Winchester, KY Homes

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  /24

  $277,500 Sold Aug 21, 2025

  10 Howard Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1961

  Last Sold Summary

  • 3% Below List Price
  • $175/SF
  • 0 Days On Market

  Current Estimated Value $279,139

  Last Listing Agent Holly Goeing The Agency

  10 Howard Dr, Winchester, KY 40391
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  /44

  Est $423,224 Not Listed For Sale

  1927 Kiddville Rd, Winchester, KY 40391

  • 5 Beds
  • 4 Baths
  • 2,056 Sq Ft
  • Built 2001

  1927 Kiddville Rd, Winchester, KY 40391

  Last Sold Summary

  • 9% Below List Price
  • $226/SF
  • 22 Days On Market

  Last Sold Price $465,000

  Last Listing Agent Megan McCoy Keller Williams Legacy Group
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  /23

  $498,900

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare find! Gorgeous 25 acres of gently rolling land with a barn and creek is perfect for building your dream home and creating your homestead! Don't miss this opportunity! This is farm is conveniently located 20 miles from Hamburg and 5 miles from the Winchester bypass. No city sewage. Deed restrictions apply. Relax and enjoy the spectacular views. Get ready to enjoy life! Land consists of 2

  Lura Justice Rector Hayden Realtors

  2996/3056 Irvine Rd, Winchester, KY 40391
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  /19

  $170,000 Sold Apr 28, 2025

  223 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  Last Sold Summary

  • 8% Below List Price
  • $166/SF
  • 82 Days On Market

  Current Estimated Value $177,611

  Last Listing Agent Jordan James Lifstyl Real Estate

  223 Blair Ave, Winchester, KY 40391
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  /112

  Est $788,259 Not Listed For Sale

  703 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,311 Sq Ft
  • Built 1980

  703 Kiddville Rd, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $303/SF
  • 276 Days On Market

  Last Sold Price $699,900

  Last Listing Agent Tyson Walters Kassie & Associates
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  /19

  $499,000

  • Land
  • 36.94 Acres
  • $13,508 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
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  /14

  $320,000 Sold Oct 17, 2025

  3431 Colby Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 5,237 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $61/SF
  • 7 Days On Market

  Current Estimated Value $330,514

  Last Listing Agent Holly Goeing The Agency

  3431 Colby Rd, Winchester, KY 40391
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  /43

  Est $389,155 Not Listed For Sale

  700 Vienna Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,826 Sq Ft
  • Built 2004

  700 Vienna Rd, Winchester, KY 40391

  Last Sold Summary

  • 20% Above List Price
  • $178/SF
  • 18 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Sheridan Sims Keller Williams Commonwealth
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  /45

  $499,900 New Construction

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Welcome to Fairholme Estates—where luxury meets comfort! This brand-new ranch-style home offers 4 bedrooms, 3 full baths, and 9' ceilings throughout for a spacious, airy feel. The designer kitchen features a huge island, beautiful finishes, and flows seamlessly into the vaulted great room filled with natural light from large windows. A Jack and Jill bath with separate sinks provides convenience,

  Kristin Ray Lifstyl Real Estate

  414 Fairholme Way, Winchester, KY 40391
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  /41

  $265,000 Sold Nov 12, 2025

  130 Village Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $133/SF
  • 4 Days On Market

  Current Estimated Value $267,987

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  130 Village Ct, Winchester, KY 40391
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  /96

  Est $474,750 Not Listed For Sale

  2430 Log Lick Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • Built 1938

  2430 Log Lick Rd, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $150/SF
  • 184 Days On Market

  Last Sold Price $405,000

  Last Listing Agent E Anthony Phillips RE/MAX
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  /70

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  215 Old Log Lick Rd, Winchester, KY 40391

  Enjoy where you live! Zen like grounds will bring inner peace in this 1,450 sq foot home on over 3 private acres. Covered front and back porches span the width of the house. Get off the grid with the solar panels on the roof (25 yr warranty), six raised garden beds, and fenced chicken coop! Average utility bill $50 in 2025 and $35 in 2024! (Solar panels paid for by Seller). No worries for fast

  Kerry Ball Local First Realty, LLC

  215 Old Log Lick Rd, Winchester, KY 40391
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  /37

  $207,000 Sold May 23, 2025

  632 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1974

  Last Sold Summary

  • $185/SF
  • 41 Days On Market

  Current Estimated Value $209,261

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  632 Laura Dr, Winchester, KY 40391
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  /30

