Winchester, KY Homes

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  /24

  Est $205,293 Not Listed For Sale

  5 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,634 Sq Ft
  • Built 1930

  5 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $103/SF
  • 1 Day On Market

  Last Sold Price $169,000

  Last Listing Agent Melissa Brown Keller Williams Legacy Group
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  /28

  $89,900

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  300 Aspen Ln, Winchester, KY 40391

  Welcome home to this well-maintained 3 bedroom, 2 bathroom double wide manufactured home in Treehaven, offering close to 2,000 square feet of comfortable living space...a rare find for buyers looking for room, functionality, and flexibility. Inside, you'll love the open-concept layout that connects the large living room, kitchen, and dining area, making it ideal for both everyday living and

  Christa Joynt Keller Williams Commonwealth

  300 Aspen Ln, Winchester, KY 40391
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  /114

  $635,000 Sold Sep 30, 2025

  315 The Woods Ln, Winchester, KY 40391

  • 5 Beds
  • 4.5 Baths
  • 5,524 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Below List Price
  • $115/SF
  • 63 Days On Market

  Current Estimated Value $622,821

  Last Listing Agent Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
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  /23

  Est $183,616 Not Listed For Sale

  11 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,708 Sq Ft
  • Built 1920

  11 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 72% Above List Price
  • $63/SF
  • 9 Days On Market

  Last Sold Price $107,000

  Last Listing Agent Darrell Lewis DIY Flat Fee.com
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  /3

  $146,000

  • 3 Beds
  • 1 Bath
  • 1,020 Sq Ft

  228 Jackson St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  228 Jackson St, Winchester, KY 40391
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  /32

  $183,000 Sold Jul 30, 2025

  517 Hidden Hills Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 2001

  Last Sold Summary

  • $163/SF
  • 78 Days On Market

  Current Estimated Value $189,412

  Last Listing Agent Brenda Sipes Bridgewater Real Estate

  517 Hidden Hills Way, Winchester, KY 40391
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  /24

  Est $197,615 Not Listed For Sale

  21 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1920

  21 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $141/SF
  • 80 Days On Market

  Last Sold Price $189,500

  Last Listing Agent Anthony Gigilo ListWithFreedom.com
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  /18

  $99,000

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  114 Magnolia St, Winchester, KY 40391

  Great opportunity for investors, flippers, or anyone looking for a project with tons of potential! This 2 bedroom, 1 bath home features a 2 year old roof, giving you a solid head start on future updates. With its convenient location and plenty of possibilities, this property is ready for someone to bring their vision! Selling as is. Cash or conventional financing only.

  Michelle Blackburn RE/MAX Creative, Winchester

  114 Magnolia St, Winchester, KY 40391
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  /61

  $220,000 Sold Nov 10, 2025

  313 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1960

  Last Sold Summary

  • 12% Below List Price
  • $179/SF
  • 51 Days On Market

  Current Estimated Value $225,939

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  313 Snowden Dr, Winchester, KY 40391
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  /18

  Est $114,157 Not Listed For Sale

  129 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1940

  129 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 52% Above List Price
  • $69/SF
  • 46 Days On Market

  Last Sold Price $75,000

  Last Listing Agent Austin Polley The Polley Group
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  /4

  $199,900

  • Land
  • 11.36 Acres
  • $17,597 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions

  Lura Justice Rector Hayden Realtors

  2996 Irvine Rd, Winchester, KY 40391
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  /53

  $80,000 Sold Apr 30, 2025

  307 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • Built 1950

  Last Sold Summary

  • 33% Below List Price
  • $49/SF
  • 67 Days On Market

  Current Estimated Value $95,490

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  307 Jackson St, Winchester, KY 40391
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  /15

  Est $187,252 Not Listed For Sale

  20 Elizabeth St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1940

  20 Elizabeth St, Winchester, KY 40391

  Last Sold Summary

  • 3% Below List Price
  • $153/SF
  • 7 Days On Market

  Last Sold Price $192,588

  Last Listing Agent Jessica Moreno SimpliHOM
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  /9

  $1,350,000

  • Land
  • 3.02 Acres
  • $447,020 per Acre

  155 April Way, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided.Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One,

  Greg Leveridge Block + Lot Real Estate

  155 April Way, Winchester, KY 40391
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  /32

  $285,000 Sold Jul 03, 2025

  602 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,690 Sq Ft
  • Built 1976

  Last Sold Summary

  • 11% Below List Price
  • $169/SF
  • 168 Days On Market

  Current Estimated Value $278,690

  Last Listing Agent Ryan O'Gara Real Broker, LLC

  602 Laura Dr, Winchester, KY 40391
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  /17

  Est $211,531 Not Listed For Sale

  102 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1940

  102 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 2% Below List Price
  • $124/SF
  • 41 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Holly Spradlin KY Realty Co
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  /2

  $100,000

  • Land
  • 0.31 Acre
  • $322,581 per Acre

  215 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

  215 Duclair Dr, Winchester, KY 40391
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  /2

  $401,500 Sold May 15, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1998

  Last Sold Summary

  • $201/SF

  Current Estimated Value $401,797

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
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  /16

