Winchester, KY Homes

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  /30

  Est $201,235 Not Listed For Sale

  280 Winn Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft
  • Built 1960

  280 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 30% Above List Price
  • $108/SF
  • 3 Days On Market

  • Last Sold Price $155,000
  • Jul 31, 2023

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
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  /72

  $406,900 New Construction

  • 3 - 6 Beds
  • 2.5 - 5.5 Baths
  • 2,570 Sq Ft

  Jackie Plan at Boone's Crossing, Winchester, KY 40391

  Unleash your creativity with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391
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  /35

  $325,000 Sold Nov 21, 2025

  130 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 19 Days On Market

  Current Estimated Value $334,641

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
• 

  

  

  /25

  Est $110,308 Not Listed For Sale

  248 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft
  • Built 1940

  248 Cook Ave, Winchester, KY 40391

  Last Sold Summary

  • 121% Above List Price
  • $34/SF
  • 27 Days On Market

  • Last Sold Price $50,000
  • Sep 18, 2024

  Last Listing Agent Chris Johnson Plum Tree Realty
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  /90

  $650,000 Pending

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

  142 Clubhouse Dr, Winchester, KY 40391

  Welcome to a lifestyle most only dream about — a stunning six-bedroom, four-bathroom residence perched along the lush fairways of Southwind Golf Course, complete with a lifetime membership for as long as you call this home. That's right, your morning coffee comes with panoramic views of manicured greens, and your evenings end with sunsets on the back porch. Inside, elegant double crown molding

  Timothy Saylor Threshold Real Estate Services

  142 Clubhouse Dr, Winchester, KY 40391
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  /51

  $303,000 Sold Jan 16, 2026

  22 N Bloomfield Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft
  • Built 1919

  Last Sold Summary

  • 5% Below List Price
  • $158/SF
  • 16 Days On Market

  Current Estimated Value $297,692

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
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  /41

  Est $207,695 Not Listed For Sale

  31 Watts Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,343 Sq Ft
  • Built 1960

  31 Watts Rd, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $149/SF
  • 24 Days On Market

  • Last Sold Price $200,000
  • Sep 30, 2024

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /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
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  /23

  $244,895 Sold Jun 10, 2025

  244 Bay Hill Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,536 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $97/SF
  • 10 Days On Market

  Current Estimated Value $267,833

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  244 Bay Hill Ct, Winchester, KY 40391
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  /27

  Est $292,407 Not Listed For Sale

  198 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 1960

  198 Hilltop Dr, Winchester, KY 40391

  Last Sold Summary

  • 24% Above List Price
  • $132/SF
  • 0 Days On Market

  • Last Sold Price $235,000
  • Jun 05, 2023

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC
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  /21

  $244,900

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

  720 Estes Dr, Winchester, KY 40391

  This charming brick ranch is truly move-in ready. Offering 3 bedrooms, 1.5 baths, a welcoming living room, a cozy den, and kitchen with appliances, this home blends comfort and convenience with ease. Enjoy the natural light and peaceful views from the screened-in sunporch, perfect for relaxing. Updates include new kitchen flooring, refinished hardwood floors, and updated trim that gives the home

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  720 Estes Dr, Winchester, KY 40391
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  /2

  $89,000 Sold Dec 18, 2025

  13067 Irvine Rd, Winchester, KY 40391

  • Land
  • 7.86 Acres
  • $11,323 per Acre

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13067 Irvine Rd, Winchester, KY 40391
• 

  

  /23

  Est $258,848 Not Listed For Sale

  130 Hilltop Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft
  • Built 1960

  130 Hilltop Dr, Winchester, KY 40391

  Last Sold Summary

  • 26% Above List Price
  • $140/SF
  • 2 Days On Market

  • Last Sold Price $205,000
  • Dec 11, 2023

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
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  /13

  $239,900

  • 5 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

  Joshua Lynch The Brokerage

  221 S Highland St, Winchester, KY 40391
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  /2

  $4,900,000 Sold Dec 23, 2025

  175 Chatham Place, Winchester, KY 40391

  • 2 Beds
  • 3 Baths
  • 37,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $132/SF
  • 111 Days On Market

  Current Estimated Value $4,910,294

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
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  /54

  Est $412,117 Not Listed For Sale

  1455 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,901 Sq Ft
  • Built 1940

  1455 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $124/SF
  • 35 Days On Market

  • Last Sold Price $360,000
  • Jan 17, 2025

  Last Listing Agent Shari Frasure Keller Williams Commonwealth
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  /19

  $125,000

  • 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
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  /51

  $340,000 Sold Oct 30, 2025

  356 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $106/SF
  • 30 Days On Market

