32

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 $280,900

    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 $288,325

    Last Listing Agent Brittany Beer eXp Realty, LLC

    729 Wayland Dr, 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
  • /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 $362,404

    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 $262,444

    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 $5,168,026

    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 $288,703

    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 $292,001

    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 $230,992

    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 $351,826

    Last Listing Agent Darryl Bond Guide Realty, Inc.

    405 Tremont Ln, Winchester, KY 40391
  • /20

    $339,000

    Sold Aug 04, 2026

    107 Gibson Way, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 2,266 Sq Ft
    • Built 2020

    Last Sold Summary

    • 8% Below List Price
    • $150/SF
    • 26 Days On Market

    Current Estimated Value $356,467

    Last Listing Agent Vanessa Highland Stewart & Co Realty LLC

    107 Gibson Way, 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 $263,461

    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 $309,962

    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 $337,444

    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 $257,208

    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 $267,028

    Last Listing Agent Craig Bridgewater Bridgewater Real Estate

    404 Wellington Way, 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 $330,559

    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 $311,510

    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 $230,992

    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 $265,180

    Last Listing Agent Destiny Darby Keller Williams Commonwealth

    214 Bartram Ct, Winchester, KY 40391
  • /35

    $245,000

    Sold Aug 31, 2026

    216 Robyn Dr, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,988 Sq Ft
    • Built 1978

    Last Sold Summary

    • $123/SF
    • 4 Days On Market

    Current Estimated Value $246,389

    Last Listing Agent Robin Jones Keller Williams Legacy Group

    216 Robyn Dr, 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 $376,898

    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 $316,392

    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 $383,627

    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 $248,091

    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 $255,085

    Last Listing Agent Justin Lee JL Realty Group, LLC

    504 Harvard Dr, Winchester, KY 40391
  • /37

    $273,750

    Sold Aug 25, 2026

    116 Sturbridge Ln, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Below List Price
    • $217/SF
    • 47 Days On Market

    Current Estimated Value $271,484

    Last Listing Agent Donna C. Slone-Crumbie Wright Realty

    116 Sturbridge Ln, 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
$274,900
Average Price Per Sq Ft
$171
Number of Homes for Sale
3
Last 12 months Home Sales
29
Months of Supply
1.20
Median List Price
$289,500
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
1%
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