Winchester, KY Homes

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  $429,500

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft

  134 Fontaine Blvd, Winchester, KY 40391

  Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looking for. Formerly home to the beloved "2 Momma's Cooking for You," the property features a fully

  Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
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  /29

  $215,000 Sold Feb 21, 2025

  167 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft

  Last Sold Summary

  • $122/SF
  • 5 Days On Market

  Current Estimated Value $232,887

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  167 E Washington St, Winchester, KY 40391
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  /70

  Est $284,059 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,321 Sq Ft

  1131 Ironworks Rd, Winchester, KY 40391

  1131 Ironworks Rd, Winchester, KY 40391
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  $109,900

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft

  17 Waveland Ave, Winchester, KY 40391

  Cozy 2-bedroom, 1-bath home with a metal roof (about 15 years old) and central heating and air for year-round comfort. Inside, you'll find wood flooring that adds warmth and character. The home just needs some cosmetic updates, making it a great chance to add your personal touch and build instant value.

  Darrell Lewis DIYFlatFee.Com

  17 Waveland Ave, Winchester, KY 40391
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  $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 $286,062

  Last Listing Agent Audra Tate National Real Estate

  129 Ashley Dr, Winchester, KY 40391
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  /26

  Est $248,772 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  1124 Ironworks Rd, Winchester, KY 40391

  1124 Ironworks Rd, Winchester, KY 40391
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  /29

  $262,500

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

  410 Wellington Way, Winchester, KY 40391

  Discover 410 Wellington Way, a beautifully updated property in a convenient Winchester location! This fully updated, move-in-ready home delivers style, comfort, and convenience from the moment you walk in. Enjoy a bright eat-in kitchen equipped with brand-new, warrantied appliances, plus modern finishes throughout—including all-new paint, new flooring, new light fixtures, new doors, updated

  Monica Marcum Century 21 Pinnacle

  410 Wellington Way, 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 $170,301

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  /41

  Est $262,590 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,982 Sq Ft

  273 Winn Ave, Winchester, KY 40391

  273 Winn Ave, Winchester, KY 40391
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  /14

  $129,800

  • Land
  • 2.3 Acres
  • $56,435 per Acre

  110 Knox Ct, Winchester, KY 40391

  The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

  Amanda Thomas The Agency

  110 Knox Ct, 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 $211,090

  Last Listing Agent Mary Layton FC Tucker Bluegrass

  445 Colby Ridge Blvd, Winchester, KY 40391
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  Est $255,013 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  113 Mary Way, Winchester, KY 40391

  113 Mary Way, Winchester, KY 40391
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  /2

  $345,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  215 Evergreen Dr, Winchester, KY 40391

  Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  215 Evergreen Dr, Winchester, KY 40391
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  /17

  $269,000 Sold Jan 31, 2025

  129 S Highland St, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 3,608 Sq Ft
  • Built 1940

  Last Sold Summary

  • 6% Below List Price
  • $75/SF
  • 86 Days On Market

  Current Estimated Value $319,552

  Last Listing Agent Joshua Lynch The Brokerage

  129 S Highland St, Winchester, KY 40391
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  /30

  Est $237,040 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft

  306 Sarah Ct, Winchester, KY 40391

  306 Sarah Ct, Winchester, KY 40391
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  /3

  $430,000 New Construction

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

  220 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

  Rex Hall United Real Estate Bluegrass

  220 Evergreen Dr, 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 $870,030

  Last Listing Agent Nora Williams Keller Williams Commonwealth

  3714 Wades Mill Rd, Winchester, KY 40391
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  /29

  Est $299,337 Not Listed For Sale

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

  455 Greenway Dr, Winchester, KY 40391

  455 Greenway Dr, Winchester, KY 40391
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  /4

  $625,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  424 Alexis Way, Winchester, KY 40391

  Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

  Shane Underwood Keller Williams Commonwealth

  424 Alexis Way, 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 $568,375

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  520 Gay Evans Rd, Winchester, KY 40391
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  /25

  Est $263,301 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft

  316 Jameson Way, Winchester, KY 40391

  316 Jameson Way, Winchester, KY 40391
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  /15

  $925,000

  • Land
  • 3.77 Acres
  • $245,358 per Acre

  300 Rolling Hills Ln, Winchester, KY 40391

  Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

  Josh Wood Freedom Realty & Property Management

  300 Rolling Hills Ln, 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 $108,590

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
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  /38

