Winchester, KY Homes

• 

  

  /2

  $78,500

  • Land
  • 21,780 Sq Ft
  • $157,000 per Acre

  2395 Paris Rd Unit Lot 5, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 5, Winchester, KY 40391
• 

  

  

  /10

  $1,045 Per Month

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Condo for Rent

  183-185 Westside Dr Unit 185 Westside Dr, Winchester, KY 40391

  2 bedroom 2 bath! Ready for Move In October 1.Convenient location on a quiet cul-de-sac in Winchester, KY!

  183-185 Westside Dr Unit 185 Westside Dr, Winchester, KY 40391
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  /14

  $320,000

  Sold Oct 17, 2025

  3431 Colby Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 5,237 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $61/SF
  • 7 Days On Market

  Current Estimated Value $356,403

  Last Listing Agent Holly Goeing The Agency

  3431 Colby Rd, Winchester, KY 40391
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  /70

  Est $326,839

  Not Listed For Sale

  705 Oil Springs Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1979

  705 Oil Springs Rd, Winchester, KY 40391

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Victoria Byrd HomeFirst Real Estate
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  /2

  $78,500

  • Land
  • 19,166 Sq Ft
  • $178,409 per Acre

  2395 Paris Rd Unit Lot 3, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 3, Winchester, KY 40391
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  /7

  $1,175 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • 247/249 April way

  247-249 April Way Unit 247 April Way, Winchester, KY 40391

  Welcome home to 247 April Way in Winchester, Kentucky! These well-maintained duplexes offer comfortable living with several floor plan options available.Each home includes washer and dryer hookups, along with a stove, refrigerator, dishwasher, and microwave. Residents can also enjoy a private deck or patio, garage parking, and lawn care included with rent.*Photos shown may

  247-249 April Way Unit 247 April Way, Winchester, KY 40391
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  /41

  $265,000

  Sold Nov 12, 2025

  130 Village Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $133/SF
  • 4 Days On Market

  Current Estimated Value $282,192

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  130 Village Ct, Winchester, KY 40391
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  /44

  Est $477,221

  Not Listed For Sale

  1927 Kiddville Rd, Winchester, KY 40391

  • 5 Beds
  • 4 Baths
  • 2,056 Sq Ft
  • Built 2001

  1927 Kiddville Rd, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Megan McCoy Keller Williams Legacy Group
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  /2

  $78,500

  • Land
  • 15,158 Sq Ft
  • $225,575 per Acre

  2395 Paris Rd Unit Lot 6, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 6, Winchester, KY 40391
• 

  

  /10

  $1,525 Per Month

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • 312/314 Prescott Lane

  312-314 Prescott Ln Unit 312 Prescott Lane, Winchester, KY 40391

  Welcome home to The Farms of Winchester, where comfortable living meets incredible community amenities!This spacious 2-bedroom, 2-full-bath duplex features a single-car garage, a functional layout, and the privacy and convenience you’ve been looking for. Even better, lawn care is included, giving you more time to enjoy your home and everything our community has to offer.Residents at The

  312-314 Prescott Ln Unit 312 Prescott Lane, Winchester, KY 40391
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  /62

  $498,325

  Sold Sep 11, 2026

  919 Elkin Station Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,844 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Above List Price
  • $175/SF
  • 1 Day On Market

  Current Estimated Value $407,705

  Last Listing Agent Lori Tolson Lifstyl Real Estate

  919 Elkin Station Rd, Winchester, KY 40391
• 

  

  /47

  Est $460,239

  Not Listed For Sale

  372 Arrowhead Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,744 Sq Ft
  • Built 2001

  372 Arrowhead Ln, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Lori Tolson Lifstyl Real Estate
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  /45

  $855,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 3 Baths
  • 2,872 Sq Ft

  5960 Van Meter Rd, Winchester, KY 40391

  Discover the charm of country living on nearly 15 acres of beautiful, mostly flat to gently rolling farmland, offering picturesque views and plenty of space to enjoy the outdoors. This well-maintained property features a barn, equipment shed, workshop, and an attached three-bay garage, providing exceptional storage and workspace for equipment, hobbies, or farm use. Inside the home, you'll find

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  5960 Van Meter Rd, Winchester, KY 40391
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  /4

  $1,125 Per Month

  • 2 Beds
  • 1.5 Baths
  • 360/362 Colby Ridge

  360-362 Colby Ridge Blvd Unit 360 Colby Ridge, Winchester, KY 40391

  This comfortable home offers the kind of easy living that makes settling in simple. You’ll be tucked into a convenient Winchester location with shopping, dining, downtown, and major roadways all just a short drive away.Whether you’re starting fresh or simply looking for a place that feels a little more like home, Colby Ridge gives you a comfortable space in a location that keeps everyday

