Clark County, KY Homes

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  /43

  Est $149,798 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,576 Sq Ft

  116 Park Ave, Winchester, KY 40391

  116 Park Ave, Winchester, KY 40391
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  /2

  $100,000

  • Land
  • 0.68 Acre
  • $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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  /13

  $38,700 Sold May 20, 2025

  11 Spring St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1945

  Last Sold Summary

  • 3% Below List Price
  • $35/SF
  • 33 Days On Market

  Current Estimated Value $45,024

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  11 Spring St, Winchester, KY 40391
• 

  

  

  /19

  Est $174,537 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,683 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  

  /59

  $820,000

  • 2 Beds
  • 1.5 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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  /36

  $345,000 Sold Jun 02, 2025

  1173 Lafayette Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $181/SF
  • 36 Days On Market

  Current Estimated Value $355,290

  Last Listing Agent Janna Smith United Real Estate Bluegrass

  1173 Lafayette Blvd, Winchester, KY 40391
• 

  

  /26

  Est $262,227 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  20 Jackson St, Winchester, KY 40391

  20 Jackson St, Winchester, KY 40391
• 

  

  /14

  $240,000

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  10 Upper St, Winchester, KY 40391

  Modern Ranch residence full un-finished basement, large lot.

  E. Clark Toleman Real Estate Appraisal Services

  10 Upper St, Winchester, KY 40391
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  /28

  $195,000 Sold Feb 11, 2025

  916 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1943

  Last Sold Summary

  • 13% Below List Price
  • $195/SF
  • 39 Days On Market

  Current Estimated Value $218,068

  Last Listing Agent Janet Jones RE/MAX Elite Lexington

  916 Muddy Creek Rd, Winchester, KY 40391
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  /25

  Est $221,771 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  21 Vine St, Winchester, KY 40391

  21 Vine St, Winchester, KY 40391
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  /29

  $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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  /18

  $240,000 Sold Mar 14, 2025

  110 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft
  • Built 2001

  Last Sold Summary

  • $194/SF
  • 8 Days On Market

  Current Estimated Value $277,053

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  110 Buckingham Ln, Winchester, KY 40391
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  /39

  Est $283,511 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,183 Sq Ft

  217 E Washington St, Winchester, KY 40391

  217 E Washington St, Winchester, KY 40391
• 

  

  /3

  $645,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  106 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

  Shane Underwood Keller Williams Commonwealth

  106 Bella Shae Way, Winchester, KY 40391
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  /36

  $472,500 Sold Sep 09, 2025

  208 Royal Oak Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,593 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Above List Price
  • $182/SF
  • 1 Day On Market

  Current Estimated Value $475,682

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  208 Royal Oak Dr, Winchester, KY 40391
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  /27

  Est $176,032 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  47 Buckner St, Winchester, KY 40391

  47 Buckner St, Winchester, KY 40391
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  /9

  $206,000

  • Land
  • 7.77 Acres
  • $26,512 per Acre

  368 Flanagan Station Rd, Winchester, KY 40391

  Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

  Shari Frasure Keller Williams Commonwealth

  368 Flanagan Station Rd, Winchester, KY 40391
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  /6

  $51,000 Sold May 14, 2025

  214 Ashton Oak Way, Winchester, KY 40391

  • Land
  • 0.25 Acre
  • $204,000 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 325 Days On Market

  Current Estimated Value $53,530

  Last Listing Agent Melia Hord Keller Williams Legacy Group

  214 Ashton Oak Way, Winchester, KY 40391
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  /26

  Est $193,661 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft

  150 W Broadway St, Winchester, KY 40391

  150 W Broadway St, Winchester, KY 40391
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  /6

  $388,000

  • 5 Beds
  • 3 Baths
  • 2,762 Sq Ft

  101 E Lexington Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. 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

  101 E Lexington Ave, Winchester, KY 40391
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  /23

  $135,000 Sold Jul 02, 2025

  2100 Old Log Lick Rd, Winchester, KY 40391

  • Land
  • 5 Acres
  • $27,000 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 69 Days On Market

  Current Estimated Value $140,312

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2100 Old Log Lick Rd, Winchester, KY 40391
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  /12

