Winchester, KY Homes

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  /41

  $247,000 Sold Sep 19, 2025

  3588 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $161/SF
  • 4 Days On Market

  Current Estimated Value $248,114

  Last Listing Agent Zach Johnson The Brokerage

  3588 Stamper Dr, Winchester, KY 40391
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  /29

  Est $231,970 Not Listed For Sale

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

  46 Hiawatha Trail, Winchester, KY 40391

  46 Hiawatha Trail, Winchester, KY 40391
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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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  /20

  $205,000 Sold Aug 19, 2025

  202 Custer Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Above List Price
  • $184/SF
  • 2 Days On Market

  Current Estimated Value $202,552

  Last Listing Agent Brittany Beer EXP Realty, LLC

  202 Custer Ct, Winchester, KY 40391
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  /33

  Est $264,133 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 950 Sq Ft

  14 Hiawatha Trail, Winchester, KY 40391

  14 Hiawatha Trail, Winchester, KY 40391
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  /6

  $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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  /15

  $176,000 Sold Oct 17, 2025

  7575 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Below List Price
  • 2 Days On Market

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391
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  /20

  Est $219,314 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,593 Sq Ft

  4 Hiawatha Trail, Winchester, KY 40391

  4 Hiawatha Trail, Winchester, KY 40391
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  /57

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,695 Sq Ft

  1700 Cabin Creek Rd, Winchester, KY 40391

  The possibilities are endless with this exceptional rural property on 12+/- fully fenced acres. This beautifully updated 3-bedroom, 2.5-bath home features a renovated kitchen and baths, wide-plank cherry hardwood floors, heated travertine floors in two bathrooms, a spacious primary suite with sitting area and attached office or studio, dedicated laundry/mudroom with secondary pantry and a sunroom

  Alysia Niva Century 21 Advantage Realty - Georgetown

  1700 Cabin Creek Rd, Winchester, KY 40391
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  /40

  $400,000 Sold May 23, 2025

  109 Monet Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,432 Sq Ft
  • Built 1995

  Last Sold Summary

  • 5% Below List Price
  • $164/SF
  • 26 Days On Market

  Current Estimated Value $420,819

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  109 Monet Blvd, Winchester, KY 40391
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  /24

  Est $268,158 Not Listed For Sale

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

  108 Dixon Way, Winchester, KY 40391

  108 Dixon Way, Winchester, KY 40391
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  /21

  $249,900

  • 3 Beds
  • 1 Bath
  • 1,494 Sq Ft

  720 Estes Dr, Winchester, KY 40391

  This charming brick ranch is truly move-in ready. Offering 3 bedrooms, 1.5 baths, a welcoming living room, a cozy den, and kitchen with appliances, this home blends comfort and convenience with ease. Enjoy the natural light and peaceful views from the screened-in sunporch, perfect for relaxing. Updates include new kitchen flooring, refinished hardwood floors, and updated trim that gives the home

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  720 Estes Dr, 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 $331,381

  Last Listing Agent Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
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  /19

  Est $226,889 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,517 Sq Ft

  170 Center Dr, Winchester, KY 40391

  170 Center Dr, Winchester, KY 40391
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  /53

  $279,500

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  724 Terry Dr, Winchester, KY 40391

  Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-bedroom, 2 full bath split-level home featuring a cozy finished basement perfect for relaxing or entertaining. Enjoy both front and rear porches, ideal for morning coffee or evening gatherings. The spacious, fenced-in backyard offers privacy and room to play, garden, or unwind. Nestled in a quiet

  Darrell Tackett Dream Maker Realty, LLC

  724 Terry Dr, Winchester, KY 40391
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  /32

  $160,000 Sold Feb 28, 2025

  7 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,626 Sq Ft
  • Built 1969

  Last Sold Summary

  • 14% Below List Price
  • $98/SF
  • 114 Days On Market

  Current Estimated Value $205,477

  Last Listing Agent Marie Waddell-Pearson RE/MAX Creative Realty

  7 Pocahontas Trail, Winchester, KY 40391
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  /58

  Est $197,056 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,191 Sq Ft

  219 Locust Grove Rd, Winchester, KY 40391

  219 Locust Grove Rd, Winchester, KY 40391
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  /24

  $188,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft

  27 Ashland Ave, Winchester, KY 40391

  Motivated Seller! Move right in and enjoy this well-maintained 3-bed, 2-bath ranch in the heart of Massie Addition! Thoughtfully updated with a recent roof on both the home and garage, a brand-new hot water heater (2025), and a modern, fresh interior paint palette, this home is ready for you. A home warranty covering all major systems and appliances is included for added peace of mind. This

  Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
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  /77

