Recently Sold Winchester, KY Homes

/18
$250,000

Sold Aug 20, 2026

280 Pine Ridge Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,296 Sq Ft
- Built 1964
Last Sold Summary
- 4% Below List Price
- $193/SF
- 54 Days On Market
Current Estimated Value $260,123

Last Listing Agent Derek Blankenship Keller Williams Commonwealth

280 Pine Ridge Rd, Winchester, KY 40391
Explore Winchester
/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 $108,274

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
/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 $740,996

Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

1783 Gay Evans Rd, 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 $308,415

Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

202 Dubuy Dr, 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 $204,370

Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

2721 Pretty Run Rd, Winchester, KY 40391
/49
$459,000

Sold Aug 19, 2026

105 Monet Blvd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 3,296 Sq Ft
- Built 1995
Last Sold Summary
- 2% Below List Price
- $139/SF
- 27 Days On Market
Current Estimated Value $458,737

Last Listing Agent Kristey Wood Keller Williams Legacy Group

105 Monet Blvd, 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 $324,148

Last Listing Agent Bradley Warford Century 21 Pinnacle

329 Hanover Dr, Winchester, KY 40391
/52
$255,000

Sold Aug 31, 2026

104 Jackson Ferry Rd, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 2,417 Sq Ft
- Built 1850
Last Sold Summary
- 7% Below List Price
- $106/SF
- 106 Days On Market
Current Estimated Value $270,671

Last Listing Agent Bob Sophiea eXp Realty, LLC

104 Jackson Ferry Rd, 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 $445,323

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 $185,445

Last Listing Agent Garnett Davis Tom Goebel & Company

612 Boone Ave, 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 $356,403

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 $282,192

Last Listing Agent Joyce Ratliff Tom Goebel & Company

130 Village Ct, Winchester, KY 40391
/62
$498,325

Sold Sep 11, 2026

919 Elkin Station Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,844 Sq Ft
- Built 1980
Last Sold Summary
- 3% Above List Price
- $175/SF
- 1 Day On Market
Current Estimated Value $407,705

Last Listing Agent Lori Tolson Lifstyl Real Estate

919 Elkin Station Rd, 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 $286,150

Last Listing Agent Joy Murphy United Real Estate Bluegrass

192 Prescott Ln, Winchester, KY 40391
/34
$278,000

Sold Aug 31, 2026

304 Sandra Dr, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 1,377 Sq Ft
- Built 1973
Last Sold Summary
- 1% Above List Price
- $202/SF
- 15 Days On Market
Current Estimated Value $272,270

Last Listing Agent Michael Hilario The Agency

304 Sandra Dr, Winchester, KY 40391
/29
$285,000

Sold Jun 12, 2026

426 E Broadway St, Winchester, KY 40391
- 5 Beds
- 2 Baths
- 1,838 Sq Ft
- Built 1945
Last Sold Summary
- 1% Below List Price
- $155/SF
- 12 Days On Market
Current Estimated Value $282,513

Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

426 E Broadway St, 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 $292,386

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 $134,081

Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

464 Ecton Rd, Winchester, KY 40391
/67
$410,000

Sold Jul 09, 2026

233 Schollsville Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,347 Sq Ft
- Built 2016
Last Sold Summary
- 2% Above List Price
- $304/SF
- 1 Day On Market
Current Estimated Value $406,775

Last Listing Agent Bill Deaton Keller Williams Legacy Group

233 Schollsville 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 $336,990

Last Listing Agent Joshua Davis The Agency

1831 Kiddville Rd, Winchester, KY 40391
/85
$1,370,000

Sold Sep 09, 2026

1200 Craig Crossing, Winchester, KY 40391
- 4 Beds
- 4.5 Baths
- 3,350 Sq Ft
- Built 2026
Last Sold Summary
- 2% Above List Price
- $409/SF
- 49 Days On Market
Last Listing Agent Michael Hilario The Agency

1200 Craig Crossing, Winchester, KY 40391
/8
$160,000

Sold Jul 13, 2026

107 Patio St, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 864 Sq Ft
- Built 1997
Last Sold Summary
- $185/SF
- 0 Days On Market
Current Estimated Value $161,771

