Winchester, KY Homes

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  /34

  $380,000 Sold Nov 21, 2025

  110 Hampton Avenue Exd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,516 Sq Ft

  Last Sold Summary

  • 1% Above List Price
  • $151/SF
  • 5 Days On Market

  Current Estimated Value $374,669

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
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  /35

  Est $425,419 Not Listed For Sale

  2195 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,062 Sq Ft
  • Built 2000

  2195 Pretty Run Rd, Winchester, KY 40391

  Last Sold Summary

  • 18% Above List Price
  • $175/SF
  • 46 Days On Market

  • Last Sold Price $360,000
  • Sep 30, 2024

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /84

  $799,900

  • 4 Beds
  • 3.5 Baths
  • 4,922 Sq Ft

  2509 Mount Sterling Rd, Winchester, KY 40391

  Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

  Josh Wood Freedom Realty & Property Management

  2509 Mount Sterling Rd, Winchester, KY 40391
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  /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 $288,005

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  223 Bartram Ct, Winchester, KY 40391
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  /38

  Est $322,697 Not Listed For Sale

  3635 Jackson Ferry Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,201 Sq Ft
  • Built 1920

  3635 Jackson Ferry Rd, Winchester, KY 40391

  Last Sold Summary

  • 15% Above List Price
  • $127/SF
  • 17 Days On Market

  • Last Sold Price $279,900
  • Oct 01, 2024

  Last Listing Agent Betsy Brown United Real Estate Bluegrass
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  /41

  $169,900

  • 1 Bed
  • 2 Baths
  • 1,056 Sq Ft

  101 Alabama St, Winchester, KY 40391

  Step back in time and discover the possibilities in this classic 1930-built home full of character and opportunity! With solid bones and vintage details, this property is the perfect canvas for investors, renovators, or anyone dreaming of restoring a piece of history. Featuring spacious rooms, original architectrual touches, and a layout just waiting to be reimagined. This home offers incredible

  A. Rebecca Woods Woods Realty Group

  101 Alabama St, Winchester, KY 40391
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  /42

  $400,000 Sold Dec 05, 2025

  210 College St, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft
  • Built 1895

  Last Sold Summary

  • 5% Below List Price
  • $147/SF
  • 59 Days On Market

  Current Estimated Value $395,841

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
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  /105

  Est $697,184 Not Listed For Sale

  1039 Cole Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft
  • Built 1977

  1039 Cole Rd, Winchester, KY 40391

  Last Sold Summary

  • 3% Below List Price
  • $281/SF
  • 11 Days On Market

  • Last Sold Price $719,000
  • Sep 16, 2024

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /15

  $275,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  110 Buckingham Ln, Winchester, KY 40391

  Watch the sunrise from your own Winchester oasis. This 3 bed, 2 bath ranch blends warmth and comfort with a bright, open layout filled with natural light. Step outside to a large, private backyard with healthy fruit trees, a garden, entertaining deck, and covered paver patio, perfect for morning coffee or evening unwind. Located in a great neighborhood, walkable to Kroger and just 20 minutes to

  Oliver Winn ERA Select Real Estate

  110 Buckingham Ln, Winchester, KY 40391
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  /31

  $379,717 Sold Mar 27, 2026

  300 Calmes Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Below List Price
  • $144/SF
  • 111 Days On Market

  Current Estimated Value $378,999

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391
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  /44

  Est $362,346 Not Listed For Sale

  207 Citation Ct, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,304 Sq Ft
  • Built 2005

  207 Citation Ct, Winchester, KY 40391

  Last Sold Summary

  • 15% Above List Price
  • $95/SF
  • 6 Days On Market

  • Last Sold Price $315,000
  • Oct 13, 2023

  Last Listing Agent Megan McCoy Keller Williams Legacy Group
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  /2

  $100,000

  • Land
  • 1.1 Acres
  • $90,909 per Acre

  270 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  270 Duclair Dr, Winchester, KY 40391
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  /64

