Winchester, KY Homes

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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 $338,294

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  366 Hanover Dr, Winchester, KY 40391
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  /27

  Est $167,303 Not Listed For Sale

  37 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1940

  37 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $116/SF
  • 30 Days On Market

  Last Sold Price $162,000

  Last Listing Agent O. Debbie Pennington CENTURY 21 Advantage Realty
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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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  /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 $219,271

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
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  /43

  Est $133,937 Not Listed For Sale

  116 Park Ave, Winchester, KY 40391

  • 1 Bed
  • 1 Bath
  • 1,576 Sq Ft
  • Built 1940

  116 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 23% Above List Price
  • $69/SF
  • 23 Days On Market

  Last Sold Price $108,500

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /4

  $64,900 Pending

  • 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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  /10

  $100,000 Sold Feb 20, 2026

  17 Waveland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $94/SF
  • 4 Days On Market

  Current Estimated Value $144,535

  Last Listing Agent Darrell Lewis DIYFlatFee.Com

  17 Waveland Ave, Winchester, KY 40391
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  /19

  Est $163,182 Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 1 Bath
  • 1,683 Sq Ft
  • Built 2023

  Unlisted Address

  Last Sold Summary

  • 39% Above List Price
  • $70/SF
  • 6 Days On Market

  Last Sold Price $117,000

  Last Listing Agent Darrell Lewis DIY Flat Fee.com
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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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  /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
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  /26

  Est $247,645 Not Listed For Sale

  20 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1940

  20 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $146/SF
  • 10 Days On Market

  Last Sold Price $240,900

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling
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  /7

  $150,000

  • Land
  • 4.21 Acres
  • $35,629 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.21 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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  /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 $541,244

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

  31 Bonnie Brook Ln, Winchester, KY 40391
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  /25

  Est $207,708 Not Listed For Sale

  21 Vine St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1960

  21 Vine St, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $190/SF
  • 0 Days On Market

  Last Sold Price $204,900

  Last Listing Agent Kymberly McCreary EXP Realty, LLC
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  /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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  /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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  /39

  Est $260,174 Not Listed For Sale

  217 E Washington St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,183 Sq Ft
  • Built 1940

  217 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 11% Above List Price
  • $108/SF
  • 21 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Joshua Lynch The Brokerage
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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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  /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 $461,655

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
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  /27

  Est $163,633 Not Listed For Sale

  47 Buckner St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1930

  47 Buckner St, Winchester, KY 40391

  Last Sold Summary

  • 64% Above List Price
  • $61/SF
  • 17 Days On Market

  Last Sold Price $100,000

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
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  /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. Walk to the breweries, shopping and restaurants. 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
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  /25

  $287,000 Sold Aug 20, 2025

  220 Mcdowell Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $205/SF
  • 36 Days On Market

  Current Estimated Value $298,852

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
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  /26

  Est $175,609 Not Listed For Sale

  150 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1940

  150 W Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $85/SF
  • 39 Days On Market

  Last Sold Price $145,000

  Last Listing Agent Michelle Blackburn RE/MAX
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  /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
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  /33

  $240,000 Sold Sep 10, 2025

  752 Wayland Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $97/SF
  • 18 Days On Market

  Current Estimated Value $251,082

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391
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  /12

  Est $157,142 Not Listed For Sale

  25 Oliver St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1940

  25 Oliver St, Winchester, KY 40391

  Last Sold Summary

  • 47% Above List Price
  • $119/SF
  • 1 Day On Market

  Last Sold Price $107,000

  Last Listing Agent Brianna Wallace Dream Maker Realty, LLC
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  /23

  $224,500 Pending

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

  508 Acadia Way, Winchester, KY 40391

  This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. The property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  508 Acadia Way, Winchester, KY 40391
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  /24

  $275,000 Sold Mar 02, 2026

  434 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2012

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $237,019

  Last Listing Agent Joshua Davis The Agency

  434 Paisley Ct, Winchester, KY 40391
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  /11

  Est $133,317 Not Listed For Sale

  30 Madison Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1996

  30 Madison Ave, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $143/SF
  • 18 Days On Market

  Last Sold Price $110,000

  Last Listing Agent Michelle Newman Team Pannell Real Estate
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  /60

  $279,950

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  115 Watercrest Cir, Winchester, KY 40391

  Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? The sellers are

  Darrell Tackett Dream Maker Realty, LLC

  115 Watercrest Cir, Winchester, KY 40391
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  /29

  $262,500 Sold Feb 18, 2026

  410 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 69 Days On Market

  Current Estimated Value $264,396

  Last Listing Agent Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
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  /25

  Est $172,034 Not Listed For Sale

  15 Madison Ave, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1996

  15 Madison Ave, Winchester, KY 40391

  Last Sold Summary

  • 15% Above List Price
  • $155/SF
  • 1 Day On Market

  Last Sold Price $149,000

  Last Listing Agent Tyanne Whitworth RE/MAX
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  /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
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  /27

  $245,000 Sold Jun 13, 2025

  8 Seneca Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $142/SF
  • 8 Days On Market

  Current Estimated Value $245,269

  Last Listing Agent Michael Hilario The Agency

  8 Seneca Dr, Winchester, KY 40391
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  /20

  Est $141,690 Not Listed For Sale

  2 1st St, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 1945

  2 1st St, Winchester, KY 40391

  Last Sold Summary

  • 91% Above List Price
  • $42/SF
  • 0 Days On Market

  Last Sold Price $74,000

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
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  /2

  $100,000

  • Land
  • 0.68 Acre
  • $147,059 per Acre

  100 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

  100 Duclair Dr, Winchester, KY 40391
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  /47

  $375,000 Sold Mar 07, 2025

  372 Arrowhead Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,744 Sq Ft
  • Built 2001

  Last Sold Summary

  • $137/SF
  • 2 Days On Market

  Current Estimated Value $396,186

  Last Listing Agent Lori Tolson Lifstyl Real Estate

  372 Arrowhead Ln, Winchester, KY 40391
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  /16

  Est $186,723 Not Listed For Sale

  123 2nd St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,298 Sq Ft

  123 2nd St, Winchester, KY 40391

  Last Sold Summary

  • 42% Above List Price
  • $101/SF
  • 0 Days On Market

  Last Sold Price $131,723

  Last Listing Agent Roscoe Riley Blu Horizon Real Estate
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  /59

  $820,000

  • 2 Beds
  • 1.5 Baths
  • 2,361 Sq Ft

  455 Davis Ln, Winchester, KY 40391

  Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

  Dale Hatton Dream Maker Realty, LLC

  455 Davis Ln, Winchester, KY 40391
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  /26

  $239,900 Sold Jun 23, 2025

  134 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Below List Price
  • $128/SF
  • 74 Days On Market

  Current Estimated Value $248,008

  Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

  134 Boone Ave, Winchester, KY 40391

Showing Results 521 - 560, Page 14 of 18