Winchester, KY Homes

• 

  

  

  /79

  $584,900

  Sold Feb 17, 2026

  180 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $122/SF
  • 46 Days On Market

  Current Estimated Value $595,170

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
• 

  

  

  /79

  Est $221,634

  Not Listed For Sale

  205 French Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 1959

  205 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 319 Days On Market
• 

  

  

  /14

  $180,000

  • 4 Beds
  • 3 Baths
  • 3,462 Sq Ft

  229 S Highland St, Winchester, KY 40391

  Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass

  Michelle Blackburn RE/MAX Creative, Winchester

  229 S Highland St, Winchester, KY 40391
• 

  

  

  /15

  $110,000

  Sold Sep 04, 2025

  706 Williamsburg Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 2024

  Last Sold Summary

  • 21% Below List Price
  • $119/SF

  Current Estimated Value $118,458

  Last Listing Agent Andrew Fugitt KY Property Hunters

  706 Williamsburg Dr, Winchester, KY 40391
• 

  

  

  /24

  Est $211,559

  Not Listed For Sale

  5 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,634 Sq Ft
  • Built 1930

  5 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /55

  $515,000

  $10K PRICE DROP

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

  935 Stoner-Ephesus Rd, Winchester, KY 40391

  Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that

  Timothy Saylor Threshold Real Estate Services

  935 Stoner-Ephesus Rd, Winchester, KY 40391
• 

  

  /30

  $185,000

  Sold Feb 06, 2026

  40 Garner St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft
  • Built 1950

  Last Sold Summary

  • 16% Below List Price
  • $137/SF
  • 217 Days On Market

  Current Estimated Value $195,462

  Last Listing Agent Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
• 

  

  /23

  Est $200,246

  Not Listed For Sale

  11 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,708 Sq Ft
  • Built 1920

  11 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market
• 

  

  /14

  $269,900

  • 3 Beds
  • 1 Bath
  • 1,644 Sq Ft

  205 Providence Ln, Winchester, KY 40391

  You Wont Find A More Beautiful And Private Setting!!! This Home Features 3 Bedrooms And 1 Bath And Sits On 5.05 Acres; Two Front Porches; Large Rear Porch; A Separate Room Downstairs That Would Make A Great Master Bedroom/Suite Potentially; Huge Mudroom/Flex Space! Possibilities Are Endless With This Property. This Home Has Replacement Vinyl Clad Windows, Roof And HVAC All Replaced In Last 10

  Patrick Arvin Keller Williams Commonwealth

  205 Providence Ln, Winchester, KY 40391
• 

  

  /36

  $435,000

  Sold May 22, 2026

  3886 Jackson Ferry Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft
  • Built 1992

  Last Sold Summary

  • $257/SF
  • 21 Days On Market

  Current Estimated Value $429,866

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  3886 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /18

  Est $119,996

  Not Listed For Sale

  129 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1940

  129 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 46 Days On Market
• 

  

  /35

  $289,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  110 Buckingham Ln, Winchester, KY 40391

  The original buyer's plans changed, and their loss may be your second chance. This beautiful Winchester ranch is the kind of home buyers walk into and immediately feel good about. From the vaulted ceilings and incredibly beautiful luxury vinyl plank flooring to the updated bathrooms, well-maintained systems, epoxied garage floor, and easy one-level layout, this home is truly move-in ready and

  Jeremy Perryman United Real Estate Bluegrass

  110 Buckingham Ln, Winchester, KY 40391
• 

  

  /19

  $189,000

  Sold Mar 03, 2026

  111 Quail Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft
  • Built 1994

  Last Sold Summary

  • $158/SF
  • 5 Days On Market

  Current Estimated Value $193,189

  Last Listing Agent Kim Dice eXp Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
• 

  

  /15

  Est $207,349

  Not Listed For Sale

  20 Elizabeth St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1940

  20 Elizabeth St, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market
• 

  

  /5

  $575,000

  • Land
  • 1.71 Acres
  • $336,257 per Acre

  1025 Colby Rd, Winchester, KY 40391

  This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center,

  Jo Gawthrop Keller Williams Bluegrass Realty

  1025 Colby Rd, Winchester, KY 40391
• 

  

  /35

  $244,000

  Sold Mar 09, 2026

  426 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,641 Sq Ft
  • Built 2004

  Last Sold Summary

  • $149/SF
  • 2 Days On Market

  Current Estimated Value $247,320

  Last Listing Agent Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
• 

  

  /17

  Est $234,766

  Not Listed For Sale

  102 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1940

  102 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 41 Days On Market
• 

  

  /55

  $350,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,835 Sq Ft

  27 Hampton Ave, Winchester, KY 40391

  Located on desirable Hampton Avenue, this all-brick ranch is full of timeless character and thoughtful updates. Beautiful original hardwood floors run throughout the main level, highlighted by detailed craftsmanship and charm you don't find every day. The spacious living room features built-ins, a fireplace, and flows into the dining area, creating a warm and inviting space for everyday living or

  Terra Long Keller Williams Commonwealth

  27 Hampton Ave, Winchester, KY 40391
• 

  

  /22

  $220,000

  Sold Mar 31, 2026

  443 Jameson Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Below List Price
  • $157/SF
  • 64 Days On Market

  Current Estimated Value $225,098

  Last Listing Agent Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
• 

  

  /16

  Est $367,376

  Not Listed For Sale

  122 French Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 4,176 Sq Ft
  • Built 1920

  122 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 4 Days On Market
• 

  

