Winchester, KY Homes

• 

  

  

  /52

  $329,900

  $10K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  228 Holiday Rd, Winchester, KY 40391

  Back on the market at no fault of the sellers. Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and

  Caroline Mucci CENTURY 21 Commonwealth R E

  228 Holiday Rd, Winchester, KY 40391
• 

  

  

  /38

  $375,750

  Sold Apr 01, 2026

  6239 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $141/SF
  • 121 Days On Market

  Current Estimated Value $384,036

  Last Listing Agent Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  

  /31

  Est $232,138

  Not Listed For Sale

  208 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft
  • Built 1950

  208 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market
• 

  

  

  /65

  $609,900

  Pending

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft

  6595 Mount Sterling Rd, Winchester, KY 40391

  Welcome to 6595 Mount Sterling Rd. offering the perfect blend of space, convenience, and flexibility on 2.59 acres. Ideally located just off I 64 between Winchester and Mount Sterling, this property provides easy interstate access while still offering privacy and room to spread out. This custom home features 5 bedrooms, 3 full baths, and a versatile floor plan. The main level includes a vaulted

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
• 

  

  

  /3

  $94,000

  Sold Aug 22, 2025

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $23,383 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 140 Days On Market

  Current Estimated Value $180,352

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /22

  Est $162,335

  Not Listed For Sale

  423 E Broadway St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 2,363 Sq Ft
  • Built 1878

  423 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market
• 

  

  /41

  $235,000

  • 4 Beds
  • 1 Bath
  • 1,609 Sq Ft

  120 Windsor Dr, Winchester, KY 40391

  Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful

  Cathie Witt-Pyle Keller Williams Commonwealth

  120 Windsor Dr, Winchester, KY 40391
• 

  

  /26

  $178,000

  Sold Apr 30, 2026

  356 Colby Ridge Blvd, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,102 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 51 Days On Market

  Current Estimated Value $184,519

  Last Listing Agent Nena Honaker Tom Goebel & Company

  356 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /10

  Est $198,349

  Not Listed For Sale

  24 Fairview Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1940

  24 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /31

  $350,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft

  38 N Burns Ave, Winchester, KY 40391

  Welcome to this beautiful new home in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back porch

  Trina Penn RE/MAX Creative Realty

  38 N Burns Ave, Winchester, KY 40391
• 

  

  /43

  $253,000

  Sold Jun 22, 2026

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 2000

  Last Sold Summary

  • 6% Below List Price
  • $129/SF
  • 54 Days On Market

  Current Estimated Value $267,810

  Last Listing Agent Felicia Mayes The Real Estate Co.

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /20

  Est $159,478

  Not Listed For Sale

  100 Dallas Aly, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,194 Sq Ft
  • Built 1920

  100 Dallas Aly, Winchester, KY 40391

  Last Sold Summary

  • 13 Days On Market
• 

  

  /54

  $164,900

  $5K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 1,056 Sq Ft

  101 Alabama St, Winchester, KY 40391

  Step back in time and discover the possibilities in this classic 1930-built home full of character and opportunity! With solid bones and vintage details, this property is the perfect canvas for investors, renovators, or anyone dreaming of restoring a piece of history. Featuring spacious rooms, original architectrual touches, and a layout just waiting to be reimagined. This home offers incredible

  A. Rebecca Woods Woods Realty Group

  101 Alabama St, Winchester, KY 40391
• 

  /2

  $85,000

  Sold Apr 15, 2026

  2465 Flanagan Station Rd, Winchester, KY 40391

  • Land
  • 3.68 Acres
  • $23,098 per Acre

  Last Sold Summary

  • 9 Days On Market

  Current Estimated Value $85,805

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  2465 Flanagan Station Rd, Winchester, KY 40391
• 

  

  /55

  Est $198,707

  Not Listed For Sale

  30 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • Built 1983

  30 Ashland Ave, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market
• 

  

  /20

  $312,000

  $95K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,858 Sq Ft

  200 Dubuy Dr, Winchester, KY 40391

  Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full

  Wayne Elkins RE/MAX Creative Realty

  200 Dubuy Dr, Winchester, KY 40391
• 

  

  /17

  $30,000

  Sold Jun 30, 2025

  12591 Ironworks Rd, Winchester, KY 40391

  • Land
  • 1.72 Acres
  • $17,442 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 51 Days On Market

  Current Estimated Value $188,245

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
• 

  

  /30

  Est $170,227

  Not Listed For Sale

  370 E Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,126 Sq Ft
  • Built 1930

  370 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market
• 

  

  /34

  $444,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,442 Sq Ft

  1478 Donaldson Rd, Winchester, KY 40391

  Tucked away at the end of a long, private driveway, this unique brick ranch sits on just over 5 manicured acres and offers the perfect blend of space, comfort, and functionality. Designed for easy one-level living, the home features extra-wide hallways and doorways, a desirable split-bedroom floor plan and an open-concept layout ideal for everyday living and entertaining. The spacious kitchen

  Jim Woodrum RE/MAX Creative, Winchester

  1478 Donaldson Rd, Winchester, KY 40391
• 

  

