Winchester, KY Homes

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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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  /65

  Est $429,308 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,372 Sq Ft

  408 S Maple St, Winchester, KY 40391

  408 S Maple St, Winchester, KY 40391
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  /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
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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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  /57

  Est $479,536 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,864 Sq Ft

  402 S Maple St, Winchester, KY 40391

  402 S Maple St, Winchester, KY 40391
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  /31

  $274,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  407 Corinne Ct, Winchester, KY 40391

  Welcome to 407 Corinne Court a beautifully maintained 3-bedroom, 2-bath all-electric home offering a perfect blend of comfort, style, and functionality. This one-level open-concept ranch sits on a crawl space foundation with a brick and vinyl exterior and features an attached two-car garage. Step inside to find fresh paint throughout, new carpet in the living room and bedrooms, and hardwood

  Shane Underwood Keller Williams Commonwealth

  407 Corinne Ct, 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

  Last Listing Agent Tyler I Back The Brokerage

  511 Acadia Way, Winchester, KY 40391
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  /60

  Est $434,054 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,718 Sq Ft

  405 Boone Ave, Winchester, KY 40391

  405 Boone Ave, Winchester, KY 40391
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  /12

  $110,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  400 Wexford Dr, Winchester, KY 40391

  Welcome! This home offers a practical layout with 3 bedrooms and 2 baths on a manageable 0.2-acre lot. The interior has been well maintained, and fenced backyard creates a private outdoor space ideal for gatherings, pets, or future improvements. A detached 2-car garage provides secure parking and storage. Approximately 5 minutes to downtown Winchester and 15 minutes to Lexington, positioning the

  Katie Allen Keller Williams Legacy Group

  400 Wexford Dr, Winchester, KY 40391
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  /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
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  /57

  Est $295,517 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft

  10 Northern Ave, Winchester, KY 40391

  10 Northern Ave, Winchester, KY 40391
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  /12

  $230,000

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft

  605 College St, Winchester, KY 40391

  Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

  Steve Adams Steven D Adams Real Estate Services, LLC

  605 College St, 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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  /15

  Est $221,192 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,036 Sq Ft

  215 Short St, Winchester, KY 40391

  215 Short St, Winchester, KY 40391
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  /31

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  17 Euclid Ave, Winchester, KY 40391

  Welcome home to 17 Euclid Ave in beautiful College Park area of Winchester. This three bedroom two full bath home may be the one you are looking for. Beautiful Hardwood floors throughout most of the home. Two additional bedrooms are upstairs with a full bath. Fenced in back yard and a large deck for you summertime entertaining. Don't wait, let's take a look.

  Donna Thwaites Thwaites Realtors LLC

  17 Euclid Ave, Winchester, KY 40391
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  /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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  /32

  Est $368,126 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,044 Sq Ft

  505 Boone Ave, Winchester, KY 40391

  505 Boone Ave, Winchester, KY 40391
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  /9

  $102,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  39 S Highland St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 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

  39 S Highland 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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  /35

  Est $402,993 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,248 Sq Ft

  121 Hampton Ave, Winchester, KY 40391

  121 Hampton Ave, Winchester, KY 40391
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  /12

  $144,000

  • 3 Beds
  • 1 Bath
  • 805 Sq Ft

  150 Cook Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 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

  150 Cook Ave, Winchester, KY 40391
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  /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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  /27

  Est $257,194 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,598 Sq Ft

  118 Southern Ct, Winchester, KY 40391

  118 Southern Ct, Winchester, KY 40391
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  /6

  $450,000

  550 E Broadway St, Winchester, KY 40391

  Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

  Keith Wilson Coldwell Banker McMahan

  550 E Broadway St, Winchester, KY 40391
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  /37

  $295,000 Sold Dec 27, 2025

  115 College St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,839 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Below List Price
  • $160/SF
  • 0 Days On Market

