Winchester, KY Homes

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  /53

  $80,000 Sold Apr 30, 2025

  307 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • Built 1950

  Last Sold Summary

  • 33% Below List Price
  • $49/SF
  • 67 Days On Market

  Current Estimated Value $116,376

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  307 Jackson St, Winchester, KY 40391
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  /71

  Est $331,487 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,402 Sq Ft

  16 French Ave, Winchester, KY 40391

  16 French Ave, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.32 Acre
  • $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
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  /32

  $285,000 Sold Jul 03, 2025

  602 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,690 Sq Ft
  • Built 1976

  Last Sold Summary

  • 11% Below List Price
  • $169/SF
  • 168 Days On Market

  Current Estimated Value $285,032

  Last Listing Agent Ryan O'Gara Real Broker, LLC

  602 Laura Dr, Winchester, KY 40391
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  /41

  Est $282,775 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,395 Sq Ft

  254 S Highland St, Winchester, KY 40391

  254 S Highland St, Winchester, KY 40391
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  $384,900 New Construction

  • 4 Beds
  • 4.5 Baths

  3600 Crowe Ridge Rd, Winchester, KY 40391

  Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 20' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

  Maggie Napier Napier Realtors

  3600 Crowe Ridge Rd, Winchester, KY 40391
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  /2

  $401,500 Sold May 15, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1998

  Last Sold Summary

  • $201/SF

  Current Estimated Value $403,666

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
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  /24

  Est $195,922 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,530 Sq Ft

  54 Winn Ave, Winchester, KY 40391

  54 Winn Ave, Winchester, KY 40391
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  /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
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  /17

  $595,000 Sold Nov 17, 2025

  304 Winterberry Dr, Winchester, KY 40391

  • 7 Beds
  • 4 Baths
  • 4,386 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $136/SF
  • 10 Days On Market

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
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  /33

  Est $272,065 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  144 E Broadway St, Winchester, KY 40391

  144 E Broadway St, Winchester, KY 40391
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  /10

  $215,000

  211 Ashton Oak Way, Winchester, KY 40391

  Here is the Blank Canvas to build your Dream Home in the Plantation Subdivision. This two story brick building, formerly the Sales Office for the Subdivision, has been gutted to offer the unique opportunity to build a 3118 Sq Ft Home consisting of Four Bedrooms, Two and Half Baths, an open concept on the main level with the addition of a two car garage. Contact listing agent to discuss current

  Melia Hord Keller Williams Legacy Group

  211 Ashton Oak Way, Winchester, KY 40391
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  /2

  $185,000 Sold Nov 28, 2025

  23 Hillcrest Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,557 Sq Ft
  • Built 1962

  Last Sold Summary

  • 12% Below List Price
  • $119/SF
  • 18 Days On Market

  Last Listing Agent Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
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  /13

  Est $258,995 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,445 Sq Ft

  130 E Broadway St, Winchester, KY 40391

  130 E Broadway St, Winchester, KY 40391
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  /22

  $145,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  417 Mount Vernon Dr, Winchester, KY 40391

  A 3 bedroom 2 bath home with a 2 car garage under 150k? Unbelievable! Start off your new year with a new home! Spacious manufactured home in Yorktowne Estates where YOU own your lot! Large primary bedroom, nice living room, huge family room, plenty of dining space, gas range, updated cabinets and sink. Check out that garage!! Private driveway with plenty of parking space, covered porches, metal

  Jason Townsend Kentucky Residential Real Estate, LLC

  417 Mount Vernon Dr, Winchester, KY 40391
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  /18

  $246,500 Sold May 16, 2025

  6278 Irvine Rd, Winchester, KY 40391

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

  Last Sold Summary

  • 7% Below List Price
  • $210/SF
  • 35 Days On Market

  Current Estimated Value $259,809

  Last Listing Agent Angela Yonts EXP Realty, LLC

  6278 Irvine Rd, Winchester, KY 40391
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  /48

  Est $338,525 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,068 Sq Ft

  23 Boone Ave, Winchester, KY 40391

  23 Boone Ave, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.5 Acre
  • $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
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  /32

