Winchester, KY Homes

• 

  

  

  /30

  $180,000

  Sold Jul 02, 2026

  217 S Highland St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,683 Sq Ft
  • Built 1930

  Last Sold Summary

  • 31% Below List Price
  • $67/SF
  • 151 Days On Market

  Current Estimated Value $192,892

  Last Listing Agent Michael Hilario The Agency

  217 S Highland St, Winchester, KY 40391
• 

  

  

  /33

  Est $264,295

  Not Listed For Sale

  7344 Ironworks Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1925

  7344 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Jason Rainey Executive Real Estate, LLC
• 

  

  

  /51

  $399,900

  $27K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,289 Sq Ft

  20 Edgewood Dr, Winchester, KY 40391

  Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a

  Libby VanMeter Marshall Lane Real Estate - Lexington

  20 Edgewood Dr, Winchester, KY 40391
• 

  

  

  /69

  $282,500

  Sold Sep 30, 2025

  227 Cross Brook Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $187/SF
  • 9 Days On Market

  Current Estimated Value $291,112

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  227 Cross Brook Ln, Winchester, KY 40391
• 

  

  

  /51

  Est $544,426

  Not Listed For Sale

  5600 Ecton Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,841 Sq Ft
  • Built 1992

  5600 Ecton Rd, Winchester, KY 40391

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Kymberly McCreary Keller Williams Commonwealth
• 

  

  /19

  $189,000

  $20K PRICE DROP

  • Land
  • 41.69 Acres
  • $4,534 per Acre

  2697 Pine Ridge Rd, Winchester, KY 40391

  Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and

  Derek Blankenship Keller Williams Commonwealth

  2697 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /58

  $345,000

  Sold Nov 14, 2025

  205 Chardonnay Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,179 Sq Ft
  • Built 1991

  Last Sold Summary

  • 8% Below List Price
  • $158/SF
  • 59 Days On Market

  Current Estimated Value $369,511

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  205 Chardonnay Ct, Winchester, KY 40391
• 

  

  /38

  Est $358,372

  Not Listed For Sale

  3070 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,866 Sq Ft
  • Built 1998

  3070 Goshen Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Kevin Bradley Keller Williams Legacy Group
• 

  

  /17

  $260,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  280 Pine Ridge Rd, Winchester, KY 40391

  This listing includes 3 lots in total, 251, 270 and 280 Pine Ridge Rd. All total 12.04 Acres per the PVA. The home is being sold as is.Public Remarks: Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or

  Derek Blankenship Overland Properties Group @ KW Commonwealth

  280 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /44

  $320,000

  Sold Nov 21, 2025

  104 Teakwood Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 24 Days On Market

  Current Estimated Value $329,742

  Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

  104 Teakwood Ct, Winchester, KY 40391
• 

  

  /88

  Est $843,279

  Not Listed For Sale

  865 Sugar Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,146 Sq Ft
  • Built 1997

  865 Sugar Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 88 Days On Market

  Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown
• 

  

  /19

  $460,000

  $39K PRICE DROP

  • Land
  • 36.94 Acres
  • $12,453 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
• 

  

  /33

  $219,900

  Sold May 28, 2026

  21 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1920

  Last Sold Summary

  • $164/SF
  • 2 Days On Market

  Current Estimated Value $219,103

  Last Listing Agent Jenny Mateyoke Keller Williams Legacy Group

  21 Kentucky St, Winchester, KY 40391
• 

  

  /76

  Est $689,646

  Not Listed For Sale

  775 Sugar Ridge Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft
  • Built 1996

  775 Sugar Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Cassie Foley CENTURY 21 Advantage Realty
• 

  

  /31

  $259,500

  Pending

  • 3 Beds
  • 2 Baths
  • 1,403 Sq Ft

  503 Kimberly Dr, Winchester, KY 40391

  Location is key! Searching for your first home or thinking of downsizing? Priced right with stylish upgrades and style. This 3-bedroom 2 bath updated brick is ready for you to start enjoying home ownership. This gem has a new roof, new flooring throughout, new kitchen quartz countertop with a range backsplash, new doors, updated lighting, Shewin Williams paint throughout, updated bathrooms with a

  Vickie Skeens RE/MAX Elite Lexington

  503 Kimberly Dr, Winchester, KY 40391
• 

  

  /30

  $168,000

  Sold Jul 13, 2026

  128 Bay Hill Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,289 Sq Ft
  • Built 2003

  Last Sold Summary

  • 16% Below List Price
  • $130/SF
  • 37 Days On Market

  Current Estimated Value $188,661

  Last Listing Agent Melia Hord MELIA Realty LLC

  128 Bay Hill Dr, Winchester, KY 40391
• 

  

  /53

  Est $288,033

  Not Listed For Sale

  1489 White Conkwright Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,126 Sq Ft
  • Built 1995

  1489 White Conkwright Rd, Winchester, KY 40391

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Sabina Chambers Semonin Realtors
• 

  

  /48

  $304,900

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  335 Newcastle Ln, Winchester, KY 40391

  Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite.

