Winchester, KY Homes

• 

  

  

  /3

  $220,000

  Sold Jul 30, 2025

  412 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $169/SF
  • 38 Days On Market

  Current Estimated Value $228,446

  Last Listing Agent John Wilson Bluegrass Properties Group

  412 Paisley Ct, Winchester, KY 40391
• 

  

  

  /91

  Est $402,899

  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

  • 11 Days On Market
• 

  

  

  /36

  $549,900

  • 4 Beds
  • 5 Baths
  • 4,173 Sq Ft

  600 Boone Ave, Winchester, KY 40391

  Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
• 

  

  

  /90

  $650,000

  Sold Jun 17, 2026

  142 Clubhouse Dr, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 4,351 Sq Ft
  • Built 2001

  Last Sold Summary

  • $149/SF
  • 10 Days On Market

  Current Estimated Value $641,305

  Last Listing Agent Timothy Saylor Threshold Real Estate Services

  142 Clubhouse Dr, Winchester, KY 40391
• 

  

  

  /47

  Est $396,552

  Not Listed For Sale

  520 Bailey Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1980

  520 Bailey Ln, Winchester, KY 40391

  Last Sold Summary

  • 51 Days On Market
• 

  

  /38

  $360,000

  $20K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 2,179 Sq Ft

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses , whatever you always dreamed of. Maybe just kicking back on the wrap around porch watching the

  Wayne Elkins RE/MAX Creative Realty

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /57

  $350,000

  Sold May 20, 2026

  220 Hibiscus Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 2001

  Last Sold Summary

  • $213/SF
  • 4 Days On Market

  Current Estimated Value $348,898

  Last Listing Agent Timothy Saylor Threshold Real Estate Services

  220 Hibiscus Ln, Winchester, KY 40391
• 

  

  /23

  Est $269,407

  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

  • 9 Days On Market
• 

  

  /23

  $99,900

  • 3 Beds
  • 2 Baths
  • 675 Sq Ft

  2799 Pine Ridge Rd, Winchester, KY 40391

  If your looking for a fixer upper, this is it. House on 2 acres in the country with lots of potential. Laundry is off the kitchen, but floor is soft from a water leak. From the kitchen you will see a guest bath, dining and living area. To the left is a hallway that leads to 2 bedrooms, drywalled just needs to be finished. To the right of the living area is your master bedroom and bath. With some

  Robin Horn Keller Williams Commonwealth

  2799 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /41

  $300,300

  Sold Nov 07, 2025

  37 Lynnway Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,220 Sq Ft
  • Built 1976

  Last Sold Summary

  • $93/SF
  • 58 Days On Market

  Current Estimated Value $333,802

  Last Listing Agent Donna Thwaites Thwaites Realtors LLC

  37 Lynnway Dr, Winchester, KY 40391
• 

  

  /54

  Est $284,444

  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

  • 121 Days On Market
• 

  

  /27

  $388,000

  Pending

  • 8 Beds
  • 8 Baths
  • 4,000 Sq Ft

  17 W Lexington Ave, Winchester, KY 40391

  Great investment opportunity right in heart Downtown Winchester!!! Welcome to this income producing apartment complex of 8 studio apartments. Two levels of apartments, 4 on the first floor and 4 on the second. Each unit features a living area, full kitchen, and full bathroom. 5 units are currently rented out. The roof was put on 2 years ago. The basement has 2 entrances and could easily be

  Libby VanMeter Marshall Lane Real Estate - Lexington

  17 W Lexington Ave, Winchester, KY 40391
• 

  

  /41

  $247,000

  Sold Sep 19, 2025

  3588 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $161/SF
  • 4 Days On Market

  Current Estimated Value $249,854

  Last Listing Agent Zach Johnson The Brokerage

  3588 Stamper Dr, Winchester, KY 40391
• 

  

  /24

  Est $257,102

  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

  • 31 Days On Market
• 

  

  /19

  $125,000

  $10K PRICE DROP

  • Land
  • 4.01 Acres
  • $31,172 per Acre

  1940 Athens Boonesboro Rd, Winchester, KY 40391

  Escape to tranquility with this beautiful 4-acre lot in Clark County, offering the perfect setting to build your dream home. Tucked away on a quiet road, this property is surrounded by expansive farmland, ensuring ultimate privacy and peaceful living. A serene pond adds to the charm, providing a perfect spot to relax and enjoy the natural beauty of the land. This lot sits directly across from the

  Laura Sizemore Kentucky Land and Home

  1940 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /20

  $205,000

  Sold Aug 19, 2025

  202 Custer Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Above List Price
  • $184/SF
  • 2 Days On Market

  Current Estimated Value $199,760

  Last Listing Agent Brittany Beer eXp Realty, LLC

  202 Custer Ct, Winchester, KY 40391
• 

  

  /47

  Est $373,294

  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

  • 115 Days On Market
• 

  

  /4

  $137,500

  • Land
  • 3.94 Acres
  • $34,898 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
• 

  

  /15

  $176,000

  Sold Oct 17, 2025

  7575 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Below List Price
  • 2 Days On Market

  Current Estimated Value $193,102

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391
• 

  

