Winchester, KY Homes

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  /29

  $235,000

  Sold Feb 09, 2026

  142 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $193/SF
  • 1 Day On Market

  Current Estimated Value $245,507

  Last Listing Agent Donna Mink Mink Realty

  142 Sturbridge Ln, Winchester, KY 40391
• 

  

  

  /33

  Est $340,816

  Not Listed For Sale

  543 S Maple St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft
  • Built 1946

  543 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass
• 

  

  /2

  $110,000

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

  135 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

  135 Jacob Ct, Winchester, KY 40391
• 

  

  

  /57

  $775,000

  Sold Mar 02, 2026

  1700 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,695 Sq Ft
  • Built 1994

  Last Sold Summary

  • $288/SF
  • 33 Days On Market

  Current Estimated Value $787,625

  Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

  1700 Cabin Creek Rd, Winchester, KY 40391
• 

  

  

  /28

  Est $242,882

  Not Listed For Sale

  358 Crescent Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,764 Sq Ft
  • Built 1950

  358 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass
• 

  

  /33

  $225,000

  • 3 Beds
  • 2.5 Baths
  • 1,522 Sq Ft

  115 Quail Ridge Rd, Winchester, KY 40391

  Looking for low-maintenance living without giving up space? This Winchester townhouse offers three bedrooms, 2.5 baths and a comfortable two-story layout with room to spread out. The main level features a spacious living room with a fireplace, dining area, kitchen and half bath. Just off the dining area, the back deck gives you a nice spot to relax or enjoy some time outside. Upstairs, the

  Michelle Blackburn RE/MAX Creative, Winchester

  115 Quail Ridge Rd, Winchester, KY 40391
• 

  

  /32

  $217,500

  Sold Jul 13, 2026

  525 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $182/SF
  • 11 Days On Market

  Current Estimated Value $218,405

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  525 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /77

  Est $292,954

  Not Listed For Sale

  328 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,709 Sq Ft
  • Built 1900

  328 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  /2

  $110,000

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

  115 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

  115 Jacob Ct, Winchester, KY 40391
• 

  

  /79

  $204,000

  Sold Oct 30, 2025

  133 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft
  • Built 1915

  Last Sold Summary

  • 18% Below List Price
  • $62/SF
  • 20 Days On Market

  Current Estimated Value $244,786

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  133 S Burns Ave, Winchester, KY 40391
• 

  

  /57

  Est $376,557

  Not Listed For Sale

  286 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,689 Sq Ft
  • Built 1910

  286 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
• 

  

  /23

  $184,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  143 Spruce Ct, Winchester, KY 40391

  Welcome to 143 Spruce Court in Winchester! This charming brick ranch offers comfortable one-level living with 3 bedrooms and 1 full bath. Inside, you'll find beautiful hardwood flooring and a warm, inviting layout. Outside, enjoy a well-manicured large corner lot (0.20 ac) with plenty of space to relax or entertain. Conveniently located near a local park featuring a splash park and recreational

  John Wilson Bluegrass Properties Group

  143 Spruce Ct, Winchester, KY 40391
• 

  

  /27

  $135,000

  Sold Sep 09, 2026

  60 Fitch Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,775 Sq Ft
  • Built 1950

  Last Sold Summary

  • 10% Below List Price
  • $76/SF
  • 5 Days On Market

  Current Estimated Value $207,315

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  60 Fitch Ave, Winchester, KY 40391
• 

  

  /34

  Est $278,704

  Not Listed For Sale

  312 S Main St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,355 Sq Ft
  • Built 1920

  312 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Susan Baldwin Threshold Real Estate Services
• 

  

  /23

  $204,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft

  38 Mackay Ave, Winchester, KY 40391

  Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing

  Nena Honaker Tom Goebel & Company

  38 Mackay Ave, Winchester, KY 40391
• 

  

  /62

  $260,000

  Sold Jun 09, 2026

  144 Holly Ave, Winchester, KY 40391

  • 8 Beds
  • 5 Baths
  • 3,637 Sq Ft
  • Built 2001

  Last Sold Summary

  • 19% Below List Price
  • $71/SF
  • 69 Days On Market

  Current Estimated Value $270,917

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  144 Holly Ave, Winchester, KY 40391
• 

  

  /52

  Est $278,837

  Not Listed For Sale

  14 Lisle Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,673 Sq Ft
  • Built 1955

  14 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty
• 

  

  /4

  $635,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,537 Sq Ft

  422 Alexis Way, Winchester, KY 40391

  Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

  Shane Underwood Keller Williams Commonwealth

  422 Alexis Way, Winchester, KY 40391
• 

  

  /28

  $246,000

  Sold Nov 06, 2025

  204 Moss Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,430 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $172/SF
  • 1 Day On Market

  Current Estimated Value $249,303

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
• 

  

  /20

  Est $223,083

  Not Listed For Sale

  18 Lisle Ln, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,082 Sq Ft
  • Built 1950

  18 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Lukas Owens The Brokerage
• 

  

  /23

  $199,900

  $6K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,154 Sq Ft

  606 College St, Winchester, KY 40391

  606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom

  Alyssa Ryan Marshall Lane Real Estate - Lexington

  606 College St, Winchester, KY 40391
• 

  

