16,306

Winchester, KY Homes

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  • /34

    $220,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    37 7th St, Winchester, KY 40391

    Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

    Andrew Fugitt Coldwell Banker McMahan

    37 7th St, Winchester, KY 40391
  • /25

    $375,000 Sold Aug 29, 2025

    317 Hanover Dr, Winchester, KY 40391

    • 5 Beds
    • 3.5 Baths
    • 3,111 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Below List Price
    • $121/SF
    • 8 Days On Market

    Current Estimated Value $371,679

    Last Listing Agent Mike Wheatley Bluegrass Properties Group

    317 Hanover Dr, Winchester, KY 40391
    • /16

      Est $190,594 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,122 Sq Ft

      141 Alabama St, Winchester, KY 40391

      141 Alabama St, Winchester, KY 40391
  • /47

    $499,000

    • 5 Beds
    • 3.5 Baths
    • 3,823 Sq Ft

    595 Earlymeade Dr, Winchester, KY 40391

    Entertaining the idea of entertaining family and friends? Looking for space for living the good life in a fun house in a great neighborhood? Then look no further. This house is ready for you to make it your new home. Located in the desirable neighborhood of Earlymeade, this house is minutes from the Winchester Bypass, I- 64 corridor and the Hamburg area of Lexington. Along with 5 bedrooms and 3.5

    Craig Bridgewater Bridgewater Real Estate

    595 Earlymeade Dr, Winchester, KY 40391
  • /60

    $545,000 Sold Oct 31, 2025

    445 Lynnway Dr, Winchester, KY 40391

    • 4 Beds
    • 3.5 Baths
    • 3,649 Sq Ft
    • Built 1993

    Last Sold Summary

    • $149/SF
    • 4 Days On Market

    Last Listing Agent Janna Smith United Real Estate Bluegrass

    445 Lynnway Dr, Winchester, KY 40391
    • /16

      Est $407,336 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 4,176 Sq Ft

      122 French Ave, Winchester, KY 40391

      122 French Ave, Winchester, KY 40391
  • /15

    $600,000

    • 8 Beds
    • 4 Baths
    • 5,046 Sq Ft

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

    Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new

    Priya Patel-Rossetti Big Blue Realty

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
  • /15

    $182,000 Sold Feb 19, 2025

    514 Cs-1383, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Above List Price
    • $162/SF
    • 5 Days On Market

    Current Estimated Value $191,028

    Last Listing Agent Craig Bridgewater Bridgewater Real Estate

    514 Cs-1383, Winchester, KY 40391
    • /31

      Est $205,546 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,946 Sq Ft

      134 Central Ave, Winchester, KY 40391

      134 Central Ave, Winchester, KY 40391
  • /4

    $67,500

    • Land
    • 1.92 Acres
    • $35,156 per Acre

    12569 Ironworks Rd, Winchester, KY 40391

    Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and watch this land grow in value. This lot containing 1.919 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

    Kathryn Cheuvront Coldwell Banker McMahan

    12569 Ironworks Rd, Winchester, KY 40391
  • /54

    $360,000 Sold Jan 17, 2025

    1455 Irvine Rd, Winchester, KY 40391

    • 4 Beds
    • 3 Baths
    • 2,901 Sq Ft
    • Built 1940

    Last Sold Summary

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

    Current Estimated Value $417,005

    Last Listing Agent Shari Frasure Keller Williams Commonwealth

    1455 Irvine Rd, Winchester, KY 40391
    • /19

      Est $221,203 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,322 Sq Ft

      130 Central Ave, Winchester, KY 40391

      130 Central Ave, Winchester, KY 40391
  • /3

    $825,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,995 Sq Ft

    111 Bella Shae Way, Winchester, KY 40391

    Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. Thespacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a

    Shane Underwood Keller Williams Commonwealth

    111 Bella Shae Way, Winchester, KY 40391
  • /27

    $380,000 Sold Nov 10, 2025

    5705 Mount Sterling Rd, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 2,980 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $128/SF
    • 50 Days On Market

