Winchester, KY Homes

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  /45

  Est $500,058 Not Listed For Sale

  1159 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,244 Sq Ft
  • Built 2007

  1159 Cabin Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $203/SF
  • 14 Days On Market

  • Last Sold Price $455,000
  • Jun 06, 2024

  Last Listing Agent Kimberly Fields Coldwell Banker McMahan
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  /100

  $1,695,000

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  PRICE REDUCED!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of the highest points in Clark County, where you can see the dormitories at EKU

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
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  /44

  $267,000 Sold Mar 24, 2026

  146 W Lexington Ave, Winchester, KY 40391

  • 8 Beds
  • 3 Baths
  • 3,393 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Below List Price
  • $79/SF
  • 54 Days On Market

  Current Estimated Value $269,171

  Last Listing Agent KB Realty Group -Kevin Bradley KB Realty Group

  146 W Lexington Ave, Winchester, KY 40391
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  /15

  Est $312,722 Not Listed For Sale

  158 Cabin Creek Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 2005

  158 Cabin Creek Heights, Winchester, KY 40391

  Last Sold Summary

  • 18% Above List Price
  • $168/SF
  • 5 Days On Market

  • Last Sold Price $265,000
  • May 15, 2024

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC
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  /21

  $175,000

  • Land
  • 11.36 Acres
  • $15,402 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of convenience and countryside charm with this beautiful 11+ acre tract located just outside of Winchester in Clark County. Offering gently rolling terrain and multiple potential building sites, this property provides an ideal setting for your dream home, mini-farm, or private retreat.Enjoy the peace and privacy of rural living without sacrificing accessibility and just

  Christa Joynt Keller Williams Commonwealth

  2996 Irvine Rd, Winchester, KY 40391
• 

  

  /22

  $156,000 Sold Jan 16, 2026

  146 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft
  • Built 1940

  Last Sold Summary

  • 8% Below List Price
  • $122/SF
  • 28 Days On Market

  Current Estimated Value $157,773

  Last Listing Agent Autumn Johannes National Real Estate

  146 Cook Ave, Winchester, KY 40391
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  /43

  Est $473,738 Not Listed For Sale

  2100 Ecton Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,060 Sq Ft
  • Built 1978

  2100 Ecton Rd, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $228/SF
  • 35 Days On Market

  • Last Sold Price $470,000
  • Aug 23, 2023

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
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  /52

  $269,000

  • 4 Beds
  • 2 Baths
  • 2,417 Sq Ft

  104 Jackson Ferry Rd, Winchester, KY 40391

  Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen

  Bob Sophiea eXp Realty, LLC

  104 Jackson Ferry Rd, Winchester, KY 40391
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  /71

  $410,000 Sold Nov 07, 2025

  188 Big Stoner Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $172/SF
  • 9 Days On Market

  Current Estimated Value $416,628

  Last Listing Agent Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
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  /44

  Est $538,580 Not Listed For Sale

  601 Wades Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,070 Sq Ft
  • Built 2000

  601 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $237/SF
  • 7 Days On Market

  • Last Sold Price $490,000
  • Sep 11, 2024

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
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  /2

  $1,200,000

  • Land
  • 24.15 Acres
  • $49,689 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, Winchester, KY 40391
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  /73

  $325,000 Sold Sep 23, 2025

  407 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $180/SF
  • 123 Days On Market

  Current Estimated Value $332,442

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  407 Fairholme Way, Winchester, KY 40391
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  /3

  Est $325,754 Not Listed For Sale

  1591 Gay Evans Rd, Winchester, KY 40391

  • 3 Beds
  • 1,260 Sq Ft
  • Built 1940

  1591 Gay Evans Rd, Winchester, KY 40391

  Last Sold Summary

  • 1% Below List Price
  • $262/SF
  • 17 Days On Market

  • Last Sold Price $330,000
  • Dec 29, 2023

  Last Listing Agent Holly Goeing The Agency
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  /6

  $171,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  102 W Hickman St, Winchester, KY 40391

  102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  102 W Hickman St, Winchester, KY 40391
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  /40

