451

Recently Sold Winchester, KY Homes

Section Image
  • /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
  • /31

    $222,500

    Sold Dec 19, 2025

    359 Silverton Way, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,502 Sq Ft
    • Built 1999

    Last Sold Summary

    • 1% Below List Price
    • $148/SF
    • 18 Days On Market

    Current Estimated Value $225,940

    Last Listing Agent Christal Browning Four Seasons Realty

    359 Silverton Way, Winchester, KY 40391
  • /50

    $359,000

    Sold Mar 27, 2026

    175 Overlooking Dr, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 2,080 Sq Ft
    • Built 1970

    Last Sold Summary

    • $173/SF
    • 0 Days On Market

    Current Estimated Value $362,143

    Last Listing Agent Keith Wilson Coldwell Banker McMahan

    175 Overlooking Dr, Winchester, KY 40391
  • /36

    $205,000

    Sold Jun 03, 2026

    415 L East Junction Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 2016

    Last Sold Summary

    • 9% Below List Price
    • $178/SF
    • 21 Days On Market

    Current Estimated Value $208,587

    Last Listing Agent Rachel Rainey Kentucky Land and Home

    415 L East Junction Rd, Winchester, KY 40391
  • /28

    $244,000

    Sold Sep 12, 2025

    252 S Highland St, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft
    • Built 1935

    Last Sold Summary

    • 2% Below List Price
    • $126/SF
    • 17 Days On Market

    Current Estimated Value $246,497

    Last Listing Agent Austina Bruton Re/Max Elite Realty - Hamburg

    252 S Highland St, Winchester, KY 40391
  • /52

    $165,000

    Sold Jun 12, 2026

    334 S Burns Ave, Winchester, KY 40391

    • 3 Beds
    • 1.5 Baths
    • 1,636 Sq Ft
    • Built 1940

    Last Sold Summary

    • 28% Below List Price
    • $101/SF
    • 79 Days On Market

    Current Estimated Value $183,541

    Last Listing Agent Jeanne Beaven Rector Hayden Realtors

    334 S Burns Ave, 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
  • /21

    $173,000

    Sold Aug 15, 2025

    222 Buffalo Trace, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 964 Sq Ft
    • Built 1998

    Last Sold Summary

    • $179/SF
    • 2 Days On Market

    Current Estimated Value $179,925

    Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

    222 Buffalo Trace, Winchester, KY 40391
  • /2

    $247,000

    Sold Jul 31, 2025

    724 Terry Dr, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 2,250 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $110/SF
    • 6 Days On Market

