16,370

Winchester, KY Homes

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  • /8

    $1,500,000

    1015 Old Stone Church Rd, Winchester, KY 40391

    Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

    Walker Mack Bluegrass Property Exchange

    1015 Old Stone Church Rd, Winchester, KY 40391
  • /50

    $220,000

    Sold Jun 18, 2026

    314 Snowden Dr, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $184/SF
    • 1 Day On Market

    Current Estimated Value $222,237

    Last Listing Agent Josh Wood Freedom Realty & Property Management

    314 Snowden Dr, Winchester, KY 40391
    • /41

      Est $356,974

      Not Listed For Sale

      5751 Mount Sterling Rd, Winchester, KY 40391

      • 3 Beds
      • 2.5 Baths
      • 1,988 Sq Ft
      • Built 1976
      5751 Mount Sterling Rd, Winchester, KY 40391

      Last Sold Summary

      • 54 Days On Market

  • /55

    $558,900

    $11K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,280 Sq Ft

    108 Bella Shae Way, Winchester, KY 40391

    Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with

    Vickie Skeens RE/MAX Elite Lexington

    108 Bella Shae Way, Winchester, KY 40391
  • /17

    $190,000

    Sold Sep 10, 2025

    114 Sunset Heights, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,059 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $179/SF
    • 50 Days On Market

    Current Estimated Value $196,011

    Last Listing Agent Susan Baldwin Threshold Real Estate Services

    114 Sunset Heights, Winchester, KY 40391
    • /79

      Est $938,610

      Not Listed For Sale

      3714 Wades Mill Rd, Winchester, KY 40391

      • 5 Beds
      • 3.5 Baths
      • 3,818 Sq Ft
      • Built 2001
      3714 Wades Mill Rd, Winchester, KY 40391

      Last Sold Summary

      • 55 Days On Market

  • /87

    $2,999,000

    $101K PRICE DROP
    • 6 Beds
    • 5 Baths
    • 3,693 Sq Ft

    3049 Ironworks Rd, Winchester, KY 40391

    Some properties are special simply because of the story behind them. This 150-acre farm with 3,168 ft of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek

    Zova Rothchild Keller Williams Legacy Group

    3049 Ironworks Rd, Winchester, KY 40391
  • /48

    $222,500

    Sold Jul 28, 2025

    217 Locust Grove Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 2,055 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Above List Price
    • $108/SF
    • 2 Days On Market

    Current Estimated Value $231,671

    Last Listing Agent Robin Murray The Agency

    217 Locust Grove Rd, Winchester, KY 40391
    • /36

      Est $376,033

      Not Listed For Sale

      610 Old Ruckerville Rd, Winchester, KY 40391

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1997
      610 Old Ruckerville Rd, Winchester, KY 40391

      Last Sold Summary

      • 37 Days On Market

  • /16

    $1,200,000

    • 16 Beds
    • 16 Baths
    • 7,480 Sq Ft

    16 Linden Ave, Winchester, KY 40391

    You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof

    Kevin Bradley KB Realty Group

    16 Linden Ave, Winchester, KY 40391
  • /34

    $342,000

    Sold Sep 16, 2025

    3560 Wades Mill Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • Built 1950

    Last Sold Summary

    • 10% Below List Price
    • $262/SF
    • 37 Days On Market

    Current Estimated Value $339,526

    Last Listing Agent Sarah MacHarg Kentucky Land and Home

    3560 Wades Mill Rd, Winchester, KY 40391
    • /35

      Est $279,279

      Not Listed For Sale

      3230 Irvine Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,510 Sq Ft
      • Built 1978
      3230 Irvine Rd, Winchester, KY 40391

      Last Sold Summary

      • 47 Days On Market

  • /3

    $380,000

    New Construction Pending
    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    270 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 on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

    Rex Hall United Real Estate Bluegrass

    270 Evergreen Dr, Winchester, KY 40391
  • /5

    $41,500

    Sold Sep 15, 2025

    434 Fairholme Way, Winchester, KY 40391

    • Land
    • 15,681 Sq Ft
    • $115,278 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 6 Days On Market

    Current Estimated Value $55,427

    Last Listing Agent Justin Lee JL Realty Group, LLC

    434 Fairholme Way, Winchester, KY 40391
    • /16

      Est $170,799

      Not Listed For Sale

      2584 Irvine Rd, Winchester, KY 40391

      • 2 Beds
      • 1 Bath
      • 990 Sq Ft
      • Built 1950
      2584 Irvine Rd, Winchester, KY 40391

