Clark County, KY Homes

• 

  

  

  /57

  $270,000

  $5K PRICE DROP

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

  720 Terry Dr, Winchester, KY 40391

  Welcome home to this cozy 3-bedroom, 2-bath property located in the heart of Winchester, KY, just minutes from the Winchester Bypass for quick and easy commuting. Priced at $270,000, this home offers exceptional value in a highly walkable and convenient neighborhood. The thoughtful layout includes a versatile lower-level den paired with a full second bathroom, creating the perfect opportunity for

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 903-5709

  720 Terry Dr, Winchester, KY 40391
• 

  

  

  /35

  Starting at $800 Per Month

  • 1 - 3 Beds

  260 Oxford Dr, Winchester, KY 40391

  The Summit located in Winchester; KY is just minutes away from major employers. We are just a short drive from Lexington, KY. Come see our pet friendly community with lots of green space. We have spacious one-, two-, and three-bedroom apartment homes with caring on-site management. Our homes feature walk-in closets, new Laminate Vinyl Plank Flooring, fully equipped kitchens, washer/dryer

  Summit Apartments

  (859) 577-9164

  260 Oxford Dr, Winchester, KY 40391
• 

  

  

  /8

  $15,000

  Sold Dec 30, 2025

  61 Melbourne St, Winchester, KY 40391

  • Land
  • 4,356 Sq Ft
  • $150,000 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 57 Days On Market

  Current Estimated Value $80,682

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
• 

  

  

  /41

  Est $682,714

  Not Listed For Sale

  357 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,007 Sq Ft
  • Built 2002

  357 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 15 Days On Market
• 

  

  

  /32

  $325,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  4305 Old Boonesboro Rd, Winchester, KY 40391

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3072

  4305 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /3

  Starting at $814 Per Month

  • Studio - 1 Bed

  27 E Washington St, Winchester, KY 40391

  *One Month Free Rent!* All Utilities Included! Nice Studio Apt Near Downtown Winchester!Marketing DescriptionStudio Apartment Available at Studio 29 Apartments, Winchester, KY! One Bath; Only 5 Minutes from Downtown! Off-Street Parking, Small Pets Ok; All Utilities Included! Kitchen includes a Stove, Refrigerator, and Microwave; Non-smoking.Conveniently located near Shopping, Grocery

  Studio 28

  (859) 249-8752

  27 E Washington St, Winchester, KY 40391
• 

  

  /20

  $189,500

  Sold Dec 18, 2025

  13015 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 17% Below List Price
  • 134 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13015 Irvine Rd, Winchester, KY 40391
• 

  

  /27

  Est $240,305

  Not Listed For Sale

  13 Fairview Ave, Winchester, KY 40391

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

  13 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  

  /18

  $550,000

  $6K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,102 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  (859) 695-3879

  110 White Conkwright Rd, Winchester, KY 40391
• 

  

  /3

  Starting at $1,049 Per Month

  • 2 Beds

  510 College St, Winchester, KY 40391

  Lovely 2 Bedroom and One Bath Apartment at the Lofts of Winchester, located at 508 College Street, Winchester, KY! Near Downtown, Shopping, Restaurants, Hwy 64 and Hwy 60. Off-street Parking; Small Pets Ok! Beautiful Updated Flooring and Stainless Steel Appliances. Kitchen includes Stove and Refrigerator. Central Heat & AC.Local Schools are: Willis H. Justice Elementary; Robert D.

  The Lofts at Winchester

  (859) 249-8853

  510 College St, Winchester, KY 40391
• 

  

  /41

  $272,000

  Sold Jun 26, 2025

  205 Beaumont Place, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1995

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 4 Days On Market

  Current Estimated Value $288,526

  Last Listing Agent Terry Billiter Premier Property Consultants

  205 Beaumont Place, Winchester, KY 40391
• 

  

  /24

  Est $198,347

  Not Listed For Sale

  605 Dixiana Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1990

  605 Dixiana Dr, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market
• 

  

  /28

  $84,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  300 Aspen Ln, Winchester, KY 40391

  Welcome home to this well-maintained 3 bedroom, 2 bathroom double wide manufactured home in Treehaven, offering close to 2,000 square feet of comfortable living space...a rare find for buyers looking for room, functionality, and flexibility. Inside, you'll love the open-concept layout that connects the large living room, a large den, a large kitchen, and dining area, making it ideal for both

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 903-5711

  300 Aspen Ln, Winchester, KY 40391
• 

  

  /5

  $996 Per Month

  • 1 Bed
  • 1 Bath
  • 872 Sq Ft
  • Condo for Rent

  362 S Main St Unit A, Winchester, KY 40391

  Property Id: 2574447Large 1 bedroom, i bath newly painted apartment. Close to shopping, gym and local grocery. Resevved off street parking, in house laundry.