  $360,000 Sold Oct 17, 2025

  309 Gallahadion Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $188/SF
  • 60 Days On Market

  Current Estimated Value $369,030

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  309 Gallahadion Ct, Winchester, KY 40391
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  /8

  Est $485,017 Not Listed For Sale

  419 Fairholme Way, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 4,447 Sq Ft
  • Built 2022

  419 Fairholme Way, Winchester, KY 40391

  Last Sold Summary

  • 21% Below List Price
  • $137/SF
  • 231 Days On Market

  • Last Sold Price $610,986
  • Nov 02, 2023

  Last Listing Agent Vickie Skeens RE/MAX
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  /9

  $500,000

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
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  /64

  $415,000 Sold Feb 25, 2026

  1857 Ironworks Rd, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft
  • Built 1865

  Last Sold Summary

  • 3% Below List Price
  • $142/SF
  • 70 Days On Market

  Current Estimated Value $415,794

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
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  /20

  Est $378,035 Not Listed For Sale

  307 Gallahadion Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,487 Sq Ft
  • Built 2004

  307 Gallahadion Ct, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $135/SF
  • 18 Days On Market

  • Last Sold Price $335,000
  • May 24, 2024

  Last Listing Agent Lindsay Rhodus Keller Williams Legacy Group
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  /2

  $67,500

  • Land
  • 1.89 Acres
  • $35,695 per Acre

  250 Spencer Ln, Winchester, KY 40391

  Unique triangular shaped lot in a wooded rural setting, interesting opportunities for privacy in a beautiful area of Clark County where you can enjoy the outdoors and create memories galore.

  Craig Bridgewater Bridgewater Real Estate

  250 Spencer Ln, Winchester, KY 40391
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  /23

  $225,000 Sold Aug 21, 2025

  26 Stefanie Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • $208/SF
  • 12 Days On Market

  Current Estimated Value $222,871

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
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  /33

  Est $310,844 Not Listed For Sale

  305 Gallahadion Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,475 Sq Ft
  • Built 2004

  305 Gallahadion Ct, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $182/SF
  • 55 Days On Market

  • Last Sold Price $268,000
  • Aug 02, 2024

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
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  /3

  $430,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout. The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
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  /47

  $365,000 Sold Apr 20, 2026

  114 Mallard Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $173/SF
  • 162 Days On Market

  Current Estimated Value $356,500

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  114 Mallard Ln, Winchester, KY 40391
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  /16

  Est $191,252 Not Listed For Sale

  430 Country Club Dr, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1982

  430 Country Club Dr, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $131/SF
  • 5 Days On Market

  • Last Sold Price $165,000
  • Dec 06, 2024

  Last Listing Agent Brian England Keller Williams Bluegrass Realty
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  /6

  $110,000

  • Land
  • 2.06 Acres
  • $53,398 per Acre

  1185 Craig Crossing Rd, Winchester, KY 40391

  Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1185 Craig Crossing Rd, Winchester, KY 40391
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  /50

  $465,000 Sold Aug 11, 2025

  701 Lisletown Ln, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 2,784 Sq Ft
  • Built 2008

  Last Sold Summary

  • $167/SF
  • 2 Days On Market

  Current Estimated Value $474,115

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  701 Lisletown Ln, Winchester, KY 40391
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  /86

  Est $284,592 Not Listed For Sale

  222 Vaught Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,904 Sq Ft
  • Built 1970

  222 Vaught Rd, Winchester, KY 40391

  Last Sold Summary

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

  • Last Sold Price $271,900
  • Sep 20, 2024

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /2

  $110,000

  • Land
  • 15,246 Sq Ft
  • $314,286 per Acre

  150 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  150 Duclair Dr, Winchester, KY 40391
• 

  /2

  $75,000 Sold Jan 05, 2026

  1341 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 5.75 Acres
  • $13,043 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1341 Sewell Shop Rd, Winchester, KY 40391
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  /38

