34

Recently Sold Old Pine Grove Homes

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  • /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 $285,265

    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 $288,861

    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 $286,618

    Last Listing Agent Teresa Richmond Freedom Realty & Property Management

    225 Prescott Ln, 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 $362,928

    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 $367,912

    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 $259,046

    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 $5,002,004

    Last Listing Agent Garry Milton Milton and Associates Real Estate

    175 Chatham Place, Winchester, KY 40391
  • /15

    $280,000

    Sold Jul 17, 2026

    327 Newcastle Ln, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 1,693 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $165/SF
    • 87 Days On Market

    Current Estimated Value $284,543

    Last Listing Agent Huong Dunn Bluegrass Property Exchange

    327 Newcastle Ln, 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 $295,471

    Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

    223 Bartram Ct, 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 $232,809

    Last Listing Agent Kimberly Brunson Hunter Real Estate

    646 Laura Dr, Winchester, KY 40391
  • /34

    $349,000

    Sold Jul 16, 2026

    405 Tremont Ln, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 2,274 Sq Ft
    • Built 2005

    Last Sold Summary

    • $153/SF
    • 6 Days On Market

    Current Estimated Value $351,641

    Last Listing Agent Darryl Bond Guide Realty, Inc.

    405 Tremont Ln, 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 $271,421

    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 $259,282

    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 $314,868

    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 $340,920

    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 $255,603

    Last Listing Agent Amy Diamond ERA Select Real Estate

    414 Wellington Way, 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 $245,874

    Last Listing Agent Donna Mink Mink Realty

    142 Sturbridge Ln, 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 $273,150

    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 $278,390

    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 $270,404

    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 $393,365

    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 $247,312

    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 $323,488

    Last Listing Agent Susan Baldwin Threshold Real Estate Services

    118 Strawberry Ln, Winchester, KY 40391
  • /36

    $359,000

    Sold Jul 22, 2026

    133 Shala-Mar Rue, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $180/SF
    • 56 Days On Market

    Last Listing Agent Nena Honaker Tom Goebel & Company

    133 Shala-Mar Rue, 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 $303,132

    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 $232,809

    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 $272,862

    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 $385,567

    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 $315,651

    Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

    123 Strawberry 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 $385,250

    Last Listing Agent Tracey Goebel Tom Goebel & Company

    122 Le Ann Ln, Winchester, KY 40391
  • /25

    $247,500

    Sold May 15, 2026

    201 Prescott Ln, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • Built 2005

    Last Sold Summary

    • 7% Below List Price
    • $190/SF
    • 19 Days On Market

    Current Estimated Value $252,942

    Last Listing Agent Patrick Arvin Keller Williams Commonwealth

    201 Prescott Ln, Winchester, KY 40391
  • /32

    $255,000

    Sold May 14, 2026

    504 Harvard Dr, Winchester, KY 40391

    • 4 Beds
    • 2 Baths
    • 1,739 Sq Ft
    • Built 1978

    Last Sold Summary

    • 4% Below List Price
    • $147/SF
    • 11 Days On Market

    Current Estimated Value $260,022

    Last Listing Agent Justin Lee JL Realty Group, LLC

    504 Harvard Dr, Winchester, KY 40391
  • /10

    $370,000

    Sold Mar 31, 2026

    395 Croxton Way, Winchester, KY 40391

    • Land
    • 1.29 Acres
    • $286,822 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 793 Days On Market

    Current Estimated Value $440,902

    Last Listing Agent Rich Decker Rector Hayden Realtors

    395 Croxton Way, Winchester, KY 40391

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 33 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 Price Trends

Median Sale Price
$280,000
Median Single Family Sale Price
$280,000
Average Price Per Sq Ft
$166
Number of Homes for Sale
3
Last 12 months Home Sales
31
Months of Supply
1.20
Median List Price
$293,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
1%
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