  Est $196,133 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,073 Sq Ft

  412 Jameson Way, Winchester, KY 40391

  412 Jameson Way, Winchester, KY 40391
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  /2

  $168,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,026 Sq Ft

  12 Apache Trail, Winchester, KY 40391

  Welcome to this charming 3-bedroom, 2-full bath ranch located in the desirable Indian Hills Subdivision! This home features a large covered front porch, perfect for relaxing and enjoying your morning coffee or evening sunsets. Inside, you'll find a spacious layout with plenty of potential to make it your own. The full unfinished basement offers endless possibilities for storage, a home gym, or

  Stephen Brashear Keller Williams Commonwealth

  12 Apache Trail, Winchester, KY 40391
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  /34

  $260,000 Sold Apr 17, 2025

  597 Marseille Blvd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,565 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $166/SF
  • 63 Days On Market

  Current Estimated Value $278,747

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  597 Marseille Blvd, Winchester, KY 40391
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  /31

  Est $249,636 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  121 Summerhill Way, Winchester, KY 40391

  121 Summerhill Way, Winchester, KY 40391
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  $525,000

  • 2 Beds
  • 1.5 Baths
  • 5,054 Sq Ft

  808 Bypass Rd, Winchester, KY 40391

  Unique Mixed-Use Opportunity! This versatile property offers prime potential for a restaurant, café, or retail space in a high-visibility location. The commercial space is turn key for a culinary venture or boutique business. Attached is a separate rental unit with private entrance, offering additional income or an ideal live/work setup. Additional space available for potential 2nd Apartment.

  Diana C Brooker Lifstyl Real Estate

  808 Bypass Rd, Winchester, KY 40391
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  /46

  $282,900 Sold Jan 02, 2026

  165 Hilltop Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $195/SF
  • 6 Days On Market

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
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  /23

  Est $277,818 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,490 Sq Ft

  302 Salem Ave, Winchester, KY 40391

  302 Salem Ave, Winchester, KY 40391
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  $349,900

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. Properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
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  /62

  $384,000 Sold Apr 10, 2025

  890 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1965

  Last Sold Summary

  • $269/SF
  • 5 Days On Market

  Current Estimated Value $385,901

  Last Listing Agent Daniel Mullins ERA Select Real Estate

  890 Miller Hunt Rd, Winchester, KY 40391
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  /20

  Est $267,615 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft

  208 Bracken Ct, Winchester, KY 40391

  208 Bracken Ct, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.27 Acre
  • $407,407 per Acre

  125 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

  125 Jacob Ct, Winchester, KY 40391
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  /41

  $650,000 Sold Jun 23, 2025

  357 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,007 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $216/SF
  • 15 Days On Market

  Current Estimated Value $667,492

  Last Listing Agent Emily Belcher Rector Hayden Realtors

  357 Wades Mill Rd, Winchester, KY 40391
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  Est $312,349 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft

  311 Fern Ct, Winchester, KY 40391

  311 Fern Ct, Winchester, KY 40391
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  /21

  $440,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  870 Pilot View Rd, Winchester, KY 40391

  Welcome to your own slice of paradise! This 2022 doublewide sits on an impressive 39.5 acres of rolling countryside in Winchester, offering the perfect blend of modern comfort, privacy, and wide-open space. Step outside and take in the beautiful pastures, ideal for horses, cattle, or hobby farming, all complemented by a peaceful creek that winds through the property—perfect for relaxing evenings

  Chelsea Morguson McCallie Real Estate

  870 Pilot View Rd, Winchester, KY 40391
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  /23

  $210,000 Sold May 12, 2025

  202 Washington Square, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1998

  Last Sold Summary

  • 11% Above List Price
  • $175/SF
  • 1 Day On Market

  Current Estimated Value $206,504

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  202 Washington Square, Winchester, KY 40391
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  Est $329,550 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft

  317 Fern Ct, Winchester, KY 40391

  317 Fern Ct, Winchester, KY 40391
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  $800,000 Pending

  • Land
  • 4.87 Acres
  • $164,271 per Acre

  1108 W Lexington Ave, Winchester, KY 40391

  Rare opportunity to purchase a large multi-family development in the heart of Winchester! Directly across the street from Legacy Grove Park! All building and engineering plans included to build 66 approved townhomes with the possibility of adding 4 more. Currently zoned PD (Planned Development), could possibly be changed to commercial due to neighboring commercial property. Main property is 4.87

  Jason Townsend Kentucky Residential Real Estate, LLC

  1108 W Lexington Ave, Winchester, KY 40391

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