Winchester, KY Homes

• 

  

  

  /64

  $524,900

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft

  275 Runnymeade Dr, Winchester, KY 40391

  OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new

  Craig Bridgewater Bridgewater Real Estate

  275 Runnymeade Dr, Winchester, KY 40391
• 

  

  

  /89

  $850,000

  Sold Sep 21, 2026

  200 Old Log Lick Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 4,019 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $211/SF

  Current Estimated Value $879,566

  Last Listing Agent Derek Blankenship Keller Williams Commonwealth

  200 Old Log Lick Rd, Winchester, KY 40391
• 

  

  

  /60

  Est $186,147

  Not Listed For Sale

  1333 Jackson Ferry Rd, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,492 Sq Ft
  • Built 1964

  1333 Jackson Ferry Rd, Winchester, KY 40391

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management
• 

  

  

  /16

  $1,200,000

  • 16 Beds
  • 16 Baths
  • 7,480 Sq Ft

  16 Linden Ave, Winchester, KY 40391

  You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof

  Kevin Bradley KB Realty Group

  16 Linden Ave, Winchester, KY 40391
• 

  

  

  /58

  $239,900

  Sold Jun 08, 2026

  3610 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1986

  Last Sold Summary

  • $209/SF
  • 4 Days On Market

  Current Estimated Value $240,544

  Last Listing Agent Pete doCouto Plum Tree Realty

  3610 Stamper Dr, Winchester, KY 40391
• 

  

  /47

  Est $418,303

  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

  Last Listing Agent Paul Waddelow Realty Headquarters LLC
• 

  

  /3

  $380,000

  New Construction 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
• 

  

  /58

  $830,000

  Sold Feb 27, 2026

  2395 Becknerville Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,234 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 8 Days On Market

  Current Estimated Value $822,413

  Last Listing Agent Crystal Towe The Real Estate Group

  2395 Becknerville Rd, Winchester, KY 40391
• 

  

  /23

  Est $267,660

  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

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty
• 

  

  /40

  $498,000

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  1780 Stoner Ephesus Rd, Winchester, KY 40391

  Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15

  Darrell Tackett Dream Maker Realty, LLC

  1780 Stoner Ephesus Rd, Winchester, KY 40391
• 

  

  /33

  $364,900

  Sold Feb 06, 2026

  446 Tremont Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,811 Sq Ft
  • Built 2005

  Last Sold Summary

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

  Current Estimated Value $370,336

  Last Listing Agent Dylan Langdon The Agency

  446 Tremont Ln, Winchester, KY 40391
• 

  

  /54

  Est $282,359

  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

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /50

  $639,000

  • 5 Beds
  • 3.5 Baths
  • 5,011 Sq Ft

  104 Teal Ln, Winchester, KY 40391

  Space, craftsmanship, and versatility come together in this stunning all-brick 1.5-story home with a finished basement, located in the desirable Mallard Place subdivision! Designed to maximize every square foot, this home offers three levels of comfortable and flexible living space. The main level welcomes you with beautiful hardwood floors, vaulted ceilings, and a cozy gas fireplace. The

  Jennifer Ray RE/MAX Elite Lexington

  104 Teal Ln, Winchester, KY 40391
• 

  

  /60

  $249,900

  Sold Jul 22, 2026

  17 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1992

  Last Sold Summary

  • $215/SF
  • 8 Days On Market

  Current Estimated Value $250,495

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  17 Holiday Rd, Winchester, KY 40391
• 

  

  /24

  Est $259,138

  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

  Last Listing Agent Tyler I Back The Brokerage
• 

  

  /58

  $309,900

  Pending

  • 3 Beds
  • 2 Baths
  • 2,138 Sq Ft

  118 College St, Winchester, KY 40391

  Beautifully updated Craftsman-style ranch offering over 2,000 square feet of comfortable living space in a desirable Winchester location. Walking distance to downtown, the library, College park gym and pool. This move-in-ready home blends timeless character with extensive modern updates, including a new roof, new 6" gutters, new HVAC system, new water heater, fresh interior paint, updated

  Josh Wood Freedom Realty & Property Management

  118 College St, Winchester, KY 40391
• 

  

  /38

  $173,000

  Sold Sep 22, 2025

  44 5th St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $136/SF
  • 2 Days On Market

  Current Estimated Value $177,714

  Last Listing Agent Tirza Howard The Howard Realty Co

  44 5th St, Winchester, KY 40391
• 

  

  /27

  Est $224,326

  Not Listed For Sale

  2350 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,385 Sq Ft
  • Built 1970

  2350 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Dylan Justice Bluegrass Commercial Real Estate
• 

  

  /3

  $350,000

  $50K PRICE DROP

  • Land
  • 7.31 Acres
  • $47,880 per Acre

  4095 Basin Springs Rd, Winchester, KY 40391

  Looking for land to build your dream home that is private, but convenient? This 7+ acre beautiful lot is located in Clark County, just 15 minutes from Costco, Hamburg and I-75. No HOA or deed restrictions. The perfect place to build or have a small farm. City water and electricity available at the street. No city sewer.