  /26

  $390,000

  Sold Jul 22, 2026

  178 Hawthorne Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,156 Sq Ft
  • Built 2018

  Last Sold Summary

  • $181/SF
  • 6 Days On Market

  Current Estimated Value $393,652

  Last Listing Agent Tiffani Casey Waizenhofer Real Estate

  178 Hawthorne Dr, Winchester, KY 40391
• 

  

  /54

  Est $331,527

  Not Listed For Sale

  35 Lisle Ln, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft
  • Built 1953

  35 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
• 

  

  /22

  $229,500

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,130 Sq Ft

  527 Hidden Hills Way, Winchester, KY 40391

  NEW roof, NEW kitchen appliances, NEW deck, and more! Welcome to 527 Hidden Hills Way! Located on a quiet cul-de-sac, this renovated one level home is ready for you to move right in. Vaulted ceilings give an open and airy feel, while fresh paint throughout offers a neutral palette for any design style. The spacious kitchen includes plenty of oak cabinetry, a separate pantry, stainless steel

  Jarran Thomas The Agency

  527 Hidden Hills Way, Winchester, KY 40391
• 

  

  /43

  $450,000

  Sold May 26, 2026

  222 Ashton Oak Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,444 Sq Ft
  • Built 2006

  Last Sold Summary

  • $131/SF
  • 4 Days On Market

  Current Estimated Value $453,186

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  222 Ashton Oak Way, Winchester, KY 40391
• 

  

  /28

  Est $379,155

  Not Listed For Sale

  512 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft
  • Built 1950

  512 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Jordan James Lifstyl Real Estate
• 

  /2

  $110,000

  • Land
  • 21,780 Sq Ft
  • $220,000 per Acre

  260 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

  260 Duclair Dr, Winchester, KY 40391
• 

  

  /52

  $230,000

  Sold Jan 20, 2026

  19 Cherokee Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $229,839

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
• 

  

  /49

  Est $411,351

  Not Listed For Sale

  228 Moundale Ave, Winchester, KY 40391

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

  228 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 261 Days On Market

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

  

  /12

  $264,900

  $40K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,214 Sq Ft

  55 Hillcrest Dr, Winchester, KY 40391

  **Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (8 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming home offers excellent

  Nina Vanetten RE/MAX Elite Lexington

  55 Hillcrest Dr, Winchester, KY 40391
• 

  

  /36

  $202,000

  Sold Mar 18, 2026

  58 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $139/SF
  • 15 Days On Market

  Current Estimated Value $201,159

  Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

  58 Hughes Ave, Winchester, KY 40391
• 

  

  /34

  Est $348,434

  Not Listed For Sale

  214 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,928 Sq Ft
  • Built 1930

  214 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 107 Days On Market

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
• 

  

  /26

  $215,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  271 April Way, Winchester, KY 40391

  This charming 2 - story townhouse is in a prime location.. Welcome to this beautifully maintained 2 bedroom, 1.5 bath townhouse offering the perfect blend of comfort, style and convenience. Spread over two spacious levels, this home features an inviting living area, a modern kitchen with ample cabinetry and a cozy dining space-perfect for every day living or entertaining guests. Upstairs,

  Kimberly Fugate Keller Williams Commonwealth

  271 April Way, Winchester, KY 40391
• 

  

  /39

  $395,000

  Sold Jun 18, 2026

  18 Casa Landa Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft
  • Built 1975

  Last Sold Summary

  • $210/SF
  • 0 Days On Market

  Current Estimated Value $390,635

  Last Listing Agent Steve Charles Freedom Realty & Property Management

  18 Casa Landa Way, Winchester, KY 40391
• 

  

  /65

  Est $354,295

  Not Listed For Sale

  408 S Maple St, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,372 Sq Ft
  • Built 1910

  408 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate
• 

  

  /21

  $326,000

  $1K PRICE INCREASE

  • Land
  • 48.54 Acres
  • $6,716 per Acre

  380 Howard Creek Rd Unit 380, Winchester, KY 40391

  Escape to the peace and privacy of this beautiful 48.54-acre unimproved property in a remote rural setting. Featuring a mix of rolling pasture and wooded acreage with gentle slopes, this versatile tract is ideal for farming, cattle, horses, recreation, hunting, or building your dream country retreat. Whether you're looking for productive agricultural land or a private getaway, this property

  Kathy Burton Coldwell Banker McMahan

  380 Howard Creek Rd Unit 380, Winchester, KY 40391
• 

  

  /24

  $90,000

  Sold Mar 23, 2026

  701 Williamsburg Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 996 Sq Ft
  • Built 1971

  Last Sold Summary

  • 7% Below List Price
  • $90/SF
  • 2 Days On Market

  Current Estimated Value $95,436

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  701 Williamsburg Dr, Winchester, KY 40391
• 

  

  /57

  Est $441,239

  Not Listed For Sale

  402 S Maple St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,864 Sq Ft
  • Built 1896

  402 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Kristy Hall The Agency
• 

  

  /4

  $10,000

  $15K PRICE DROP Pending

  • Land
  • 7,274 Sq Ft
  • $59,880 per Acre

  117 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

  Anita McDermott Keller Williams Bluegrass Realty

  117 4th St, Winchester, KY 40391
• 

  

  /27

  $335,000

  Sold Dec 18, 2025

  2198 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 31 Days On Market

  Current Estimated Value $337,246

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors

  2198 Goshen Rd, Winchester, KY 40391

Showing Results 601 - 640, Page 16 of 18