Winchester, KY Homes

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  $3,500,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /10

  $325,000 Sold Aug 29, 2025

  210 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1999

  Last Sold Summary

  • $205/SF

  Current Estimated Value $327,597

  Last Listing Agent Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
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  /19

  Est $191,160 Not Listed For Sale

  7 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,215 Sq Ft
  • Built 1968

  7 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $144/SF
  • 54 Days On Market

  Last Sold Price $175,000

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  $85,000

  • Land
  • 3.68 Acres
  • $23,098 per Acre

  2465 Flanagan Station Rd, Winchester, KY 40391

  Rare opportunity to own 3.68 acres of vacant land just outside Winchester, ideal for buyers seeking space to build a private custom home in a peaceful rural setting. With electric and water available at the road, this property offers a ready-to-build homesite while maintaining the privacy and open surroundings many buyers are looking for today. Providing quick access to downtown Winchester's

  Shari Frasure Keller Williams Commonwealth

  2465 Flanagan Station Rd, Winchester, KY 40391
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  $464,900 Sold Jun 09, 2025

  275 Runnymeade Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft
  • Built 2017

  Last Sold Summary

  • $186/SF
  • 21 Days On Market

  Current Estimated Value $474,409

  Last Listing Agent Tyson Walters Kassie & Associates

  275 Runnymeade Dr, Winchester, KY 40391
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  /33

  Est $248,801 Not Listed For Sale

  16 Apache Trail, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,831 Sq Ft
  • Built 1999

  16 Apache Trail, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $126/SF
  • 2 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Tammy Prewitt Keller Williams Commonwealth
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  $100,000

  • Land
  • 0.37 Acre
  • $270,270 per Acre

  225 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

  225 Jacob Ct, Winchester, KY 40391
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  /36

  $261,000 Sold Feb 04, 2026

  433 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $212/SF
  • 60 Days On Market

  Current Estimated Value $259,712

  Last Listing Agent Stephen Brashear Real Broker LLC

  433 Wellington Way, Winchester, KY 40391
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  /29

  Est $229,441 Not Listed For Sale

  46 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1970

  46 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $145/SF
  • 2 Days On Market

  Last Sold Price $218,000

  Last Listing Agent Christina Baker United Real Estate Louisville
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  $369,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
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  /2

  $180,000 Sold Jul 01, 2025

  23 Meadowbrook Dr, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 2,250 Sq Ft
  • Built 1953

  Last Sold Summary

  • $80/SF

  Current Estimated Value $190,471

  Last Listing Agent A. Rebecca Woods Woods Realty Group

  23 Meadowbrook Dr, Winchester, KY 40391
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  /33

  Est $241,848 Not Listed For Sale

  14 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 950 Sq Ft
  • Built 1975

  14 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $249/SF
  • 21 Days On Market

  Last Sold Price $237,000

  Last Listing Agent Dylan Langdon The Agency
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  $195,000

  6699 Boonesboro Rd, Winchester, KY 40391

  READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

  Jennifer Ray RE/MAX Elite Lexington

  6699 Boonesboro Rd, Winchester, KY 40391
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  /7

  $55,000 Sold Nov 06, 2025

  76 Clay St, Winchester, KY 40391

  • 1,768 Sq Ft
  • Built 1945

  Last Sold Summary

  • $31/SF
  • 2 Days On Market

  Current Estimated Value $60,898

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  76 Clay St, Winchester, KY 40391
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  /24

  Est $242,962 Not Listed For Sale

  108 Dixon Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,377 Sq Ft
  • Built 2006

  108 Dixon Way, Winchester, KY 40391

  Last Sold Summary

  • 6% Below List Price
  • $187/SF
  • 124 Days On Market

  Last Sold Price $257,500

  Last Listing Agent Angie Conley Dixon Dixon Properties
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  /3

  $670,000 New Construction

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft

  113 Bella Shae Way, Winchester, KY 40391

  Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, Winchester, KY 40391
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  /18

  $99,000 Sold Jun 17, 2025

  27 Oliver St, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1940

  Last Sold Summary

  • 7% Below List Price
  • $80/SF
  • 8 Days On Market

  Current Estimated Value $107,681

  Last Listing Agent Daniel Ellis Metro Max Realty

  27 Oliver St, Winchester, KY 40391
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  /19

  Est $216,518 Not Listed For Sale

  170 Center Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,517 Sq Ft
  • Built 1961

  170 Center Dr, Winchester, KY 40391

  Last Sold Summary

  • 49% Above List Price
  • $96/SF
  • 52 Days On Market

  Last Sold Price $145,000

  Last Listing Agent Larry Moore CENTURY 21 Simpson & Associates
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  /26

  $255,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft

  21 Virginia Ave, Winchester, KY 40391

  Nicely updated and offering plenty of functional space, this home gives you flexibility and room to grow. The main living area flows into an updated kitchen featuring modern finishes, new appliances, butcher-block countertops, and convenient access to the sunroom. Enjoy your morning coffee in the oversized sunroom, then step out to the fully fenced backyard — great for chickens, kids, pets,