  $210,000 Sold Sep 11, 2025

  635 Lisletown Ln, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • Built 1981

  Last Sold Summary

  • 12% Below List Price
  • $129/SF
  • 31 Days On Market

  Current Estimated Value $221,998

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  635 Lisletown Ln, Winchester, KY 40391
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  /96

  Est $827,257 Not Listed For Sale

  1995 Gay Evans Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,272 Sq Ft
  • Built 1998

  1995 Gay Evans Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $239/SF
  • 82 Days On Market

  • Last Sold Price $782,000
  • Aug 15, 2024

  Last Listing Agent Andrea Coughtry Lifstyl Real Estate
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  /2

  $110,000

  • Land
  • 16,552 Sq Ft
  • $289,474 per Acre

  200 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

  200 Duclair Dr, Winchester, KY 40391
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  /43

  $485,000 Sold Jun 23, 2025

  430 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,414 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $201/SF
  • 55 Days On Market

  Current Estimated Value $494,564

  Last Listing Agent Robyn Bradley Woods Realty Group

  430 Fairholme Way, Winchester, KY 40391
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  /60

  Est $190,434 Not Listed For Sale

  1333 Jackson Ferry Rd, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,492 Sq Ft
  • Built 1964

  1333 Jackson Ferry Rd, Winchester, KY 40391

  Last Sold Summary

  • 52% Above List Price
  • $84/SF
  • 60 Days On Market

  • Last Sold Price $125,000
  • Sep 05, 2024

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management
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  /16

  $174,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  47 Buckner St, Winchester, KY 40391

  This 3-bedroom, 2 full bath home is nestled in a convenient location and ready for new owners. Updates can be admired throughout. Property boats spacious bedrooms including primary bedroom with on-suite, large back yard with garage and so much more. Schedule your showing today!

  Michael Hilario The Agency

  47 Buckner St, Winchester, KY 40391
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  /74

  $350,000 Sold Mar 06, 2026

  4611 Colby Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,712 Sq Ft
  • Built 1980

  Last Sold Summary

  • $94/SF
  • 2 Days On Market

  Current Estimated Value $350,630

  Last Listing Agent Nancy Smith Rector Hayden Realtors

  4611 Colby Rd, Winchester, KY 40391
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  /91

  Est $376,365 Not Listed For Sale

  2184 Cole Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,514 Sq Ft
  • Built 1970

  2184 Cole Rd, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $147/SF
  • 11 Days On Market

  • Last Sold Price $370,000
  • Sep 07, 2023

  Last Listing Agent Greg Wood Freedom Realty & Property Management
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  /25

  $425,000

  • Land
  • 25.87 Acres
  • $16,426 per Acre

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare opportunity to own over 25 acres of beautiful Kentucky countryside on Irvine Road, combining two adjoining tracts into one exceptional offering. With gently rolling hills and multiple ideal building sites, this property provides the perfect setting to create your dream home, private estate, or mini-farm. The land offers a wonderful balance of usability and natural beauty, featuring a scenic

  Christa Joynt Keller Williams Commonwealth

  2996/3056 Irvine Rd, Winchester, KY 40391
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  /24

  $186,000 Sold May 14, 2025

  205 Arbor Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1994

  Last Sold Summary

  • 3% Above List Price
  • $157/SF
  • 77 Days On Market

  Current Estimated Value $202,977

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  205 Arbor Ct, Winchester, KY 40391
• 

  

  /23

  Est $254,998 Not Listed For Sale

  421 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,487 Sq Ft
  • Built 2003

  421 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $168/SF
  • 9 Days On Market

  • Last Sold Price $250,000
  • Jul 09, 2024

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty
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  /94

  $779,000

  • 4 Beds
  • 3.5 Baths
  • 4,584 Sq Ft

  4040 Muddy Creek Rd, Winchester, KY 40391

  A Farmhouse Retreat with Timeless Craftsmanship on 13.6 Acres Nestled on 13.6 rolling acres in Clark County, this custom built farmhouse captivates with soaring tongue-and-groove ceilings, rich woodwork, and thoughtful craftsmanship that sets this home apart. Oversized doors, custom cabinetry, and detailed finishes showcase the quality throughout, while two wood-burning fireplaces with homemade

