Winchester, KY Homes

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  /26

  Est $262,227 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  20 Jackson St, Winchester, KY 40391

  20 Jackson St, Winchester, KY 40391
• 

  

  

  /4

  $10,000

  • Land
  • 0.17 Acre
  • $58,824 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
• 

  

  

  /22

  $193,000 Sold Jun 06, 2025

  116 Linden Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Built 1945

  Last Sold Summary

  • 2% Below List Price
  • $166/SF
  • 3 Days On Market

  Current Estimated Value $199,798

  Last Listing Agent Jeremy Perryman United Real Estate Bluegrass

  116 Linden Ave, Winchester, KY 40391
• 

  

  

  /25

  Est $221,771 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  21 Vine St, Winchester, KY 40391

  21 Vine St, Winchester, KY 40391
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  /7

  $180,000

  • Land
  • 4.45 Acres
  • $40,449 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.450 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
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  /19

  $220,000 Sold Apr 23, 2025

  112 Central Ave, Winchester, KY 40391

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

  Last Sold Summary

  • 1% Above List Price
  • $183/SF
  • 1 Day On Market

  Current Estimated Value $226,382

  Last Listing Agent Nena Honaker Tom Goebel & Company

  112 Central Ave, Winchester, KY 40391
• 

  

  /39

  Est $283,511 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,183 Sq Ft

  217 E Washington St, Winchester, KY 40391

  217 E Washington St, Winchester, KY 40391
• 

  

  /14

  $159,900

  • Land
  • 2.66 Acres
  • $60,113 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
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  /26

  $210,000 Sold Jan 24, 2025

  3641 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1961

  Last Sold Summary

  • 11% Below List Price
  • $188/SF
  • 61 Days On Market

  Current Estimated Value $217,543

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  3641 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /27

  Est $176,032 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  47 Buckner St, Winchester, KY 40391

  47 Buckner St, Winchester, KY 40391
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  /39

  $295,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,979 Sq Ft

  8 Village Dr, Winchester, KY 40391

  Newly renovated 3 bedroom, 2 full bathroom home located close to downtown, shopping, and medical services as well as College Park which features a indoor pool, tennis, pickleball courts, and much more. Home features all new paint, flooring, updated bathrooms, updated appliances, new lighting, and much, much more. Basement has large Family Room with bar. This home is ready for all your family

  Keith Wilson Coldwell Banker McMahan

  8 Village Dr, Winchester, KY 40391
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  /2

  $85,000 Sold Dec 12, 2025

  1385 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 6.43 Acres
  • $13,219 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 6 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1385 Sewell Shop Rd, Winchester, KY 40391
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  /26

  Est $193,661 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft

  150 W Broadway St, Winchester, KY 40391

  150 W Broadway St, Winchester, KY 40391
• 

  

  /36

  $289,900 Pending

  • 4 Beds
  • 3 Baths
  • 1,944 Sq Ft

  424 Waycross Dr, Winchester, KY 40391

  424 Waycross Drive offers more space than you might expect, with a layout designed to give you room to spread out and truly live. Between the finished basement and the backyard you're sure to enjoy, this home delivers flexibility for everyday life, entertaining, and everything in between. From the inviting front porch to the bright, vaulted main living area, it feels welcoming and comfortable the

  Kymberly McCreary EXP Realty, LLC

  424 Waycross Dr, Winchester, KY 40391
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  /53

  $867,500 Sold Aug 01, 2025

  511 Boone Ave, Winchester, KY 40391

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

  Last Sold Summary

  • 11% Below List Price
  • $185/SF
  • 318 Days On Market

  Current Estimated Value $868,477

  Last Listing Agent Greg Leveridge Block + Lot Real Estate

  511 Boone Ave, Winchester, KY 40391
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  /12

  Est $161,444 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  25 Oliver St, Winchester, KY 40391

  25 Oliver St, Winchester, KY 40391
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  /2

  $78,500

  • Land
  • 0.22 Acre
  • $356,818 per Acre

  Lot 3 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  Melia Hord Keller Williams Legacy Group

  Lot 3 Plantations Dr, Winchester, KY 40391
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  /41

  $310,000 Sold Dec 29, 2025

  1996 White Conkwright Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,055 Sq Ft
  • Built 1966

  Last Sold Summary

  • 9% Below List Price
  • $294/SF
  • 45 Days On Market

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
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  /11

  Est $135,211 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  30 Madison Ave, Winchester, KY 40391

  30 Madison Ave, Winchester, KY 40391
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  /30

  $349,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,475 Sq Ft

  212 Woodbine Ct, Winchester, KY 40391

  Step right up - come on in! Its appeal is undeniable, both inside and out! Move-in ready. This well-maintained all-brick ranch on a full basement is full of charm and functionality! — Inside, you'll love having two separate living areas, 1 upstairs and 1 in the basement with a wood burning fireplace in both rooms. Enjoy the cold winter evenings in front of either of the fireplaces with family and

