Winchester, KY Homes

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  /17

  $223,000

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft

  140 Cherokee Dr, Winchester, KY 40391

  Serena Cassidy Coldwell Banker McMahan

  140 Cherokee Dr, Winchester, KY 40391
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  /53

  Est $291,914 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  7 Bon Haven Ave, Winchester, KY 40391

  7 Bon Haven Ave, Winchester, KY 40391
• 

  

  

  /17

  $229,000

  • Land
  • 17 Acres
  • $13,729 per Acre

  13015 Irvine Rd, Winchester, KY 40391

  Mendel Tipton Natural Bridge Realty

  13015 Irvine Rd, Winchester, KY 40391
• 

  

  

  /27

  Est $316,791 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  19 Meadowbrook Dr, Winchester, KY 40391

  19 Meadowbrook Dr, Winchester, KY 40391
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  /5

  $105,000

  • Land
  • 1.00 Acre
  • $105,000 per Acre

  1750 Mcclure Rd, Winchester, KY 40391

  Mila Ensor Ensor Real Estate LLC

  1750 Mcclure Rd, Winchester, KY 40391
• 

  

  /61

  Est $258,552 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,948 Sq Ft

  1316 Dale Dr, Winchester, KY 40391

  1316 Dale Dr, Winchester, KY 40391
• 

  

  /25

  $255,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  724 Terry Dr, Winchester, KY 40391

  Nestled in the Westmeade neighborhood, this home offers the perfect blend of comfort and convenience, just minutes from the Winchester Bypass and a short drive to Lexington. With approximately 2,250 square feet of living space, this home features an inviting foyer that leads into a bright eat-in kitchen and a welcoming main living area.Down the hall, you'll find three bedrooms, along with

  Samantha Cotton National Real Estate

  724 Terry Dr, Winchester, KY 40391
• 

  

  /17

  Est $244,801 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  3495 Stamper Dr, Winchester, KY 40391

  3495 Stamper Dr, Winchester, KY 40391
• 

  

  /5

  $45,000 Pending

  • Land
  • 0.36 Acre
  • $125,000 per Acre

  434 Fairholme Way, Winchester, KY 40391

  Ready to build your forever home? Look no further! This lot is conveniently located in the highly sought after Fairholme Estates, which is a short golf cart ride to the Winchester Country Club and downtown Winchester.

  Justin Lee JL Realty Group, LLC

  434 Fairholme Way, Winchester, KY 40391
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  /24

  Est $280,535 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,435 Sq Ft

  317 Frontier Way, Winchester, KY 40391

  317 Frontier Way, Winchester, KY 40391
• 

  

  /55

  $174,900 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  20 Heather Ln, Winchester, KY 40391

  This charming 2-bedroom, 1.5-bath brick townhome offers a comfortable living space in a prime location. Inside, you'll find all-new LVP flooring, fresh carpet, and a fresh coat of paint throughout. The spacious living room flows into a well-sized kitchen featuring brand-new countertops and ample counter space—perfect for everyday cooking and entertaining.Appliances including the washer,

  Josh Wood Freedom Realty & Property Mgt

  20 Heather Ln, Winchester, KY 40391
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  /42

  Est $329,932 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,085 Sq Ft

  426 Tremont Ln, Winchester, KY 40391

  426 Tremont Ln, Winchester, KY 40391
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  /33

  $335,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft

  543 S Maple St, Winchester, KY 40391

  Nestled on the charming street of South Maple this beautiful ranch home offers the perfect blend of comfort and convenience. Featuring three bedrooms and two modern bathrooms, this single-level living space is designed for ease and elegance. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating a welcoming atmosphere for gatherings. Large windows fill

  Lucy Martin Jenkins United Real Estate Bluegrass

  543 S Maple St, Winchester, KY 40391
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  /15

  Est $279,981 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft

  408 Tremont Ln, Winchester, KY 40391

  408 Tremont Ln, Winchester, KY 40391
• 

  

  /3

  $109,000 Pending

  • Land
  • 4.02 Acres
  • $27,114 per Acre

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2010 and 2058 approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

  Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /20

  Est $284,560 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft

  317 Newcastle Ln, Winchester, KY 40391

  317 Newcastle Ln, Winchester, KY 40391
• 

  

  /27

  $278,900 Pending

  • 3 Beds
  • 3 Baths
  • 1,813 Sq Ft

  9 Hillcrest Dr, Winchester, KY 40391

  Built To Last, This Extra Solid Ranch Home, Was Built With Top Of The Line Materials! Turn It Into Your Dream Home Or Use As A Great Investment Property, Where As, You Can Easily Double Your Square Footage When Finishing The Basement. A Beautiful Layout, Offering 3 Bedrooms, 2 Full Baths, Chef's Kitchen, Separate Laundry, Off The Attached Garage, Open Concept Living & Dining Space, On The Main.

