Winchester, KY Homes

• 

  

  

  /58

  $345,000

  Sold Nov 14, 2025

  205 Chardonnay Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,179 Sq Ft
  • Built 1991

  Last Sold Summary

  • 8% Below List Price
  • $158/SF
  • 59 Days On Market

  Current Estimated Value $356,978

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  205 Chardonnay Ct, Winchester, KY 40391
• 

  

  

  /42

  Est $392,220

  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

  • 30 Days On Market
• 

  

  

  /18

  $260,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  280 Pine Ridge Rd, Winchester, KY 40391

  Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or expansion, this property is perfect for those dreaming of country living. Renovate the existing home or reimagine the space to fit your needs — the possibilities

  Derek Blankenship Keller Williams Commonwealth

  280 Pine Ridge Rd, Winchester, KY 40391
• 

  

  

  /27

  $210,000

  Sold Sep 04, 2025

  305 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $183/SF
  • 1 Day On Market

  Current Estimated Value $218,245

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  305 Geronimo Ct, Winchester, KY 40391
• 

  

  

  /70

  Est $614,054

  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

  • 186 Days On Market
• 

  

  /19

  $199,000

  $10K PRICE DROP

  • Land
  • 41.69 Acres
  • $4,774 per Acre

  2697 Pine Ridge Rd, Winchester, KY 40391

  Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and

  Derek Blankenship Keller Williams Commonwealth

  2697 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /44

  $320,000

  Sold Nov 21, 2025

  104 Teakwood Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • Built 2005

  Last Sold Summary

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

  Current Estimated Value $326,533

  Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

  104 Teakwood Ct, Winchester, KY 40391
• 

  

  /69

  Est $395,168

  Not Listed For Sale

  3975 Wills Rupard Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft
  • Built 1986

  3975 Wills Rupard Rd, Winchester, KY 40391

  Last Sold Summary

  • 218 Days On Market
• 

  

  /19

  $460,000

  $39K PRICE DROP

  • Land
  • 36.94 Acres
  • $12,453 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
• 

  

  /33

  $219,900

  Sold May 28, 2026

  21 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1920

  Last Sold Summary

  • $164/SF
  • 2 Days On Market

  Current Estimated Value $216,772

  Last Listing Agent Jenny Mateyoke Keller Williams Legacy Group

  21 Kentucky St, Winchester, KY 40391
• 

  

  /61

  Est $454,035

  Not Listed For Sale

  2601 Crowe Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,435 Sq Ft
  • Built 2002

  2601 Crowe Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 32 Days On Market
• 

  

  /49

  $469,000

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft

  105 Monet Blvd, Winchester, KY 40391

  Welcome to 105 Monet Blvd., located in one of Winchester's most desirable neighborhoods! This beautifully updated home offers the perfect combination of space, style, and future potential. Featuring 4 spacious bedrooms, a dedicated home office, formal dining room, family room, and an eat-in kitchen, this home was designed for both comfortable living and entertaining. The newly remodeled kitchen

  Kristey Wood eXp Realty, LLC

  105 Monet Blvd, Winchester, KY 40391
• 

  

  /39

  $549,000

  Sold Jul 30, 2025

  154 Hawthorne Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,478 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $158/SF
  • 100 Days On Market

  Current Estimated Value $593,991

  Last Listing Agent Jarran Thomas The Agency

  154 Hawthorne Dr, Winchester, KY 40391
• 

  

  /45

  Est $387,160

  Not Listed For Sale

  1600 Crowe Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,846 Sq Ft
  • Built 2012

  1600 Crowe Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 147 Days On Market
• 

  

  /35

  $329,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft

  8 Monroe Ave, Winchester, KY 40391

  If you love to entertain and are looking for a cozy home that is move in ready, you don't want to let the one pass you by! Includes 3 bedrooms and two full baths this home has it all. Equipped with a primary bedroom suite with spacious bathroom and walk in closet. This home has beautiful hardwood floors in kitchen living and dining areas. In the gallery kitchen you will find granite countertops,

  Lisa Barker Freedom Realty & Property Management

  8 Monroe Ave, Winchester, KY 40391
• 

  

  /47

  $374,900

  Sold Sep 19, 2025

  714 Concord Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Built 2017

  Last Sold Summary

  • $214/SF
  • 23 Days On Market

  Current Estimated Value $382,014

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  714 Concord Ave, Winchester, KY 40391
• 

  

  /56

  Est $639,212

  Not Listed For Sale

  9953 Ironworks Rd, Winchester, KY 40391

  • 6 Beds
  • 2.5 Baths
  • 3,800 Sq Ft
  • Built 2003

  9953 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market
• 

  

  /52

  $269,000

  $6K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,417 Sq Ft

  104 Jackson Ferry Rd, Winchester, KY 40391

  Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen

  Bob Sophiea eXp Realty, LLC

  104 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /38

  $340,000

  Sold Apr 30, 2026

  168 Buckingham Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,358 Sq Ft
  • Built 2000

  Last Sold Summary

  • $144/SF
  • 3 Days On Market

  Current Estimated Value $340,362

  Last Listing Agent Tammy Hill Keller Williams Legacy Group

  168 Buckingham Ln, Winchester, KY 40391
• 

  