  Kathy Burton Coldwell Banker McMahan

  212 Woodbine Ct, Winchester, KY 40391
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  /38

  $599,500 Sold Sep 08, 2025

  102 Bella Shae Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft
  • Built 2025

  Last Sold Summary

  • $272/SF
  • 72 Days On Market

  Current Estimated Value $606,898

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
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  /25

  Est $189,333 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  15 Madison Ave, Winchester, KY 40391

  15 Madison Ave, Winchester, KY 40391
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  /61

  $524,900 Pending

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

  5515 Van Meter Rd, Winchester, KY 40391

  Welcome to your dream home, perfectly nestled in a highly desired location. This stunning property spans a generous 5 acres, offering an idyllic setting for homesteading. Experience the best of country living with the convenience of nearby amenities. The home boasts beautiful views that will take your breath away every morning. Imagine waking up to the serene beauty of nature, right at your

  Robyn Bradley Woods Realty Group

  5515 Van Meter Rd, Winchester, KY 40391
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  /34

  $333,900 Sold Jul 28, 2025

  366 Hanover Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,162 Sq Ft
  • Built 2001

  Last Sold Summary

  • $154/SF
  • 2 Days On Market

  Current Estimated Value $338,937

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  366 Hanover Dr, Winchester, KY 40391
• 

  

  /20

  Est $134,143 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,776 Sq Ft

  2 1st St, Winchester, KY 40391

  2 1st St, Winchester, KY 40391
• 

  

  /34

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  12 Linden Ave, Winchester, KY 40391

  Cute ranch with easy access to I-64 and downtown Winchester. 3 bedrooms with 2 full baths with 1 car detached garage with fenced in back yard. This property has a interesting feature of a building that's 14 x 40 that has been a rental but can be used as storage or a mother in-law suite.

  Roni Porter RE/MAX Creative Realty

  12 Linden Ave, Winchester, KY 40391
• 

  

  /37

  $220,000 Sold Sep 23, 2025

  213 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 4 Days On Market

  Current Estimated Value $220,116

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
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  /16

  Est $184,952 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,298 Sq Ft

  123 2nd St, Winchester, KY 40391

  123 2nd St, Winchester, KY 40391
• 

  

  /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
• 

  /2

  $110,000 Sold May 13, 2025

  140 Duclair Dr, Winchester, KY 40391

  • Land
  • 0.42 Acre
  • $261,905 per Acre

  Last Sold Summary

  • 900 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  140 Duclair Dr, Winchester, KY 40391
• 

  

  /74

  Est $517,395 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,941 Sq Ft

  4 Moundale Ave, Winchester, KY 40391

  4 Moundale Ave, Winchester, KY 40391
• 

  

  /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 Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Real Estate

  145 Codella Dr, Winchester, KY 40391
• 

  

  /44

  $515,000 Sold May 19, 2025

  31 Bonnie Brook Ln, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 4,091 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $126/SF
  • 294 Days On Market

  Current Estimated Value $538,364

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

  31 Bonnie Brook Ln, Winchester, KY 40391
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  /73

  Est $564,108 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,236 Sq Ft

  12 Moundale Ave, Winchester, KY 40391

  12 Moundale Ave, Winchester, KY 40391
• 

  

  /25

  $248,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,342 Sq Ft

  120 Jackson St, Winchester, KY 40391

  Step into modern comfort just minutes from the heart of downtown Winchester. This nearly new home blends contemporary style with timeless charm. Featuring bright, open living spaces, and thoughtful upgrades throughout, it offers a move-in-ready opportunity in one of Winchester's most convenient locations.

  Hannah Toole Coldwell Banker McMahan

  120 Jackson St, Winchester, KY 40391
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  /14

  $200,000 Sold Sep 19, 2025

  9711 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 11% Below List Price
  • 19 Days On Market

  Last Listing Agent Jessica Maloney Denniston Realty

  9711 Ironworks Rd, Winchester, KY 40391
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  /43

  Est $284,501 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,009 Sq Ft

  373 Crescent Ave, Winchester, KY 40391

  373 Crescent Ave, Winchester, KY 40391
• 

  

  /68

  $899,000 Pending

  • 5 Beds
  • 4 Baths
  • 4,058 Sq Ft

  2447 Clintonville Rd, Winchester, KY 40391

  What a great opportunity to own 3 acres just 15 minutes from Man O War and 20 minutes to the Hamburg Shopping Area. The move in ready property features a beautiful brick home built by builder, Michael Childers, to use as his main residence. The property also has a 3 car detached Garage which is deep enough to hold 6 cars and one door is tall for storage of a Recreational Vehicle. It has been

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  2447 Clintonville Rd, Winchester, KY 40391
• 

  

  /75

  $490,000 Sold Sep 26, 2025

  497 Goose Creek Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,972 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 2 Days On Market

  Current Estimated Value $473,261

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
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  /38

  Est $258,832 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,540 Sq Ft

  377 Crescent Ave, Winchester, KY 40391

  377 Crescent Ave, Winchester, KY 40391

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