Winchester, KY Homes

• 

  

  

  /12

  Est $213,193

  Not Listed For Sale

  303 Hummingbird Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,169 Sq Ft
  • Built 1960

  303 Hummingbird Rd, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Garry Milton Milton and Associates Real Estate
• 

  

  

  /15

  $260,000

  • 4 Beds
  • 2 Baths
  • 1,996 Sq Ft

  59 Hillcrest Dr, Winchester, KY 40391

  PRICED TO SELL | BRING AN OFFER! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds | 2 Baths | ~2,066 Total Sq Ft | Full Basement | Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant

  Dylan Langdon The Agency

  59 Hillcrest Dr, Winchester, KY 40391
• 

  

  

  /32

  $263,000

  Sold Sep 05, 2025

  2 Chickadee Ln, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,397 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $188/SF
  • 2 Days On Market

  Current Estimated Value $264,065

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
• 

  

  

  /7

  Est $189,365

  Not Listed For Sale

  301 Hummingbird Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,106 Sq Ft
  • Built 1955

  301 Hummingbird Rd, Winchester, KY 40391

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Garry Milton Milton and Associates Real Estate
• 

  

  

  /17

  $379,000

  $85K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  104 Colby Hills Dr, Winchester, KY 40391

  Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  104 Colby Hills Dr, Winchester, KY 40391
• 

  

  /35

  $325,000

  Sold Nov 21, 2025

  130 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 19 Days On Market

  Current Estimated Value $343,201

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
• 

  

  /30

  Est $174,287

  Not Listed For Sale

  222 Locust Grove Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft
  • Built 1940

  222 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

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

  

  /50

  $229,900

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

  491 Hidden Hills Way, Winchester, KY 40391

  Welcome home to this charming 3-bedrooms, 2-bath ranch perfectly situated in the heart of Winchester! Offering the convenience of one-level living, this inviting 1200 sq ft home combines comfort, functionality, and an unbeatable location. Primary bedroom is en suite and offers plenty of closet space. Additional 2-bedrooms and 1-bath provide plenty of space. Enjoy easy access to schools, shopping,

  ROBIN TRIMBLE HomeFirst Real Estate

  491 Hidden Hills Way, Winchester, KY 40391
• 

  

  /43

  $356,000

  Sold Jul 10, 2026

  274 Greenway Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,208 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Above List Price
  • $161/SF
  • 1 Day On Market

  Current Estimated Value $350,117

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  274 Greenway Dr, Winchester, KY 40391
• 

  

  /31

  Est $224,884

  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

  Last Listing Agent Shane Underwood Keller Williams Commonwealth
• 

  

  /3

  $84,900

  Pending

  • Land
  • 3.39 Acres
  • $25,044 per Acre

  160 Rector Ln, Winchester, KY 40391

  UNIQUE Opportunity - 3.39 acres with a small pond - tucked away on a private lane, flat land and totally surrounded by trees. What a unique setting!! Convenience is the key to this property. Water is available at the main road. Internet has been extended down Rector Lane, electricity is accessible for connection. Deed Restrictions apply. Do Not Miss Your Chance to own this SPECIAL piece of land.

  M Gail Cleaver United Real Estate Bluegrass

  160 Rector Ln, Winchester, KY 40391
• 

  

  /31

  $292,500

  Sold May 22, 2026

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 1 Day On Market

  Current Estimated Value $293,151

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

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

  

  /22

  Est $185,160

  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

  Last Listing Agent Tanya McKee Bluegrass Auction, Appraisal & Realty, LLC
• 

  

  /30

  $310,000

  $5K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,840 Sq Ft

  209 Connie Ln, Winchester, KY 40391

  Get here first, make an offer on this 4 bedroom, 3 bath, 1 1/2 story home, 2 car garage, showroom fresh condition, vaulted ceiling, hardwood floors, tile, carpet, deck, nice back yard, call today to view.

