Winchester, KY Homes

• 

  

  

  /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 $219,017

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  305 Geronimo Ct, Winchester, KY 40391
• 

  

  

  /39

  Est $362,088

  Not Listed For Sale

  3232 Old Ruckerville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1994

  3232 Old Ruckerville Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Megan McCoy Keller Williams Legacy Group
• 

  

  

  /46

  $347,900

  New Construction

  • 3 - 6 Beds
  • 2 - 4 Baths
  • 1,580 Sq Ft

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

  The Martha floor plan is your canvas for creating a home that perfectly fits your lifestyle, offering unmatched flexibility, thoughtful design, and timeless appeal. Built by one of the leading home builders in Central Kentucky, the Martha is an excellent choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space that adapts to how they

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824258, 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 $333,295

  Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

  104 Teakwood Ct, Winchester, KY 40391
• 

  

  

  /36

  Est $451,150

  Not Listed For Sale

  5487 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,892 Sq Ft
  • Built 1978

  5487 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Wayne Elkins RE/MAX Creative Realty
• 

  

  /28

  $363,900

  New Construction

  • 4 - 5 Beds
  • 2.5 - 3.5 Baths
  • 2,100 Sq Ft

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

  Experience the Elizabeth floor plan, a beautifully crafted new construction home designed for families who value open-concept living, thoughtful organization, and flexible bedroom space. Offered by one of the most trusted home builders in Central Kentucky, the Elizabeth is a standout option for buyers searching for new construction homes in Lexington KY and surrounding communities.From the moment

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824250, 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 $213,701

  Last Listing Agent Jenny Mateyoke Keller Williams Legacy Group

  21 Kentucky St, Winchester, KY 40391
• 

  

  /34

  Est $367,668

  Not Listed For Sale

  4759 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,633 Sq Ft
  • Built 1985

  4759 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Hannah Simpkins National Real Estate
• 

  

  /85

  $1,349,000

  New Construction Pending

  • 4 Beds
  • 4.5 Baths
  • 3,350 Sq Ft

  1200 Craig Crossing, Winchester, KY 40391

  Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom.

  Michael Hilario The Agency

  1200 Craig Crossing, Winchester, KY 40391
• 

  

  /30

  $168,000

  Sold Jul 13, 2026

  128 Bay Hill Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,289 Sq Ft
  • Built 2003

  Last Sold Summary

  • 16% Below List Price
  • $130/SF
  • 37 Days On Market

  Current Estimated Value $191,604

  Last Listing Agent Melia Hord MELIA Realty LLC

  128 Bay Hill Dr, Winchester, KY 40391
• 

  

  /41

  Est $329,611

  Not Listed For Sale

  2100 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1988

  2100 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Patrick Doyle Lifstyl Real Estate
• 

  

  /85

  $397,900

  New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,263 Sq Ft

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

  Step into the award-winning Abigail floor plan, a standout choice for buyers searching for new construction homes in Lexington, KY and Central Kentucky. Designed with today’s lifestyle in mind, this home offers the perfect blend of flexible floor plans, energy efficiency, and modern comfort—everything you expect from a trusted home builder in Lexington, KY.From the moment you arrive, the Abigail

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824251, Winchester, KY 40391
• 

  

  /20

  $205,000

  Sold Jul 27, 2026

  301 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Below List Price
  • $148/SF
  • 17 Days On Market

  Current Estimated Value $211,177

  Last Listing Agent Julia Lark The Brokerage

  301 Snowden Dr, Winchester, KY 40391
• 

  

  /62

  Est $389,928

  Not Listed For Sale

  890 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1965

  890 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Daniel Mullins ERA Select Real Estate
• 

  

  /52

  $369,900

  New Construction

  • 3 - 6 Beds
  • 2 Baths
  • 1,770 Sq Ft

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

  Experience the true essence of homecoming with the Barbara floor plan, a beautifully designed new construction home available through one of the most trusted home builders in Central Kentucky. Thoughtfully crafted for modern living, this plan blends timeless exterior charm with a warm, open interior designed for comfort, flexibility, and everyday functionality.Step onto the inviting covered front

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824253, 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 $379,991

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  714 Concord Ave, Winchester, KY 40391
• 

  

  /29

  Est $447,052

  Not Listed For Sale

  1623 Little Stoner Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1982

  1623 Little Stoner Rd, Winchester, KY 40391

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Sharon Ben David Berkshire Hathaway de Movellan Properties
• 

