Clark County, KY Homes

• 

  

  

  /10

  $591,650

  New Construction Pending

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  104 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  104 Bella Shae Way, Winchester, KY 40391
• 

  

  

  /32

  $335,000

  Sold May 21, 2026

  8720 Wades Mill Rd, Mount Sterling, KY 40353

  • 4 Beds
  • 2 Baths
  • 2,940 Sq Ft
  • Built 1984

  Last Sold Summary

  • 4% Below List Price
  • $114/SF
  • 35 Days On Market

  Current Estimated Value $335,048

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  8720 Wades Mill Rd, Mount Sterling, KY 40353
• 

  

  

  /32

  Est $197,364

  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

  Last Listing Agent Andrew Fugitt KY Property Hunters
• 

  

  

  /65

  $364,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,269 Sq Ft

  15 Moundale Ave, Winchester, KY 40391

  Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of living space, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. The main level features a spacious family room with a cozy fireplace, custom cabinetry and new granite countertops in the kitchen, and a

  Josh Wood Freedom Realty & Property Management

  15 Moundale Ave, Winchester, KY 40391
• 

  

  

  /31

  $249,900

  Sold Jul 28, 2026

  312 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 2001

  Last Sold Summary

  • $195/SF
  • 10 Days On Market

  Current Estimated Value $249,453

  Last Listing Agent Paula Cole The Agency

  312 Buffalo Trace, Winchester, KY 40391
• 

  

  /27

  Est $229,259

  Not Listed For Sale

  13 Fairview Ave, Winchester, KY 40391

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

  13 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  

  /86

  $789,000

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft

  6500 Mount Sterling Rd, Winchester, KY 40391

  **Drone video and outside pictures available.** Enjoy the space and privacy you've been searching for at 6500 Mount Sterling Rd. Situated on a beautiful rural setting, this property offers the tranquility of country living while remaining conveniently close to Winchester and Lexington. Located less than a minute off exit 101 on I-64. The gorgeous property offers plenty of room for horses,

  Josh Wood Freedom Realty & Property Management

  6500 Mount Sterling 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 $378,745

  Last Listing Agent Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /39

  Est $176,169

  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

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  /2

  $1,800,000

  $2M PRICE INCREASE

  • Land
  • 4.36 Acres
  • $412,844 per Acre

  722 Colby Rd Unit 1, Winchester, KY 40391

  Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

  Cheryl Johnston CMI Properties

  722 Colby Rd Unit 1, 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 $200,671

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /29

  Est $157,510

  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

  Last Listing Agent Christal Browning Four Seasons Realty
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 16,117 Sq Ft
  • $270,270 per Acre

  225 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

  225 Jacob Ct, 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 $179,250

  Last Listing Agent Nena Honaker Tom Goebel & Company

  356 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /43

  Est $137,604

  Not Listed For Sale

  44 Watts Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 858 Sq Ft
  • Built 1959

  44 Watts Rd, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /7

  $365,900

  New Construction $4K PRICE DROP

  • 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
• 

  

  /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 $257,093

  Last Listing Agent Felicia Mayes The Real Estate Co.

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

  

  /25

  Est $128,741

  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

  Last Listing Agent Chris Johnson Plum Tree Realty
• 

  /2

  $195,000

  $2M PRICE DROP

  6699 Boonesboro Rd, Winchester, KY 40391

  READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

  Jennifer Ray RE/MAX Elite Lexington

  6699 Boonesboro Rd, 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 $87,283

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  2465 Flanagan Station Rd, Winchester, KY 40391
• 

  

  /41

  Est $202,053

  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

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /3

  $670,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft

  113 Bella Shae Way, Winchester, KY 40391

  Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, 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 $285,638

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
• 

  

  /23

  Est $254,099

  Not Listed For Sale

  130 Hilltop Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft
  • Built 1960

  130 Hilltop Dr, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
• 

  

  /50

  $429,900

  • 4 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  240 Athens Boonesboro Rd, Winchester, KY 40391

  Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your

  Darrell Tackett Dream Maker Realty, LLC

  240 Athens Boonesboro Rd, 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 $267,937

  Last Listing Agent Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /54

  Est $384,489

  Not Listed For Sale

  1455 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,901 Sq Ft
  • Built 1940

  1455 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Shari Frasure Keller Williams Commonwealth
• 

  

  /41

  $225,000

  $10K PRICE DROP

  • 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
• 

  

  /52

  $320,000

  Sold Jul 29, 2026

  228 Holiday Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $174/SF
  • 11 Days On Market

  Current Estimated Value $331,598

  Last Listing Agent Caroline Mucci CENTURY 21 Commonwealth R E

  228 Holiday Rd, Winchester, KY 40391
• 

  

  /70

  Est $285,738

  Not Listed For Sale

  1131 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,321 Sq Ft
  • Built 1960

  1131 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /32

  $320,000

  New Construction $30K PRICE DROP

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

  38 N Burns Ave, Winchester, KY 40391

  Welcome to this beautiful BRAND 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

  Trina Penn RE/MAX Creative Realty

  38 N Burns Ave, 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 $247,231

  Last Listing Agent Emily Crump eXp Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
• 

  

  /26

  Est $255,660

  Not Listed For Sale

  1124 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2006

  1124 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
• 

  

  /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
• 

  

  /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 $201,521

  Last Listing Agent Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
• 

  

  /28

  Est $248,800

  Not Listed For Sale

  1112 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2006

  1112 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 116 Days On Market

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

  

  /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
• 

  

  /65

  $609,000

  Sold Jul 17, 2026

  6595 Mount Sterling Rd, Winchester, KY 40391

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft
  • Built 2010

  Last Sold Summary

  • $135/SF
  • 21 Days On Market

  Current Estimated Value $606,153

  Last Listing Agent Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /41

  Est $241,903

  Not Listed For Sale

  273 Winn Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,982 Sq Ft
  • Built 1880

  273 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  

  /31

  $329,900

  $18K PRICE DROP Pending

  • 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

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