  /15

  $925,000

  • Land
  • 3.77 Acres
  • $245,358 per Acre

  300 Rolling Hills Ln, Winchester, KY 40391

  Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

  Josh Wood Freedom Realty & Property Management

  300 Rolling Hills Ln, Winchester, KY 40391
• 

  /2

  $160,000

  Sold Sep 19, 2025

  8 Village Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $113/SF
  • 0 Days On Market

  Current Estimated Value $279,726

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  8 Village Dr, Winchester, KY 40391
• 

  

  /31

  Est $188,591

  Not Listed For Sale

  134 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • Built 1930

  134 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  /2

  $168,500

  Pending

  • 3 Beds
  • 2 Baths
  • 1,026 Sq Ft

  12 Apache Trail, Winchester, KY 40391

  Welcome to this charming 3-bedroom, 2-full bath ranch located in the desirable Indian Hills Subdivision! This home features a large covered front porch, perfect for relaxing and enjoying your morning coffee or evening sunsets. Inside, you'll find a spacious layout with plenty of potential to make it your own. The full unfinished basement offers endless possibilities for storage, a home gym, or

  Stephen Brashear Keller Williams Commonwealth

  12 Apache Trail, Winchester, KY 40391
• 

  

  /28

  $290,000

  Sold Apr 17, 2026

  24 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft
  • Built 1920

  Last Sold Summary

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

  Current Estimated Value $289,691

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
• 

  

  /19

  Est $205,146

  Not Listed For Sale

  130 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • Built 1930

  130 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /50

  $545,000

  665 Lillies Ferry Rd, Winchester, KY 40391

  You do not want to sleep on this one, it is a beautiful working farm with multiple building sites and amazing views and tranquility. Two farms are selling together for a total of 91.28 acres that is already a very productive cattle farm. The fencing, gates, waterers and infrastructure is already in place to move right in and produce income. There are multiple possible building sites with amazing

  Carrie Taylor Taylor Real Estate, LLC

  665 Lillies Ferry Rd, Winchester, KY 40391
• 

  

  /101

  $1,050,000

  Sold Jun 01, 2026

  3760 Old Boonesboro Rd, Winchester, KY 40391

  • 5 Beds
  • 5 Baths
  • 5,666 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $185/SF
  • 15 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /19

  Est $230,477

  Not Listed For Sale

  112 Central Ave, Winchester, KY 40391

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

  112 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  /2

  $110,000

  • Land
  • 11,761 Sq Ft
  • $407,407 per Acre

  125 Jacob Ct, 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

  125 Jacob Ct, Winchester, KY 40391
• 

  /2

  $85,000

  Sold Dec 12, 2025

  1385 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 6.43 Acres
  • $13,219 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 6 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1385 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /23

  Est $201,705

  Not Listed For Sale

  112 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,738 Sq Ft
  • Built 1930

  112 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market
• 

  

  /8

  $175,000

  $20K PRICE DROP

  • Land
  • 6.59 Acres
  • $26,555 per Acre

  990 Craig Crossing Rd, Winchester, KY 40391

  Lot # 13 contains 6.588 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  990 Craig Crossing Rd, Winchester, KY 40391
• 

  

  /53

  $867,500

  Sold Aug 01, 2025

  511 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 4.5 Baths
  • 4,698 Sq Ft
  • Built 1885

  Last Sold Summary

  • 11% Below List Price
  • $185/SF
  • 318 Days On Market

  Current Estimated Value $899,501

  Last Listing Agent Greg Leveridge Block + Lot Homes

  511 Boone Ave, Winchester, KY 40391
• 

  

  /48

  Est $262,249

  Not Listed For Sale

  104 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • Built 1930

  104 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market
• 

  

  /22

  $139,900

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft

  174 Cook Ave, Winchester, KY 40391

  Charming Fixer-Upper with Endless Potential - Priced to Sell!! This older gem is full of character and opportunity! Featuring solid bones and classic charm, this property is perfect for buyers with a vision who are not afraid to add a little TLC! Whether you're an investor, DIY entusiast, or someone dreaming of restoring a home to its former glory, this is your chance to build equity and create

  A. Rebecca Woods Woods Realty Group

  174 Cook Ave, Winchester, KY 40391
• 

  

  /36

  $420,000

  Sold Feb 25, 2026

  134 Fontaine Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft
  • Built 1994

  Last Sold Summary

  • 7% Below List Price
  • $153/SF
  • 126 Days On Market

  Current Estimated Value $426,173

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
• 

  

  /44

  Est $183,326

  Not Listed For Sale

  118 Alabama St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1940

  118 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /32

  $219,500

  Pending

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft

  525 Colby Ridge Blvd, Winchester, KY 40391

  Location, location, location. This duplex is located within minutes of the Winchester Bypass and Colby Road. This one level home offers 3 bedrooms, 2 full baths, great room with fireplace, eat in kitchen, and a one car garage. In 2023 the owners remodeled the bathrooms, added a new kitchen sink and countertops. The LVP flooring was also completed in 2023. The house includes all the kitchen

  Craig Bridgewater Bridgewater Real Estate

  525 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /41

  $310,000

  Sold Dec 29, 2025

  1996 White Conkwright Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,055 Sq Ft
  • Built 1966

  Last Sold Summary

  • 9% Below List Price
  • $294/SF
  • 45 Days On Market

  Current Estimated Value $310,871

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391

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