Winchester, KY Homes

• 

  

  

  /65

  $385,000

  Sold Dec 11, 2025

  1731 Ford Hampton Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 27% Below List Price
  • $182/SF
  • 157 Days On Market

  Current Estimated Value $409,389

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
• 

  

  

  /19

  Est $205,751

  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
• 

  

  /2

  $110,000

  • Land
  • 14,810 Sq Ft
  • $323,529 per Acre

  230 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

  230 Duclair Dr, Winchester, KY 40391
• 

  

  

  /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 $594,971

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
• 

  

  

  /19

  Est $223,493

  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
• 

  

  /4

  $625,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  424 Alexis Way, Winchester, KY 40391

  Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

  Shane Underwood Keller Williams Commonwealth

  424 Alexis Way, Winchester, KY 40391
• 

  

  /31

  $249,900

  Sold Jul 17, 2026

  123 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Below List Price
  • $173/SF
  • 52 Days On Market

  Current Estimated Value $247,714

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  123 Sunset Heights, Winchester, KY 40391
• 

  

  /23

  Est $203,875

  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
• 

  

  /12

  $529,000

  • 2 Beds
  • 1.5 Baths
  • 1,054 Sq Ft

  443 Oxford Dr Unit 443,445,447,449, Winchester, KY 40391

  Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal

  Tracey Goebel Tom Goebel & Company

  443 Oxford Dr Unit 443,445,447,449, 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 $119,745

  Last Listing Agent Andrew Fugitt KY Property Hunters

  706 Williamsburg Dr, Winchester, KY 40391
• 

  

  /48

  Est $258,153

  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
• 

  

  /14

  $165,000

  $15K PRICE DROP

  • 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
• 

  

  /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 $191,930

  Last Listing Agent Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
• 

  

  /44

  Est $185,160

  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
• 

  

  /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
• 

  

  /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 $423,237

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  3886 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /28

  Est $256,031

  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
• 

  

  /14

  $269,900

  Pending

  • 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
• 

  

  /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 $191,472

  Last Listing Agent Kim Dice eXp Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
• 

  

  /33

  Est $269,061

  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
• 

  

  /39

  $409,500

  $6K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 2,304 Sq Ft

  215 Delaplain Rd, Winchester, KY 40391

  215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line

  Alyssa Ryan Marshall Lane Real Estate - Lexington

  215 Delaplain 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 $245,612

  Last Listing Agent Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
• 

  

  /27

  Est $261,786

  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
• 

  

  /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
• 

  

  /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 $222,297

  Last Listing Agent Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
• 

  

  /35

  Est $225,382

  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
• 

  

  /55

  $350,000

  $10K PRICE DROP Pending

  • 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
• 

  /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 $283,126

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  8 Village Dr, Winchester, KY 40391
• 

  

  /41

  Est $259,252

  Not Listed For Sale

  254 S Highland St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,395 Sq Ft
  • Built 1935

  254 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester
• 

  

  /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
• 

  

  /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 $286,659

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
• 

  

  /24

  Est $200,180

  Not Listed For Sale

  54 Winn Ave, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1940

  54 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Lukas Owens The Brokerage
• 

  

  /22

  $178,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft

  17 Waveland Ave, Winchester, KY 40391

  Welcome home to this beautifully updated 2-bedroom, 1-bath home offering 1,061 square feet of comfortable living space! The renovated kitchen features soft-close shaker cabinets and granite countertops, while durable luxury vinyl plank flooring flows throughout the home for a fresh, modern feel. Outside, you'll find a spacious, fully fenced backyard complete with a storage shed providing extra

  Kelsie Calvo Haven Homes Group

  17 Waveland Ave, 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 $672,000

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /33

  Est $276,576

  Not Listed For Sale

  144 E Broadway St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1930

  144 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Thomas Harper Tom Harper and Associates
• 

  /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
• 

  

  /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 $345,306

  Last Listing Agent Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
• 

  

  /22

  Est $222,238

  Not Listed For Sale

  44 Buckner St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,309 Sq Ft
  • Built 1935

  44 Buckner St, Winchester, KY 40391

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent W Tyce McCullough Rector Hayden Realtors
• 

  

  /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
• 

  /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

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