  Peggy Baldridge HomeFirst Real Estate

  4095 Basin Springs Rd, Winchester, KY 40391
• 

  

  /18

  $200,000

  Sold Jan 14, 2026

  245 Ecton Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,074 Sq Ft
  • Built 1940

  Last Sold Summary

  • 9% Below List Price
  • $186/SF
  • 2 Days On Market

  Current Estimated Value $201,419

  Last Listing Agent Anthony Gigilo ListWithFreedom.com

  245 Ecton Rd, Winchester, KY 40391
• 

  

  /20

  Est $198,118

  Not Listed For Sale

  2342 Ironworks Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1970

  2342 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Dylan Justice Bluegrass Commercial Real Estate
• 

  

  /10

  $575,000

  $75K PRICE DROP

  • Land
  • 2.6 Acres
  • $221,154 per Acre

  529 Bullion Blvd Unit 3B, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  529 Bullion Blvd Unit 3B, Winchester, KY 40391
• 

  

  /80

  $524,000

  Sold Dec 16, 2025

  160 Agawam Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft
  • Built 1978

  Last Sold Summary

  • 9% Below List Price
  • $106/SF
  • 51 Days On Market

  Current Estimated Value $531,006

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
• 

  

  /47

  Est $393,357

  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

  Last Listing Agent John Groft RE/MAX Creative Realty
• 

  

  /11

  $50,000

  • Land
  • 17,859 Sq Ft
  • $121,951 per Acre

  308 Duclair Dr, Winchester, KY 40391

  Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

  Joseph Miller Keller Williams Legacy Group

  308 Duclair Dr, Winchester, KY 40391
• 

  

  /28

  $203,900

  Sold Dec 10, 2025

  25 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $220/SF
  • 35 Days On Market

  Current Estimated Value $207,289

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  25 Hiawatha Trail, Winchester, KY 40391
• 

  

  /24

  Est $209,245

  Not Listed For Sale

  113 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1983

  113 Colonial Park Dr, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Janet Baldwin Kentucky Land and Home
• 

  

  /22

  $665,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  414 Alexis Way, Winchester, KY 40391

  Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

  Shane Underwood Keller Williams Commonwealth

  414 Alexis Way, 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 $639,067

  Last Listing Agent Timothy Saylor Threshold Real Estate Services

  142 Clubhouse Dr, Winchester, KY 40391
• 

  

  /25

  Est $251,729

  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

  Last Listing Agent Brad Harmon LexHomes Real Estate
• 

  

  /9

  $785,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  425 Alexis Way, Winchester, KY 40391

  Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

  Shane Underwood Keller Williams Commonwealth

  425 Alexis Way, 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 $351,594

  Last Listing Agent Timothy Saylor Threshold Real Estate Services

  220 Hibiscus Ln, Winchester, KY 40391
• 

  

  /14

  Est $237,814

  Not Listed For Sale

  313 Vanover Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 1995

  313 Vanover Way, Winchester, KY 40391

  Last Sold Summary

  • 112 Days On Market

  Last Listing Agent Bob Sophiea eXp Realty, LLC
• 

  

  /60

  $248,900

  $11K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 2,249 Sq Ft

  11304 Irvine Rd, Winchester, KY 40391

  Welcome to this freshly renovated farmhouse in the heart of Trapp, Kentucky! Blending timeless farmhouse charm with fresh updates, this property is ready for its next chapter. The possibilities are endless—come see all this special home has to offer. An absolute must-see!

  Darrell Tackett Dream Maker Realty, LLC

  11304 Irvine 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 $326,015

  Last Listing Agent Donna Thwaites Thwaites Realtors LLC

  37 Lynnway Dr, Winchester, KY 40391
• 

  

  /21

  Est $232,420

  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

  Last Listing Agent Tyler I Back The Brokerage
• 

  

  /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
• 

  

  /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 $191,030

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391
• 

  

  /22

  Est $217,159

  Not Listed For Sale

  517 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2001

  517 Acadia Way, Winchester, KY 40391

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Tyler I Back The Brokerage
• 

  

  /36

  $519,900

  $30K PRICE DROP Pending

  • 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

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