Winchester, KY Homes

• 

  

  

  /76

  Est $555,672

  Not Listed For Sale

  775 Sugar Ridge Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft
  • Built 1996

  775 Sugar Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  

  

  /3

  $399,000

  • Land
  • 11.3 Acres
  • $35,310 per Acre

  0 Fairholme Way, Winchester, KY 40391

  11 acres of golf course adjacent land with development plan. Owner/Broker. Road and utility estimates available upon request. A list of individuals interested in lots available upon contract.

  Steve Adams Steven D Adams Real Estate Services, LLC

  0 Fairholme Way, Winchester, KY 40391
• 

  

  

  /26

  $259,000

  Sold Jun 22, 2026

  86 Bon-Haven Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,295 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $113/SF
  • 1 Day On Market

  Current Estimated Value $260,273

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  86 Bon-Haven Ave, Winchester, KY 40391
• 

  

  

  /32

  Est $306,243

  Not Listed For Sale

  810 Howard Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 2001

  810 Howard Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market
• 

  

  

  /14

  $129,300

  • Land
  • 2.3 Acres
  • $56,217 per Acre

  110 Knox Ct, Winchester, KY 40391

  This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the

  Jarran Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
• 

  

  /75

  $600,000

  Sold May 29, 2026

  905 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 3,391 Sq Ft
  • Built 1997

  Last Sold Summary

  • $177/SF
  • 3 Days On Market

  Current Estimated Value $599,438

  Last Listing Agent Niki Wiley Bluegrass Sotheby's International Realty

  905 Pretty Run Rd, Winchester, KY 40391
• 

  

  /53

  Est $293,573

  Not Listed For Sale

  1489 White Conkwright Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,126 Sq Ft
  • Built 1995

  1489 White Conkwright Rd, Winchester, KY 40391

  Last Sold Summary

  • 45 Days On Market
• 

  

  /103

  $2,650,000

  $345K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
• 

  

  /28

  $359,900

  Sold Jul 30, 2025

  210 Jett Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 2024

  Last Sold Summary

  • $225/SF
  • 311 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  210 Jett Dr, Winchester, KY 40391
• 

  

  /23

  Est $313,479

  Not Listed For Sale

  440 White Conkwright Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 2004

  440 White Conkwright Rd, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market
• 

  

  /30

  $209,000

  $51K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 2,683 Sq Ft

  217 S Highland St, Winchester, KY 40391

  This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

  Michael Hilario The Agency

  217 S Highland St, Winchester, KY 40391
• 

  

  /44

  $267,000

  Sold Mar 24, 2026

  146 W Lexington Ave, Winchester, KY 40391

  • 8 Beds
  • 3 Baths
  • 3,393 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Below List Price
  • $79/SF
  • 54 Days On Market

  Current Estimated Value $272,203

  Last Listing Agent KB Realty Group -Kevin Bradley KB Realty Group

  146 W Lexington Ave, Winchester, KY 40391
• 

  

  /78

  Est $579,757

  Not Listed For Sale

  7625 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,689 Sq Ft
  • Built 2006

  7625 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 42 Days On Market
• 

  

  /57

  $340,000

  $10K PRICE DROP

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

  443 S Maple St, Winchester, KY 40391

  Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make

  Terra Long Keller Williams Commonwealth

  443 S Maple St, Winchester, KY 40391
• 

  

  /22

  $156,000

  Sold Jan 16, 2026

  146 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft
  • Built 1940

  Last Sold Summary

  • 8% Below List Price
  • $122/SF
  • 28 Days On Market

  Current Estimated Value $162,440

  Last Listing Agent Autumn Johannes National Real Estate

  146 Cook Ave, Winchester, KY 40391
• 

  

  /18

  Est $279,682

  Not Listed For Sale

  6278 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1978

  6278 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 35 Days On Market
• 

  /2

  $10,000

  Pending

  • Land
  • 2,613 Sq Ft
  • $166,667 per Acre

  75 4th St, Winchester, KY 40391

  Explore the opportunity to build your next home or investment property on this 0.06-acre residential lot located at 75 4th Street. Nestled in an established neighborhood, this lot offers convenient access to local amenities, schools, and nearby roadways. With public utilities available in the area, it's a great option for new construction or future development. Whether you're a builder, investor,

  Bob Sophiea eXp Realty, LLC

  75 4th St, Winchester, KY 40391
• 

  

  /71

  $410,000

  Sold Nov 07, 2025

  188 Big Stoner Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $172/SF
  • 9 Days On Market

  Current Estimated Value $420,985

  Last Listing Agent Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
• 

  

  /39

  Est $358,902

  Not Listed For Sale

  3232 Old Ruckerville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1994

  3232 Old Ruckerville Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  /2

  $110,000

  • Land
  • 20,473 Sq Ft
  • $234,043 per Acre

  139 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

  139 Jacob Ct, Winchester, KY 40391
• 

  

  /73

  $325,000

  Sold Sep 23, 2025

  407 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $180/SF
  • 123 Days On Market