  360-362 Colby Ridge Blvd Unit 360 Colby Ridge, Winchester, KY 40391
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  /35

  $285,000

  Sold May 01, 2026

  192 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Above List Price
  • $184/SF
  • 1 Day On Market

  Current Estimated Value $286,150

  Last Listing Agent Joy Murphy United Real Estate Bluegrass

  192 Prescott Ln, Winchester, KY 40391
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  /112

  Est $791,615

  Not Listed For Sale

  703 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,311 Sq Ft
  • Built 1980

  703 Kiddville Rd, Winchester, KY 40391

  Last Sold Summary

  • 276 Days On Market

  Last Listing Agent Tyson Walters Kassie & Associates
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  /29

  $150,000

  • 3 Beds
  • 1 Bath
  • 1,842 Sq Ft

  5 S Burns Ave, Winchester, KY 40391

  Welcome home to this charming 3-bedroom, 1-bathroom property featuring a comfortable living room, dedicated dining room, and a functional layout with plenty of potential. Outside, you'll find a detached 1-car garage and a long driveway. Whether you're looking for your first home or your next investment opportunity, this property offers a great combination of space, functionality, and potential.

  

  Tirza Howard

  The Howard Realty Co

  5 S Burns Ave, Winchester, KY 40391
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  /10

  $1,045 Per Month

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Condo for Rent

  188-190 Westside Dr Unit 188 Westside Dr, Winchester, KY 40391

  2 bedroom 2 bath! Ready for Move In October 1.Convenient location on a quiet cul-de-sac in Winchester, KY!

  188-190 Westside Dr Unit 188 Westside Dr, Winchester, KY 40391
• 

  

  /34

  $278,000

  Sold Aug 31, 2026

  304 Sandra Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,377 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $202/SF
  • 15 Days On Market

  Current Estimated Value $272,270

  Last Listing Agent Michael Hilario The Agency

  304 Sandra Dr, Winchester, KY 40391
• 

  

  /96

  Est $462,303

  Not Listed For Sale

  2430 Log Lick Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • Built 1938

  2430 Log Lick Rd, Winchester, KY 40391

  Last Sold Summary

  • 184 Days On Market

  Last Listing Agent E Anthony Phillips RE/MAX Creative Realty
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  /35

  $299,900

  $20K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,082 Sq Ft

  128 Cherokee Dr, Winchester, KY 40391

  Welcome to 128 Cherokee Drive, where space, versatility, and convenience come together! This all-brick split-foyer home offers 5 bedrooms, 2 full bathrooms, and over 2,000 square feet of comfortable living space, making it ideal for growing families, multi-generational living, or anyone needing extra room. The main level features a bright and inviting living room, while the finished lower level

  

  Tyler Hurst

  Oak & Acre

  128 Cherokee Dr, Winchester, KY 40391
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  /6

  $799 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  7 Calloway St Unit 7 Calloway St #1, Winchester, KY 40391

  Bright One Bedroom Apartment with character and all utilities included. This is a basement apartment but is very bright and light with new cabinets, counters, bathtub, vanity and more! All utilities included Weekly or Monthly payment options available. Apply online at www.360mgt.group today. Approved lease applications are required before a showing is scheduled.

  7 Calloway St Unit 7 Calloway St #1, Winchester, KY 40391
• 

  

  /29

  $285,000

  Sold Jun 12, 2026

  426 E Broadway St, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,838 Sq Ft
  • Built 1945

  Last Sold Summary

  • 1% Below List Price
  • $155/SF
  • 12 Days On Market

  Current Estimated Value $282,513

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  426 E Broadway St, Winchester, KY 40391
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  /30

  Est $263,081

  Not Listed For Sale

  3604 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1998

  3604 Pine Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Patty Adams Rector Hayden Realtors
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  /21

  $175,000

  Pending

  • Land
  • 11.36 Acres
  • $15,402 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of convenience and countryside charm with this beautiful 11+ acre tract located just outside of Winchester in Clark County. Offering gently rolling terrain and multiple potential building sites, this property provides an ideal setting for your dream home, mini-farm, or private retreat.Enjoy the peace and privacy of rural living without sacrificing accessibility and just

  

  Christa Joynt

  Keller Williams Commonwealth

  2996 Irvine Rd, Winchester, KY 40391
• 

  

  /6

  $795 Per Month

  • 2 Beds
  • 1 Bath
  • House for Rent

  1305 Fulton Rd, Winchester, KY 40391

  This unit won't last long! Located right off the Bypass, this duplex is close to everything Winchester has to offer! Get your application in today before it's too late.

