Winchester, KY Homes

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  /32

  $263,000 Sold Sep 05, 2025

  2 Chickadee Ln, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,397 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $188/SF
  • 2 Days On Market

  Current Estimated Value $257,333

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
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  /18

  Est $161,475 Not Listed For Sale

  108 Crawford Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1955

  108 Crawford Ave, Winchester, KY 40391

  Last Sold Summary

  • 24% Above List Price
  • $144/SF
  • 0 Days On Market

  Last Sold Price $130,000

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
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  /26

  $175,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  10 Pocahontas Trail, Winchester, KY 40391

  This inviting 2 bedroom, 1 and a half bath home blends comfort with smart design. An open floor plan creates a bright, welcoming space where the living, dining, and kitchen areas flow effortlessly—perfect for everyday living and easy entertaining. The fully fenced backyard adds privacy and flexibility, ideal for pets, play, or quiet evenings outdoors. Whether you're stepping into homeownership

  Libby VanMeter Marshall Lane Real Estate - Lexington

  10 Pocahontas Trail, Winchester, KY 40391
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  /35

  $325,000 Sold Nov 21, 2025

  130 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 19 Days On Market

  Current Estimated Value $334,469

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
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  /10

  Est $199,735 Not Listed For Sale

  24 Fairview Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1940

  24 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 25% Above List Price
  • $126/SF
  • 1 Day On Market

  Last Sold Price $159,900

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC
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  /2

  $110,000

  • Land
  • 0.35 Acre
  • $314,286 per Acre

  150 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

  150 Duclair Dr, Winchester, KY 40391
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  /51

  $303,000 Sold Jan 16, 2026

  22 N Bloomfield Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft
  • Built 1919

  Last Sold Summary

  • 5% Below List Price
  • $158/SF
  • 16 Days On Market

  Current Estimated Value $312,928

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
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  /55

  Est $173,791 Not Listed For Sale

  30 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • Built 1983

  30 Ashland Ave, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $118/SF
  • 8 Days On Market

  Last Sold Price $166,500

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /21

  $249,900

  • 3 Beds
  • 1.5 Baths
  • 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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  /23

  $244,895 Sold Jun 10, 2025

  244 Bay Hill Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,536 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $97/SF
  • 10 Days On Market

  Current Estimated Value $274,904

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  244 Bay Hill Ct, Winchester, KY 40391
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  /30

  Est $155,117 Not Listed For Sale

  370 E Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,126 Sq Ft
  • Built 1930

  370 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $133/SF
  • 3 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Meredith Story Story Realty
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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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  /2

  $89,000 Sold Dec 18, 2025

  13067 Irvine Rd, Winchester, KY 40391

  • Land
  • 7.86 Acres
  • $11,323 per Acre

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13067 Irvine Rd, Winchester, KY 40391
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  /32

  Est $199,872 Not Listed For Sale

  203 Crawford Ct, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1960

  203 Crawford Ct, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $91/SF
  • 17 Days On Market

  Last Sold Price $173,000

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan
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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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  /2

  $4,900,000 Sold Dec 23, 2025

  175 Chatham Place, Winchester, KY 40391

  • 2 Beds
  • 3 Baths
  • 37,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $132/SF
  • 111 Days On Market

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
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  /53

  Est $209,260 Not Listed For Sale

  29 Fairview Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,631 Sq Ft
  • Built 1960

  29 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 111% Above List Price
  • $61/SF
  • 140 Days On Market

  Last Sold Price $99,000

  Last Listing Agent Bob Sophiea eXp Realty, LLC
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  /30

  $189,900 Pending

  • 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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  /51

  $340,000 Sold Oct 30, 2025

  356 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $106/SF
  • 30 Days On Market

  Current Estimated Value $346,812

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
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  /29

  Est $164,440 Not Listed For Sale

  4 Sylvania Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft
  • Built 1960

  4 Sylvania Ave, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $168/SF
  • 4 Days On Market

  Last Sold Price $140,000

  Last Listing Agent Christal Browning Four Seasons Realty
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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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  /4

  $315,000 Sold Jun 30, 2025

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391
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  /22

  Est $189,649 Not Listed For Sale

  21 Sylvania Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft
  • Built 1970

  21 Sylvania Ave, Winchester, KY 40391

  Last Sold Summary

  • 22% Above List Price
  • $154/SF
  • 1 Day On Market

  Last Sold Price $156,000

  Last Listing Agent Ciara Isaacs Hagedorn RE/MAX
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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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  /33

  $270,000 Sold Mar 28, 2025

  129 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,884 Sq Ft
  • Built 1993

