Winchester, KY Homes

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  /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 $325,437

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  407 Fairholme Way, Winchester, KY 40391
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  /17

  Est $226,459 Not Listed For Sale

  2504 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,221 Sq Ft
  • Built 1955

  2504 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 62% Above List Price
  • $115/SF
  • 4 Days On Market

  Last Sold Price $140,000

  Last Listing Agent Brian Weir DIY Listing
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  /17

  $129,900

  • 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
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  /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 $216,067

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  635 Lisletown Ln, Winchester, KY 40391
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  /32

  Est $278,553 Not Listed For Sale

  2615 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft
  • Built 1965

  2615 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Below List Price
  • $174/SF
  • 1 Day On Market

  Last Sold Price $295,000

  Last Listing Agent Jim Woodrum RE/MAX
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  /44

  $269,900 Pending

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

  146 W Lexington Ave, Winchester, KY 40391

  Don't miss this fantastic property located in the heart of Downtown Winchester. There's a great opportunity to use this property for house hacking -- leverage your money by living in one unit and renting out the other! Home could easily be converted into an expansive single-family home with all the charm and space you've been dreaming of. Currently there is a downstairs unit with 5 bedrooms and 2

  Kevin Bradley KB Realty Group

  146 W Lexington Ave, Winchester, KY 40391
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  /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 $493,850

  Last Listing Agent Robyn Bradley Woods Realty Group

  430 Fairholme Way, Winchester, KY 40391
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  /49

  Est $311,311 Not Listed For Sale

  373 Old Ironworks Rd, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,333 Sq Ft
  • Built 1965

  373 Old Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 45% Above List Price
  • $92/SF
  • 138 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Robin Murray The Agency
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  /4

  $64,900 Pending

  • Land
  • 0.64 Acre
  • $101,406 per Acre

  102 Royal Oak Dr, Winchester, KY 40391

  A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..64 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

  Melia Hord Keller Williams Legacy Group

  102 Royal Oak Dr, Winchester, KY 40391
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  /24

  $186,000 Sold May 14, 2025

  205 Arbor Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1994

  Last Sold Summary

  • 3% Above List Price
  • $157/SF
  • 77 Days On Market

  Current Estimated Value $191,354

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  205 Arbor Ct, Winchester, KY 40391
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  /45

  Est $471,301 Not Listed For Sale

  1159 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,244 Sq Ft
  • Built 2007

  1159 Cabin Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $203/SF
  • 14 Days On Market

  Last Sold Price $455,000

  Last Listing Agent Kimberly Fields Coldwell Banker McMahan
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  /8

  $1,500,000

  1015 Old Stone Church Rd, Winchester, KY 40391

  Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

  Walker Mack Bluegrass Property Exchange

  1015 Old Stone Church Rd, Winchester, KY 40391
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  /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 $313,589

  Last Listing Agent Lauren Ball Deborah Ball Realty

  115 Hampton Ave, Winchester, KY 40391
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  /15

  Est $278,661 Not Listed For Sale

  158 Cabin Creek Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 2005

  158 Cabin Creek Heights, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $168/SF
  • 5 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC
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  /87

  $3,100,000

  • 6 Beds
  • 5 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  150 acres of pure Kentucky beauty in Winchester, on the market for the first time ever. This incredible cattle farm has been owned by the same family since 1803 and is now ready for its next chapter. With rolling land, four barns, two storage sheds, four ponds, a creek, and two homes, this estate is truly unmatched. If you've been waiting for your dream property, this is it.

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
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  /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 $381,292

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1138 Lafayette Blvd, Winchester, KY 40391
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  /43

  Est $484,399 Not Listed For Sale

  2100 Ecton Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,060 Sq Ft
  • Built 1978

  2100 Ecton Rd, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $228/SF
  • 35 Days On Market

  Last Sold Price $470,000

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
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  /33

  $360,000

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

  1270 Sewell Shop Rd, Winchester, KY 40391

  Country Living with Convenience — 5 Fenced Acres in Winchester, KY Enjoy the perfect blend of peaceful country living and easy access to town with this well-maintained home on 5 fully fenced acres in Winchester, KY. Conveniently located just 30 minutes to Lexington, 5 miles to I-64, 10 minutes to Mt. Sterling, and 15 minutes to Winchester, this property offers country living without sacrificing

  Meggan Batey Keller Williams Legacy Group

  1270 Sewell Shop Rd, Winchester, KY 40391
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  /17

  $190,000 Sold Sep 10, 2025

  114 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,059 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $179/SF
  • 50 Days On Market

  Current Estimated Value $189,951

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  114 Sunset Heights, Winchester, KY 40391
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  /44

  Est $503,253 Not Listed For Sale

  601 Wades Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,070 Sq Ft
  • Built 2000

  601 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $237/SF
  • 7 Days On Market

  Last Sold Price $490,000

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
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  /3

  $70,000

  • Land
  • 2.04 Acres
  • $34,314 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and let the land grow in value. This lot totaling 2.041 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
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  /48

  $222,500 Sold Jul 28, 2025

  217 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Above List Price
  • $108/SF
  • 2 Days On Market

  Current Estimated Value $224,159

  Last Listing Agent Robin Murray The Agency

  217 Locust Grove Rd, Winchester, KY 40391
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  /127

  Est $699,559 Not Listed For Sale

  1924 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,514 Sq Ft
  • Built 1993

  1924 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 12% Above List Price
  • $249/SF
  • 123 Days On Market

  Last Sold Price $625,000

  Last Listing Agent Greg Wood Freedom Realty & Property Management
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  /31