  Current Estimated Value $347,055

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
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  /70

  Est $270,412 Not Listed For Sale

  1131 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,321 Sq Ft
  • Built 1960

  1131 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $114/SF
  • 45 Days On Market

  • Last Sold Price $265,000
  • Sep 13, 2024

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /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
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  /28

  $131,000 Sold Mar 12, 2026

  46 Judy Ann Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 0 Days On Market

  Current Estimated Value $135,593

  Last Listing Agent Lukas Owens The Brokerage

  46 Judy Ann Ct, Winchester, KY 40391
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  /26

  Est $238,771 Not Listed For Sale

  1124 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2006

  1124 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $187/SF
  • 7 Days On Market

  • Last Sold Price $219,900
  • May 03, 2024

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
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  /17

  $415,000

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

  104 Colby Hills Dr, Winchester, KY 40391

  (Reducted 50,000) for fast sell. 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
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  /4

  $315,000 Sold Jun 30, 2025

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391
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  /28

  Est $238,689 Not Listed For Sale

  1112 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2006

  1112 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $187/SF
  • 116 Days On Market

  • Last Sold Price $220,000
  • Jan 13, 2025

  Last Listing Agent Michelle Blackburn RE/MAX
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  /63

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Property is under contract with a 72 hour kickout clause. Enjoy peaceful country living on 17 beautiful acres in Clark County! This 3-bedroom, 2-bath ranch home sits on a scenic stretch of Trapp-Goffs Corner Road and offers the perfect blend of privacy, space, and convenience just minutes from Winchester and an easy drive to Lexington. The home features comfortable main-level living with a

  Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /38

  $375,750 Sold Apr 01, 2026

  6239 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $141/SF
  • 121 Days On Market

  Current Estimated Value $384,630

  Last Listing Agent Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
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  /41

  Est $234,821 Not Listed For Sale

  273 Winn Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,982 Sq Ft
  • Built 1880

  273 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $108/SF
  • 38 Days On Market

  • Last Sold Price $215,000
  • Nov 17, 2023

  Last Listing Agent Nena Honaker Tom Goebel & Company
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  /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
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  /3

  $94,000 Sold Aug 22, 2025

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $23,383 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 140 Days On Market

  Current Estimated Value $172,003

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  /38

  Est $228,760 Not Listed For Sale

  113 Mary Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1996

  113 Mary Way, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $214/SF
  • 10 Days On Market

  • Last Sold Price $225,000
  • Mar 29, 2024

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth
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  /51

  $69,900

  • Land
  • 4.48 Acres
  • $15,603 per Acre

  1450 Ford Rd, Winchester, KY 40391

  Darrell Tackett Dream Maker Realty, LLC

  1450 Ford Rd, Winchester, KY 40391
• 

  

  /21

  $199,500 Sold May 09, 2025

  445 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,539 Sq Ft
  • Built 1998

  Last Sold Summary

  • $130/SF
  • 3 Days On Market

  Current Estimated Value $219,705

  Last Listing Agent Mary Layton FC Tucker Bluegrass

  445 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /30

  Est $220,086 Not Listed For Sale

  306 Sarah Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1998

  306 Sarah Ct, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $177/SF
  • 0 Days On Market

  • Last Sold Price $193,000
  • Sep 29, 2023

  Last Listing Agent Jennifer Rose United Real Estate Bluegrass
• 

  /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
• 

  

  /26

  $178,000 Sold Apr 30, 2026

  356 Colby Ridge Blvd, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,102 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 51 Days On Market

  Current Estimated Value $184,047

  Last Listing Agent Nena Honaker Tom Goebel & Company

  356 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /29

  Est $279,617 Not Listed For Sale

  455 Greenway Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1993

  455 Greenway Dr, Winchester, KY 40391

  Last Sold Summary

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

  • Last Sold Price $238,000
  • May 10, 2023

  Last Listing Agent Heather Isaacs Lifstyl Real Estate
• 

  /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
• 

  /2

  $85,000 Sold Apr 15, 2026

  2465 Flanagan Station Rd, Winchester, KY 40391

  • Land
  • 3.68 Acres
  • $23,098 per Acre

  Last Sold Summary

  • 9 Days On Market

  Current Estimated Value $164,900

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  2465 Flanagan Station Rd, Winchester, KY 40391
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  /25

  Est $237,651 Not Listed For Sale

  316 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 1990

  316 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $138/SF
  • 140 Days On Market

  • Last Sold Price $225,000
  • Jan 19, 2024

  Last Listing Agent Jenny Bradley Rector Hayden Realtors

Showing Results 281 - 320, Page 8 of 18