  $230,000 Sold Mar 21, 2025

  200 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 2002

  Last Sold Summary

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

  Current Estimated Value $244,163

  Last Listing Agent Amy Diamond ERA Select Real Estate

  200 Bracken Ct, Winchester, KY 40391
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  /17

  Est $158,613 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft

  21 Franklin Ave, Winchester, KY 40391

  21 Franklin Ave, Winchester, KY 40391
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  /55

  $425,000

  • 5 Beds
  • 3.5 Baths
  • 2,564 Sq Ft

  6504 Combs Ferry Rd, Winchester, KY 40391

  Welcome to an extraordinary residence where luxury, craftsmanship, and natural beauty come together. This house has been taken down to the studs, and thoughtfully rebuilt. This two story home with a walk-out basement sits on 8 acres, adjoining the Lower Howard Creek Preserve, offering unmatched privacy and an exceptional standard of living. The owner spared no expense—every detail has been

  Lucy Martin Jenkins United Real Estate Bluegrass

  6504 Combs Ferry Rd, Winchester, KY 40391
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  /65

  $385,000 Sold Dec 11, 2025

  1731 Ford Hampton Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 27% Below List Price
  • $182/SF
  • 157 Days On Market

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
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  /23

  Est $161,550 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,905 Sq Ft

  353 E Broadway St, Winchester, KY 40391

  353 E Broadway St, Winchester, KY 40391
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  /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
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  /35

  $490,000 Sold Jan 31, 2025

  163 Hawthorne Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,830 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $173/SF
  • 151 Days On Market

  Current Estimated Value $533,908

  Last Listing Agent Michael Hilario The Agency

  163 Hawthorne Dr, Winchester, KY 40391
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  /32

  Est $226,825 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  230 Winn Ave, Winchester, KY 40391

  230 Winn Ave, Winchester, KY 40391
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  /37

  $949,950 Pending

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

  700 Nick Ln, Winchester, KY 40391

  🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you

  Darrell Tackett Dream Maker Realty, LLC

  700 Nick Ln, Winchester, KY 40391
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  /62

  $325,000 Sold Apr 24, 2025

  138 Shanahan Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1996

  Last Sold Summary

  • 23% Below List Price
  • $172/SF
  • 88 Days On Market

  Current Estimated Value $345,992

  Last Listing Agent Christine McDonald FC Tucker Bluegrass

  138 Shanahan Ln, Winchester, KY 40391
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  /17

  Est $171,101 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 956 Sq Ft

  30 Rowland Ave, Winchester, KY 40391

  30 Rowland Ave, Winchester, KY 40391
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  /27

  $182,000

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

  6 Monroe Ave, Winchester, KY 40391

  Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional.

  Lindsey Bivens Berkshire Hathaway de Movellan Properties

  6 Monroe Ave, Winchester, KY 40391
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  /21

  $338,000 Sold Mar 19, 2025

  240 Athens Boonesboro Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,841 Sq Ft
  • Built 1983

  Last Sold Summary

  • 170% Above List Price
  • $184/SF
  • 26 Days On Market

  Current Estimated Value $280,120

  Last Listing Agent Damon Ballinger C Roger Lewis Agency

  240 Athens Boonesboro Rd, Winchester, KY 40391
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  /27

  Est $182,465 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  37 Jackson St, Winchester, KY 40391

  37 Jackson St, Winchester, KY 40391
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  /53

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  174 Hidden Grove Ln, Winchester, KY 40391

  Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just

  Kathryn Cheuvront Coldwell Banker McMahan

  174 Hidden Grove Ln, Winchester, KY 40391
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  /15

  $110,000 Sold Sep 04, 2025

  706 Williamsburg Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 2024

  Last Sold Summary

  • 21% Below List Price
  • $119/SF

  Current Estimated Value $115,817

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan

  706 Williamsburg Dr, Winchester, KY 40391
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  /43

  Est $149,798 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,576 Sq Ft

  116 Park Ave, Winchester, KY 40391

  116 Park Ave, Winchester, KY 40391
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  /4

  $64,900

  • Land
  • 0.52 Acre
  • $124,808 per Acre

  101 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..52 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

  101 Royal Oak Dr, Winchester, KY 40391
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  /28

  $615,000 Sold Jan 31, 2025

  1199 Mcclure Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 4,665 Sq Ft
  • Built 1993

  Last Sold Summary

  • 16% Below List Price
  • $132/SF
  • 129 Days On Market

  Current Estimated Value $630,516

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  1199 Mcclure Rd, Winchester, KY 40391
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  /19

  Est $174,537 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,683 Sq Ft

  Unlisted Address

  Unlisted Address
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  /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
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  /47

  $190,000 Sold Feb 03, 2025

  15 Finley Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Below List Price
  • $136/SF
  • 45 Days On Market

  Current Estimated Value $212,765

  Last Listing Agent Victoria Byrd HomeFirst Real Estate

  15 Finley Rd, Winchester, KY 40391

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