Recently Sold Winchester, KY Homes

/35
$215,000 Sold Feb 03, 2025

1896 Mount Sterling Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 1,942 Sq Ft
- Built 1960
Last Sold Summary
- 1% Below List Price
- $111/SF
- 10 Days On Market
Current Estimated Value $241,345

Last Listing Agent Keith Wilson Coldwell Banker McMahan

1896 Mount Sterling Rd, Winchester, KY 40391
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/27
$274,900 Sold May 23, 2025

707 Terry Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,770 Sq Ft
- Built 1978
Last Sold Summary
- 5% Below List Price
- $155/SF
- 40 Days On Market
Current Estimated Value $278,444

Last Listing Agent Kymberly McCreary EXP Realty, LLC

707 Terry Dr, 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 $554,435

Last Listing Agent Jarran Thomas The Agency

154 Hawthorne Dr, Winchester, KY 40391
/47
$374,900 Sold Sep 19, 2025

714 Concord Ave, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,750 Sq Ft
- Built 2017
Last Sold Summary
- $214/SF
- 23 Days On Market
Current Estimated Value $373,121

Last Listing Agent Josh Wood Freedom Realty & Property Management

714 Concord Ave, Winchester, KY 40391
/36
$309,000 Sold May 21, 2025

172 Buckingham Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,958 Sq Ft
- Built 1999
Last Sold Summary
- 6% Below List Price
- $158/SF
- 29 Days On Market
Current Estimated Value $322,932

Last Listing Agent Mila Ensor Ensor Real Estate, LLC

172 Buckingham Ln, Winchester, KY 40391
/3
$20,000 Sold Jan 27, 2025

735 Williamsburg Dr, Winchester, KY 40391
- Land
- 0.09 Acre
- $222,222 per Acre
Last Sold Summary
- 49% Below List Price
- 140 Days On Market
Current Estimated Value $32,866

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

735 Williamsburg Dr, Winchester, KY 40391
/42
$390,000 Sold Oct 21, 2025

19 Snowfall Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,625 Sq Ft
- Built 1950
Last Sold Summary
- 11% Above List Price
- $240/SF
- 2 Days On Market
Last Listing Agent Bradford Queen Bluegrass Sotheby's International Realty

19 Snowfall Dr, Winchester, KY 40391
/34
$369,500 Sold Aug 22, 2025

148 Gibson Way, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,456 Sq Ft
- Built 2022
Last Sold Summary
- 4% Below List Price
- $150/SF
- 11 Days On Market
Current Estimated Value $376,830

Last Listing Agent W Patrick Arvin Keller Williams Commonwealth

148 Gibson Way, Winchester, KY 40391
/26
$200,000 Sold Oct 02, 2025

34 N Burns Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- Built 1945
Last Sold Summary
- 11% Below List Price
- $133/SF
- 8 Days On Market
Last Listing Agent Ashley Barreto Indigo & Co

34 N Burns Ave, Winchester, KY 40391
/16
$214,900 Sold Dec 05, 2025

15 Holly Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2025
Last Sold Summary
- 4% Below List Price
- $179/SF
- 52 Days On Market
Last Listing Agent Nena Honaker Tom Goebel & Company

15 Holly Ave, Winchester, KY 40391
/48
$550,000 Sold Sep 04, 2025

594 Earlymeade Dr, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 3,489 Sq Ft
- Built 2007
Last Sold Summary
- 4% Below List Price
- $158/SF
- 43 Days On Market
Current Estimated Value $556,957

Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

594 Earlymeade Dr, Winchester, KY 40391
/28
$359,900 Sold Jul 30, 2025

210 Jett Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
- Built 2024
Last Sold Summary
- $225/SF
- 311 Days On Market
Last Listing Agent Mila Ensor Ensor Real Estate, LLC

210 Jett Dr, Winchester, KY 40391
/47
$330,000 Sold Mar 31, 2025

150 Privacy Ln, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,784 Sq Ft
- Built 1987
Last Sold Summary
- 6% Below List Price
- $119/SF
- 103 Days On Market
Current Estimated Value $348,946

Last Listing Agent Jason Joseph Keller Williams Commonwealth

150 Privacy Ln, Winchester, KY 40391
/73
$325,000 Sold Sep 23, 2025

407 Fairholme Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,805 Sq Ft
- Built 2021
Last Sold Summary
- 4% Below List Price
- $180/SF
- 123 Days On Market
Current Estimated Value $328,033