    Current Estimated Value $269,814

    Last Listing Agent Samantha Gray National Real Estate

    724 Terry Dr, Winchester, KY 40391
  • /23

    $197,377

    Sold May 15, 2026

    313 S Burns Ave, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,518 Sq Ft
    • Built 1903

    Last Sold Summary

    • 21% Below List Price
    • $130/SF
    • 106 Days On Market

    Current Estimated Value $213,961

    Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

    313 S Burns Ave, Winchester, KY 40391
  • /26

    $195,000

    Sold Nov 06, 2025

    388 Colby Ridge Blvd, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 1,224 Sq Ft
    • Built 2000

    Last Sold Summary

    • 9% Below List Price
    • $159/SF
    • 31 Days On Market

    Current Estimated Value $204,530

    Last Listing Agent Joyce Ratliff Tom Goebel & Company

    388 Colby Ridge Blvd, Winchester, KY 40391
  • /46

    $365,000

    Sold Oct 27, 2025

    7875 Bybee Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft
    • Built 2021

    Last Sold Summary

    • 9% Below List Price
    • $226/SF
    • 79 Days On Market

    Current Estimated Value $355,034

    Last Listing Agent Joyce Ratliff Tom Goebel & Company

    7875 Bybee Rd, Winchester, KY 40391
  • /34

    $205,000

    Sold Jun 30, 2025

    42 Wheeler Ave, Winchester, KY 40391

    • 2 Beds
    • 1 Bath
    • 1,013 Sq Ft
    • Built 1950

    Last Sold Summary

    • 16% Below List Price
    • $202/SF
    • 13 Days On Market

    Current Estimated Value $213,089

    Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

    42 Wheeler Ave, Winchester, KY 40391
  • /25

    $263,000

    Sold Jun 16, 2026

    164 Buckingham Ln, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,190 Sq Ft
    • Built 2000

    Last Sold Summary

    • 3% Below List Price
    • $221/SF
    • 14 Days On Market

    Current Estimated Value $266,905

    Last Listing Agent Heather Baber Rector Hayden Realtors

    164 Buckingham Ln, Winchester, KY 40391
  • /2

    $470,000

    Sold Dec 02, 2025

    415 David Ln, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 3,989 Sq Ft
    • Built 1999

    Last Sold Summary

    • 19% Below List Price
    • $118/SF
    • 58 Days On Market

    Current Estimated Value $505,119

    Last Listing Agent Craig Bridgewater Bridgewater Real Estate

    415 David Ln, Winchester, KY 40391
  • /11

    $205,000

    Sold Oct 10, 2025

    322 Buffalo Trace, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,110 Sq Ft
    • Built 2001

    Last Sold Summary

    • 5% Above List Price
    • $185/SF
    • 1 Day On Market

    Current Estimated Value $203,476

    Last Listing Agent Sondra Clark Taylor Real Estate, LLC

    322 Buffalo Trace, Winchester, KY 40391
  • /33

    $333,500

    Sold Aug 20, 2025

    543 S Maple St, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,527 Sq Ft
    • Built 1946

    Last Sold Summary

    • 5% Below List Price
    • $218/SF
    • 38 Days On Market

    Current Estimated Value $337,986

    Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

    543 S Maple St, Winchester, KY 40391
  • /82

    $475,000

    Sold Oct 23, 2025

    102 Camelot Dr, Winchester, KY 40391

    • 5 Beds
    • 3.5 Baths
    • 3,679 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Above List Price
    • $129/SF
    • 3 Days On Market

    Current Estimated Value $495,767

    Last Listing Agent Scott Fryar Keller Williams Bluegrass Realty

    102 Camelot Dr, Winchester, KY 40391
  • /68

    $460,000

    Sold Oct 10, 2025

    946 Pine Ridge Rd, Winchester, KY 40391

    • 4 Beds
    • 4 Baths
    • 3,523 Sq Ft
    • Built 2003

    Last Sold Summary

    • 8% Below List Price
    • $131/SF
    • 8 Days On Market

    Current Estimated Value $472,300

    Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

    946 Pine Ridge Rd, 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 $260,213

    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 $252,548

    Last Listing Agent Justin Lee JL Realty Group, LLC

    504 Harvard Dr, Winchester, KY 40391
  • /34

    $252,000

    Sold Jul 30, 2025

    216 Connie Ln, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 2017

    Last Sold Summary

    • $202/SF
    • 2 Days On Market

    Current Estimated Value $255,483

    Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

    216 Connie Ln, Winchester, KY 40391
  • /21

    $259,900

    Sold Jul 10, 2025

    302 April Way, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,321 Sq Ft
    • Built 2002

    Last Sold Summary

    • $197/SF
    • 12 Days On Market

    Current Estimated Value $266,482

    Last Listing Agent Michael Hilario The Agency

    302 April Way, Winchester, KY 40391
  • /22

    $600,000

    Sold Aug 19, 2025

    1203 Irvine Rd, Winchester, KY 40391

    • Land
    • 12.38 Acres
    • $48,465 per Acre

    Last Sold Summary

    • 37% Below List Price
    • 125 Days On Market

    Current Estimated Value $647,237

    Last Listing Agent Josh Wood Freedom Realty & Property Management

    1203 Irvine Rd, Winchester, KY 40391
  • /17

    $228,500

    Sold Feb 06, 2026

    394 S Main St, Winchester, KY 40391

    • 4 Beds
    • 2 Baths
    • 1,858 Sq Ft
    • Built 1900

    Last Sold Summary

    • $123/SF
    • 9 Days On Market

    Current Estimated Value $232,088

    Last Listing Agent Tracey Goebel Tom Goebel & Company

    394 S Main St, Winchester, KY 40391
  • /32

    $253,000

    Sold Jun 12, 2026

    363 S Main St, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 2,142 Sq Ft
    • Built 1940

    Last Sold Summary

    • 1% Above List Price
    • $118/SF
    • 2 Days On Market

    Current Estimated Value $245,252

    Last Listing Agent Zachary Otis HomeLand Real Estate Inc

    363 S Main St, Winchester, KY 40391
  • /33

    $420,000

    Sold May 21, 2026

    107 Woodduck Ct, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 2,652 Sq Ft
    • Built 2000

    Last Sold Summary

    • 7% Below List Price
    • $158/SF
    • 66 Days On Market

    Current Estimated Value $430,385

    Last Listing Agent Laura Eaves Berkshire Hathaway de Movellan Properties

    107 Woodduck Ct, Winchester, KY 40391
  • /2

    $125,000

    Sold May 15, 2026

    39 Casa Landa Way, Winchester, KY 40391

    • Land
    • 17,859 Sq Ft
    • $304,878 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $136,256

    Last Listing Agent Tracey Goebel Tom Goebel & Company

    39 Casa Landa Way, Winchester, KY 40391
  • /2

    $75,000

    Sold Dec 16, 2025

    1477 Sewell Shop Rd, Winchester, KY 40391

    • Land
    • 4.82 Acres
    • $15,560 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Zella Rosenthal Tom Goebel & Company