  /17

  Est $454,116

  Not Listed For Sale

  1026 Crowe Ridge Rd, Winchester, KY 40391

  • 1 Bath
  • Built 1945

  1026 Crowe Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 56 Days On Market
• 

  /2

  $1,200,000

  $596K PRICE INCREASE

  • Land
  • 24.15 Acres
  • $49,689 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, Winchester, KY 40391
• 

  

  /92

  $1,075,000

  Sold Mar 18, 2026

  6237 Bybee Rd, Winchester, KY 40391

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $131/SF
  • 212 Days On Market

  Current Estimated Value $1,112,303

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
• 

  

  /26

  Est $328,362

  Not Listed For Sale

  11705 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,668 Sq Ft
  • Built 1988

  11705 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 81 Days On Market
• 

  

  /59

  $499,900

  • 4 Beds
  • 3 Baths
  • 5,646 Sq Ft

  16 Manor Dr, Winchester, KY 40391

  One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

  Zella Rosenthal Tom Goebel & Company

  16 Manor Dr, Winchester, KY 40391
• 

  

  /42

  $390,000

  Sold Oct 21, 2025

  19 Snowfall Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 1950

  Last Sold Summary

  • 11% Above List Price
  • $240/SF
  • 2 Days On Market

  Current Estimated Value $360,411

  Last Listing Agent Bradford Queen Bluegrass Sotheby's International Realty

  19 Snowfall Dr, Winchester, KY 40391
• 

  

  /33

  Est $246,789

  Not Listed For Sale

  7344 Ironworks Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1925

  7344 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  /2

  $110,000

  • Land
  • 16,552 Sq Ft
  • $289,474 per Acre

  200 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

  200 Duclair Dr, Winchester, KY 40391
• 

  

  /34

  $369,500

  Sold Aug 22, 2025

  148 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $150/SF
  • 11 Days On Market

  Current Estimated Value $363,178

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
• 

  

  /82

  Est $412,736

  Not Listed For Sale

  380 L E Junction Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 3,173 Sq Ft
  • Built 1976

  380 L E Junction Rd, Winchester, KY 40391

  Last Sold Summary

  • 13 Days On Market
• 

  

  /26

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  This home is complete with an Aurora above ground pool for all the summer fun. The 3 beds 2 bath brick ranch home is located conveniently to shopping, dining, parks, pool and more. Large open family room and kitchen with wood bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. There is an oversized storage/tool shed, and a partially

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
• 

  

  /26

  $200,000

  Sold Oct 02, 2025

  34 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1945

  Last Sold Summary

  • 11% Below List Price
  • $133/SF
  • 8 Days On Market

  Current Estimated Value $213,402

  Last Listing Agent Ashley Barreto Indigo & Co

  34 N Burns Ave, Winchester, KY 40391
• 

  

  /51

  Est $555,277

  Not Listed For Sale

  5600 Ecton Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,841 Sq Ft
  • Built 1992

  5600 Ecton Rd, Winchester, KY 40391

  Last Sold Summary

  • 62 Days On Market
• 

  

  /67

  $400,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,347 Sq Ft

  233 Schollsville Rd, Winchester, KY 40391

  Welcome to 233 Schollsville Rd! This beautiful 3 bed 2 bathroom home privately sits on 5.48 acres. Enjoy the views of your very own fully stocked pond from your wrap around porch. Inside you will find a warm, welcoming split bedroom floor plan with large windows bringing in plenty of natural light. If you are looking for a private setting where you can enjoy the outdoors yet still being within 30

  Bill Deaton Keller Williams Legacy Group

  233 Schollsville Rd, Winchester, KY 40391
• 

  

  /16

  $214,900

  Sold Dec 05, 2025

  15 Holly Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $179/SF
  • 52 Days On Market

  Current Estimated Value $214,417

  Last Listing Agent Nena Honaker Tom Goebel & Company

  15 Holly Ave, Winchester, KY 40391
• 

  

  /38

  Est $388,553

  Not Listed For Sale

  3070 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,866 Sq Ft
  • Built 1998

  3070 Goshen Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  

  /8

  $160,000

  Pending

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  107 Patio St, Winchester, KY 40391

  What a cute little dollhouse. Move in Ready . Corner lot with storage building. Close to all amenities.

  Sherry Stephens Murphy Realty Group

  107 Patio St, Winchester, KY 40391
• 

  

  /54

  $410,000

  Sold Apr 10, 2026

  204 Delaplain Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 3,563 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $115/SF
  • 21 Days On Market

  Current Estimated Value $417,089

  Last Listing Agent Sam Watkins COLOR Real Estate

  204 Delaplain Rd, Winchester, KY 40391
• 

  

  /88

  Est $816,259

  Not Listed For Sale

  865 Sugar Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,146 Sq Ft
  • Built 1997

  865 Sugar Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 88 Days On Market
• 

  

  /38

  $484,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Property under contract with a kickout clause. Step into a lifestyle where modern luxury and brand-new construction come together seamlessly. This home is perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience.

  Morgan Withrow The Brokerage

  414 Fairholme Way, Winchester, KY 40391
• 

  

  /48

  $550,000

  Sold Sep 04, 2025

  594 Earlymeade Dr, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,489 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $158/SF
  • 43 Days On Market

  Current Estimated Value $556,020

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391

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