      Last Sold Summary

      • 29 Days On Market

  • /49

    $254,500

    • 3 Beds
    • 1.5 Baths
    • 1,533 Sq Ft

    377 Crescent Ave, Winchester, KY 40391

    Don't miss out on this beautiful two-story, 3 BR, 1.5 BA home in a great neighborhood in the heart of Winchester! Great-sized living room with real hardwood floors, complete with a tiled fireplace with mantel (seller has never used). Spacious Kitchen with a tiled backsplash, white cabinets, and stainless-steel appliances! Large Dining Room that will accommodate nearly any size table. Half bath

    Bill VanWinkle Joyce Marcum Realty

    377 Crescent Ave, Winchester, KY 40391
  • /58

    $239,900

    Sold Jun 08, 2026

    3610 Stamper Dr, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • Built 1986

    Last Sold Summary

    • $209/SF
    • 4 Days On Market

    Current Estimated Value $240,099

    Last Listing Agent Peter doCouto Plum Tree Realty

    3610 Stamper Dr, Winchester, KY 40391
    • /32

      Est $316,454

      Not Listed For Sale

      2615 Ironworks Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,694 Sq Ft
      • Built 1965
      2615 Ironworks Rd, Winchester, KY 40391

      Last Sold Summary

      • 1 Day On Market

  • /12

    $129,999

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    471 Goose Creek Rd, Winchester, KY 40391

    CASH BUYERS! This 3-bedroom, 2-bath manufactured home on 1.49 acres offers strong potential for those looking to renovate, rent, or resell. Property is being sold as-is and will require repairs, making it best suited for cash buyers. Located just minutes from I-64 and convenient to Lexington, this property combines rural privacy with accessibility — a desirable combination for future resale or

    Shari Frasure Keller Williams Commonwealth

    471 Goose Creek Rd, Winchester, KY 40391
  • /58

    $830,000

    Sold Feb 27, 2026

    2395 Becknerville Rd, Winchester, KY 40391

    • 4 Beds
    • 3.5 Baths
    • 3,234 Sq Ft
    • Built 2012

    Last Sold Summary

    • 2% Below List Price
    • $257/SF
    • 8 Days On Market

    Current Estimated Value $821,791

    Last Listing Agent Crystal Towe The Real Estate Group

    2395 Becknerville Rd, Winchester, KY 40391
    • /45

      Est $520,764

      Not Listed For Sale

      1159 Cabin Creek Rd, Winchester, KY 40391

      • 3 Beds
      • 2.5 Baths
      • 2,244 Sq Ft
      • Built 2007
      1159 Cabin Creek Rd, Winchester, KY 40391

      Last Sold Summary

      • 14 Days On Market

  • /7

    $400,000

    • Land
    • 7.31 Acres
    • $54,720 per Acre

    4095 Basin Springs Rd, Winchester, KY 40391

    Looking for land to build your dream home that is private, but convenient? This 7+ acre beautiful lot is located in Clark County, just 15 minutes from Costco, Hamburg and I-75. No HOA or deed restrictions. The perfect place to build or have a small farm. Location! Location! Location!

    Peggy Baldridge HomeFirst Real Estate

    4095 Basin Springs Rd, Winchester, KY 40391
  • /33

    $364,900

    Sold Feb 06, 2026

    446 Tremont Ln, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 2,811 Sq Ft
    • Built 2005

    Last Sold Summary

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

    Current Estimated Value $367,799

    Last Listing Agent Dylan Langdon The Agency

    446 Tremont Ln, Winchester, KY 40391
    • /15

      Est $317,460

      Not Listed For Sale

      158 Cabin Creek Heights, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,580 Sq Ft
      • Built 2005
      158 Cabin Creek Heights, Winchester, KY 40391

      Last Sold Summary

      • 5 Days On Market

  • /60

    $249,900

    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    17 Holiday Rd, Winchester, KY 40391

    This classic brick ranch house is move-in ready and waiting for you to call it home! Take a step inside the front door to appreciate the gleaming laminate wood floors in the open concept living space. Around the corner, the beautiful kitchen cabinets and updated, stainless, kitchen appliances are ready for family meals and social gatherings around the dining table. In the full bath, you'll find a

    Josh Wood Freedom Realty & Property Management

    17 Holiday Rd, Winchester, KY 40391
  • /38

    $173,000

    Sold Sep 22, 2025

    44 5th St, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,270 Sq Ft
    • Built 1952