  Last Listing Agent Zova Rothchild Keller Williams Legacy Group

  115 College St, Winchester, KY 40391
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  /46

  Est $354,394 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft

  14 Western Ave, Winchester, KY 40391

  14 Western Ave, Winchester, KY 40391
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  /12

  $194,900

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
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  /20

  $243,000 Sold Mar 24, 2025

  235 Dubuy Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Built 2006

  Last Sold Summary

  • 7% Below List Price
  • $158/SF
  • 56 Days On Market

  Current Estimated Value $276,796

  Last Listing Agent Melissa Combs Keller Williams Commonwealth

  235 Dubuy Dr, Winchester, KY 40391
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  /18

  Est $205,643 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,109 Sq Ft

  6 Western Ave, Winchester, KY 40391

  6 Western Ave, Winchester, KY 40391
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  /2

  $189,900 Pending

  • Land
  • 10.73 Acres
  • $17,698 per Acre

  1045 Gay Evans Rd, Winchester, KY 40391

  Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 10 acres of unrestricted land with many building sites. Schedule your showing today!

  Holly Goeing The Agency

  1045 Gay Evans Rd, Winchester, KY 40391
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  /21

  $285,000 Sold Jul 29, 2025

  219 Bartram Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,696 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $168/SF
  • 8 Days On Market

  Current Estimated Value $291,929

  Last Listing Agent Nora Williams Keller Williams Commonwealth

  219 Bartram Ct, Winchester, KY 40391
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  /37

  Est $312,532 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft

  120 Milwood Dr, Winchester, KY 40391

  120 Milwood Dr, Winchester, KY 40391
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  /42

  $450,000

  • 5 Beds
  • 3 Baths
  • 3,718 Sq Ft

  1503 Schollsville Rd, Winchester, KY 40391

  Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft

  Keith Wilson Coldwell Banker McMahan

  1503 Schollsville Rd, Winchester, KY 40391
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  /43

  $354,000 Sold Jul 02, 2025

  485 Mccullough Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft
  • Built 1950

  Last Sold Summary

  • 21% Below List Price
  • $167/SF
  • 38 Days On Market

  Current Estimated Value $377,824

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  485 Mccullough Ln, Winchester, KY 40391
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  /48

  Est $264,168 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,496 Sq Ft

  132 Boone Ave, Winchester, KY 40391

  132 Boone Ave, Winchester, KY 40391
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  /23

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  313 S Burns Ave, Winchester, KY 40391

  This 3 bedroom, 2 bath home sits on a corner lot with hardwood floors and a two-car detached garage behind the home. Plus, it's walkable to downtown Winchester, the public library, and College Park. Inside, you'll find tall ceilings, a traditional living and dining room, and a unique layout that gives you options for how you use the space. The kitchen opens to the back deck, and a ramp at the

  Michelle Blackburn RE/MAX Creative, Winchester

  313 S Burns Ave, Winchester, KY 40391
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  /78

  $660,000 Sold Dec 10, 2025

  420 Alexis Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft
  • Built 2022

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 26 Days On Market

  Last Listing Agent Edwin Burden McCormick Realty Inc.

  420 Alexis Way, Winchester, KY 40391
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  /39

  Est $403,023 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,660 Sq Ft

  14 Euclid Ave, Winchester, KY 40391

  14 Euclid Ave, Winchester, KY 40391
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  /5

  $70,000

  • Land
  • 1.72 Acres
  • $40,698 per Acre

  12541 Ironworks Rd, Winchester, KY 40391

  Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

  Daniela Virguez National Real Estate

  12541 Ironworks Rd, Winchester, KY 40391
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  /31

  $172,500 Sold Jan 17, 2025

  366 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,180 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $146/SF
  • 2 Days On Market

  Current Estimated Value $193,337

  Last Listing Agent Tiffany Jarvis ERA Select Real Estate

  366 Colby Ridge Blvd, Winchester, KY 40391

Showing Results 601 - 640, Page 16 of 18