  Current Estimated Value $340,141

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  407 Fairholme Way, Winchester, KY 40391
• 

  

  /36

  Est $442,928

  Not Listed For Sale

  5487 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,892 Sq Ft
  • Built 1978

  5487 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 47 Days On Market
• 

  

  /20

  $210,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft

  301 Snowden Dr, Winchester, KY 40391

  Charming all-brick ranch offering timeless character and everyday functionality! Step inside to a light-filled living room featuring beautiful hardwood floors and a warm, welcoming feel throughout. This home offers three bedrooms and one full bathroom, along with an eat-in kitchen perfect for casual dining and gathering. A dedicated laundry/mud room just off the kitchen provides convenient access

  Julia Lark The Brokerage

  301 Snowden Dr, Winchester, KY 40391
• 

  

  /40

  $210,000

  Sold Sep 11, 2025

  635 Lisletown Ln, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • Built 1981

  Last Sold Summary

  • 12% Below List Price
  • $129/SF
  • 31 Days On Market

  Current Estimated Value $224,419

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  635 Lisletown Ln, Winchester, KY 40391
• 

  

  /34

  Est $371,333

  Not Listed For Sale

  4759 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,633 Sq Ft
  • Built 1985

  4759 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  /2

  $150,000

  • Land
  • 2.11 Acres
  • $71,090 per Acre

  125 Knox 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

  125 Knox Ct, Winchester, KY 40391
• 

  

  /43

  $485,000

  Sold Jun 23, 2025

  430 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,414 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $201/SF
  • 55 Days On Market

  Current Estimated Value $504,185

  Last Listing Agent Robyn Bradley Woods Realty Group

  430 Fairholme Way, Winchester, KY 40391
• 

  

  /41

  Est $346,507

  Not Listed For Sale

  2100 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1988

  2100 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 44 Days On Market
• 

  

  /24

  $365,900

  New Construction $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
• 

  

  /74

  $350,000

  Sold Mar 06, 2026

  4611 Colby Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,712 Sq Ft
  • Built 1980

  Last Sold Summary

  • $94/SF
  • 2 Days On Market

  Current Estimated Value $359,903

  Last Listing Agent Nancy Smith Rector Hayden Realtors

  4611 Colby Rd, Winchester, KY 40391
• 

  

  /62

  Est $424,286

  Not Listed For Sale

  890 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1965

  890 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 5 Days On Market
• 

  

  /16

  $124,500

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, Winchester, KY 40391
• 

  

  /33

  $340,000

  Sold May 12, 2026

  1270 Sewell Shop Rd, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 2020

  Last Sold Summary

  • 7% Below List Price
  • $174/SF
  • 73 Days On Market

  Current Estimated Value $350,156

  Last Listing Agent Meggan Batey Keller Williams Legacy Group

  1270 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /29

  Est $471,859

  Not Listed For Sale

  1623 Little Stoner Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1982

  1623 Little Stoner Rd, Winchester, KY 40391

  Last Sold Summary

  • 25 Days On Market
• 

  

  /64

  $499,000

  Pending

  • 5 Beds
  • 2.5 Baths
  • 3,097 Sq Ft

  182 Chardonnay Ct, Winchester, KY 40391

  First time on the market! This one-owner, all brick home offers 5 bedrooms, 2.5 baths, and sits on a spacious 0.6-acre lot. The well-designed floor plan provides plenty of room for family living and entertaining. The finished basement features a dedicated office and recreation room, offering flexible space for work, hobbies, or play. Enjoy the quality and durability of brick construction, a large

  Kathryn Cheuvront Coldwell Banker McMahan

  182 Chardonnay Ct, Winchester, KY 40391
• 

  

  /30

  $310,900

  Sold Sep 12, 2025

  115 Hampton Ave, Winchester, KY 40391

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

  Last Sold Summary

  • 4% Below List Price
  • $102/SF
  • 2 Days On Market

  Current Estimated Value $357,844

  Last Listing Agent Lauren Ball Deborah Ball Realty

  115 Hampton Ave, Winchester, KY 40391
• 

  

  /42

  Est $338,025

  Not Listed For Sale

  1570 Little Stoner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1990

  1570 Little Stoner Rd, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /10

  $550,000

  New Construction

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

  107 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

  107 Bella Shae Way, Winchester, KY 40391
• 

  

  /82

  $385,000

  Sold Nov 07, 2025

  1138 Lafayette Blvd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Above List Price
  • $167/SF
  • 1 Day On Market

  Current Estimated Value $383,121

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1138 Lafayette Blvd, Winchester, KY 40391
• 

  

  /47

  Est $357,116

  Not Listed For Sale

  150 Privacy Ln, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,784 Sq Ft
  • Built 1987

  150 Privacy Ln, Winchester, KY 40391

  Last Sold Summary

  • 103 Days On Market

Showing Results 161 - 200, Page 5 of 18