Winchester, KY Homes

• 

  

  

  /60

  Est $433,509

  Not Listed For Sale

  405 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 2,718 Sq Ft
  • Built 1945

  405 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Diane K Scott The Brokerage
• 

  

  

  /7

  $150,000

  $30K PRICE DROP

  • Land
  • 4.21 Acres
  • $35,629 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.21 acres of gently rolling land with small stream 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

  1030 Craig Crossing Rd, Winchester, KY 40391
• 

  

  /2

  $224,900

  Sold May 08, 2026

  11 Shelley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1970

  Last Sold Summary

  • $189/SF

  Current Estimated Value $230,384

  Last Listing Agent Mark Wallace Transactionbroker.com

  11 Shelley Dr, Winchester, KY 40391
• 

  

  

  /57

  Est $307,968

  Not Listed For Sale

  10 Northern Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft
  • Built 1957

  10 Northern Ave, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Jeanne Beaven Rector Hayden Realtors
• 

  

  

  /27

  $234,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,108 Sq Ft

  227 Leslie Dr, Winchester, KY 40391

  This 3 Bedroom, 2 bath home is quietly nestled within the Saddle Brook subdivision. Conveniently located just outside of Winchester New Bypass, this property also qualifies for zero down rural housing financing. Updates can be seen throughout along with spacious master bedroom with on-suite, large back yard and open concept living. Schedule your showing today!

  Michael Hilario The Agency

  227 Leslie Dr, Winchester, KY 40391
• 

  

  /30

  $254,000

  Sold Dec 02, 2025

  312 Forest Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $164/SF
  • 52 Days On Market

  Current Estimated Value $252,107

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  312 Forest Ave, Winchester, KY 40391
• 

  

  /92

  Est $384,553

  Not Listed For Sale

  31 Mockingbird Valley Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft
  • Built 1962

  31 Mockingbird Valley Rd, Winchester, KY 40391

  Last Sold Summary

  • 209 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /14

  $152,500

  $7K PRICE DROP Pending

  • Land
  • 2.66 Acres
  • $57,374 per Acre

  590 Craig Crossing, Winchester, KY 40391

  Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

  Keith Wilson Coldwell Banker McMahan

  590 Craig Crossing, Winchester, KY 40391
• 

  

  /75

  $410,000

  Sold Nov 21, 2025

  291 Log Lick Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 3 Days On Market

  Current Estimated Value $419,447

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
• 

  

  /28

  Est $386,720

  Not Listed For Sale

  29 Manor Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft
  • Built 1962

  29 Manor Dr, Winchester, KY 40391

  Last Sold Summary

  • 247 Days On Market

  Last Listing Agent John Patterson Rector Hayden Realtors
• 

  /2

  $150,000

  • Land
  • 2.77 Acres
  • $54,074 per Acre

  3385 Colby Rd, Winchester, KY 40391

  Parcel 4 in the photos. This 2.774 acre lot is available on Colby Road just 1.5 miles from the Winchester Bypass. No building restrictions other than no manufactured housing and a paved driveway must be completed within a year of finishing a residence.

  Steve Adams Steven D Adams Real Estate Services, LLC

  3385 Colby Rd, Winchester, KY 40391
• 

  

  /34

  $200,000

  Sold Aug 03, 2026

  190 Privacy Ln, Winchester, KY 40391

  • Land
  • 6.08 Acres
  • $32,895 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 136 Days On Market

  Current Estimated Value $237,935

  Last Listing Agent Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
• 

  

  /53

  Est $904,192

  Not Listed For Sale

  511 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 4.5 Baths
  • 4,698 Sq Ft
  • Built 1885

  511 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 318 Days On Market

  Last Listing Agent Greg Leveridge Block + Lot Homes
• 

  

  /16

  $168,000

  Pending

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft

  41 Hiawatha Trail, Winchester, KY 40391

  This inviting 3- bedroom, 1- bath home offers a great combination of comfort, character,and convenience. Beautiful hardwood floors add warmth throughout, while the updated kitchen provides a fresh, functional space for everyday living. Outside, the fenced backyard offers plenty of room for pets, entertaining, gardening, or simply relaxing outdoors. Move in ready and easy to maintain, this home is

  Hannah Toole Coldwell Banker McMahan

  41 Hiawatha Trail, Winchester, KY 40391
• 

  

  /36

  $257,400

  Sold Nov 21, 2025

  103 Hampton Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $150/SF
  • 4 Days On Market

  Current Estimated Value $271,720

  Last Listing Agent Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
• 

  

  /35

  Est $347,583

  Not Listed For Sale

  121 Hampton Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,248 Sq Ft
  • Built 1958

  121 Hampton Ave, Winchester, KY 40391

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
• 

  

  /3

  $700,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  415 Alexis Way, Winchester, KY 40391

  Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

  Shane Underwood Keller Williams Commonwealth

  415 Alexis Way, Winchester, KY 40391
• 

  

  /32

  $175,000

  Sold Dec 29, 2025

  200 Madison Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $156/SF
  • 19 Days On Market

  Current Estimated Value $181,457

  Last Listing Agent Silvia Torres Tru Life Real Estate

  200 Madison Ave, Winchester, KY 40391
• 

  

  /30

  Est $347,221

  Not Listed For Sale

  115 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,042 Sq Ft
  • Built 1960

  115 Hampton Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Lauren Ball Deborah Ball Realty
• 

  