  Last Sold Summary

  • $143/SF
  • 8 Days On Market

  Current Estimated Value $287,992

  Last Listing Agent Audra Tate National Real Estate

  129 Ashley Dr, Winchester, KY 40391
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  /30

  Est $202,140 Not Listed For Sale

  280 Winn Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft
  • Built 1960

  280 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 30% Above List Price
  • $108/SF
  • 3 Days On Market

  Last Sold Price $155,000

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

  $100,000

  • Land
  • 0.32 Acre
  • $312,500 per Acre

  111 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

  111 Jacob Ct, Winchester, KY 40391
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  /3

  $94,000 Sold Aug 22, 2025

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $23,383 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 140 Days On Market

  Current Estimated Value $170,966

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  /25

  Est $121,390 Not Listed For Sale

  248 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft
  • Built 1940

  248 Cook Ave, Winchester, KY 40391

  Last Sold Summary

  • 143% Above List Price
  • $34/SF
  • 27 Days On Market

  Last Sold Price $50,000

  Last Listing Agent Chris Johnson Plum Tree Realty
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  /7

  $270,000

  • Land
  • 0.84 Acre
  • $321,429 per Acre

  800 Interstate Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

  Whitney Ensor Ensor Real Estate, LLC

  800 Interstate Dr, Winchester, KY 40391
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  /21

  $199,500 Sold May 09, 2025

  445 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,539 Sq Ft
  • Built 1998

  Last Sold Summary

  • $130/SF
  • 3 Days On Market

  Current Estimated Value $212,295

  Last Listing Agent Mary Layton FC Tucker Bluegrass

  445 Colby Ridge Blvd, Winchester, KY 40391
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  /4

  Est $86,145 Not Listed For Sale

  Unlisted Address

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

  Unlisted Address

  Last Sold Summary

  • 169% Above List Price
  • $34/SF

  Last Sold Price $32,000

  Last Listing Agent Null Non-Member Non-Member Office
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  /86

  $530,000

  • 4 Beds
  • 3.5 Baths
  • 3,848 Sq Ft

  125 Casa Landa Way, Winchester, KY 40391

  Stoney Brook Subdivision! Second time ever offered for sale. Beautiful two story brick home with first and second floor en-suites. Each of the 4 bedrooms has its own walk in closet. Formal family room and dinning rooms, great room with fireplace, breakfast area, all season room with natural lighting, and large flex space located on second floor. All of this setting on .40 of an acre lot with side

  Maggie Napier Napier Realtors

  125 Casa Landa Way, Winchester, KY 40391
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  /79

  $849,900 Sold May 23, 2025

  3714 Wades Mill Rd, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,818 Sq Ft
  • Built 2001

  Last Sold Summary

  • $223/SF
  • 55 Days On Market

  Current Estimated Value $868,349

  Last Listing Agent Nora Williams Keller Williams Commonwealth

  3714 Wades Mill Rd, Winchester, KY 40391
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  /41

  Est $194,877 Not Listed For Sale

  31 Watts Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,343 Sq Ft
  • Built 1960

  31 Watts Rd, Winchester, KY 40391

  Last Sold Summary

  • 3% Below List Price
  • $149/SF
  • 24 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /27

  $269,000

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

  916 Stratton Ln, Winchester, KY 40391

  Welcome to 916 Stratton Lane, a beautifully updated 3 bedroom, 2 bath home offering 1,400 square feet of comfortable living space in the highly desired Westmeade area. This charming brick home features a warm and inviting interior with stylish updates throughout. The spacious living room showcases rich dark flooring, a stunning stone fireplace, and abundant natural light, creating the perfect

  Joshua Davis The Agency

  916 Stratton Ln, Winchester, KY 40391
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  /51

  $560,000 Sold Jun 10, 2025

  520 Gay Evans Rd, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 3,160 Sq Ft
  • Built 2012

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 11 Days On Market

  Current Estimated Value $561,275

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  520 Gay Evans Rd, Winchester, KY 40391
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  /27

  Est $290,247 Not Listed For Sale

  198 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 1960

  198 Hilltop Dr, Winchester, KY 40391

  Last Sold Summary

  • 24% Above List Price
  • $132/SF
  • 0 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC
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  /65

  $609,900 Pending

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft

  6595 Mount Sterling Rd, Winchester, KY 40391

  INCREDIBLE! This custom-built home sits on 2.59 acres in a prime location just minutes from I-64 and perfectly positioned between Winchester and Mount Sterling. The main level features a grand formal dining room, a family room with a vaulted coffered ceiling, and an eat-in kitchen open to the living area for easy entertaining. You'll also find the first primary suite plus two additional bedrooms

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
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  /17

  $30,000 Sold Jun 30, 2025

  12591 Ironworks Rd, Winchester, KY 40391

  • Land
  • 1.72 Acres
  • $17,442 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 51 Days On Market

  Current Estimated Value $129,286

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391

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