  Est $174,596 Not Listed For Sale

  3604 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1998

  3604 Pine Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $125/SF
  • 3 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Patty Adams Rector Hayden Realtors
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  /24

  $369,900 New Construction

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

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
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  /31

  $231,000 Sold Jun 30, 2025

  619 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • Built 1980

  Last Sold Summary

  • $165/SF
  • 17 Days On Market

  Current Estimated Value $236,934

  Last Listing Agent Kevin Bradley KB Realty Group

  619 Laura Dr, Winchester, KY 40391
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  /101

  Est $338,992 Not Listed For Sale

  3642 Crowe Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft
  • Built 1953

  3642 Crowe Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 7% Below List Price
  • $189/SF
  • 121 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Maggie Napier Napier Realtors
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  /54

  $434,900

  • 3 Beds
  • 2 Baths
  • 3,563 Sq Ft

  204 Delaplain Rd, Winchester, KY 40391

  Unique opportunity to own a ranch with partly finished basement in a well established neighborhood! Stoneybrook subdivision is very convenient to schools, shopping, and dining. Ranch has been updated (including roof and windows) and in very good condition with lots of space. Three bedrooms, two baths, large spacious kitchen, extensive bar, huge pantry, laundry, dining, and great room are on the

  Sam Watkins COLOR Real Estate

  204 Delaplain Rd, Winchester, KY 40391
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  /64

  $929,000 Sold Sep 05, 2025

  1110 Craig Crossing, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,670 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $348/SF
  • 23 Days On Market

  Current Estimated Value $955,644

  Last Listing Agent Michael Hilario The Agency

  1110 Craig Crossing, Winchester, KY 40391
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  /16

  Est $150,000 Not Listed For Sale

  4523 Trapp Goffs Corner Rd, Winchester, KY 40391

  • Studio
  • 1,271 Sq Ft
  • Built 1974

  4523 Trapp Goffs Corner Rd, Winchester, KY 40391

  Last Sold Summary

  • 33% Above List Price
  • $89/SF
  • 178 Days On Market

  Last Sold Price $112,500

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
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  /10

  $550,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, Winchester, KY 40391
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  /6

  $225,000 Sold Apr 22, 2025

  845 Gay Evans Rd, Winchester, KY 40391

  • Land
  • 8.59 Acres
  • $26,193 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 35 Days On Market

  Last Listing Agent Holly Goeing The Agency

  845 Gay Evans Rd, Winchester, KY 40391
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  /66

  Est $547,013 Not Listed For Sale

  5078 Trapp Goffs Corner Rd, Winchester, KY 40391

  • 5 Beds
  • 4.5 Baths
  • 4,479 Sq Ft
  • Built 1992

  5078 Trapp Goffs Corner Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $115/SF
  • 5 Days On Market

  Last Sold Price $516,000

  Last Listing Agent Wayne Sewell The Agency
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  /74

  $349,999 Pending

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

  4611 Colby Rd, Winchester, KY 40391

  Contingent upon inspections, taking back up offers. Rare opportunity to own a brick ranch on 2.68 acres! Located close to Lexington and Winchester. In-ground swimming pool, beautiful, level lot that overlooks farmland behind it. This is an estate sale and in need of updating. Home has great bones! The roof is newer, there are hardwoods on the majority of the first floor. The pool was operational

  Nancy Smith Rector Hayden Realtors

  4611 Colby Rd, Winchester, KY 40391
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  /2

  $299,900 Sold Aug 08, 2025

  Unlisted Address

  • 3 Beds
  • 3 Baths
  • 2,054 Sq Ft
  • Built 1970

  Last Sold Summary

  • $146/SF

  Current Estimated Value $299,209

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  Unlisted Address
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  /39

  Est $395,098 Not Listed For Sale

  900 Vienna Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,314 Sq Ft
  • Built 2005

  900 Vienna Rd, Winchester, KY 40391

  Last Sold Summary

  • $170/SF
  • 0 Days On Market

  Last Sold Price $394,500

  Last Listing Agent Devin Ramsey Berkshire Hathaway HomeServices Foster Realtors
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  /3

  $380,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  270 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
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  /21

