Winchester, KY Homes

• 

  

  

  /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 $227,192

  Last Listing Agent Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
• 

  

  

  /17

  Est $231,123

  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

  Last Listing Agent Holly Spradlin KY Realty Co
• 

  

  

  /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
• 

  

  

  /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 $289,526

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
• 

  

  

  /31

  Est $181,310

  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

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
• 

  

  /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
• 

  

  /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

  Current Estimated Value $1,052,416

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /19

  Est $206,484

  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

  Last Listing Agent Lukas Owens The Brokerage
• 

  

  /50

  $545,000

  Pending

  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
• 

  

  /42

  $339,500

  Sold Jul 15, 2026

  221 W Hickman St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1940

  Last Sold Summary

  • 3% Below List Price
  • $121/SF
  • 4 Days On Market

  Current Estimated Value $337,406

  Last Listing Agent Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
• 

  

  /19

  Est $223,280

  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

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  /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 $198,125

  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

  Last Listing Agent Wayne Elkins RE/MAX Creative Realty
• 

  

  /28

  $365,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
• 

  

  /20

  $228,500

  Sold Aug 13, 2026

  122 Spruce Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $189/SF
  • 24 Days On Market

  Current Estimated Value $227,703

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  122 Spruce Ct, Winchester, KY 40391
• 

  

  /48

  Est $264,352

  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

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington
• 

  

  /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
• 

  

  /34

  $349,000

  Sold Jul 16, 2026

  405 Tremont Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,274 Sq Ft
  • Built 2005

  Last Sold Summary

  • $153/SF
  • 6 Days On Market

  Current Estimated Value $352,114

  Last Listing Agent Darryl Bond Guide Realty, Inc.

  405 Tremont Ln, Winchester, KY 40391
• 

  

  /16

  Est $213,074

  Not Listed For Sale

  128 Alabama St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft
  • Built 1930

  128 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Paul Eads Freedom Realty & Property Management
• 

  

  /19

  $350,000

  • 3 Beds
  • 3 Baths
  • 2,592 Sq Ft

  135 E Broadway St, Winchester, KY 40391

  Attention Investors! This 3 plex in the heart of Winchester is a great investment. There are 3 apartments that are all currently rented out. The bottom floor has a huge living room, bathroom, and kitchen. The other two upstairs also have a living room, kitchen, bathroom, and bedroom. There is also a huge deck on the back for entertaining. Schedule an appointment to take a look before this one is

  Dale Hatton Dream Maker Realty, LLC

  135 E Broadway St, 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 $426,530

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
• 

  

  /44

  Est $183,746

  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

  Last Listing Agent Susan Moore Keller Williams Legacy Group
• 

  

  /24

  $199,900

  • 2 Beds
  • 1 Bath
  • 1,149 Sq Ft

  287 Ecton Rd, Winchester, KY 40391

  Country living with city convenience! Move in ready two bedroom home, large kitchen with lots of cabinets, expansive living room and bonus room--currently used as office/den and laundry area! Lots of natural light throughout! Step out back to the deck to sit and enjoy the outdoors! Christmas Tree Farm and Wild Flower field next door. Nice fenced yard! Full house cellar with outdoor entrance,

  Vicky Kamousi Metro Realty

  287 Ecton Rd, Winchester, KY 40391
• 

  

  /59

  $277,500

  Sold Jun 30, 2026

  403 Pueblo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Above List Price
  • $212/SF
  • 8 Days On Market

  Current Estimated Value $277,785

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  403 Pueblo Ct, Winchester, KY 40391
• 

  

  /28

  Est $240,326

  Not Listed For Sale

  116 Alabama St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1940

  116 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 95 Days On Market

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth
• 

  

  /22

  $134,900

  $5K PRICE DROP

  • 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 enthusiast, 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
• 

  

  /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 $330,391

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
• 

  

  /33

  Est $278,623

  Not Listed For Sale

  14 Calloway St, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Built 1940

  14 Calloway St, Winchester, KY 40391

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington
• 

  

  /12

  $137,500

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  48 Judy Ann Ct, Winchester, KY 40391

  Affordable and inviting townhome conveniently located in Winchester! This well-maintained home offers a functional layout with a spacious kitchen featuring plenty of room for everyday cooking and dining. The main level includes a comfortable living room, convenient half bath, and access to a private patio, perfect for relaxing or enjoying your morning coffee. A dedicated storage area provides

  Holly Spradlin KY Realty Co

  48 Judy Ann Ct, Winchester, KY 40391
• 

  

  /43

  $299,900

  Sold Jul 14, 2026

  3622 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft
  • Built 1983

  Last Sold Summary

  • $106/SF
  • 12 Days On Market

  Current Estimated Value $304,322

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /27

  Est $262,937

  Not Listed For Sale

  335 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1920

  335 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Shari Frasure Keller Williams Commonwealth
• 

  

  /46

  $369,900

  • 4 Beds
  • 2 Baths
  • 1,636 Sq Ft

  327 Primrose Ln, Winchester, KY 40391

  Please give 24 hour's notice. If you've been searching for an immaculate ranch home in a great location, this is one you won't want to miss! Let's start with the updates. This beautifully maintained home features newer heating and cooling, a newer water heater, granite countertops, updated kitchen and appliances, a privacy fence, professional landscaping, exterior lighting, and so much more. Now

  Teresa Richmond Freedom Realty & Property Management

  327 Primrose Ln, Winchester, KY 40391
• 

  

  /4

  $35,000

  Sold Jul 29, 2026

  2828 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 1 Acre
  • $35,000 per Acre

  Last Sold Summary

  • 14 Days On Market

  Current Estimated Value $35,281

  Last Listing Agent Kristian Kiskaden Keller Williams Commonwealth

  2828 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /35

  Est $231,619

  Not Listed For Sale

  24 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 2024

  24 Hughes Ave, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  

  /4

  $155,000

  $24K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,472 Sq Ft

  13 Maryland Ave, Winchester, KY 40391

  Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. Home features a newer roof and gutters as well as a large fenced backyard. Schedule your

  Clay David Sutherland ERA Select Real Estate

  13 Maryland Ave, Winchester, KY 40391
• 

  

  /37

  $220,000

  Sold Sep 23, 2025

  213 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 4 Days On Market

  Current Estimated Value $221,472

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
• 

  

  /31

  Est $502,880

  Not Listed For Sale

  10 French Ave, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,262 Sq Ft
  • Built 1906

  10 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Brian England Keller Williams Bluegrass Realty
• 

  

  /31

  $455,000

  $50K PRICE DROP

  • 8 Beds
  • 4 Baths
  • 5,058 Sq Ft

  265 S Highland St, Winchester, KY 40391

  Fully stabilized and 100% occupied, this is a quality investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep

  J Corey Griffo RE/MAX Elite Lexington

  265 S Highland St, Winchester, KY 40391
• 

  

  /10

  $100,000

  Sold Feb 20, 2026

  17 Waveland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $94/SF
  • 4 Days On Market

  Current Estimated Value $170,638

  Last Listing Agent Darrell Lewis DIY Realty-Flat Fee MLS

  17 Waveland Ave, Winchester, KY 40391

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