    1477 Sewell Shop Rd, Winchester, KY 40391
  • /83

    $850,000

    Sold Mar 25, 2026

    4755 Combs Ferry Rd, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 2,768 Sq Ft
    • Built 1993

    Last Sold Summary

    • $307/SF
    • 13 Days On Market

    Current Estimated Value $844,476

    Last Listing Agent Craig Bridgewater Bridgewater Real Estate

    4755 Combs Ferry Rd, Winchester, KY 40391
  • /27

    $199,900

    Sold May 15, 2026

    215 Short St, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,036 Sq Ft
    • Built 1955

    Last Sold Summary

    • $193/SF
    • 1 Day On Market

    Current Estimated Value $199,007

    Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

    215 Short St, Winchester, KY 40391
  • /67

    $307,900

    Sold May 29, 2026

    118 Windridge Dr, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $190/SF
    • 3 Days On Market

    Current Estimated Value $307,352

    Last Listing Agent Amber Hunt Whalen & Company

    118 Windridge Dr, Winchester, KY 40391
  • /42

    $249,000

    Sold Oct 22, 2025

    9 Apache Trail, Winchester, KY 40391

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 1960

    Last Sold Summary

    • 6% Below List Price
    • $142/SF
    • 117 Days On Market

    Current Estimated Value $261,586

    Last Listing Agent Joyce Ratliff Tom Goebel & Company

    9 Apache Trail, Winchester, KY 40391
  • /34

    $405,000

    Sold May 26, 2026

    505 Lasalle Ct, Winchester, KY 40391

    • 5 Beds
    • 3 Baths
    • 2,944 Sq Ft
    • Built 1995

    Last Sold Summary

    • $138/SF
    • 1 Day On Market

    Current Estimated Value $399,048

    Last Listing Agent Amanda Thomas The Agency

    505 Lasalle Ct, Winchester, KY 40391
  • /92

    $364,900

    Sold Jul 31, 2025

    31 Mockingbird Valley Rd, Winchester, KY 40391

    • 4 Beds
    • 2 Baths
    • 2,520 Sq Ft
    • Built 1962

    Last Sold Summary

    • 6% Below List Price
    • $145/SF
    • 209 Days On Market

    Current Estimated Value $385,088

    Last Listing Agent Josh Wood Freedom Realty & Property Management

    31 Mockingbird Valley Rd, Winchester, KY 40391
  • /23

    $335,000

    Sold Aug 27, 2025

    413 Lyon Dr, Winchester, KY 40391

    • 4 Beds
    • 3 Baths
    • 2,936 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $114/SF
    • 8 Days On Market

    Current Estimated Value $327,243

    Last Listing Agent Ray Rush Rush Real Estate

    413 Lyon Dr, Winchester, KY 40391
  • /17

    $86,008

    Sold Jul 30, 2025

    977 Muddy Creek Rd, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,030 Sq Ft
    • Built 1940

    Last Sold Summary

    • 28% Below List Price
    • $84/SF
    • 37 Days On Market

    Current Estimated Value $95,452

    Last Listing Agent Jason Szaks EXIT Town & Country Realtors

    977 Muddy Creek Rd, Winchester, KY 40391
  • /27

    $199,900

    Sold Jul 15, 2025

    139 W Hickman St, Winchester, KY 40391

    • 3 Beds
    • 1.5 Baths
    • 1,348 Sq Ft
    • Built 1940

    Last Sold Summary

    • $148/SF
    • 18 Days On Market

    Current Estimated Value $205,511

    Last Listing Agent Clay David Sutherland ERA Select Real Estate

    139 W Hickman St, Winchester, KY 40391
  • /31

    $295,000

    Sold Feb 24, 2026

    420 Willowbrook Rd, Winchester, KY 40391

    • 3 Beds
    • 3 Baths
    • 1,738 Sq Ft
    • Built 1980

    Last Sold Summary

    • $170/SF
    • 32 Days On Market

    Current Estimated Value $295,019

    Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

    420 Willowbrook Rd, Winchester, KY 40391
  • /42

    $247,500

    Sold Jan 16, 2026

    125 Summerhill Way, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,333 Sq Ft
    • Built 2003

    Last Sold Summary

    • 5% Below List Price
    • $186/SF
    • 15 Days On Market

    Current Estimated Value $255,205

    Last Listing Agent Gwen Mathews Bluegrass Sotheby's International Realty

    125 Summerhill Way, Winchester, KY 40391

Showing Results 401 - 440, Page 11 of 12

How to Buy a Home How to Finance a Home How to Sell a Home