  $207,000 Sold May 12, 2025

  513 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2001

  Last Sold Summary

  • 4% Below List Price
  • $154/SF
  • 35 Days On Market

  Current Estimated Value $217,208

  Last Listing Agent Tyler I Back The Brokerage

  513 Acadia Way, Winchester, KY 40391
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  /23

  Est $728,113 Not Listed For Sale

  1275 Old Log Lick Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1982

  1275 Old Log Lick Rd, Winchester, KY 40391

  Last Sold Summary

  • 2% Below List Price
  • $532/SF
  • 474 Days On Market

  Last Sold Price $740,000

  Last Listing Agent John Wilson Bluegrass Properties Group
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  /25

  $310,000

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft

  398 Pine Ridge Rd, Winchester, KY 40391

  Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from the

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  /19

  $288,500 Sold Feb 24, 2026

  729 Wayland Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $147/SF
  • 92 Days On Market

  Current Estimated Value $279,281

  Last Listing Agent Brittany Beer EXP Realty, LLC

  729 Wayland Dr, Winchester, KY 40391
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  /43

  Est $283,561 Not Listed For Sale

  2270 Mina Station Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • Built 1971

  2270 Mina Station Rd, Winchester, KY 40391

  Last Sold Summary

  • 35% Above List Price
  • $155/SF
  • 72 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
• 

  

  /23

  $337,900

  • 3 Beds
  • 2.5 Baths
  • 3,868 Sq Ft

  225 Plantations Dr, Winchester, KY 40391

  Welcome to 225 Plantations Drive, a beautifully maintained home in the desirable Royal Oaks Subdivision. This charming three-bedroom, two-and-a-half-bath residence is in wonderful condition and move-in ready! This is home comes with a wonderful floorplan that has a primary bedroom with built-in's on the first floor, Kitchen with granite and stainless appliances and deck has been updated with Trex

  John Wilson Bluegrass Properties Group

  225 Plantations Dr, Winchester, KY 40391
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  /33

  $332,000 Sold Oct 14, 2025

  1831 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $189/SF
  • 82 Days On Market

  Current Estimated Value $328,356

  Last Listing Agent Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
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  /42

  Est $358,959 Not Listed For Sale

  920 Log Lick Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1998

  920 Log Lick Rd, Winchester, KY 40391

  Last Sold Summary

  • 8% Below List Price
  • $260/SF
  • 30 Days On Market

  Last Sold Price $389,900

  Last Listing Agent Angela Stamper RE/MAX
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  /35

  $329,900

  • 4 Beds
  • 2 Baths
  • 1,751 Sq Ft

  219 Woodbine Ct, Winchester, KY 40391

  Welcome to Woodbine Ct! Tucked away at the end of a quiet cul-de-sac, this adorable brick split-level home offers the perfect blend of charm, space, and flexibility. Featuring 4 bedrooms and 2 full bathrooms, this home is packed with possibilities including the option for two primary suites. Enjoy a traditional primary bedroom on the main level, plus a spacious downstairs retreat complete with a

  Joshua Warren Freedom Realty & Property Management

  219 Woodbine Ct, Winchester, KY 40391
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  /32

  $283,000 Sold Apr 03, 2025

  193 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft
  • Built 2004

  Last Sold Summary

  • $172/SF
  • 3 Days On Market

  Current Estimated Value $286,218

  Last Listing Agent Justin Satterwhite SimpliHOM

  193 Prescott Ln, Winchester, KY 40391
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  /70

  Est $544,361 Not Listed For Sale

  519 Right Angle Rd, Winchester, KY 40391

  • 6 Beds
  • 3 Baths
  • 3,712 Sq Ft
  • Built 2000

  519 Right Angle Rd, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $143/SF
  • 186 Days On Market

  Last Sold Price $530,000

  Last Listing Agent The Prather Team - Michael Prather Keller Williams Bluegrass Realty
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  /28

  $298,900

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft

  24 N Burns Ave, Winchester, KY 40391

  Historic charm with all the modern amenities! An inviting front porch and entry lead to a welcoming space warmed by refinished original hardwood floors and a new electric fireplace. Other updates include a brand-new kitchen with granite countertops and new appliances, new lighting fixtures, tile in the foyer and bathrooms, new roof, new plumbing, new electrical, new HVAC, new windows, new spray

  Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
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  /25

  $223,000 Sold Nov 04, 2025

  204 Crawford Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,636 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 1 Day On Market

  Current Estimated Value $223,008

  Last Listing Agent Tisha Monte Bluegrass Properties Group

  204 Crawford Ct, Winchester, KY 40391

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