  1305 Fulton Rd, Winchester, KY 40391
• 

  

  /19

  $288,500

  Sold Feb 24, 2026

  729 Wayland Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $147/SF
  • 92 Days On Market

  Current Estimated Value $292,386

  Last Listing Agent Brittany Beer eXp Realty, LLC

  729 Wayland Dr, Winchester, KY 40391
• 

  

  /13

  Est $124,243

  Not Listed For Sale

  2431 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,113 Sq Ft
  • Built 1920

  2431 Pine Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent A. Rebecca Woods Woods Realty Group
• 

  /2

  $78,500

  • Land
  • 22,651 Sq Ft
  • $150,962 per Acre

  2395 Paris Rd Unit Lot 4, Winchester, KY 40391

  Welcome to Deerlawn Development, a fully approved 274-acre residential community, extending off of the Royal Oaks/Plantation Subdivision in Winchester, KY. Phase One includes 12 build-ready single-family homesites, with 5 already closed and additional lots coming in future stages. Build your custom home with your preferred builder or build for yourself. Deerlawn is planned for 438 single-family

  

  Melia Hord

  MELIA Realty LLC

  2395 Paris Rd Unit Lot 4, Winchester, KY 40391
• 

  

  /22

  $1,400 Per Month

  • 3 Beds
  • 1 Bath
  • 805 Sq Ft
  • House for Rent

  150 Cook Ave, Winchester, KY 40391

  150 Cook Ave, Winchester, KY 40391
• 

  

  /14

  $125,000

  Sold Apr 01, 2026

  464 Ecton Rd, Winchester, KY 40391

  • Land
  • 1.03 Acres
  • $121,359 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 3 Days On Market

  Current Estimated Value $134,081

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  464 Ecton Rd, Winchester, KY 40391
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  /101

  Est $375,771

  Not Listed For Sale

  3642 Crowe Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft
  • Built 1953

  3642 Crowe Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 121 Days On Market

  Last Listing Agent Maggie Napier Napier Realtors
• 

  

  /46

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  2180 Big Stoner Rd, Winchester, KY 40391

  Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides

  

  Ashley Barreto

  Indigo & Co

  2180 Big Stoner Rd, Winchester, KY 40391
• 

  

  /25

  $1,395 Per Month

  • 3 Beds
  • 2 Baths
  • 975 Sq Ft
  • House for Rent

  222 Buffalo Trace, Winchester, KY 40391

  ESTIMATED TOTAL MONTHLY LEASING PRICE: $1490.99Base Rent: $1395.00*Resident Benefits Package: Starts at $30.99*Resident Internet Amenity: $65.00This three-bedroom home is perfectly situated in the desirable Buffalo Trace neighborhood of downtown Winchester, offering both convenience and comfort in a prime location. The property features luxury vinyl plank flooring throughout,

  222 Buffalo Trace, Winchester, KY 40391
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  /67

  $410,000

  Sold Jul 09, 2026

  233 Schollsville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,347 Sq Ft
  • Built 2016

  Last Sold Summary

  • 2% Above List Price
  • $304/SF
  • 1 Day On Market

  Current Estimated Value $406,775

  Last Listing Agent Bill Deaton Keller Williams Legacy Group

  233 Schollsville Rd, Winchester, KY 40391
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  /16

  Est $138,000

  Not Listed For Sale

  4523 Trapp Goffs Corner Rd, Winchester, KY 40391

  • Studio
  • 1,271 Sq Ft
  • Built 1974

  4523 Trapp Goffs Corner Rd, Winchester, KY 40391

  Last Sold Summary

  • 178 Days On Market

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
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  /4

  $64,900

  • Land
  • 27,878 Sq Ft
  • $101,406 per Acre

  102 Royal Oak Dr, Winchester, KY 40391

  One of the Few Remaining Estate Homesites in Royal Oaks Estates! An exceptional opportunity awaits to build your custom dream home in the Estate Section of Royal Oaks, one of Clark County's most established and desirable communities. Situated on 0.64 acres, 102 Royal Oak Drive offers the space, setting, and flexibility to create a home tailored to your lifestyle while enjoying the beauty and

  

  Melia Hord

  MELIA Realty LLC

  102 Royal Oak Dr, Winchester, KY 40391
• 

  

  /14

  $1,250 Per Month

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Condo for Rent

  167-169 Westside Dr Unit 167 Westside Dr, Winchester, KY 40391

  3 bedroom 2 bath duplex available for immediate move in!Winchester, KY great location, quiet cul-de-sac.

  167-169 Westside Dr Unit 167 Westside Dr, Winchester, KY 40391
• 

  

  /33

  $332,000

  Sold Oct 14, 2025

  1831 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $189/SF
  • 82 Days On Market

  Current Estimated Value $336,990

  Last Listing Agent Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
• 

  

  /40

  Est $386,774

  Not Listed For Sale

  409 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,840 Sq Ft
  • Built 1971

  409 Kiddville Rd, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

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