  /13

  $400,000

  • Land
  • 2.19 Acres
  • $182,648 per Acre

  145 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 Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  145 Codella Dr, Winchester, KY 40391
• 

  

  /82

  $392,000

  Sold Dec 19, 2025

  397 Calmes Blvd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,637 Sq Ft
  • Built 1992

  Last Sold Summary

  • 11% Below List Price
  • $149/SF
  • 62 Days On Market

  Current Estimated Value $391,735

  Last Listing Agent Omar Shalash Tru Life Real Estate

  397 Calmes Blvd, Winchester, KY 40391
• 

  

  /50

  Est $438,478

  Not Listed For Sale

  33 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,580 Sq Ft
  • Built 1958

  33 Hampton Ave, Winchester, KY 40391

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Robert Coburn Kentucky Realty Group, LLC
• 

  

  /52

  $536,000

  $3K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,732 Sq Ft

  267 Runnymeade Dr, Winchester, KY 40391

  Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops,

  Jason Caudill RE/MAX Creative Realty

  267 Runnymeade Dr, Winchester, KY 40391
• 

  

  /24

  $265,000

  Sold Feb 25, 2026

  120 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $184/SF
  • 32 Days On Market

  Current Estimated Value $266,798

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  120 Sunset Heights, Winchester, KY 40391
• 

  

  /51

  Est $446,266

  Not Listed For Sale

  17 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,181 Sq Ft
  • Built 1960

  17 Hampton Ave, Winchester, KY 40391

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate
• 

  

  /39

  $239,000

  Pending

  • 6 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  Excellent investment opportunity!!! A triplex near downtown Winchester. Close to everything. The main level features a unit with 3 bedrooms, 1 full bath, 2 living areas, a large eat-in kitchen and a laundry room. The upstairs unit features 2 bedrooms, 1 full bath, a living room, and an eat-in kitchen. The lower level features a 1 bedroom, 1 full bathroom, a large living room and an eat-in

  Libby VanMeter Marshall Lane Real Estate - Lexington

  221 S Highland St, Winchester, KY 40391
• 

  

  /35

  $349,000

  Sold Feb 13, 2026

  121 Fitch Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Below List Price
  • $166/SF
  • 3 Days On Market

  Current Estimated Value $345,002

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  121 Fitch Ave, Winchester, KY 40391
• 

  

  /27

  Est $244,471

  Not Listed For Sale

  118 Southern Ct, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,598 Sq Ft
  • Built 1943

  118 Southern Ct, Winchester, KY 40391

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Susan Baldwin Threshold Real Estate Services
• 

  /2

  $100,000

  • Land
  • 29,620 Sq Ft
  • $147,059 per Acre

  100 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

  100 Duclair Dr, Winchester, KY 40391
• 

  

  /9

  $135,000

  Sold Aug 28, 2026

  220 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,097 Sq Ft
  • Built 1940

  Last Sold Summary

  • 16% Below List Price
  • $123/SF
  • 29 Days On Market

  Current Estimated Value $143,332

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  220 E Washington St, Winchester, KY 40391
• 

  

  /46

  Est $334,594

  Not Listed For Sale

  14 Western Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Built 2023

  14 Western Ave, Winchester, KY 40391

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC
• 

  

  /60

  $699,000

  $126K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,361 Sq Ft

  455 Davis Ln, Winchester, KY 40391

  Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

  Dale Hatton Dream Maker Realty, LLC

  455 Davis Ln, Winchester, KY 40391
• 

  

  /31

  $175,000

  Sold Jun 18, 2026

  5434 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $175/SF
  • 23 Days On Market

  Current Estimated Value $178,726

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  5434 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /18

  Est $202,629

  Not Listed For Sale

  6 Western Ave, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 2,109 Sq Ft
  • Built 1950

  6 Western Ave, Winchester, KY 40391

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Steven G King CENTURY 21 Advantage Realty
• 

  

  /23

  $215,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,319 Sq Ft

  3 Nunnelly Ct, Winchester, KY 40391

  Welcome to 3 Nunnelly Ct, Winchester, KY This charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes,

  Yasir Ahmed Black Mountain Realty

  3 Nunnelly Ct, Winchester, KY 40391
• 

  

  /34

  $800,000

  Sold Jun 03, 2026

  1150 Craig Crossing, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 2,842 Sq Ft
  • Built 2025

  Last Sold Summary

  • 14% Below List Price
  • $281/SF
  • 82 Days On Market

  Current Estimated Value $803,793

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  1150 Craig Crossing, Winchester, KY 40391
• 

  

  /37

  Est $293,391

  Not Listed For Sale

  120 Milwood Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft
  • Built 1965

  120 Milwood Dr, Winchester, KY 40391

  Last Sold Summary

  • 80 Days On Market

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

  

  /37

  $249,000

  $47K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  33 Bon-Haven Ave, Winchester, KY 40391

  Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third

  Erika Beatty Plum Tree Realty

  33 Bon-Haven Ave, Winchester, KY 40391
• 

  

  /45

  $271,000

  Sold Feb 26, 2026

  4180 Bybee Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,523 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $178/SF
  • 5 Days On Market

  Current Estimated Value $274,983

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  4180 Bybee Rd, Winchester, KY 40391
• 

  

  /26

  Est $275,899

  Not Listed For Sale

  134 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft
  • Built 1920

  134 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

Showing Results 641 - 680, Page 17 of 18