  (859) 577-7730

  362 S Main St Unit A, Winchester, KY 40391
• 

  

  /51

  $750,000

  Sold May 21, 2026

  1783 Gay Evans Rd, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 2,904 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $258/SF
  • 135 Days On Market

  Current Estimated Value $758,759

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1783 Gay Evans Rd, Winchester, KY 40391
• 

  

  /33

  Est $277,585

  Not Listed For Sale

  14 Calloway St, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Built 1940

  14 Calloway St, Winchester, KY 40391

  Last Sold Summary

  • 75 Days On Market
• 

  

  /84

  $724,999

  $74K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 7,058 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 470-2071

  186 Chardonnay Ct, Winchester, KY 40391
• 

  /2

  $1,190 Per Month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  1028 W Lexington Ave Unit 3, Winchester, KY 40391

  This cozy 1-bedroom, 1-bathroom apartment features a comfortable living area and a functional kitchen. Pets are welcome with an additional pet fee. Tenants are responsible for all utility payments, giving you full control over your monthly expenses. Ideal for anyone seeking a convenient and pet-friendly home.

  1028 W Lexington Ave Unit 3, Winchester, KY 40391
• 

  

  /75

  $315,000

  Sold Jun 27, 2025

  408 Calmes Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $170/SF
  • 46 Days On Market

  Current Estimated Value $338,031

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  408 Calmes Blvd, Winchester, KY 40391
• 

  

  /18

  Est $108,202

  Not Listed For Sale

  27 Oliver St, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1940

  27 Oliver St, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market
• 

  

  /24

  $280,000

  • 4 Beds
  • 3.5 Baths
  • 3,276 Sq Ft

  133 Bay Hill Dr, Winchester, KY 40391

  Welcome to 133 Bay Hill Drive in Winchester, Kentucky — a spacious and beautifully maintained home offering over 3,200 square feet of living space in one of the area's desirable subdivisions. Conveniently located just minutes from town and close to local factories and major employers, this property offers the perfect blend of comfort, convenience, and neighborhood living. Inside, you'll find

  

  Dustin Pennington

  Keller Williams Legacy Group

  (859) 636-6943

  133 Bay Hill Dr, Winchester, KY 40391
• 

  /2

  $1,750 Per Month

  • 3 Beds
  • 1 Bath
  • 1,974 Sq Ft
  • House for Rent

  136 Alabama St, Winchester, KY 40391

  Welcome home to this spacious 3-bedroom, 1-bath residence offering the perfect combination of comfort and convenience. With generous living space, well-sized bedrooms, and a functional layout, this home is ideal for families, roommates, or anyone looking for extra room to spread out.Enjoy comfortable living in a home designed to meet your everyday needs. Contact us today for more

  136 Alabama St, Winchester, KY 40391
• 

  

  /41

  $302,500

  Sold Jan 05, 2026

  202 Dubuy Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Below List Price
  • $168/SF
  • 5 Days On Market

  Current Estimated Value $306,425

  Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

  202 Dubuy Dr, Winchester, KY 40391
• 

  

  /28

  Est $386,474

  Not Listed For Sale

  512 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft
  • Built 1950

  512 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 58 Days On Market
• 

  

  /21

  $175,000

  • 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

  (859) 648-3896

  2996 Irvine Rd, Winchester, KY 40391
• 

  

  /6

  $1,190 Per Month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  1028 W Lexington Ave Unit 4, Winchester, KY 40391

  Welcome to 1028 W Lexington Ave — a cozy and well-maintained 1-bedroom, 1-bathroom apartment located in the heart of Winchester, KY.This home features a spacious living area, a functional kitchen, and all the essentials needed for comfortable everyday living. Ideal for students, professionals, or anyone looking to downsize, this apartment offers the perfect balance of comfort and

  1028 W Lexington Ave Unit 4, Winchester, KY 40391
• 

  

  /31

  $88,500

  Sold Aug 08, 2025

  15 Sycamore St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1945

  Last Sold Summary

  • 12% Below List Price
  • $77/SF
  • 28 Days On Market

  Current Estimated Value $98,044

  Last Listing Agent Rony Jo Ballou Power House Realty

  15 Sycamore St, Winchester, KY 40391
• 

  