  $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 $469,941

  Last Listing Agent Tyson Walters Kassie & Associates

  275 Runnymeade Dr, Winchester, KY 40391
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  /29

  Est $218,534 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,228 Sq Ft

  505 Bob o Link Dr, Winchester, KY 40391

  505 Bob o Link Dr, Winchester, KY 40391
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  /23

  $345,900

  • 3 Beds
  • 2.5 Baths
  • 3,868 Sq Ft

  225 Plantations Dr, Winchester, KY 40391

  Welcome to 225 Plantations Drive, a beautifully maintained home in the desirable Royal Oaks Subdivision. This charming three-bedroom, two-and-a-half-bath residence is in wonderful condition and move-in ready! This is home comes with a wonderful floorplan that has a primary bedroom with built-in's on the first floor, Kitchen with granite and stainless appliances and deck has been updated with Trex

  John Wilson Bluegrass Properties Group

  225 Plantations 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 $188,354

  Last Listing Agent A. Rebecca Woods Woods Realty Group

  23 Meadowbrook Dr, Winchester, KY 40391
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  /12

  Est $229,416 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,169 Sq Ft

  303 Hummingbird Rd, Winchester, KY 40391

  303 Hummingbird Rd, Winchester, KY 40391
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  /3

  $1,200 Pending

  • Land
  • 2.57 Acres
  • $467 per Acre

  507 Tech Dr, Winchester, KY 40391

  For lease-Frontage on Rolling Hills Rd, and Tech Drive.I-64 visibility, ideally located commercial property. Paved driveway and gravel lot.$1200 per .25 acre/per month

  Holly Spradlin KY Realty Co

  507 Tech Dr, 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

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  76 Clay St, Winchester, KY 40391
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  /7

  Est $188,320 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,106 Sq Ft

  301 Hummingbird Rd, Winchester, KY 40391

  301 Hummingbird Rd, Winchester, KY 40391
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  /27

  $269,000

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  222 Bracken Ct, Winchester, KY 40391

  Great flloor plan -- great location -- GREAT price! Nice open space on the first level with fully-equipped kitchen and dining area and a very generously-sized family room. Backs up to Ecton Road so you are not looking at the back of another house. Primary bedroom and laundry upstairs with two other bedrooms. All three bedrooms have walk-in closets! The storage building conveys. This home is less

  Jim Woodrum RE/MAX Creative, Winchester

  222 Bracken Ct, 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 $104,701

  Last Listing Agent Daniel Ellis Metro Max Realty

  27 Oliver St, Winchester, KY 40391
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  /30

  Est $187,097 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  222 Locust Grove Rd, Winchester, KY 40391

  222 Locust Grove Rd, Winchester, KY 40391
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  /30

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  357 E Washington St, Winchester, KY 40391

  Completely renovated and move-in ready, this beautifully updated home combines modern finishes with an unbeatable walkable location. Featuring a brand-new roof, new flooring throughout, and fresh paint from top to bottom, every inch of this home has been thoughtfully refreshed. The kitchen has been fully remodeled with new cabinets, new appliances, and a stylish butcher block countertop—perfect

  Dylan Justice GSP Homes

  357 E Washington St, 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 $268,446

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
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  /31

  Est $235,274 Not Listed For Sale

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

  208 Locust Grove Rd, Winchester, KY 40391

  208 Locust Grove Rd, Winchester, KY 40391
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  /47

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  23 Kittison Dr, Winchester, KY 40391

  ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.

  Teresa Richmond Freedom Realty & Property Management

  23 Kittison Dr, 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 $252,898

  Last Listing Agent David Baesler Kentucky Dreams Realty

  206 Moss Cir, Winchester, KY 40391
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  /21

  Est $198,793 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 720 Sq Ft

  117 Spicer Rd, Winchester, KY 40391

  117 Spicer Rd, Winchester, KY 40391
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  /33

  $215,000

  • 4 Beds
  • 1 Bath
  • 1,743 Sq Ft

  218 E Washington St, Winchester, KY 40391

  Motivated seller! Bring your offers. This home is a charming 4 bedroom 1 bath. It boasts a large bonus room which could be an office or 5th bedroom. This home offers a nice sized laundry room with space to add a second bathroom. This home has a nicely shaded fully fenced in back yard with a gate for easy accessibility . There is also a detached storage garage and a long driveway. Within walking

  Fernando Andrade Rector Hayden Realtors

  218 E Washington St, 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 $570,045

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, Winchester, KY 40391
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  /18

  Est $169,844 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  108 Crawford Ave, Winchester, KY 40391

  108 Crawford Ave, Winchester, KY 40391
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  /22

  $221,500

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft

  521 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. 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

  521 Acadia Way, Winchester, KY 40391
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  /48

  $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 $344,096

  Last Listing Agent Geneva Wilder Selling the South Realty

  401 Cedar Ct, Winchester, KY 40391

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