Last Listing Agent Josh Wood Freedom Realty & Property Management

407 Fairholme Way, Winchester, KY 40391
/55
$785,000 Sold Feb 25, 2025

280 Penny Ln, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,885 Sq Ft
- Built 2014
Last Sold Summary
- 1% Below List Price
- $272/SF
- 13 Days On Market
Current Estimated Value $841,992

Last Listing Agent Nora Williams Keller Williams Commonwealth

280 Penny Ln, Winchester, KY 40391
/40
$210,000 Sold Sep 11, 2025

635 Lisletown Ln, Winchester, KY 40391
- 2 Beds
- 2 Baths
- 1,628 Sq Ft
- Built 1981
Last Sold Summary
- 12% Below List Price
- $129/SF
- 31 Days On Market
Current Estimated Value $216,085

Last Listing Agent Robin Jones Keller Williams Legacy Group

635 Lisletown Ln, Winchester, KY 40391
/43
$485,000 Sold Jun 23, 2025

430 Fairholme Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,414 Sq Ft
- Built 2017
Last Sold Summary
- 4% Below List Price
- $201/SF
- 55 Days On Market
Current Estimated Value $493,449

Last Listing Agent Robyn Bradley Woods Realty Group

430 Fairholme Way, Winchester, KY 40391
/24
$186,000 Sold May 14, 2025

205 Arbor Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,188 Sq Ft
- Built 1994
Last Sold Summary
- 3% Above List Price
- $157/SF
- 77 Days On Market
Current Estimated Value $188,290

Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

205 Arbor Ct, Winchester, KY 40391
/30
$310,900 Sold Sep 12, 2025

115 Hampton Ave, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 3,042 Sq Ft
- Built 1960
Last Sold Summary
- 4% Below List Price
- $102/SF
- 2 Days On Market
Current Estimated Value $314,396

Last Listing Agent Lauren Ball Deborah Ball Realty

115 Hampton Ave, Winchester, KY 40391
/82
$385,000 Sold Nov 07, 2025

1138 Lafayette Blvd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,300 Sq Ft
- Built 1995
Last Sold Summary
- 4% Above List Price
- $167/SF
- 1 Day On Market
Last Listing Agent Josh Wood Freedom Realty & Property Management

1138 Lafayette Blvd, Winchester, KY 40391
/17
$190,000 Sold Sep 10, 2025

114 Sunset Heights, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,059 Sq Ft
- Built 1960
Last Sold Summary
- 3% Below List Price
- $179/SF
- 50 Days On Market
Current Estimated Value $188,941

Last Listing Agent Susan Baldwin Threshold Real Estate Services

114 Sunset Heights, Winchester, KY 40391
/48
$222,500 Sold Jul 28, 2025

217 Locust Grove Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,055 Sq Ft
- Built 1955
Last Sold Summary
- 1% Above List Price
- $108/SF
- 2 Days On Market
Current Estimated Value $223,628

Last Listing Agent Robin Murray The Agency

217 Locust Grove Rd, Winchester, KY 40391
/34
$342,000 Sold Sep 16, 2025

3560 Wades Mill Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,305 Sq Ft
- Built 1950
Last Sold Summary
- 10% Below List Price
- $262/SF
- 37 Days On Market
Current Estimated Value $344,847

Last Listing Agent Sarah MacHarg Kentucky Land and Home

3560 Wades Mill Rd, Winchester, KY 40391
/32
$195,700 Sold Mar 10, 2025

162 French Ave, Winchester, KY 40391
- 4 Beds
- 1 Bath
- 2,327 Sq Ft
- Built 1920
Last Sold Summary
- 11% Below List Price
- $84/SF
- 15 Days On Market
Current Estimated Value $216,593

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

162 French Ave, Winchester, KY 40391
/5
$41,500 Sold Sep 15, 2025

434 Fairholme Way, Winchester, KY 40391
- Land
- 0.36 Acre
- $115,278 per Acre
Last Sold Summary
- 8% Below List Price
- 6 Days On Market
Current Estimated Value $52,232

Last Listing Agent Justin Lee JL Realty Group, LLC

434 Fairholme Way, Winchester, KY 40391
/17
$162,500 Sold Dec 31, 2024

13 Waveland Ave, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,148 Sq Ft
- Built 1950
Last Sold Summary
- $142/SF
- 5 Days On Market
Current Estimated Value $161,829

Last Listing Agent Danielle Ratliff RE/MAX Creative Realty

13 Waveland Ave, Winchester, KY 40391
/23
$170,000 Sold Dec 31, 2024

20 3rd St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,710 Sq Ft
- Built 1960
Last Sold Summary
- 15% Below List Price
- $99/SF
- 26 Days On Market
Current Estimated Value $194,296

Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

20 3rd St, Winchester, KY 40391
/43
$215,000 Sold Jan 14, 2025

83 Hillcrest Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 2,052 Sq Ft
- Built 1965
Last Sold Summary
- 17% Below List Price
- $105/SF
- 98 Days On Market
Current Estimated Value $250,274

Last Listing Agent Timothy Saylor EXP Realty, LLC

83 Hillcrest Dr, Winchester, KY 40391
/48
$330,000 Sold May 23, 2025

113 Holiday Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,090 Sq Ft
- Built 1970
Last Sold Summary
- 3% Below List Price
- $158/SF
- 35 Days On Market
Current Estimated Value $317,663

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

113 Holiday Rd, Winchester, KY 40391
/48
$300,000 Sold Feb 07, 2025

509 Lasalle Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,484 Sq Ft
- Built 1987
Last Sold Summary
- 5% Below List Price
- $121/SF
- 155 Days On Market
Current Estimated Value $333,948

Last Listing Agent Kasey McCarty 5.23 Real Estate

509 Lasalle Ct, Winchester, KY 40391
/46
$441,000 Sold Jan 15, 2025

576 Earlymeade Dr, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 3,420 Sq Ft
- Built 2003
Last Sold Summary
- 7% Below List Price
- $129/SF
- 134 Days On Market
Current Estimated Value $486,302

Last Listing Agent Shari Frasure Keller Williams Commonwealth

576 Earlymeade Dr, Winchester, KY 40391
/42
$425,000 Sold Jan 02, 2025

4640 Ecton Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,802 Sq Ft
- Built 2016
Last Sold Summary
- 2% Below List Price
- $236/SF
- 55 Days On Market
Current Estimated Value $461,230

Last Listing Agent Christine McDonald FC Tucker Bluegrass

4640 Ecton Rd, Winchester, KY 40391
/38
$173,000 Sold Sep 22, 2025

44 5th St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,270 Sq Ft
- Built 1952
Last Sold Summary
- 2% Above List Price
- $136/SF
- 2 Days On Market
Current Estimated Value $173,905

Last Listing Agent Tirza Cooper The Howard Realty Co

44 5th St, Winchester, KY 40391
/52
$500,000 Sold Aug 25, 2025

1778 Elkin Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,020 Sq Ft
- Built 2015
Last Sold Summary
- 7% Below List Price
- $248/SF
- 103 Days On Market
Last Listing Agent Vicki VanWinkle ERA Select Real Estate

1778 Elkin Rd, Winchester, KY 40391
/21
$233,000 Sold Jan 31, 2025

4190 Trapp-Goffs Corner Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 992 Sq Ft
- Built 1978
Last Sold Summary
- 7% Below List Price
- $235/SF
- 49 Days On Market
Current Estimated Value $242,960

Last Listing Agent Christina Bucher Keller Williams Legacy Group

4190 Trapp-Goffs Corner Rd, Winchester, KY 40391
/28
$203,900 Sold Dec 10, 2025

25 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 925 Sq Ft
- Built 1968
Last Sold Summary
- 3% Below List Price
- $220/SF
- 35 Days On Market
Last Listing Agent Sarah Hess Keller Williams Commonwealth

25 Hiawatha Trail, Winchester, KY 40391
/3
$220,000 Sold Jul 30, 2025

412 Paisley Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,300 Sq Ft
- Built 2005
Last Sold Summary
- 4% Below List Price
- $169/SF
- 38 Days On Market
Current Estimated Value $222,554

Last Listing Agent John Wilson Bluegrass Properties Group

412 Paisley Ct, Winchester, KY 40391
/37
$228,000 Sold May 02, 2025

102 E Clark Dr, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,247 Sq Ft
- Built 1962
Last Sold Summary
- 1% Below List Price
- $183/SF
- 6 Days On Market
Current Estimated Value $227,254

Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

102 E Clark Dr, Winchester, KY 40391
/35
$185,000 Sold Apr 02, 2025

125 Magnolia St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,251 Sq Ft
- Built 1945
Last Sold Summary
- 2% Below List Price
- $148/SF
- 31 Days On Market
Current Estimated Value $201,387

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

125 Magnolia St, Winchester, KY 40391
/61
$372,500 Sold Mar 28, 2025

521 Lasalle Ct, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,101 Sq Ft
- Built 1979
Last Sold Summary
- 2% Below List Price
- $177/SF
- 15 Days On Market
Current Estimated Value $374,936

Last Listing Agent Keith Wilson Coldwell Banker McMahan

521 Lasalle Ct, Winchester, KY 40391

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