  /26

  Est $268,271

  Not Listed For Sale

  134 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft
  • Built 1920

  134 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 74 Days On Market
• 

  

  /25

  $425,000

  • Land
  • 25.87 Acres
  • $16,426 per Acre

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare opportunity to own over 25 acres of beautiful Kentucky countryside on Irvine Road, combining two adjoining tracts into one exceptional offering. With gently rolling hills and multiple ideal building sites, this property provides the perfect setting to create your dream home, private estate, or mini-farm. The land offers a wonderful balance of usability and natural beauty, featuring a scenic

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 577-9032

  2996/3056 Irvine Rd, Winchester, KY 40391
• 

  /2

  $1,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  135 Winn Ave Unit A, Winchester, KY 40391

  Step into this beautifully renovated 3-bedroom, 2-bathroom home featuring a bright and open living area and a modern kitchen on the ground floor. Designed for comfort and style, this residence offers contemporary finishes, spacious layouts, and all the amenities you need for modern living. Perfect for families or anyone seeking a move-in ready home with a fresh, modern feel.

  135 Winn Ave Unit A, Winchester, KY 40391
• 

  

  /30

  $190,000

  Sold Mar 06, 2026

  2721 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2000

  Last Sold Summary

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

  Current Estimated Value $199,524

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
• 

  

  /25

  Est $221,674

  Not Listed For Sale

  138 Linden Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 2024

  138 Linden Ave, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market
• 

  

  /30

  $200,000

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

  128 Bay Hill Dr, Winchester, KY 40391

  Opportunity knocks in Royal Oaks Village--be part of Winchester's next chapter. Located within the expanding Deerlawn development, this single-story ranch townhome offers incredible upside in an area poised for growth. With future plans bringing hundreds of new homes, townhomes, and duplexes nearby, this is your chance to get in early and build equity. Inside, you'll find a spacious and

  

  Melia Hord

  MELIA Realty LLC

  (859) 809-3304

  128 Bay Hill Dr, Winchester, KY 40391
• 

  

  /20

  $829 Per Month

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  18 Calloway St Unit 4, Winchester, KY 40391

  Available May 26,2026! – Recently Renovated Winchester Apartment!Welcome to your next home in the heart of Winchester! This beautifully updated 1-bedroom, 1-bath apartment is nestled just off Lexington Avenue and Bypass Road close to shopping, dining, and just minutes from downtown Winchester.At Bluegrass Rental Management, we strive to provide an experience that is cost-effective

  18 Calloway St Unit 4, Winchester, KY 40391
• 

  

  /35

  $308,000

  Sold Oct 03, 2025

  329 Hanover Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft
  • Built 2003

  Last Sold Summary

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

  Current Estimated Value $319,964

  Last Listing Agent Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
• 

  

  /23

  Est $270,360

  Not Listed For Sale

  244 Bay Hill Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,536 Sq Ft
  • Built 2006

  244 Bay Hill Ct, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market
• 

  

  /20

  $300,000

  • Land
  • 15.27 Acres
  • $19,652 per Acre

  4025 Jackson Ferry Rd, Winchester, KY 40391

  Opportunities like this are incredibly rare—15.266 combined acres backing to the Kentucky River, offering the ultimate private retreat. Located at the end of a scenic drive, these two tracts are being offered together, creating an expansive recreational property with unmatched access to the water. Ideal for camping, family getaways, or creating a multi-use outdoor haven, this land provides

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 208-1610

  4025 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /7

  $825 Per Month

  • Studio
  • 1 Bath
  • 300 Sq Ft
  • Studio Apt All Utilities Included!

  401 N Maple St Unit 6, Winchester, KY 40391

  Welcome to this charming renovated studio apartment located at 401 North Maple Street. This cozy unit is perfect for those seeking a comfortable and affordable living space.Step inside and be greeted by the stylish LVP flooring that adds a touch of elegance to the interior. The open layout creates a seamless flow between the living area, kitchenette, and sleeping quarters.One of

  401 N Maple St Unit 6, Winchester, KY 40391
• 

  

  /81

  $599,500

  Sold Aug 18, 2025

  2615 Crowe Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,222 Sq Ft
  • Built 2018

  Last Sold Summary

  • $270/SF
  • 1 Day On Market

  Current Estimated Value $580,680

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  2615 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  /33

  Est $464,278

  Not Listed For Sale

  210 Candlewood Dr, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,046 Sq Ft
  • Built 2006

  210 Candlewood Dr, Winchester, KY 40391

  Last Sold Summary

  • 49 Days On Market

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