Winchester, KY Homes

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  $924,900 Pending

  • 5 Beds
  • 4.5 Baths
  • 6,314 Sq Ft

  7210 Ecton Rd, Winchester, KY 40391

  Welcome to 7210 Ecton Road a stunning 5 bedroom, 4.5 bathroom home situated on 7+/- acres (awaiting final survey) of gently rolling Kentucky countryside. This property offers the perfect balance of modern comfort, privacy, and wide-open space, just minutes from downtown Winchester. Step inside to discover a spacious and well-designed floor plan featuring: 5 generously sized bedrooms including a

  Megan McCoy Keller Williams Legacy Group

  7210 Ecton Rd, Winchester, KY 40391
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  /29

  $180,000 Sold Aug 11, 2025

  217 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Above List Price
  • $176/SF
  • 0 Days On Market

  Current Estimated Value $182,006

  Last Listing Agent Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
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  /28

  Est $201,060 Not Listed For Sale

  18 A St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 2024

  18 A St, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $152/SF
  • 39 Days On Market

  • Last Sold Price $182,500
  • May 29, 2024

  Last Listing Agent Nena Honaker Tom Goebel & Company
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  $100,000

  • Land
  • 29,620 Sq Ft
  • $147,059 per Acre

  100 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

  100 Duclair Dr, Winchester, KY 40391
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  $254,000 Sold Dec 02, 2025

  312 Forest Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $164/SF
  • 52 Days On Market

  Current Estimated Value $248,691

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  312 Forest Ave, Winchester, KY 40391
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  /23

  Est $200,734 Not Listed For Sale

  20 3rd St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 1960

  20 3rd St, Winchester, KY 40391

  Last Sold Summary

  • 18% Above List Price
  • $99/SF
  • 26 Days On Market

  • Last Sold Price $170,000
  • Dec 31, 2024

  Last Listing Agent E Anthony Phillips RE/MAX
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  /65

  $775,900 Open House 5/17

  • 2 Beds
  • 2.5 Baths
  • 2,361 Sq Ft

  455 Davis Ln, Winchester, KY 40391

  Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

  Dale Hatton Dream Maker Realty, LLC

  455 Davis Ln, Winchester, KY 40391
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  /75

  $410,000 Sold Nov 21, 2025

  291 Log Lick Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 3 Days On Market

  Current Estimated Value $413,496

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
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  /14

  Est $147,596 Not Listed For Sale

  110 3rd St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1969

  110 3rd St, Winchester, KY 40391

  Last Sold Summary

  • 41% Above List Price
  • $85/SF
  • 0 Days On Market

  • Last Sold Price $105,000
  • Nov 07, 2023

  Last Listing Agent Daniel Ellis Metro Max Realty
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  /20

  $105,000

  • Land
  • 9.75 Acres
  • $10,767 per Acre

  3759 Jackson Ferry Rd, Winchester, KY 40391

  Tucked along a peaceful, scenic drive, this 9.752-acre tract offers a rare opportunity to own land backing directly to the beautiful Kentucky River. This parcel is the perfect recreational escape-ideal for parking a camper, weekend getaways, or creating your own private retreat. Spend your days kayaking, canoeing, fishing, or paddle boarding right from your property, then unwind surrounded by

  Christa Joynt Keller Williams Commonwealth

  3759 Jackson Ferry Rd, Winchester, KY 40391
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  $101,000 Sold Jul 14, 2025

  2058 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $25,124 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 86 Days On Market

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2058 Athens Boonesboro Rd, Winchester, KY 40391
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  /25

  Est $193,756 Not Listed For Sale

  4 Elm St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1950

  4 Elm St, Winchester, KY 40391

  Last Sold Summary

  • 11% Above List Price
  • $146/SF
  • 61 Days On Market

  • Last Sold Price $175,000
  • Jan 31, 2025

  Last Listing Agent E Anthony Phillips RE/MAX
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  $269,500

  • 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. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
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  $257,400 Sold Nov 21, 2025

  103 Hampton Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $150/SF
  • 4 Days On Market

  Current Estimated Value $266,769

  Last Listing Agent Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /26

  Est $183,245 Not Listed For Sale

  24 Spring St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft
  • Built 1950

  24 Spring St, Winchester, KY 40391

  Last Sold Summary

  • 23% Above List Price
  • $127/SF
  • 130 Days On Market

  • Last Sold Price $149,000
  • Mar 04, 2024

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan
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  /2

  $110,000

  • Land
  • 12,632 Sq Ft
  • $379,310 per Acre

  160 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

  160 Duclair Dr, Winchester, KY 40391
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  $460,000 Sold Jul 11, 2025

  150 Stone Crest Rd, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 4,448 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $103/SF
  • 18 Days On Market

  Last Listing Agent Brenda Murphy Murphy Realty Group

  150 Stone Crest Rd, Winchester, KY 40391
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  /41

  Est $331,581 Not Listed For Sale

  173 Milwood Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft
  • Built 1964

  173 Milwood Dr, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $156/SF
  • 16 Days On Market

  • Last Sold Price $290,000
  • May 23, 2023

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
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  $329,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  374 N Middletown Rd, Winchester, KY 40391

  Investment Opportunity! This is the Parent Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 (titled) Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of potential. You could

  Danielle Haggard Keller Williams Commonwealth

  374 N Middletown Rd, Winchester, KY 40391
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  $175,000 Sold Dec 29, 2025

  200 Madison Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $156/SF
  • 19 Days On Market

  Current Estimated Value $177,445

  Last Listing Agent Silvia Torres Tru Life Real Estate

  200 Madison Ave, Winchester, KY 40391

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