  Josh Wood Freedom Realty & Property Management

  335 Newcastle Ln, Winchester, KY 40391
• 

  

  /20

  $205,000

  Sold Jul 27, 2026

  301 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Below List Price
  • $148/SF
  • 17 Days On Market

  Current Estimated Value $212,976

  Last Listing Agent Julia Lark The Brokerage

  301 Snowden Dr, Winchester, KY 40391
• 

  

  /18

  Est $277,691

  Not Listed For Sale

  6278 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1978

  6278 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Angela Yonts eXp Realty, LLC
• 

  /2

  $1,200,000

  $596K PRICE INCREASE

  • Land
  • 24.15 Acres
  • $49,689 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, Winchester, KY 40391
• 

  

  /38

  $340,000

  Sold Apr 30, 2026

  168 Buckingham Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,358 Sq Ft
  • Built 2000

  Last Sold Summary

  • $144/SF
  • 3 Days On Market

  Current Estimated Value $345,032

  Last Listing Agent Tammy Hill Keller Williams Legacy Group

  168 Buckingham Ln, Winchester, KY 40391
• 

  

  /36

  Est $464,461

  Not Listed For Sale

  5487 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,892 Sq Ft
  • Built 1978

  5487 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Wayne Elkins RE/MAX Creative Realty
• 

  

  /59

  $499,900

  Pending

  • 4 Beds
  • 3 Baths
  • 5,646 Sq Ft

  16 Manor Dr, Winchester, KY 40391

  One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

  Zella Rosenthal Tom Goebel & Company

  16 Manor Dr, Winchester, KY 40391
• 

  

  /92

  $1,075,000

  Sold Mar 18, 2026

  6237 Bybee Rd, Winchester, KY 40391

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $131/SF
  • 212 Days On Market

  Current Estimated Value $1,073,550

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
• 

  

  /34

  Est $369,626

  Not Listed For Sale

  4759 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,633 Sq Ft
  • Built 1985

  4759 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Hannah Simpkins National Real Estate
• 

  /2

  $110,000

  • Land
  • 16,552 Sq Ft
  • $289,474 per Acre

  200 Duclair Dr, 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

  200 Duclair Dr, Winchester, KY 40391
• 

  

  /42

  $390,000

  Sold Oct 21, 2025

  19 Snowfall Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 1950

  Last Sold Summary

  • 11% Above List Price
  • $240/SF
  • 2 Days On Market

  Current Estimated Value $377,052

  Last Listing Agent Bradford Queen Bluegrass Sotheby's International Realty

  19 Snowfall Dr, Winchester, KY 40391
• 

  

  /41

  Est $327,094

  Not Listed For Sale

  2100 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1988

  2100 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Patrick Doyle Lifstyl Real Estate
• 

  

  /34

  $219,000

  $10K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,297 Sq Ft

  13 Long Ave, Winchester, KY 40391

  Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities.

  Kathryn Cheuvront Coldwell Banker McMahan

  13 Long Ave, Winchester, KY 40391
• 

  

  /26

  $200,000

  Sold Oct 02, 2025

  34 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1945

  Last Sold Summary

  • 11% Below List Price
  • $133/SF
  • 8 Days On Market

  Current Estimated Value $214,067

  Last Listing Agent Ashley Barreto Indigo & Co

  34 N Burns Ave, Winchester, KY 40391
• 

  

  /62

  Est $387,797

  Not Listed For Sale

  890 Miller Hunt Rd, Winchester, KY 40391

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

  890 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Daniel Mullins ERA Select Real Estate
• 

  

  /27

  $265,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  15 Kittison Dr, Winchester, KY 40391

  Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and

  Cheri Shaffer Lifstyl Real Estate

  15 Kittison Dr, Winchester, KY 40391
• 

  

  /16

  $214,900

  Sold Dec 05, 2025

  15 Holly Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $179/SF
  • 52 Days On Market

  Current Estimated Value $217,089

  Last Listing Agent Nena Honaker Tom Goebel & Company

  15 Holly Ave, Winchester, KY 40391
• 

  

  /29

  Est $463,534

  Not Listed For Sale

  1623 Little Stoner Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1982

  1623 Little Stoner Rd, Winchester, KY 40391

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Sharon Ben David Berkshire Hathaway de Movellan Properties
• 

  

  /3

  $399,000

  • Land
  • 11.3 Acres
  • $35,310 per Acre

  0 Fairholme Way, Winchester, KY 40391

  11 acres of golf course adjacent land with development plan. Owner/Broker. Road and utility estimates available upon request. A list of individuals interested in lots available upon contract.

  Steve Adams Steven D Adams Real Estate Services, LLC

  0 Fairholme Way, Winchester, KY 40391
• 

  

  /57

  $264,000

  Sold Jul 27, 2026

  720 Terry Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Below List Price
  • $148/SF
  • 28 Days On Market

  Current Estimated Value $275,032

  Last Listing Agent Christa Joynt Keller Williams Commonwealth

  720 Terry Dr, Winchester, KY 40391
• 

  

  /42

  Est $322,734

  Not Listed For Sale

  1570 Little Stoner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1990

  1570 Little Stoner Rd, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Joyce Ratliff Tom Goebel & Company
• 

  

  /45

  $389,900

  Pending

  • 4 Beds
  • 3 Baths
  • 2,676 Sq Ft

  117 Mallard Ln, Winchester, KY 40391

  Discover a hidden gem in Winchester with more than an acre of space and inviting indoor and outdoor living areas. This beautifully maintained brick ranch sits on two combined lots totaling 1.11 acres and features four bedrooms, three full bathrooms, hardwood floors, and a full basement. A spacious sunroom with a gas-log fireplace offers year-round living space and opens to a screened porch

  Erin Lewis Christies International Real Estate Bluegrass

  117 Mallard Ln, Winchester, KY 40391
• 

  

  /54

  $410,000

  Sold Apr 10, 2026

  204 Delaplain Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 3,563 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $115/SF
  • 21 Days On Market

  Current Estimated Value $422,047

  Last Listing Agent Sam Watkins COLOR Real Estate

  204 Delaplain Rd, Winchester, KY 40391

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