  /25

  Est $257,667

  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

  • 1 Day On Market
• 

  

  /24

  $199,900

  • 3 Beds
  • 2 Baths
  • 915 Sq Ft

  225 Buffalo Trace, Winchester, KY 40391

  This move in ready ranch home offering 3 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  225 Buffalo Trace, Winchester, KY 40391
• 

  

  /21

  $240,000

  Sold Jun 09, 2026

  720 Estes Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,494 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $161/SF
  • 28 Days On Market

  Current Estimated Value $247,014

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

  720 Estes Dr, Winchester, KY 40391
• 

  

  /21

  Est $232,202

  Not Listed For Sale

  523 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 2002

  523 Acadia Way, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market
• 

  

  /17

  $398,000

  $66K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  104 Colby Hills Dr, Winchester, KY 40391

  Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  104 Colby Hills Dr, Winchester, KY 40391
• 

  

  /10

  $325,000

  Sold Aug 29, 2025

  210 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1999

  Last Sold Summary

  • $205/SF

  Current Estimated Value $339,994

  Last Listing Agent Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /21

  Est $237,924

  Not Listed For Sale

  513 Acadia Way, Winchester, KY 40391

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

  513 Acadia Way, Winchester, KY 40391

  Last Sold Summary

  • 35 Days On Market
• 

  

  /25

  $237,500

  $2K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  125 Kittison Dr, Winchester, KY 40391

  Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable

  Kathryn Cheuvront Coldwell Banker McMahan

  125 Kittison Dr, Winchester, KY 40391
• 

  

  /36

  $261,000

  Sold Feb 04, 2026

  433 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $212/SF
  • 60 Days On Market

  Current Estimated Value $261,328

  Last Listing Agent Nick Ratliff Realty Team - Nicholas Ratliff Real Broker, LLC - Lexington

  433 Wellington Way, Winchester, KY 40391
• 

  

  /17

  Est $255,850

  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

  • 30 Days On Market
• 

  

  /3

  $84,900

  • Land
  • 3.39 Acres
  • $25,044 per Acre

  160 Rector Ln, Winchester, KY 40391

  UNIQUE Opportunity - 3.39 acres with a small pond - tucked away on a private lane, flat land and totally surrounded by trees. What a unique setting!! Convenience is the key to this property. Water is available at the main road. Internet has been extended down Rector Lane, electricity is accessible for connection. Deed Restrictions apply. Do Not Miss Your Chance to own this SPECIAL piece of land.

  M Gail Cleaver United Real Estate Bluegrass

  160 Rector Ln, Winchester, KY 40391
• 

  /2

  $180,000

  Sold Jul 01, 2025

  23 Meadowbrook Dr, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 2,250 Sq Ft
  • Built 1953

  Last Sold Summary

  • $80/SF

  Current Estimated Value $257,493

  Last Listing Agent A. Rebecca Woods Woods Realty Group

  23 Meadowbrook Dr, Winchester, KY 40391
• 

  

  /32

  Est $222,360

  Not Listed For Sale

  303 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1998

  303 Geronimo Ct, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market
• 

  

  /43

  $350,000

  Pending

  • 4 Beds
  • 2 Baths
  • 2,208 Sq Ft

  274 Greenway Dr, Winchester, KY 40391

  Beautifully updated 4 bedroom, 2 bath brick ranch situated on a spacious .55± acre lot in a quiet rural subdivision! This well-maintained home offers comfort, functionality, and plenty of indoor and outdoor space. Features include an attached 2-car garage, detached 2-car garage with heating and air wall unit, 1-car carport, crawlspace, oversized driveway, storage shed, and three outdoor storage

  Michelle Blackburn RE/MAX Creative, Winchester

  274 Greenway Dr, Winchester, KY 40391
• 

  

  /7

  $55,000

  Sold Nov 06, 2025

  76 Clay St, Winchester, KY 40391

  • 1,768 Sq Ft
  • Built 1945

  Last Sold Summary

  • $31/SF
  • 2 Days On Market

  Current Estimated Value $61,167

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  76 Clay St, Winchester, KY 40391
• 

  

  /19

  Est $205,600

  Not Listed For Sale

  125 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 932 Sq Ft
  • Built 1997

  125 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 43 Days On Market
• 

  /2

  $42,500

  Pending

  • Land
  • 11,369 Sq Ft
  • $162,835 per Acre

  105 Bella Ct, Winchester, KY 40391

  Jo Gawthrop Keller Williams Bluegrass Realty

  105 Bella Ct, Winchester, KY 40391
• 

  

  /65

  $275,000

  Sold Aug 15, 2025

  151 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,873 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $147/SF
  • 130 Days On Market

  Current Estimated Value $277,282

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
• 

  

  /22

  Est $197,748

  Not Listed For Sale

  113 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1998

  113 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  /2

  $110,000

  • Land
  • 13,939 Sq Ft
  • $343,750 per Acre

  250 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

  250 Duclair Dr, Winchester, KY 40391
• 

  

  /3

  $554,651

  Sold Jul 10, 2025

  426 Alexis Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Above List Price
  • $231/SF
  • 21 Days On Market

  Current Estimated Value $566,921

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, Winchester, KY 40391

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