Recently Sold Old Pine Grove Homes

/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
Explore Old Pine Grove
/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
/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
/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
/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
/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 $363,178

Last Listing Agent Patrick Arvin Keller Williams Commonwealth

148 Gibson Way, Winchester, KY 40391
/33
$364,900

Sold Feb 06, 2026

446 Tremont Ln, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,811 Sq Ft
- Built 2005
Last Sold Summary
- 1% Below List Price
- $130/SF
- 15 Days On Market
Current Estimated Value $367,799

Last Listing Agent Dylan Langdon The Agency

446 Tremont Ln, Winchester, KY 40391
/36
$261,000

Sold Feb 04, 2026

433 Wellington Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,234 Sq Ft
- Built 2010
Last Sold Summary
- 2% Below List Price
- $212/SF
- 60 Days On Market
Current Estimated Value $261,328

Last Listing Agent Nick Ratliff Realty Team - Nicholas Ratliff Real Broker, LLC - Lexington

433 Wellington Way, Winchester, KY 40391
/2
$4,900,000

Sold Dec 23, 2025

175 Chatham Place, Winchester, KY 40391
- 2 Beds
- 3 Baths
- 37,192 Sq Ft
- Built 2007
Last Sold Summary
- 13% Below List Price
- $132/SF
- 111 Days On Market
Current Estimated Value $5,022,391

Last Listing Agent Garry Milton Milton and Associates Real Estate

175 Chatham Place, Winchester, KY 40391
/30
$289,100

Sold Nov 03, 2025

223 Bartram Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,606 Sq Ft
- Built 2004
Last Sold Summary
- $180/SF
- 46 Days On Market
Current Estimated Value $291,397

Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

223 Bartram Ct, Winchester, KY 40391
/28
$265,000

Sold Jul 02, 2025

609 Clintonville Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,305 Sq Ft
- Built 1980
Last Sold Summary
- 2% Above List Price
- $203/SF
- 2 Days On Market
Current Estimated Value $275,210

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

609 Clintonville Rd, Winchester, KY 40391
/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
Current Estimated Value $230,813

Last Listing Agent Kimberly Brunson Hunter Real Estate

646 Laura Dr, 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 $289,370

Last Listing Agent Ryan O'Gara Real Broker, LLC

602 Laura Dr, Winchester, KY 40391
/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 $269,823

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

752 Wayland Dr, Winchester, KY 40391
/29
$262,500

Sold Feb 18, 2026

410 Wellington Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,192 Sq Ft
- Built 2007
Last Sold Summary
- 2% Below List Price
- $220/SF
- 69 Days On Market
Current Estimated Value $263,024

Last Listing Agent Monica Marcum Century 21 Pinnacle

410 Wellington Way, Winchester, KY 40391
/32
$310,000

Sold May 01, 2026

113 Strawberry Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,780 Sq Ft
- Built 2023
Last Sold Summary
- 2% Below List Price
- $174/SF
- 1 Day On Market
Current Estimated Value $317,437

Last Listing Agent Rob Bolton Christies International Real Estate Bluegrass

113 Strawberry Ln, Winchester, KY 40391
/43
$339,000

Sold Feb 12, 2026

106 Gibson Way, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,064 Sq Ft
- Built 2021
Last Sold Summary
- $164/SF
- 1 Day On Market
Current Estimated Value $340,724

Last Listing Agent Brittany Nester RO&CO Real Estate

106 Gibson Way, Winchester, KY 40391
/32
$259,000

Sold Apr 30, 2026

414 Wellington Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,251 Sq Ft
- Built 2007
Last Sold Summary
- $207/SF
- 53 Days On Market
Current Estimated Value $257,273

Last Listing Agent Amy Diamond ERA Select Real Estate

414 Wellington Way, Winchester, KY 40391
/21
$285,000

Sold Jul 29, 2025

219 Bartram Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,696 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $168/SF
- 8 Days On Market
Current Estimated Value $307,202

Last Listing Agent Nora Williams Keller Williams Commonwealth

219 Bartram Ct, Winchester, KY 40391
/65
$290,000

Sold Jun 18, 2025

13 Robyn Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,844 Sq Ft
- Built 1980
Last Sold Summary
- 2% Below List Price
- $157/SF
- 1 Day On Market
Current Estimated Value $303,806

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

13 Robyn Dr, Winchester, KY 40391
/29
$235,000

Sold Feb 09, 2026

142 Sturbridge Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,220 Sq Ft
- Built 2005
Last Sold Summary
- 6% Below List Price
- $193/SF
- 1 Day On Market
Current Estimated Value $245,544

Last Listing Agent Donna Mink Mink Realty

142 Sturbridge Ln, Winchester, KY 40391
/28
$234,500

Sold Jul 29, 2025

108 Sturbridge Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2004
Last Sold Summary
- 4% Below List Price
- $195/SF
- 45 Days On Market
Current Estimated Value $243,488

Last Listing Agent Jason Szaks EXIT Town & Country Realtors

108 Sturbridge Ln, Winchester, KY 40391
/22
$334,327

Sold Jul 01, 2025

136 Gibson Way, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 1,997 Sq Ft
- Built 2024
Last Sold Summary
- $167/SF
- 219 Days On Market
Current Estimated Value $348,029

Last Listing Agent Neshia Gaines Christies International Real Estate Bluegrass

136 Gibson Way, 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 $266,347

Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

234 Prescott Ln, 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 $274,843

Last Listing Agent Melodie Lincavage Berkshire Hathaway HomeServices Foster Realtors