  $215,000

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

  5434 Pine Ridge Rd, Winchester, KY 40391

  Jim Woodrum RE/MAX Creative, Winchester

  5434 Pine Ridge Rd, Winchester, KY 40391
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  /34

  $342,000 Sold Sep 16, 2025

  3560 Wades Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1950

  Last Sold Summary

  • 10% Below List Price
  • $262/SF
  • 37 Days On Market

  Current Estimated Value $333,408

  Last Listing Agent Sarah MacHarg Kentucky Land and Home

  3560 Wades Mill Rd, Winchester, KY 40391
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  /3

  Est $387,880 Not Listed For Sale

  1591 Gay Evans Rd, Winchester, KY 40391

  • 3 Beds
  • 1,260 Sq Ft
  • Built 1940

  1591 Gay Evans Rd, Winchester, KY 40391

  Last Sold Summary

  • 18% Above List Price
  • $262/SF
  • 17 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Holly Goeing The Agency
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  /33

  $367,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,811 Sq Ft

  446 Tremont Ln, Winchester, KY 40391

  Are your ready for a lifestyle change? Do you need more space? How about approximately 2800 square feet with four bedrooms and 2-1/2 baths. A nice size corner lot with side entry 2 car garage. Walkout patio, walk in closet, two story entry and gas fireplace are just a few of the features in this home. Recent upgrades include TWO new hot water heaters, UV filtration installed in HVAC, Full privacy

  Dylan Langdon The Agency

  446 Tremont Ln, Winchester, KY 40391
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  /32

  $195,700 Sold Mar 10, 2025

  162 French Ave, Winchester, KY 40391

  • 4 Beds
  • 1 Bath
  • 2,327 Sq Ft
  • Built 1920

  Last Sold Summary

  • 11% Below List Price
  • $84/SF
  • 15 Days On Market

  Current Estimated Value $230,467

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  162 French Ave, Winchester, KY 40391
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  /50

  Est $661,762 Not Listed For Sale

  1909 Gay Evans Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft
  • Built 1998

  1909 Gay Evans Rd, Winchester, KY 40391

  Last Sold Summary

  • $207/SF
  • 9 Days On Market

  Last Sold Price $663,500

  Last Listing Agent Steve Moore Bluegrass Sotheby's International Realty
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  /10

  $775,000

  • Land
  • 2.6 Acres
  • $298,077 per Acre

  529 Bullion Blvd Unit 3B, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided.Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One,

  Greg Leveridge Block + Lot Real Estate

  529 Bullion Blvd Unit 3B, Winchester, KY 40391
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  /5

  $41,500 Sold Sep 15, 2025

  434 Fairholme Way, Winchester, KY 40391

  • Land
  • 0.36 Acre
  • $115,278 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 6 Days On Market

  Current Estimated Value $52,970

  Last Listing Agent Justin Lee JL Realty Group, LLC

  434 Fairholme Way, Winchester, KY 40391
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  /96

  Est $830,641 Not Listed For Sale

  1995 Gay Evans Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,272 Sq Ft
  • Built 1998

  1995 Gay Evans Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $239/SF
  • 82 Days On Market

  Last Sold Price $782,000

  Last Listing Agent Andrea Coughtry Lifstyl Real Estate
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  /11

  $50,000

  • Land
  • 0.41 Acre
  • $121,951 per Acre

  308 Duclair Dr, Winchester, KY 40391

  Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

  Joseph Miller Keller Williams Legacy Group

  308 Duclair Dr, Winchester, KY 40391
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  /48

  $330,000 Sold May 23, 2025

  113 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,090 Sq Ft
  • Built 1970

  Last Sold Summary

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

  Current Estimated Value $292,232

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  113 Holiday Rd, Winchester, KY 40391
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  /60

  Est $162,547 Not Listed For Sale

  1333 Jackson Ferry Rd, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,492 Sq Ft
  • Built 1964

  1333 Jackson Ferry Rd, Winchester, KY 40391

  Last Sold Summary

  • 30% Above List Price
  • $84/SF
  • 60 Days On Market

  Last Sold Price $125,000

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management
• 

  /2

  $14,100,000

  • Land
  • 274.52 Acres
  • $51,362 per Acre

  2395 Paris Rd, Winchester, KY 40391

  NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development—an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods.
 Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family

  Melia Hord Keller Williams Legacy Group

  2395 Paris Rd, Winchester, KY 40391
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  /58

  $830,000 Sold Feb 27, 2026

  2395 Becknerville Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,234 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 8 Days On Market

  Current Estimated Value $837,685

  Last Listing Agent Crystal Towe The Real Estate Group

  2395 Becknerville Rd, Winchester, KY 40391
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  /10

  Est $1,252,412 Not Listed For Sale

  4479 Muddy Creek Rd, Winchester, KY 40391

  • Studio
  • 3,351 Sq Ft
  • Built 1935

  4479 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $358/SF
  • 28 Days On Market

  Last Sold Price $1,200,000

  Last Listing Agent Joseph E.C. Hagen Imperium Real Estate Group, LLC
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  /34

  $275,000

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  20 Bon-Haven Ave, Winchester, KY 40391

  Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike.Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and

  Jacqueline Marchildon Lifstyl Real Estate

  20 Bon-Haven Ave, Winchester, KY 40391
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  /38

  $173,000 Sold Sep 22, 2025

  44 5th St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $136/SF
  • 2 Days On Market

  Current Estimated Value $174,606

  Last Listing Agent Tirza Cooper The Howard Realty Co

  44 5th St, Winchester, KY 40391

Showing Results 161 - 200, Page 5 of 18