  

  /55

  $270,000

  Pending

  • 6 Beds
  • 4 Baths
  • 3,090 Sq Ft

  21 Beckner St, Winchester, KY 40391

  Outstanding opportunity for investors or owner-occupants! This beautifully updated duplex is located in Winchester's desirable Stuarts Addition and offers two spacious units, each featuring approximately 1,545 square feet with 3 bedrooms and 2 full bathrooms. Both units have been thoughtfully renovated and feature hardwood flooring throughout the main living areas with tile in the wet areas for

  Rex Hall United Real Estate Bluegrass

  21 Beckner St, 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 $336,592

  Last Listing Agent Tammy Hill Keller Williams Legacy Group

  168 Buckingham Ln, Winchester, KY 40391
• 

  

  /42

  Est $325,720

  Not Listed For Sale

  1570 Little Stoner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1990

  1570 Little Stoner Rd, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Joyce Ratliff Tom Goebel & Company
• 

  

  /127

  $3,450,000

  • 2 Beds
  • 2.5 Baths
  • 2,725 Sq Ft

  510 - 612 Quisenberry Ln, Winchester, KY 40391

  Adjoining the banks of the Lower Howard's Creek in Clark County lies a very special 145.6± acre farm. With some of the oldest settlements in the county, this region near the Old Stone Church (or Old Providence Church) is immensely historic. Daniel Boone's first eleven surveys in Kentucky were conducted for the Bush family, early inhabitants of the area and farm. With gated stone entrances and

  Zach Davis Kirkpatrick & Company

  510 - 612 Quisenberry Ln, 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 $1,111,666

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
• 

  

  /47

  Est $363,268

  Not Listed For Sale

  150 Privacy Ln, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,784 Sq Ft
  • Built 1987

  150 Privacy Ln, Winchester, KY 40391

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Jason Joseph Keller Williams Commonwealth
• 

  

  /18

  $260,000

  Pending

  • 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
• 

  

  /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 $379,580

  Last Listing Agent Bradford Queen Bluegrass Sotheby's International Realty

  19 Snowfall Dr, Winchester, KY 40391
• 

  

  /41

  Est $363,052

  Not Listed For Sale

  5751 Mount Sterling Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 1976

  5751 Mount Sterling Rd, Winchester, KY 40391

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Chandler Williams Keller Williams Legacy Group
• 

  

  /19

  $189,000

  $20K PRICE DROP

  • Land
  • 41.69 Acres
  • $4,534 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
• 

  

  /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 $380,780

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
• 

  

  /79

  Est $829,691

  Not Listed For Sale

  3714 Wades Mill Rd, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,818 Sq Ft
  • Built 2001

  3714 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Nora Williams Keller Williams Commonwealth
• 

  

  /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
• 

  

  /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 $214,473

  Last Listing Agent Ashley Barreto Indigo & Co

  34 N Burns Ave, Winchester, KY 40391
• 

  

  /36

  Est $404,846

  Not Listed For Sale

  610 Old Ruckerville Rd, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1997

  610 Old Ruckerville Rd, Winchester, KY 40391

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Garnett Davis Tom Goebel & Company
• 

  

  /49

  $459,000

  $10K PRICE DROP Pending

  • 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
• 

  

  /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 $217,595

  Last Listing Agent Nena Honaker Tom Goebel & Company

  15 Holly Ave, Winchester, KY 40391
• 

  

  /35

  Est $269,296

  Not Listed For Sale

  3230 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Built 1978

  3230 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Cindy Hellinger United Real Estate Bluegrass
• 

  

  /43

  $319,900

  $20K 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
• 

  

  /57

  $264,000

  Sold Jul 27, 2026

  720 Terry Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Below List Price
  • $148/SF
  • 28 Days On Market

  Current Estimated Value $272,136

  Last Listing Agent Christa Joynt Keller Williams Commonwealth

  720 Terry Dr, Winchester, KY 40391
• 

  

  /16

  Est $196,171

  Not Listed For Sale

  2584 Irvine Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft
  • Built 1950

  2584 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Veronica Norwood All Star Real Estate, Inc.
• 

  

  /52

  $269,000

  $6K PRICE DROP Pending

  • 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
• 

  

  /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 $410,321

  Last Listing Agent Sam Watkins COLOR Real Estate

  204 Delaplain Rd, Winchester, KY 40391

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