  Emily Crump EXP Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
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  /65

  $275,000 Sold Aug 15, 2025

  151 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,873 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $147/SF
  • 130 Days On Market

  Current Estimated Value $270,722

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
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  Est $178,579 Not Listed For Sale

  219 Locust Grove Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,191 Sq Ft
  • Built 1955

  219 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 1% Below List Price
  • $151/SF
  • 27 Days On Market

  Last Sold Price $180,000

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /13

  $1,250,000

  345 Providence Ln, Winchester, KY 40391

  Reasonable Offers Considered!! 120 Acres of Scenic Farmland in Winchester, KY. Discover the beauty and tranquility of country living on this remarkable 120-acre farm nestled in the heart of Clark County, Kentucky. Featuring a picturesque mix of rolling pastureland, mature woodlands, and pond, this property offers endless possibilities for farming, livestock, recreation, or building your dream

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
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  /35

  $248,000 Sold May 22, 2025

  206 Moss Cir, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,773 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $140/SF
  • 20 Days On Market

  Current Estimated Value $257,154

  Last Listing Agent David Baesler Kentucky Dreams Realty

  206 Moss Cir, Winchester, KY 40391
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  /29

  Est $201,601 Not Listed For Sale

  505 Bob o Link Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,228 Sq Ft
  • Built 1960

  505 Bob o Link Dr, Winchester, KY 40391

  Last Sold Summary

  • 22% Above List Price
  • $134/SF
  • 22 Days On Market

  Last Sold Price $165,000

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
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  /31

  $379,717 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  300 Calmes Blvd, Winchester, KY 40391

  Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half

  Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391
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  /3

  $554,651 Sold Jul 10, 2025

  426 Alexis Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Above List Price
  • $231/SF
  • 21 Days On Market

  Current Estimated Value $562,830

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, Winchester, KY 40391
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  /12

  Est $215,432 Not Listed For Sale

  303 Hummingbird Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,169 Sq Ft
  • Built 1960

  303 Hummingbird Rd, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $162/SF
  • 27 Days On Market

  Last Sold Price $189,000

  Last Listing Agent Garry Milton Milton and Associates Real Estate
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  /2

  $100,000

  • Land
  • 1.1 Acres
  • $90,909 per Acre

  270 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

  270 Duclair Dr, Winchester, KY 40391
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  $341,500 Sold Jun 27, 2025

  401 Cedar Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Above List Price
  • $186/SF
  • 2 Days On Market

  Current Estimated Value $343,715

  Last Listing Agent Geneva Wilder Stewart & Co Realty LLC

  401 Cedar Ct, Winchester, KY 40391
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  /7

  Est $185,074 Not Listed For Sale

  301 Hummingbird Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,106 Sq Ft
  • Built 1955

  301 Hummingbird Rd, Winchester, KY 40391

  Last Sold Summary

  • 33% Above List Price
  • $126/SF
  • 41 Days On Market

  Last Sold Price $139,000

  Last Listing Agent Garry Milton Milton and Associates Real Estate
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  $500,000

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
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  $290,000 Sold Mar 12, 2025

  28 Edgewood Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,962 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $148/SF
  • 11 Days On Market

  Current Estimated Value $316,694

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  28 Edgewood Dr, Winchester, KY 40391
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  Est $169,208 Not Listed For Sale

  222 Locust Grove Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft
  • Built 1940

  222 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 25% Above List Price
  • $151/SF
  • 2 Days On Market

  Last Sold Price $135,000

  Last Listing Agent Michelle Blackburn RE/MAX
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  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 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

  205 Codella Dr, Winchester, KY 40391
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  /2

  $39,500 Sold Mar 05, 2025

  418 Fairholme Way, Winchester, KY 40391

  • Land
  • 0.38 Acre
  • $103,947 per Acre

  Last Sold Summary

  • 14% Above List Price
  • 1,594 Days On Market

  Current Estimated Value $97,975

  Last Listing Agent Garnett Davis Tom Goebel & Company

  418 Fairholme Way, Winchester, KY 40391
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  /31

  Est $215,128 Not Listed For Sale

  208 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft
  • Built 1950

  208 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $137/SF
  • 9 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Shane Underwood Keller Williams Commonwealth
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  /3

  $430,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout. The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
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  /2

  $610,000 Sold Aug 29, 2025

  4560 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • $330/SF
  • 1 Day On Market

  Current Estimated Value $612,799

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  4560 Pine Ridge Rd, Winchester, KY 40391
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  /21

  Est $174,334 Not Listed For Sale

  117 Spicer Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1955

  117 Spicer Rd, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $222/SF
  • 45 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Michael Hilario The Agency
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  $110,000

  • Land
  • 2.06 Acres
  • $53,398 per Acre

  1185 Craig Crossing Rd, Winchester, KY 40391

  Lot # 30 contains 2.058 acres of gently rolling land 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

  1185 Craig Crossing Rd, Winchester, KY 40391

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