Last Listing Agent Sherry Stephens Murphy Realty Group

107 Patio St, Winchester, KY 40391
/38
$484,900

Sold Aug 13, 2026

414 Fairholme Way, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,418 Sq Ft
- Built 2025
Last Sold Summary
- $201/SF
- 53 Days On Market
Current Estimated Value $474,841

Last Listing Agent Morgan Withrow The Brokerage

414 Fairholme Way, 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 $229,223

Last Listing Agent Tisha Monte Bluegrass Properties Group

204 Crawford Ct, Winchester, KY 40391
/26
$274,900

Sold Aug 25, 2026

136 Sturbridge Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,604 Sq Ft
- Built 2005
Last Sold Summary
- 2% Below List Price
- $171/SF
- 21 Days On Market
Current Estimated Value $279,661

Last Listing Agent Sarah MacHarg Kentucky Land and Home

136 Sturbridge Ln, 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 $171,741

Last Listing Agent Michael Hilario The Agency

47 Buckner St, Winchester, KY 40391
/74
$320,000

Sold Sep 10, 2026

13 Bel Air Dr, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,068 Sq Ft
- Built 1962
Last Sold Summary
- 6% Below List Price
- $155/SF
- 36 Days On Market
Current Estimated Value $333,822

Last Listing Agent Robin Jones Keller Williams Legacy Group

13 Bel Air Dr, 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 $317,779

Last Listing Agent Kerry Ball Local First Realty, LLC

215 Old Log Lick Rd, Winchester, KY 40391
/94
$759,000

Sold Jun 17, 2026

4040 Muddy Creek Rd, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 4,584 Sq Ft
- Built 2007
Last Sold Summary
- 15% Below List Price
- $166/SF
- 262 Days On Market
Current Estimated Value $767,253

Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

4040 Muddy Creek Rd, 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 $220,844

Last Listing Agent Serena Cassidy Coldwell Banker McMahan

7 Hiawatha Trail, 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 $345,254

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 $93,237

Last Listing Agent Christa Joynt Keller Williams Commonwealth

32 Hays St, Winchester, KY 40391
/30
$180,000

Sold Jul 02, 2026

217 S Highland St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 2,683 Sq Ft
- Built 1930
Last Sold Summary
- 31% Below List Price
- $67/SF
- 151 Days On Market
Current Estimated Value $192,892

Last Listing Agent Michael Hilario The Agency

217 S Highland 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 $291,112

Last Listing Agent Josh Wood Freedom Realty & Property Management

227 Cross Brook Ln, 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 $369,511

Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

205 Chardonnay 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 $329,742

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 $219,103

Last Listing Agent Jenny Mateyoke Keller Williams Legacy Group

21 Kentucky St, Winchester, KY 40391
/30
$168,000

Sold Jul 13, 2026

128 Bay Hill Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,289 Sq Ft
- Built 2003
Last Sold Summary
- 16% Below List Price
- $130/SF
- 37 Days On Market
Current Estimated Value $188,661

Last Listing Agent Melia Hord MELIA Realty LLC

128 Bay Hill Dr, Winchester, KY 40391
/20
$205,000

Sold Jul 27, 2026

301 Snowden Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,386 Sq Ft
- Built 1960
Last Sold Summary
- 2% Below List Price
- $148/SF
- 17 Days On Market
Current Estimated Value $212,976

Last Listing Agent Julia Lark The Brokerage

301 Snowden Dr, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 11

Kentucky Clark County

Frequently Asked Questions

What is the average home price in Winchester, KY?

Homes for sale in Winchester, KY have an average home price of $333,077.

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 82 active homes for sale in Winchester, KY.

How many homes have sold over the last 12 months in Winchester, KY?

284 homes have sold in Winchester, KY over the last 12 months.

Home Prices in Winchester, KY

The median home sale price in Winchester, KY is $264,500, up 10% year-over-year. Homes in Winchester sell in 35 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $264,500	Median Single Family Sale Price $267,500
Median Townhouse Sale Price $195,000	Median 2 Bedroom Sale Price $158,765
Median 1 Bedroom Sale Price $117,950	Average Price Per Sq Ft $160
Number of Homes for Sale 433	Last 12 months Home Sales 284
Months of Supply 3.50	Median List Price $270,000
Median Change From 1st List Price 3%	Median Home Sale Price YoY Change 10%

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Winchester Types of Homes for Sale

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