  Est $161,444 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  25 Oliver St, Winchester, KY 40391

  25 Oliver St, Winchester, KY 40391
• 

  

  /21

  $189,500

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  109 Quail Ridge Rd, Winchester, KY 40391

  Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

  Kim Dice EXP Realty, LLC

  109 Quail Ridge Rd, Winchester, KY 40391
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  /20

  $217,500 Sold Sep 30, 2025

  511 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $155/SF
  • 28 Days On Market

  Current Estimated Value $218,277

  Last Listing Agent Tyler I Back The Brokerage

  511 Acadia Way, Winchester, KY 40391
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  /11

  Est $135,211 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  30 Madison Ave, Winchester, KY 40391

  30 Madison Ave, Winchester, KY 40391
• 

  

  /24

  $329,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  360 N Middletown Rd, Winchester, KY 40391

  Investment Opportunity! This is the Child 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

  360 N Middletown Rd, Winchester, KY 40391
• 

  /2

  $99,500 Sold Dec 01, 2025

  1295 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 8.39 Acres
  • $11,859 per Acre

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1295 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /25

  Est $189,333 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  15 Madison Ave, Winchester, KY 40391

  15 Madison Ave, Winchester, KY 40391
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  /84

  $849,900

  • 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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  /2

  $39,500 Sold Mar 05, 2025

  410 Fairholme Way, Winchester, KY 40391

  • Land
  • 0.4 Acre
  • $98,750 per Acre

  Last Sold Summary

  • 14% Above List Price
  • 1,599 Days On Market

  Current Estimated Value $221,085

  Last Listing Agent Garnett Davis Tom Goebel & Company

  410 Fairholme Way, Winchester, KY 40391
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  /20

  Est $134,143 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,776 Sq Ft

  2 1st St, Winchester, KY 40391

  2 1st St, Winchester, KY 40391
• 

  

  /11

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,534 Sq Ft

  646 Laura Dr, Winchester, KY 40391

  Three bedrooms ranch, that has been updated with a new kitchen, with granite tops ,new appliances, new flooring ,new interior paintiing ,plus much more, located in Verna Hills S/D located between Winchester and Lexington . Owner/Agent

  Garry Milton Milton and Associates Real Estate

  646 Laura Dr, Winchester, KY 40391
• 

  

  /13

  $140,000 Sold Nov 24, 2025

  220 Pendleton St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  Last Sold Summary

  • 24% Below List Price
  • $155/SF
  • 37 Days On Market

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

  220 Pendleton St, Winchester, KY 40391
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  /16

  Est $184,952 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,298 Sq Ft

  123 2nd St, Winchester, KY 40391

  123 2nd St, Winchester, KY 40391
• 

  

  /12

  $189,900

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street. This brick ranch offers 3 bedrooms, 2 full baths, and hardwood floors throughout the living room, hallway, and bedrooms, ready to be refreshed with a re-sand and polish. The layout provides a foundation for a buyer looking to add personal updates and make it their own. Located at the end of the street, the home offers added privacy along with peaceful farm views behind

  Austina Bruton Re/Max Elite Realty - Hamburg

  41 7th St, Winchester, KY 40391
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  /2

  $59,000 Sold Dec 16, 2025

  1515 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 2.83 Acres
  • $20,848 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 3 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1515 Sewell Shop Rd, Winchester, KY 40391
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  /74

  Est $517,395 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,941 Sq Ft

  4 Moundale Ave, Winchester, KY 40391

  4 Moundale Ave, Winchester, KY 40391
• 

  /2

  $99,900 Pending

  • Land
  • 8.82 Acres
  • $11,327 per Acre

  13015 Irvine Rd Unit Parcel 5, Winchester, KY 40391

  Mendel Tipton Natural Bridge Realty

  13015 Irvine Rd Unit Parcel 5, Winchester, KY 40391
• 

  

  /53

  $439,000 Sold Dec 29, 2025

  129 Lana Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,844 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $154/SF
  • 110 Days On Market

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  129 Lana Ln, Winchester, KY 40391
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  /73

  Est $564,108 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,236 Sq Ft

  12 Moundale Ave, Winchester, KY 40391

  12 Moundale Ave, Winchester, KY 40391

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