    Last Sold Summary

    • 2% Above List Price
    • $136/SF
    • 2 Days On Market

    Current Estimated Value $181,015

    Last Listing Agent Tirza Howard The Howard Realty Co

    44 5th St, Winchester, KY 40391
    • /43

      Est $485,668

      Not Listed For Sale

      2100 Ecton Rd, Winchester, KY 40391

      • 4 Beds
      • 2 Baths
      • 2,060 Sq Ft
      • Built 1978
      2100 Ecton Rd, Winchester, KY 40391

      Last Sold Summary

      • 35 Days On Market

  • /10

    $575,000

    $75K PRICE DROP
    • Land
    • 2.6 Acres
    • $221,154 per Acre

    529 Bullion Blvd Unit 3B, Winchester, KY 40391

    Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

    Greg Leveridge Block + Lot Homes

    529 Bullion Blvd Unit 3B, Winchester, KY 40391
  • /18

    $200,000

    Sold Jan 14, 2026

    245 Ecton Rd, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,074 Sq Ft
    • Built 1940

    Last Sold Summary

    • 9% Below List Price
    • $186/SF
    • 2 Days On Market

    Current Estimated Value $202,112

    Last Listing Agent Anthony Gigilo ListWithFreedom.com

    245 Ecton Rd, Winchester, KY 40391
    • /44

      Est $547,629

      Not Listed For Sale

      601 Wades Mill Rd, Winchester, KY 40391

      • 3 Beds
      • 2.5 Baths
      • 2,070 Sq Ft
      • Built 2000
      601 Wades Mill Rd, Winchester, KY 40391

      Last Sold Summary

      • 7 Days On Market

  • /11

    $50,000

    • Land
    • 17,859 Sq Ft
    • $121,951 per Acre

    308 Duclair Dr, Winchester, KY 40391

    Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

    Joseph Miller Keller Williams Legacy Group

    308 Duclair Dr, Winchester, KY 40391
  • /52

    $500,000

    Sold Aug 25, 2025

    1778 Elkin Rd, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 2,020 Sq Ft
    • Built 2015

    Last Sold Summary

    • 7% Below List Price
    • $248/SF
    • 103 Days On Market

    Last Listing Agent Vicki VanWinkle ERA Select Real Estate

    1778 Elkin Rd, Winchester, KY 40391
    • /3

      Est $334,438

      Not Listed For Sale

      1591 Gay Evans Rd, Winchester, KY 40391

      • 3 Beds
      • 1,260 Sq Ft
      • Built 1940
      1591 Gay Evans Rd, Winchester, KY 40391

      Last Sold Summary

      • 17 Days On Market

  • /22

    $665,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,643 Sq Ft

    414 Alexis Way, Winchester, KY 40391

    Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

    Shane Underwood Keller Williams Commonwealth

    414 Alexis Way, Winchester, KY 40391
  • /28

    $203,900

    Sold Dec 10, 2025

    25 Hiawatha Trail, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 925 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $220/SF
    • 35 Days On Market

    Current Estimated Value $200,293

    Last Listing Agent Sarah Hess Keller Williams Commonwealth

    25 Hiawatha Trail, Winchester, KY 40391
    • /96

      Est $846,308

      Not Listed For Sale

      1995 Gay Evans Rd, Winchester, KY 40391

      • 4 Beds
      • 3.5 Baths
      • 3,272 Sq Ft
      • Built 1998
      1995 Gay Evans Rd, Winchester, KY 40391

      Last Sold Summary

      • 82 Days On Market

  • /9

    $785,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,476 Sq Ft

    425 Alexis Way, Winchester, KY 40391

    Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

    Shane Underwood Keller Williams Commonwealth

    425 Alexis Way, Winchester, KY 40391
  • /80

    $524,000

    Sold Dec 16, 2025

    160 Agawam Rd, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 4,933 Sq Ft
    • Built 1978

    Last Sold Summary

    • 9% Below List Price
    • $106/SF
    • 51 Days On Market

    Current Estimated Value $522,385

    Last Listing Agent Megan McCoy Keller Williams Legacy Group

    160 Agawam Rd, Winchester, KY 40391
    • /60

      Est $170,604

      Not Listed For Sale

      1333 Jackson Ferry Rd, Winchester, KY 40391

      • 2 Beds
      • 2 Baths
      • 1,492 Sq Ft
      • Built 1964
      1333 Jackson Ferry Rd, Winchester, KY 40391

      Last Sold Summary

      • 60 Days On Market

  • /72

    $406,900

    New Construction
    • 3 - 6 Beds
    • 2.5 - 5.5 Baths
    • 2,570 Sq Ft

    Jackie Plan at Boone's Crossing, Winchester, KY 40391

    Unleash your creativity with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391

Showing Results 201 - 240, Page 6 of 18

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