  /46

  $282,900

  Sold Jan 02, 2026

  165 Hilltop Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $195/SF
  • 6 Days On Market

  Current Estimated Value $284,465

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
• 

  

  /32

  Est $203,827

  Not Listed For Sale

  203 Crawford Ct, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1960

  203 Crawford Ct, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market
• 

  

  /31

  $329,900

  $18K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  110 Powe Dr, Winchester, KY 40391

  This 4 Bedroom, 3 Bath home is quietly nestled within the Greenfield subdivision. Prime location just off the Winchester Bypass. This property has so much to offer. Updates can be seen throughout. Large first floor primary bedroom with on-suite and walk in closet, spacious family room, large yard with mature trees as well as widened driveway for additional parking, above ground pool with duel

  Michael Hilario The Agency

  110 Powe Dr, Winchester, KY 40391
• 

  

  /25

  $262,500

  Sold May 22, 2026

  398 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft
  • Built 1977

  Last Sold Summary

  • 15% Below List Price
  • $224/SF
  • 97 Days On Market

  Current Estimated Value $292,244

  Last Listing Agent Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /53

  Est $192,979

  Not Listed For Sale

  29 Fairview Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,631 Sq Ft
  • Built 1960

  29 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 140 Days On Market
• 

  /2

  $100,000

  $10K PRICE INCREASE

  • Land
  • 1.1 Acres
  • $90,909 per Acre

  270 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

  270 Duclair Dr, Winchester, KY 40391
• 

  

  /41

  $650,000

  Sold Jun 23, 2025

  357 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,007 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $216/SF
  • 15 Days On Market

  Current Estimated Value $682,714

  Last Listing Agent Emily Belcher Rector Hayden Realtors

  357 Wades Mill Rd, Winchester, KY 40391
• 

  

  /39

  Est $176,342

  Not Listed For Sale

  10 Sylvania Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 953 Sq Ft
  • Built 1961

  10 Sylvania Ave, Winchester, KY 40391

  Last Sold Summary

  • 207 Days On Market
• 

  

  /9

  $500,000

  $100K PRICE DROP

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
• 

  

  /26

  $250,000

  Sold Feb 20, 2026

  21 Virginia Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft
  • Built 1962

  Last Sold Summary

  • 4% Below List Price
  • $143/SF
  • 40 Days On Market

  Current Estimated Value $249,389

  Last Listing Agent Emily Crump eXp Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
• 

  

  /29

  Est $162,313

  Not Listed For Sale

  4 Sylvania Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft
  • Built 1960

  4 Sylvania Ave, Winchester, KY 40391

  Last Sold Summary

  • 4 Days On Market
• 

  

  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  205 Codella Dr, Winchester, KY 40391
• 

  

  /19

  $199,900

  Sold Feb 12, 2026

  117 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1998

  Last Sold Summary

  • $186/SF
  • 49 Days On Market

  Current Estimated Value $201,380

  Last Listing Agent Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
• 

  

  /30

  Est $197,654

  Not Listed For Sale

  280 Winn Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft
  • Built 1960

  280 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market
• 

  /2

  $67,500

  • Land
  • 1.89 Acres
  • $35,695 per Acre

  250 Spencer Ln, Winchester, KY 40391

  Unique triangular shaped lot in a wooded rural setting, interesting opportunities for privacy in a beautiful area of Clark County where you can enjoy the outdoors and create memories galore.

  Craig Bridgewater Bridgewater Real Estate

  250 Spencer Ln, Winchester, KY 40391
• 

  

  /31

  $205,000

  Sold Jun 12, 2026

  34 Hays St, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 2,450 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Below List Price
  • $84/SF
  • 18 Days On Market

  Current Estimated Value $211,366

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  34 Hays St, Winchester, KY 40391
• 

  

  /25

  Est $115,898

  Not Listed For Sale

  248 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft
  • Built 1940

  248 Cook Ave, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market
• 

  

  /30

  $310,000

  • 4 Beds
  • 2 Baths
  • 2,285 Sq Ft

  872 Stratton Ln, Winchester, KY 40391

  Welcome home to this well-maintained, one-owner split-level offering space, comfort, and endless possibilities! Featuring 4 bedrooms and 2 full baths, this home provides room for everyone. Enjoy both a spacious living room and cozy family room wih a fireplace, perfect for relaxing or entertaining. The functional floor plan offers flexibility for today's lifestyle. New carpet and fresh paint

  Kathryn Cheuvront Coldwell Banker McMahan

  872 Stratton Ln, Winchester, KY 40391
• 

  

  /44

  $310,000

  Sold Jun 27, 2025

  2482 Mina Station Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1962

  Last Sold Summary

  • $177/SF
  • 24 Days On Market

  Current Estimated Value $321,654

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  2482 Mina Station Rd, Winchester, KY 40391
• 

  

  /41

  Est $210,616

  Not Listed For Sale

  31 Watts Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,343 Sq Ft
  • Built 1960

  31 Watts Rd, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market
• 

  

  /3

  $430,000

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout. The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391

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