  Mila Ensor Ensor Real Estate, LLC

  209 Connie Ln, Winchester, KY 40391
• 

  

  /22

  $255,000

  Sold May 26, 2026

  35 Cherokee Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft
  • Built 1968

  Last Sold Summary

  • 6% Below List Price
  • $109/SF
  • 123 Days On Market

  Current Estimated Value $259,130

  Last Listing Agent Brenda Rue Keller Williams Bluegrass Realty

  35 Cherokee Ct, Winchester, KY 40391
• 

  

  /10

  Est $198,092

  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

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC
• 

  

  /38

  $205,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,769 Sq Ft

  236 Buffalo Trace, Winchester, KY 40391

  Welcome to **236 Buffalo Trace in Winchester, KY**—where thoughtful design meets comfortable, one-level living. This well-maintained **3-bedroom, 2.5-bath** home features a desirable **split-bedroom floor plan**, offering added privacy for the primary suite while keeping family or guest bedrooms conveniently located on the opposite side of the home. The spacious main level is designed for

  Rachel Lopez Coldwell Banker McMahan

  236 Buffalo Trace, Winchester, KY 40391
• 

  

  /51

  $303,000

  Sold Jan 16, 2026

  22 N Bloomfield Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft
  • Built 1919

  Last Sold Summary

  • 5% Below List Price
  • $158/SF
  • 16 Days On Market

  Current Estimated Value $307,676

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
• 

  

  /20

  Est $153,634

  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

  Last Listing Agent Emidio Figueroa Rector Hayden Realtors
• 

  /2

  $42,500

  Pending

  • Land
  • 11,369 Sq Ft
  • $162,835 per Acre

  105 Bella Ct, Winchester, KY 40391

  Jo Gawthrop Keller Williams Bluegrass Realty

  105 Bella Ct, Winchester, KY 40391
• 

  /2

  $89,000

  Sold Dec 18, 2025

  13067 Irvine Rd, Winchester, KY 40391

  • Land
  • 7.86 Acres
  • $11,323 per Acre

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13067 Irvine Rd, Winchester, KY 40391
• 

  

  /55

  Est $203,973

  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

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  /2

  $110,000

  • Land
  • 13,939 Sq Ft
  • $343,750 per Acre

  250 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

  250 Duclair Dr, Winchester, KY 40391
• 

  /2

  $4,900,000

  Sold Dec 23, 2025

  175 Chatham Place, Winchester, KY 40391

  • 2 Beds
  • 3 Baths
  • 37,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $132/SF
  • 111 Days On Market

  Current Estimated Value $5,168,026

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
• 

  

  /30

  Est $167,561

  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

  Last Listing Agent Meredith Story Story Realty
• 

  

  /21

  $139,000

  $10K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
• 

  

  /51

  $340,000

  Sold Oct 30, 2025

  356 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $106/SF
  • 30 Days On Market

  Current Estimated Value $359,737

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
• 

  

  /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
• 

  

  /14

  $950,000

  • Land
  • 120 Acres
  • $7,917 per Acre

  345 Providence Ln, Winchester, KY 40391

  Rare opportunity to acquire approximately 120 acres of magnificent, rolling Bluegrass farmland in prime Clark County! This exceptionally versatile property features a ideal blend of cleared pasture and rich wooded land, making it perfectly suited for cattle, horses, recreational pursuits, or building your private dream estate.Equipped with a large pond, barn, and county water available at the

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
• 

  

  /15

  $280,000

  Sold Jul 17, 2026

  327 Newcastle Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $165/SF
  • 87 Days On Market

  Current Estimated Value $288,703

  Last Listing Agent Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, 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
• 

  /2

  $188,500

  Pending

  • Land
  • 12.1 Acres
  • $15,579 per Acre

  155 Spring Ridge Way, Winchester, KY 40391

  Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are- R-1E, 4000 sq. Ft lots for 80 lots R-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue.

  Jo Gawthrop Keller Williams Bluegrass Realty

  155 Spring Ridge Way, Winchester, KY 40391
• 

  

  /28

  $131,000

  Sold Mar 12, 2026

  46 Judy Ann Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 0 Days On Market

  Current Estimated Value $134,900

  Last Listing Agent Lukas Owens The Brokerage

  46 Judy Ann Ct, 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
• 

  

  /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
• 

  

  /33

  $340,000

  Sold Jul 10, 2026

  740 Pilot Ridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 2017

  Last Sold Summary

  • $211/SF
  • 6 Days On Market

  Current Estimated Value $333,363

  Last Listing Agent Holly Goeing The Agency

  740 Pilot Ridge Ln, 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
• 

  

  /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
• 

  

  /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

Showing Results 281 - 320, Page 8 of 18