2002
Last Sold Summary
- 4% Below List Price
- $184/SF
- 3 Days On Market
Current Estimated Value $241,095

Last Listing Agent Amy Diamond ERA Select Real Estate

200 Bracken Ct, Winchester, KY 40391
/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
Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

1731 Ford Hampton Rd, Winchester, KY 40391
/35
$490,000 Sold Jan 31, 2025

163 Hawthorne Dr, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,830 Sq Ft
- Built 2018
Last Sold Summary
- 6% Below List Price
- $173/SF
- 151 Days On Market
Current Estimated Value $517,545

Last Listing Agent Michael Hilario The Agency

163 Hawthorne Dr, Winchester, KY 40391
/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 $334,639

Last Listing Agent Christine McDonald FC Tucker Bluegrass

138 Shanahan Ln, Winchester, KY 40391
/21
$338,000 Sold Mar 19, 2025

240 Athens Boonesboro Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,841 Sq Ft
- Built 1983
Last Sold Summary
- 170% Above List Price
- $184/SF
- 26 Days On Market
Current Estimated Value $254,587

Last Listing Agent Damon Ballinger C Roger Lewis Agency

240 Athens Boonesboro Rd, Winchester, KY 40391
/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 $115,334

Last Listing Agent Andrew Fugitt Coldwell Banker McMahan

706 Williamsburg Dr, Winchester, KY 40391
/28
$615,000 Sold Jan 31, 2025

1199 Mcclure Rd, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 4,665 Sq Ft
- Built 1993
Last Sold Summary
- 16% Below List Price
- $132/SF
- 129 Days On Market
Current Estimated Value $631,560

Last Listing Agent Teresa Richmond Freedom Realty & Property Management

1199 Mcclure Rd, Winchester, KY 40391
/47
$190,000 Sold Feb 03, 2025

15 Finley Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,392 Sq Ft
- Built 1950
Last Sold Summary
- 5% Below List Price
- $136/SF
- 45 Days On Market
Current Estimated Value $207,541

Last Listing Agent Victoria Byrd HomeFirst Real Estate

15 Finley Rd, Winchester, KY 40391
/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
Last Listing Agent Joyce Ratliff Tom Goebel & Company

8 Village Dr, Winchester, KY 40391
/50
$207,500 Sold Jan 13, 2025

122 Sunset Heights, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,715 Sq Ft
- Built 1960
Last Sold Summary
- 10% Below List Price
- $121/SF
- 67 Days On Market
Current Estimated Value $228,551

Last Listing Agent Christa Joynt Keller Williams Commonwealth

122 Sunset Heights, Winchester, KY 40391
/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 $200,812

Last Listing Agent Jeremy Perryman United Real Estate Bluegrass

116 Linden Ave, Winchester, KY 40391
/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 $225,386

Last Listing Agent Nena Honaker Tom Goebel & Company

112 Central Ave, Winchester, KY 40391
/26
$210,000 Sold Jan 24, 2025

3641 Trapp-Goffs Corner Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
- Built 1961
Last Sold Summary
- 11% Below List Price
- $188/SF
- 61 Days On Market
Current Estimated Value $217,543

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

3641 Trapp-Goffs Corner Rd, Winchester, KY 40391
/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 $874,563

Last Listing Agent Greg Leveridge Block + Lot Real Estate

511 Boone Ave, Winchester, KY 40391
/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 $606,527

Last Listing Agent Shane Underwood Keller Williams Commonwealth

102 Bella Shae Way, Winchester, KY 40391
/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 $337,417

Last Listing Agent Melissa Brown Keller Williams Legacy Group

366 Hanover Dr, Winchester, KY 40391
/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
Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

213 Blair Ave, Winchester, KY 40391
/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
/2
$4,360,000 Sold Jan 09, 2025

1403 Westwood Dr, Winchester, KY 40391
- 1,330 Sq Ft
- Built 2006
Last Sold Summary
- $3,278/SF
- 0 Days On Market
Current Estimated Value $243,712

Last Listing Agent Wes Durrant Crye-Leike Executive Realty

1403 Westwood Dr, Winchester, KY 40391
/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 $546,612

Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

31 Bonnie Brook Ln, Winchester, KY 40391
/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
/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
Last Listing Agent O Eve Stern Threshold Real Estate Services

497 Goose Creek Rd, Winchester, KY 40391
/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 $289,450

Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

220 Mcdowell Dr, Winchester, KY 40391
/2
$175,000 Sold Jan 07, 2025

Unlisted Address
- 4 Beds
- 2 Baths
- 1,680 Sq Ft
- Built 1979
Last Sold Summary
- $104/SF
Current Estimated Value $234,957

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

Unlisted Address
/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 $252,000

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

752 Wayland Dr, Winchester, KY 40391
/2
$110,750 Sold Feb 07, 2025

Unlisted Address
- 2 Beds
- 2 Baths
- 906 Sq Ft
- Built 1995
Last Sold Summary
- $122/SF
Current Estimated Value $160,232

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

Unlisted Address
/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 $244,349

Last Listing Agent Michael Hilario The Agency

8 Seneca Dr, Winchester, KY 40391
/47
$375,000 Sold Mar 07, 2025

372 Arrowhead Ln, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,744 Sq Ft
- Built 2001
Last Sold Summary
- $137/SF
- 2 Days On Market
Current Estimated Value $391,266

Last Listing Agent Lori Tolson Lifstyl Real Estate

372 Arrowhead Ln, Winchester, KY 40391
/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 $242,654

Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

134 Boone Ave, Winchester, KY 40391

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