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
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  /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
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  /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
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  /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