Winchester, KY Homes

• 

  

  /2

  $110,000

  • Land
  • 20,473 Sq Ft
  • $234,043 per Acre

  139 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

  139 Jacob Ct, 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 $223,189

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  314 Snowden Dr, Winchester, KY 40391
• 

  

  

  /24

  Est $249,204

  Not Listed For Sale

  445 Jameson Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2002

  445 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Tyler I Back The Brokerage
• 

  

  /2

  $150,000

  • Land
  • 2.11 Acres
  • $71,090 per Acre

  125 Knox 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 Knox Ct, 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 $191,407

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  114 Sunset Heights, Winchester, KY 40391
• 

  

  /27

  Est $218,329

  Not Listed For Sale

  2350 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,385 Sq Ft
  • Built 1970

  2350 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Dylan Justice Bluegrass Commercial Real Estate
• 

  

  /24

  $365,900

  New Construction $4K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
• 

  

  /35

  $355,000

  Sold Aug 06, 2026

  411 Skylark Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,591 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $137/SF
  • 0 Days On Market

  Current Estimated Value $344,192

  Last Listing Agent Jennifer Hickman Keller Williams Commonwealth

  411 Skylark Dr, Winchester, KY 40391
• 

  

  /20

  Est $193,784

  Not Listed For Sale

  2342 Ironworks Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1970

  2342 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Dylan Justice Bluegrass Commercial Real Estate
• 

  

  /16

  $124,500

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, 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 $343,742

  Last Listing Agent Sarah MacHarg Kentucky Land and Home

  3560 Wades Mill Rd, Winchester, KY 40391
• 

  

  /47

  Est $349,843

  Not Listed For Sale

  106 Old Ironworks Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,380 Sq Ft
  • Built 1900

  106 Old Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent John Groft RE/MAX Creative Realty
• 

  

  /10

  $550,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, 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 $134,516

  Last Listing Agent Justin Lee JL Realty Group, LLC

  434 Fairholme Way, Winchester, KY 40391
• 

  

  /24

  Est $207,426

  Not Listed For Sale

  113 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1983

  113 Colonial Park Dr, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Janet Baldwin Kentucky Land and Home
• 

  

  /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
• 

  

  /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 $240,558

  Last Listing Agent Pete doCouto Plum Tree Realty

  3610 Stamper Dr, Winchester, KY 40391
• 

  

  /25

  Est $253,025

  Not Listed For Sale

  325 Vanover Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 2002

  325 Vanover Way, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Brad Harmon LexHomes Real Estate
• 

  

  /55

  $549,900

  Open Sun 1PM - 3PM $20K 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
• 

  

  /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 $807,230

  Last Listing Agent Crystal Towe The Real Estate Group

  2395 Becknerville Rd, Winchester, KY 40391
• 

  

  /14

  Est $230,798

  Not Listed For Sale

  313 Vanover Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 1995

  313 Vanover Way, Winchester, KY 40391

  Last Sold Summary

  • 112 Days On Market

  Last Listing Agent Bob Sophiea eXp Realty, LLC
• 

  

  /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
• 

  

  /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 $362,404

  Last Listing Agent Dylan Langdon The Agency

  446 Tremont Ln, Winchester, KY 40391
• 

  

  /21

  Est $229,919

  Not Listed For Sale

  523 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 2002

  523 Acadia Way, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Tyler I Back The Brokerage
• 

  

  /64

  $524,900

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft

  275 Runnymeade Dr, Winchester, KY 40391

  OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new

  Craig Bridgewater Bridgewater Real Estate

  275 Runnymeade Dr, Winchester, KY 40391
• 

  

  /60

  $249,900

  Sold Jul 22, 2026

  17 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1992

  Last Sold Summary

  • $215/SF
  • 8 Days On Market

  Current Estimated Value $250,763

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  17 Holiday Rd, Winchester, KY 40391
• 

  

  /21

  Est $230,872

  Not Listed For Sale

  513 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2001

  513 Acadia Way, Winchester, KY 40391

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Tyler I Back The Brokerage
• 

  

  /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
• 

  

  /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 $181,397

  Last Listing Agent Tirza Howard The Howard Realty Co

  44 5th St, Winchester, KY 40391
• 

  

  /36

  Est $185,827

  Not Listed For Sale

  218 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Built 1999

  218 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Sandy Statom Team Realtors
• 

  

  /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
• 

  

  /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 $201,682

  Last Listing Agent Anthony Gigilo ListWithFreedom.com

  245 Ecton Rd, Winchester, KY 40391
• 

  

  /17

  Est $248,972

  Not Listed For Sale

  206 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,737 Sq Ft
  • Built 1998

  206 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Kymberly McCreary eXp Realty, LLC
• 

  

  /40

  $498,000

  • 4 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  1780 Stoner Ephesus Rd, Winchester, KY 40391

  Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15

  Darrell Tackett Dream Maker Realty, LLC

  1780 Stoner Ephesus Rd, 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
• 

  

  /32

  Est $216,102

  Not Listed For Sale

  303 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1998

  303 Geronimo Ct, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Marie Waddell-Pearson RE/MAX Creative Realty
• 

  

  /89

  $899,000

  Pending

  • 3 Beds
  • 2 Baths
  • 4,019 Sq Ft

  200 Old Log Lick Rd, Winchester, KY 40391

  Behind a private, gated entrance on 14.38 acres, this 3,481 sq ft all-wood cabin estate is a truly rare find in Central Kentucky. Offering 3 bedrooms, 2 bathrooms, and a flexible bonus room perfect as a 4th bedroom or home office, every inch of this home reflects true craftsmanship -- rich wood features throughout, a large sunroom, and a screened-in back porch made for long evenings and unhurried

  Derek Blankenship Keller Williams Commonwealth

  200 Old Log Lick Rd, 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 $520,291

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
• 

  

  /19

  Est $195,825

  Not Listed For Sale

  125 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 932 Sq Ft
  • Built 1997

  125 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty
• 

  

  /7

  $350,000

  $50K PRICE DROP

  • Land
  • 7.31 Acres
  • $47,880 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

Showing Results 201 - 240, Page 6 of 18