Recently Sold Winchester, KY Homes

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  /22

  $220,000 Sold Jul 08, 2025

  122 Spruce Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $182/SF
  • 32 Days On Market

  Current Estimated Value $224,464

  Last Listing Agent Christal Browning Four Seasons Realty

  122 Spruce Ct, Winchester, KY 40391
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  /39

  $240,000 Sold Aug 08, 2025

  172 Ryans Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft
  • Built 2018

  Last Sold Summary

  • 7% Below List Price
  • $194/SF
  • 6 Days On Market

  Current Estimated Value $249,428

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

  172 Ryans Mill Rd, Winchester, KY 40391
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  /5

  $160,000 Sold May 21, 2025

  3235 Colby Rd, Winchester, KY 40391

  • Land
  • 2.4 Acres
  • $66,667 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 54 Days On Market

  Current Estimated Value $172,670

  Last Listing Agent Steve Adams Steven D Adams Real Estate Services, LLC

  3235 Colby Rd, Winchester, KY 40391
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  /37

  $149,900 Sold May 23, 2025

  502 N Maple St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Below List Price
  • $163/SF
  • 68 Days On Market

  Current Estimated Value $155,637

  Last Listing Agent Christa Joynt Keller Williams Commonwealth

  502 N Maple St, Winchester, KY 40391
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  /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 $371,190

  Last Listing Agent Amanda Stewart Stewart & Co Realty LLC

  140 Gibson Way, Winchester, KY 40391
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  /31

  $335,000 Sold Nov 10, 2025

  536 S Maple St, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,832 Sq Ft
  • Built 1900

  Last Sold Summary

  • 8% Below List Price
  • $183/SF
  • 17 Days On Market

  Current Estimated Value $330,679

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  536 S Maple St, Winchester, KY 40391
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  /25

  $250,000 Sold Sep 23, 2025

  816 Stratton Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,024 Sq Ft
  • Built 1986

  Last Sold Summary

  • 23% Below List Price
  • $83/SF
  • 7 Days On Market

  Current Estimated Value $258,093

  Last Listing Agent Haley Rollins Dream Maker Realty, LLC

  816 Stratton Ln, Winchester, KY 40391
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  /20

  $189,900 Sold Jul 14, 2025

  2342 Ironworks Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1970

  Last Sold Summary

  • $180/SF
  • 2 Days On Market

  Current Estimated Value $195,695

  Last Listing Agent Dylan Justice GSP Homes

  2342 Ironworks Rd, Winchester, KY 40391
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  /2

  $363,000 Sold Oct 30, 2025

  614 S Maple St Unit B3, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,734 Sq Ft
  • Built 1985

  Last Sold Summary

  • $209/SF
  • 0 Days On Market

  Current Estimated Value $333,474

  Last Listing Agent Holly Goeing The Agency

  614 S Maple St Unit B3, Winchester, KY 40391
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  /13

  $75,000 Sold Jul 01, 2025

  2431 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,113 Sq Ft
  • Built 1920

  Last Sold Summary

  • 25% Below List Price
  • $67/SF
  • 74 Days On Market

  Current Estimated Value $102,584

  Last Listing Agent A. Rebecca Woods Woods Realty Group

  2431 Pine Ridge Rd, Winchester, KY 40391
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  /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 $309,526

  Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

  123 Strawberry Ln, Winchester, KY 40391
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  /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 $224,448

  Last Listing Agent Christal Browning Four Seasons Realty

  359 Silverton Way, Winchester, KY 40391
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  /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 $358,226

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  175 Overlooking Dr, Winchester, KY 40391
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  /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 $282,950

  Last Listing Agent Brittany Lewis National Real Estate

  216 Prescott Ln, Winchester, KY 40391
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  /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 $243,638

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

  252 S Highland St, Winchester, KY 40391
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  /31

  $194,000 Sold May 22, 2025

  429 Paisley Ct, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,352 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Below List Price
  • $143/SF
  • 3 Days On Market

  Current Estimated Value $209,240

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  429 Paisley Ct, Winchester, KY 40391
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  /33

  $450,000 Sold Jun 06, 2025

  210 Candlewood Dr, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,046 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $148/SF
  • 49 Days On Market

  Current Estimated Value $452,015

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  210 Candlewood Dr, Winchester, KY 40391
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  /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 $377,037

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  122 Le Ann Ln, Winchester, KY 40391
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  /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 $177,336

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

  222 Buffalo Trace, Winchester, KY 40391
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  /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 $269,777

  Last Listing Agent Samantha Gray National Real Estate

  724 Terry Dr, Winchester, KY 40391
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  /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 $200,364

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  388 Colby Ridge Blvd, Winchester, KY 40391
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  /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 $370,194

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  7875 Bybee Rd, Winchester, KY 40391
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  /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 $209,211

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  42 Wheeler Ave, Winchester, KY 40391
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  /67

  $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 $486,895

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  415 David Ln, Winchester, KY 40391
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  /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 $204,805

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC

  322 Buffalo Trace, Winchester, KY 40391
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  /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 $333,798

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  543 S Maple St, Winchester, KY 40391
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  /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 $481,921

  Last Listing Agent Scott Fryar Keller Williams Bluegrass Realty

  102 Camelot Dr, Winchester, KY 40391
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  /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 $467,061

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  946 Pine Ridge Rd, Winchester, KY 40391
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  /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 $250,368

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  216 Connie Ln, Winchester, KY 40391
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  /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 $266,401

  Last Listing Agent Michael Hilario The Agency

  302 April Way, Winchester, KY 40391
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  /30

  $185,000 Sold Jun 18, 2025

  308 Essex Ct, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,188 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $156/SF
  • 3 Days On Market

  Current Estimated Value $203,164

  Last Listing Agent Lisa Sosa Keller Williams Commonwealth

  308 Essex Ct, Winchester, KY 40391
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  /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 $930,902

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1203 Irvine Rd, Winchester, KY 40391
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  /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 $229,911

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  394 S Main St, Winchester, KY 40391
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  /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
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  /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 $733,988

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  4755 Combs Ferry Rd, Winchester, KY 40391
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  /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 $253,527

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  9 Apache Trail, Winchester, KY 40391
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  /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 $375,415

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  31 Mockingbird Valley Rd, Winchester, KY 40391
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  /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 $330,173

  Last Listing Agent Ray Rush Rush Real Estate

  413 Lyon Dr, Winchester, KY 40391
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  /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 $93,605

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  977 Muddy Creek Rd, Winchester, KY 40391
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  /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 $203,571

  Last Listing Agent Clay David Sutherland ERA Select Real Estate

  139 W Hickman St, Winchester, KY 40391

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