  Est $298,197 Not Listed For Sale

  2020 Two Mile Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1950

  2020 Two Mile Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $212/SF
  • 37 Days On Market

  • Last Sold Price $280,000
  • May 30, 2024

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC
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  /3

  $1,200 Pending

  • Land
  • 2.57 Acres
  • $467 per Acre

  507 Tech Dr, Winchester, KY 40391

  For lease-Frontage on Rolling Hills Rd, and Tech Drive.I-64 visibility, ideally located commercial property. Paved driveway and gravel lot.$1200 per .25 acre/per month

  Holly Spradlin KY Realty Co

  507 Tech Dr, Winchester, KY 40391
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  /29

  $408,000 Sold Sep 12, 2025

  4732 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,361 Sq Ft
  • Built 1945

  Last Sold Summary

  • 18% Below List Price
  • $173/SF
  • 285 Days On Market

  Current Estimated Value $419,433

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  4732 Old Boonesboro Rd, Winchester, KY 40391
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  /13

  Est $183,532 Not Listed For Sale

  4 Burton Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,330 Sq Ft
  • Built 1948

  4 Burton Ave, Winchester, KY 40391

  Last Sold Summary

  • 27% Above List Price
  • $109/SF
  • 1 Day On Market

  • Last Sold Price $145,000
  • Aug 07, 2023

  Last Listing Agent Amanda McMillian RE/MAX
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  /31

  $145,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft

  730 Byrd Ave, Winchester, KY 40391

  Full of opportunity on a large lot! With mostly cosmetic updates needed, this is an ideal project for a flip or a rental refresh. The layout and lot size provide flexibility, and this property has excellent potential to add value quickly. Being sold as-is.

  Patricia Weiderman Kentucky Land and Home

  730 Byrd Ave, Winchester, KY 40391
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  /2

  $555,000 Sold Jan 16, 2026

  184 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,585 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $155/SF

  Current Estimated Value $562,626

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  184 Casa Landa Way, Winchester, KY 40391
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  /19

  Est $179,461 Not Listed For Sale

  223 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  223 Blair Ave, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $166/SF
  • 82 Days On Market

  • Last Sold Price $170,000
  • Apr 28, 2025

  Last Listing Agent Jordan James Lifstyl Real Estate
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  /33

  $210,000

  • 4 Beds
  • 1 Bath
  • 1,743 Sq Ft

  218 E Washington St, Winchester, KY 40391

  Motivated seller! Bring your offers. This home is a charming 4 bedroom 1 bath. It boasts a large bonus room which could be an office or 5th bedroom. This home offers a nice sized laundry room with space to add a second bathroom. This home has a nicely shaded fully fenced in back yard with a gate for easy accessibility . There is also a detached storage garage and a long driveway. Within walking

  Fernando Andrade Rector Hayden Realtors

  218 E Washington St, Winchester, KY 40391
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  /43

  $165,000 Sold May 20, 2025

  12005 Irvine Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,130 Sq Ft
  • Built 1980

  Last Sold Summary

  • 13% Below List Price
  • $146/SF
  • 96 Days On Market

  Current Estimated Value $174,681

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  12005 Irvine Rd, Winchester, KY 40391
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  /26

  Est $195,212 Not Listed For Sale

  64 Bond Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1987

  64 Bond Ct, Winchester, KY 40391

  Last Sold Summary

  • 22% Above List Price
  • $156/SF
  • 18 Days On Market

  • Last Sold Price $160,000
  • Apr 26, 2024

  Last Listing Agent Jim Woodrum RE/MAX
• 

  /2

  $100,000

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  111 Jacob Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  111 Jacob Ct, Winchester, KY 40391
• 

  

  /44

  $315,000 Sold Jun 27, 2025

  43 Skylark Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,459 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $128/SF
  • 70 Days On Market

  Current Estimated Value $336,983

  Last Listing Agent Chad Bowman The Brokerage

  43 Skylark Dr, Winchester, KY 40391

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