    Last Listing Agent Dale Hatton Dream Maker Realty, LLC

    5705 Mount Sterling Rd, Winchester, KY 40391
    • /8

      Est $244,567 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,359 Sq Ft

      109 Alabama St, Winchester, KY 40391

      109 Alabama St, Winchester, KY 40391
  • /32

    $359,900 Open Sun 2PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft

    538 S Maple St, Winchester, KY 40391

    24 hour kickout in place. Be the first to call this stunning new construction home! Perfectly situated in the heart of Winchester, this two-story residence offers a fresh, modern feel with convenience at your doorstep. Step inside to discover a bright and airy open-concept main level, featuring durable and stylish Luxury Vinyl Plank (LVP) flooring throughout. The kitchen is a true showstopper,

    Heather Kuykendoll Bluegrass Properties Group

    538 S Maple St, Winchester, KY 40391
  • /102

    $525,000 Sold Dec 22, 2025

    1953 Cabin Creek Rd, Winchester, KY 40391

    • 6 Beds
    • 4.5 Baths
    • 3,846 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Below List Price
    • $137/SF
    • 9 Days On Market

    Last Listing Agent Josh Wood Freedom Realty & Property Management

    1953 Cabin Creek Rd, Winchester, KY 40391
    • /23

      Est $230,649 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,738 Sq Ft

      112 Georgia St, Winchester, KY 40391

      112 Georgia St, Winchester, KY 40391
  • /13

    $74,900

    • Land
    • 2.14 Acres
    • $35,000 per Acre

    1751 Little Stoner Rd, Winchester, KY 40391

    Located at 1751 Little Stoner Rd in Winchester, this 2.139 acre building lot offers the kind of space and setting that's getting harder to find. Open land, rolling country views, and room to create something truly your own, all while staying conveniently connected to the places that matter most. Enjoy the rare balance of peaceful surroundings with easy access. You're just 20 minutes to Lexington,

    Kymberly McCreary EXP Realty, LLC

    1751 Little Stoner Rd, Winchester, KY 40391
  • /28

    $345,000 Sold Jun 19, 2025

    512 Boone Ave, Winchester, KY 40391

    • 4 Beds
    • 3 Baths
    • 3,149 Sq Ft
    • Built 1950

    Last Sold Summary

    • 14% Below List Price
    • $110/SF
    • 58 Days On Market

    Current Estimated Value $371,595

    Last Listing Agent Jordan James Lifstyl Real Estate

    512 Boone Ave, Winchester, KY 40391
    • /48

      Est $265,805 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,758 Sq Ft

      104 Georgia St, Winchester, KY 40391

      104 Georgia St, Winchester, KY 40391
  • /43

    $269,900

    • 7 Beds
    • 3 Baths
    • 3,393 Sq Ft

    146 W Lexington Ave, Winchester, KY 40391

    This investment property has strong rent potential to add to your portfolio. Property is conveniently located in the heart of Downtown Winchester and is zoned R-4. There's a great opportunity to use this property for house hacking -- leverage your money by living in one unit and renting out the other! Downstairs unit has 4 bedrooms and 2 full bathrooms, and its currently leased for $1,495 a