400 Verna Dr, Winchester, KY 40391
/34
$265,000

Sold May 11, 2026

404 Wellington Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,682 Sq Ft
- Built 2005
Last Sold Summary
- 5% Below List Price
- $158/SF
- 158 Days On Market
Current Estimated Value $275,807

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

404 Wellington Way, Winchester, KY 40391
/54
$269,900

Sold Aug 12, 2025

137 Sturbridge Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,536 Sq Ft
- Built 2006
Last Sold Summary
- 2% Below List Price
- $176/SF
- 11 Days On Market
Current Estimated Value $276,050

Last Listing Agent Josh Wood Freedom Realty & Property Management

137 Sturbridge Ln, Winchester, KY 40391
/41
$259,900

Sold Aug 31, 2025

315 Newcastle Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,544 Sq Ft
- Built 2006
Last Sold Summary
- $168/SF
- 6 Days On Market
Current Estimated Value $267,856

Last Listing Agent Terra Long Keller Williams Commonwealth

315 Newcastle Ln, Winchester, KY 40391
/33
$385,000

Sold Sep 04, 2025

113 Shala Mar Rue, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,741 Sq Ft
- Built 1985
Last Sold Summary
- 4% Below List Price
- $140/SF
- 12 Days On Market
Current Estimated Value $387,606

Last Listing Agent Rebakah Goodpaster Keller Williams Legacy Group

113 Shala Mar Rue, Winchester, KY 40391
/25
$248,000

Sold Dec 01, 2025

331 Newcastle Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,351 Sq Ft
- Built 2004
Last Sold Summary
- $184/SF
- 3 Days On Market
Current Estimated Value $248,164

Last Listing Agent Sydney Pennington In House Real Estate

331 Newcastle Ln, Winchester, KY 40391
/24
$320,000

Sold Dec 01, 2025

118 Strawberry Ln, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,008 Sq Ft
- Built 2022
Last Sold Summary
- 2% Below List Price
- $159/SF
- 14 Days On Market
Current Estimated Value $327,020

Last Listing Agent Susan Baldwin Threshold Real Estate Services

118 Strawberry Ln, Winchester, KY 40391
/35
$310,000

Sold Jun 01, 2026

219 Bartram Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,696 Sq Ft
- Built 2004
Last Sold Summary
- $183/SF
- 7 Days On Market
Current Estimated Value $307,202

Last Listing Agent Dennis Nobles Turf Town Properties

219 Bartram Ct, Winchester, KY 40391
/11
$249,000

Sold Apr 01, 2026

646 Laura Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,534 Sq Ft
- Built 1980
Last Sold Summary
- $162/SF
- 55 Days On Market
Current Estimated Value $230,813

Last Listing Agent Garry Milton Milton and Associates Real Estate

646 Laura Dr, Winchester, KY 40391
/2
$260,000

Sold Mar 30, 2026

214 Bartram Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,800 Sq Ft
- Built 2004
Last Sold Summary
- $144/SF
Current Estimated Value $264,311

Last Listing Agent Destiny Darby Keller Williams Commonwealth

214 Bartram Ct, Winchester, KY 40391
/7
$155,000

Sold Dec 23, 2025

134 Hud Rd, Winchester, KY 40391
- Land
- 18,730 Sq Ft
- $360,465 per Acre
Last Sold Summary
- 3 Days On Market
Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

134 Hud Rd, Winchester, KY 40391
/9
$378,000

Sold Mar 09, 2026

140 Gibson Way, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,269 Sq Ft
- Built 2025
Last Sold Summary
- $167/SF
- 0 Days On Market
Current Estimated Value $381,771

Last Listing Agent Amanda Stewart Stewart & Co Realty LLC

140 Gibson Way, Winchester, KY 40391
/34
$305,000

Sold Nov 04, 2025

123 Strawberry Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,792 Sq Ft
- Built 2024
Last Sold Summary
- 2% Below List Price
- $170/SF
- 1 Day On Market
Current Estimated Value $313,300

Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

123 Strawberry Ln, Winchester, KY 40391
/27
$275,000

Sold Jun 13, 2025

216 Prescott Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,726 Sq Ft
- Built 2008
Last Sold Summary
- 6% Below List Price
- $159/SF
- 129 Days On Market
Current Estimated Value $289,461

Last Listing Agent Brittany Lewis National Real Estate

216 Prescott Ln, Winchester, KY 40391
/37
$379,000

Sold Dec 22, 2025

122 Le Ann Ln, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,587 Sq Ft
- Built 1978
Last Sold Summary
- $147/SF
- 7 Days On Market
Current Estimated Value $382,879

Last Listing Agent Tracey Goebel Tom Goebel & Company

122 Le Ann Ln, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 2

Kentucky Clark County Winchester Old Pine Grove

Learn more about living in Old Pine Grove

Frequently Asked Questions

What is the average time to sell a house in Old Pine Grove, KY?

The houses for sale in Old Pine Grove, KY spend an average of 32 days on the market.

What is the number of active homes for sale in Old Pine Grove, KY?

There are 3 active homes for sale in Old Pine Grove, KY.

Home Prices in Old Pine Grove, KY

The median home sale price in Old Pine Grove, Winchester is $272,450, down 3% year-over-year. Homes in Old Pine Grove sell in 32 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price $272,450	Median Single Family Sale Price $269,900
Average Price Per Sq Ft $169	Number of Homes for Sale 3
Last 12 months Home Sales 40	Months of Supply 0.90
Median List Price $285,000	Median Change From 1st List Price 2%
Median Home Sale Price YoY Change -3%

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