Winchester, KY Homes

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  /41

  Est $277,754 Not Listed For Sale

  21 Beckner St, Winchester, KY 40391

  • 6 Beds
  • 3.5 Baths
  • 3,072 Sq Ft
  • Built 1940

  21 Beckner St, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $75/SF
  • 17 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Shane Underwood Keller Williams Commonwealth
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  /2

  $2,000,000

  • Land
  • 17.87 Acres
  • $111,919 per Acre

  1509 Boonesboro Rd, Winchester, KY 40391

  17.87 Acre farm available for sale. Ideal location for redevelopment. Gently rolling topography. Corner lot with excellent visibility. Water, electric, sewer, gas and telecommunications available. Conveniently located near RD Campbell Junior High School, George Rogers Clark High School & Winchester Country Club. Located 3 miles south of Interstate 64. Signalized corner lot at Boonesboro Rd. &

  Cheryl Johnston CMI Properties

  1509 Boonesboro 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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  /32

  Est $306,662 Not Listed For Sale

  322 S Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft
  • Built 1940

  322 S Burns Ave, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $148/SF
  • 46 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Mary Layton FC Tucker Bluegrass
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  /20

  $134,900

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  103 Yorktowne Ct, Winchester, KY 40391

  Affordable and move in ready! This home will qualify for FHA, VA &/or Rural Housing Loan. This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping,

  Susy Esquivel Allied Realty

  103 Yorktowne Ct, Winchester, KY 40391
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  /16

  $225,000 Sold Apr 25, 2025

  39 Hillcrest Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 943 Sq Ft
  • Built 1968

  Last Sold Summary

  • $239/SF
  • 2 Days On Market

  Current Estimated Value $228,941

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  39 Hillcrest Dr, Winchester, KY 40391
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  /51

  Est $366,175 Not Listed For Sale

  200 College St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,227 Sq Ft
  • Built 1887

  200 College St, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $101/SF
  • 137 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Amy Diamond ERA Select Real Estate
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  /13

  $140,000

  • 2 Beds
  • 1 Bath
  • 1,254 Sq Ft

  208 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

  Anita McDermott Keller Williams Bluegrass Realty

  208 4th St, Winchester, KY 40391
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  /87

  $250,000 Sold Apr 18, 2025

  418 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $149/SF
  • 3 Days On Market

  Current Estimated Value $253,110

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  418 Jameson Way, Winchester, KY 40391
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  /12

  Est $230,041 Not Listed For Sale

  217 College St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1940

  217 College St, Winchester, KY 40391

  Last Sold Summary

  • 3% Below List Price
  • $144/SF
  • 72 Days On Market

  Last Sold Price $237,500

  Last Listing Agent Angie Conley Dixon Dixon Properties
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  /10

  $374,900 Pending

  • Land
  • 1.29 Acres
  • $290,620 per Acre

  395 Croxton Way, Winchester, KY 40391

  1.29 acre Commercial Lot zoned B-3 that's slightly elevated with maximum visibility for your business. Ideal location for a gas station, fast food restaurant or retail shop. Lot near Clark Medical Center Hospital. To the south is Lexington Road (US 60), to the west is Floyd Clay Drive, and to the North is Croxton Way. Making three (3) different entrances to enhance accessibility to any business.

  Rich Decker Rector Hayden Realtors

  395 Croxton Way, 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 $262,914

  Last Listing Agent Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /27

  Est $304,641 Not Listed For Sale

  118 Olde Potomac Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,000 Sq Ft
  • Built 1935

  118 Olde Potomac Ave, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $95/SF
  • 6 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth
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  /28

  $799,900

  • Land
  • 13.19 Acres
  • $60,644 per Acre

  1600 Ironworks Rd, Winchester, KY 40391

  This property has it all! Easy access to Veterans Memorial Bypass, I-64, and downtown Winchester, plus entrances on Ironworks and clear visibility from the Bypass. This does have sewer and water located on the property. Full of potential possibilities zoned Planned Development and more acreage is available if needed. The property access is a driveway off Ironworks Road across from Center Drive

  Josh Wood Freedom Realty & Property Management

  1600 Ironworks Rd, Winchester, KY 40391
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  /58

  $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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  /86

  Est $278,937 Not Listed For Sale

  112 Olde Potomac Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,220 Sq Ft
  • Built 1935

  112 Olde Potomac Ave, Winchester, KY 40391

  Last Sold Summary

  • 5% Below List Price
  • $91/SF
  • 2 Days On Market

  Last Sold Price $294,000

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /50

  $799,900

  • 4 Beds
  • 3 Baths
  • 3,311 Sq Ft

  7300 Old Boonesboro Rd, Winchester, KY 40391

  This beautiful home sits on over 7 acres of peaceful countryside. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of

  Vickie Skeens RE/MAX Elite Lexington

  7300 Old Boonesboro Rd, Winchester, KY 40391
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  /32

  $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 $178,196

  Last Listing Agent Silvia Torres Tru Life Real Estate

  200 Madison Ave, Winchester, KY 40391
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  /30

  Est $225,702 Not Listed For Sale

  302 W Lexington Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,939 Sq Ft
  • Built 1935

  302 W Lexington Ave, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $107/SF
  • 16 Days On Market

  Last Sold Price $207,500

  Last Listing Agent Heather Justice Rector Hayden Realtors
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  /3

  $219,000 Sold May 20, 2025

  410 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,628 Sq Ft
  • Built 2005

  Last Sold Summary

  • $135/SF
  • 18 Days On Market

  Current Estimated Value $236,408

  Last Listing Agent John Wilson Bluegrass Properties Group

  410 Paisley Ct, Winchester, KY 40391

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