  Julie Wiggington RE/MAX Creative, Winchester

  4040 Muddy Creek Rd, Winchester, KY 40391
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  /30

  $310,900 Sold Sep 12, 2025

  115 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,042 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $102/SF
  • 2 Days On Market

  Current Estimated Value $320,503

  Last Listing Agent Lauren Ball Deborah Ball Realty

  115 Hampton Ave, Winchester, KY 40391
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  /54

  Est $270,619 Not Listed For Sale

  427 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 2002

  427 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $146/SF
  • 121 Days On Market

  • Last Sold Price $260,000
  • Sep 18, 2024

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /14

  $129,300

  • Land
  • 2.3 Acres
  • $56,217 per Acre

  110 Knox Ct, Winchester, KY 40391

  This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the

  Jarran Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
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  /82

  $385,000 Sold Nov 07, 2025

  1138 Lafayette Blvd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Above List Price
  • $167/SF
  • 1 Day On Market

  Current Estimated Value $382,697

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1138 Lafayette Blvd, Winchester, KY 40391
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  /24

  Est $244,066 Not Listed For Sale

  445 Jameson Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2002

  445 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $154/SF
  • 31 Days On Market

  • Last Sold Price $215,000
  • Apr 24, 2025

  Last Listing Agent Tyler I Back The Brokerage
• 

  

  /20

  $217,500 Pending

  • 3 Beds
  • 1 Bath
  • 1,190 Sq Ft

  7 Hiawatha Trail, Winchester, KY 40391

  Welcome to 7 Hiawatha Trail in Winchester—a beautifully updated brick ranch that blends timeless character with modern conveniences. Built in 1968, this home has been thoughtfully improved by its current owners, offering a move-in-ready space with stylish upgrades throughout. Inside, you'll find refinished original hardwood floors that bring warmth and charm, complemented by fresh paint and

  Serena Cassidy Coldwell Banker McMahan

  7 Hiawatha Trail, Winchester, KY 40391
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  /17

  $190,000 Sold Sep 10, 2025

  114 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,059 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $179/SF
  • 50 Days On Market

  Current Estimated Value $194,838

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  114 Sunset Heights, Winchester, KY 40391
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  /47

  Est $350,516 Not Listed For Sale

  106 Old Ironworks Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,380 Sq Ft
  • Built 1900

  106 Old Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 20% Above List Price
  • $86/SF
  • 115 Days On Market

  • Last Sold Price $291,000
  • Dec 13, 2024

  Last Listing Agent John Groft RE/MAX
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  /103

  $2,650,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /48

  $222,500 Sold Jul 28, 2025

  217 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Above List Price
  • $108/SF
  • 2 Days On Market

  Current Estimated Value $228,093

  Last Listing Agent Robin Murray The Agency

  217 Locust Grove Rd, Winchester, KY 40391
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  /25

  Est $258,372 Not Listed For Sale

  325 Vanover Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 2002

  325 Vanover Way, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $169/SF
  • 1 Day On Market

  • Last Sold Price $240,880
  • Aug 27, 2024

  Last Listing Agent Brad Harmon LexHomes Real Estate
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  /30

  $209,000

  • 4 Beds
  • 2 Baths
  • 2,683 Sq Ft

  217 S Highland St, Winchester, KY 40391

  This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

  Michael Hilario The Agency

  217 S Highland St, Winchester, KY 40391
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  /34

  $342,000 Sold Sep 16, 2025

  3560 Wades Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1950

  Last Sold Summary

  • 10% Below List Price
  • $262/SF
  • 37 Days On Market

  Current Estimated Value $342,626

  Last Listing Agent Sarah MacHarg Kentucky Land and Home

  3560 Wades Mill Rd, Winchester, KY 40391
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  /17

  Est $245,869 Not Listed For Sale

  206 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,737 Sq Ft
  • Built 1998

  206 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $138/SF
  • 30 Days On Market

  • Last Sold Price $239,000
  • Dec 16, 2024

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

Showing Results 161 - 200, Page 5 of 18