  Est $337,724 Not Listed For Sale

  122 French Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 4,176 Sq Ft
  • Built 1920

  122 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $72/SF
  • 4 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Brenda Sipes Bridgewater Real Estate
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  /12

  $345,000

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
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  /17

  $595,000 Sold Nov 17, 2025

  304 Winterberry Dr, Winchester, KY 40391

  • 7 Beds
  • 4 Baths
  • 4,386 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $136/SF
  • 10 Days On Market

  Current Estimated Value $587,163

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
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  /31

  Est $180,748 Not Listed For Sale

  134 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • Built 1930

  134 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 29% Above List Price
  • $72/SF
  • 1 Day On Market

  Last Sold Price $140,000

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
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  /34

  $275,700

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft

  404 Wellington Way, Winchester, KY 40391

  This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is supplied with all the appliances. And the house also has a washer and dryer. The large great room is perfect for watching the favorite sports teams and movies with family and friends. The sellers added fiber optics

  Craig Bridgewater Bridgewater Real Estate

  404 Wellington Way, Winchester, KY 40391
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  /2

  $185,000 Sold Nov 28, 2025

  23 Hillcrest Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,557 Sq Ft
  • Built 1962

  Last Sold Summary

  • 12% Below List Price
  • $119/SF
  • 18 Days On Market

  Current Estimated Value $193,680

  Last Listing Agent Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
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  /19

  Est $212,871 Not Listed For Sale

  130 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • Built 1930

  130 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 15% Above List Price
  • $140/SF
  • 1 Day On Market

  Last Sold Price $185,000

  Last Listing Agent Lukas Owens The Brokerage
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  /2

  $100,000

  • Land
  • 0.32 Acre
  • $312,500 per Acre

  155 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

  155 Duclair Dr, Winchester, KY 40391
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  /18

  $246,500 Sold May 16, 2025

  6278 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $210/SF
  • 35 Days On Market

  Current Estimated Value $260,653

  Last Listing Agent Angela Yonts EXP Realty, LLC

  6278 Irvine Rd, Winchester, KY 40391
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  /8

  Est $247,994 Not Listed For Sale

  109 Alabama St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,359 Sq Ft
  • Built 1930

  109 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $167/SF
  • 9 Days On Market

  Last Sold Price $227,000

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan
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  /34

  $220,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
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  /22

  $216,000 Sold Feb 27, 2026

  521 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $158/SF
  • 17 Days On Market

  Current Estimated Value $222,469

  Last Listing Agent Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
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  /23

  Est $210,605 Not Listed For Sale

  112 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,738 Sq Ft
  • Built 1930

  112 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 32% Above List Price
  • $92/SF
  • 8 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Wayne Elkins RE/MAX
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  /47

  $499,000

  • 5 Beds
  • 3.5 Baths
  • 3,823 Sq Ft

  595 Earlymeade Dr, Winchester, KY 40391

  Entertaining the idea of entertaining family and friends? Looking for space for living the good life in a fun house in a great neighborhood? Then look no further. This house is ready for you to make it your new home. Located in the desirable neighborhood of Earlymeade, this house is minutes from the Winchester Bypass, I- 64 corridor and the Hamburg area of Lexington. Along with 5 bedrooms and 3.5

  Craig Bridgewater Bridgewater Real Estate

  595 Earlymeade Dr, Winchester, KY 40391
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  /32

  $230,000 Sold Mar 21, 2025

  200 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $184/SF
  • 3 Days On Market

  Current Estimated Value $238,828

  Last Listing Agent Amy Diamond ERA Select Real Estate

  200 Bracken Ct, Winchester, KY 40391
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  /48

  Est $238,508 Not Listed For Sale

  104 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • Built 1930

  104 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 3% Below List Price
  • $139/SF
  • 9 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington
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  /15

  $600,000

  • 8 Beds
  • 4 Baths
  • 5,046 Sq Ft

  101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

  Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new

  Priya Patel-Rossetti Big Blue Realty

  101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
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  /65

  $385,000 Sold Dec 11, 2025

  1731 Ford Hampton Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 27% Below List Price
  • $182/SF
  • 157 Days On Market

  Current Estimated Value $394,025

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
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  /44

  Est $161,870 Not Listed For Sale

  118 Alabama St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1940

  118 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $101/SF
  • 1 Day On Market

  Last Sold Price $142,000

  Last Listing Agent Susan Moore Keller Williams Legacy Group
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  /4

  $67,500

  • Land
  • 1.92 Acres
  • $35,156 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and watch this land grow in value. This lot containing 1.919 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391
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  /62

  $325,000 Sold Apr 24, 2025

  138 Shanahan Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1996

  Last Sold Summary

  • 23% Below List Price
  • $172/SF
  • 88 Days On Market

  Current Estimated Value $327,734

  Last Listing Agent Christine McDonald FC Tucker Bluegrass

  138 Shanahan Ln, Winchester, KY 40391
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  /28

  Est $251,726 Not Listed For Sale

  116 Alabama St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1940

  116 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $142/SF
  • 95 Days On Market

  Last Sold Price $231,000

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth

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