    Kevin Bradley KB Realty Group

    146 W Lexington Ave, Winchester, KY 40391
  • /65

    $380,000 Sold Jun 19, 2025

    399 Stonecrest Rd, Winchester, KY 40391

    • 3 Beds
    • 4 Baths
    • 4,572 Sq Ft
    • Built 1976

    Last Sold Summary

    • 4% Below List Price
    • $83/SF
    • 3 Days On Market

    Current Estimated Value $397,273

    Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

    399 Stonecrest Rd, Winchester, KY 40391
    • /44

      Est $181,270 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,408 Sq Ft

      118 Alabama St, Winchester, KY 40391

      118 Alabama St, Winchester, KY 40391
  • /70

    $335,000

    • 6 Beds
    • 4 Baths
    • 3,544 Sq Ft

    297 S Main St, Winchester, KY 40391

    Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

    Silvia Torres Tru Life Real Estate

    297 S Main St, Winchester, KY 40391
  • /114

    $635,000 Sold Sep 30, 2025

    315 The Woods Ln, Winchester, KY 40391

    • 5 Beds
    • 4.5 Baths
    • 5,524 Sq Ft
    • Built 1995

    Last Sold Summary

    • 2% Below List Price
    • $115/SF
    • 63 Days On Market

    Last Listing Agent Terri McGraw FC Tucker Bluegrass

    315 The Woods Ln, Winchester, KY 40391
    • /28

      Est $270,219 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,626 Sq Ft

      116 Alabama St, Winchester, KY 40391

      116 Alabama St, Winchester, KY 40391
  • /5

    $29,000

    • Land
    • 0.46 Acre
    • $63,043 per Acre

    102 Augusta Dr, Winchester, KY 40391

    This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

    Dale Hatton Dream Maker Realty, LLC

    102 Augusta Dr, Winchester, KY 40391
  • /32

    $183,000 Sold Jul 30, 2025

    517 Hidden Hills Way, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 2001

    Last Sold Summary

    • $163/SF
    • 78 Days On Market

    Current Estimated Value $189,671

    Last Listing Agent Brenda Sipes Bridgewater Real Estate

    517 Hidden Hills Way, Winchester, KY 40391
    • /27

      Est $268,989 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,968 Sq Ft

      335 S Main St, Winchester, KY 40391

      335 S Main St, Winchester, KY 40391
  • /62

    $259,500

    • 3 Beds
    • 2 Baths
    • 1,247 Sq Ft

    3614 Stamper Dr, Winchester, KY 40391

    Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

    Darrell Tackett Dream Maker Realty, LLC

    3614 Stamper Dr, Winchester, KY 40391
  • /17

    $175,000 Sold May 07, 2025

    220 Jackson St, Winchester, KY 40391

    • 2 Beds
    • 1 Bath
    • 1,228 Sq Ft
    • Built 1940

    Last Sold Summary

    • $143/SF
    • 1 Day On Market

    Current Estimated Value $172,901

    Last Listing Agent Joanna Howell Bluegrass Properties Group

    220 Jackson St, Winchester, KY 40391
    • /20

      Est $204,868 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      38 Hughes Ave, Winchester, KY 40391

      38 Hughes Ave, Winchester, KY 40391
  • /3

    $345,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    225 Evergreen Dr, Winchester, KY 40391

    Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

    Rex Hall United Real Estate Bluegrass

    225 Evergreen Dr, Winchester, KY 40391
  • /35

    $189,900 Sold Jan 16, 2025

    24 Hughes Ave, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 2024

    Last Sold Summary

    • $158/SF
    • 24 Days On Market

    Current Estimated Value $216,329

    Last Listing Agent Nena Honaker Tom Goebel & Company

    24 Hughes Ave, Winchester, KY 40391
    • /12

      Est $120,628 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 679 Sq Ft

      46 Hughes Ave, Winchester, KY 40391

      46 Hughes Ave, Winchester, KY 40391
  • /27

    $72,500

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    725 Berry Ct, Winchester, KY 40391

    Looking for affordable homeownership in Winchester, KY? This move-in ready 3-bedroom, 2-bath manufactured home offers modern living at an incredible value. Built just 3 years ago and meticulously maintained, this home feels like new from the moment you step inside. Located in the heart of Winchester, you'll enjoy easy access to local restaurants, shopping, grocery stores, parks, and everyday

    Christa Joynt Keller Williams Commonwealth

    725 Berry Ct, Winchester, KY 40391
  • /61

    $220,000 Sold Nov 10, 2025

    313 Snowden Dr, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1960

    Last Sold Summary

    • 12% Below List Price
    • $179/SF
    • 51 Days On Market

    Last Listing Agent Josh Wood Freedom Realty & Property Management

    313 Snowden Dr, Winchester, KY 40391
    • /35

      Est $325,749 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,769 Sq Ft

      8 French Ave, Winchester, KY 40391

      8 French Ave, Winchester, KY 40391
  • /6

    $200,000

    • Land
    • 0.81 Acre
    • $246,914 per Acre

    550 Bullion Blvd, Winchester, KY 40391

    Rarely available Bypass frontage lot for sale! Exciting opportunity to locate alongside a new Chipotle that is soon to be under construction. Retention in place, leaving approximately 1/2-acre developable. Perfect location for a national retailer. Ideally located along the heart of Bypass Road in Winchester, Kentucky between Kroger and Walmart shopping centers. Winchester, Kentucky is the county

    Greg Leveridge Block + Lot Real Estate

    550 Bullion Blvd, Winchester, KY 40391

Showing Results 441 - 480, Page 12 of 18

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