  Melissa Thompson Keller Williams Legacy Group

  9 Hillcrest Dr, Winchester, KY 40391
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  /41

  Est $289,028 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,883 Sq Ft

  335 Newcastle Ln, Winchester, KY 40391

  335 Newcastle Ln, Winchester, KY 40391
• 

  

  /24

  $284,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft

  10 Howard Dr, Winchester, KY 40391

  Charming All-Brick Ranch with Bonus Space & Huge Yard!This beautifully updated 3-bedroom, 2-bathroom all-brick ranch offers timeless charm and modern touches throughout. Situated on a generous, fully fenced lot with mature trees, this home features fresh neutral paint, stylish shiplap accents, and abundant natural light. The spacious detached bonus room is perfect for a home office, gym,

  Holly Goeing The Agency

  10 Howard Dr, Winchester, KY 40391
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  /20

  Est $251,581 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,353 Sq Ft

  186 Prescott Ln, Winchester, KY 40391

  186 Prescott Ln, Winchester, KY 40391
• 

  

  /36

  $285,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft

  103 Hampton Ave, Winchester, KY 40391

  A timeless brick ranch in one of Winchester's most established neighborhoods on a corner lot. This 3 bedroom, 2.5 bath home offers two living areas and a cozy fireplace. Spacious backyard, covered front porch, and a wrap-around driveway for a private entrance. All just minutes from downtown, schools, and I-64. The home combines classic comfort, location, and room to grow on a walk-out basement.

  Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /31

  Est $273,240 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft

  334 Newcastle Ln, Winchester, KY 40391

  334 Newcastle Ln, Winchester, KY 40391
• 

  

  /32

  $210,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,294 Sq Ft

  2858 Ford Hampton Rd, Winchester, KY 40391

  This cozy place has so much to offer. 3 spacious bedrooms and 2 full bathrooms. The kitchen has handmade cabinets throughout. The property includes a large 1,050 square foot detached garage and a 448 square foot building. It is located just minutes from the Boonesborough State Park and the scenic Kentucky River. Camping, hiking, fine dining, golf courses, and several other amenities are also

  Dale Hatton Dream Maker Realty, LLC

  2858 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /28

  Est $275,394 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,652 Sq Ft

  220 Bartram Ct, Winchester, KY 40391

  220 Bartram Ct, Winchester, KY 40391
• 

  

  /34

  $372,500 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  148 Gibson Way, Winchester, KY 40391

  NEW PRICE!Better Than New Construction!!! This Spacious 4 Bedroom 2 1/2 Bath Home Is Move In Ready And Has A Beautiful Farm View From Your Covered Porch. Features Include A Large Open Living Room And Kitchen With Plenty Of Cabinet Space; Large Island With Faucet; Granite Countertops; Tile Backsplash; Stainless Steel Appliances; Large pantry; Gas Log Fireplace; Gas Heat; Gas Water Heater;

  Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
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  /26

  Est $286,496 Not Listed For Sale

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

  214 Bartram Ct, Winchester, KY 40391

  214 Bartram Ct, Winchester, KY 40391
• 

  

  /21

  $149,000 Pending

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval, no warranties implied or

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
• 

  

  /32

  Est $209,884 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  533 Hidden Hills Way, Winchester, KY 40391

  533 Hidden Hills Way, Winchester, KY 40391
• 

  

  /29

  $174,900 Pending

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  217 Blair Ave, Winchester, KY 40391

  Welcome to 217 Blair Avenue in the heart of Winchester—a charming and move-in-ready home offering comfort, character, and convenience. This property features 3 spacious bedrooms, 1 full bath, and an inviting layout featuring hardwood floors, a light-filled living room, and an updated kitchen with ample cabinet space. Outside, enjoy a large backyard ideal for gatherings, gardening, or relaxing

  Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
• 

  

  /6

  Est $174,514 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft

  207 Arbor Ct, Winchester, KY 40391

  207 Arbor Ct, Winchester, KY 40391
• 

  

  /25

  $315,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft

  220 Mcdowell Dr, Winchester, KY 40391

  This beautiful 3BR, 2BA ranch style home offers a blend of comfort and style. Featuring an inviting open concept layout, the spacious living area flows effortlessly into the kitchen and dining spaces- perfect for family gatherings or entertaining guests. The exterior boasts charming curb appeal with a well maintained lawn, new siding, stone accents, and a cozy covered front porch. A 2 car

  Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
• 

  

  /24

  Est $187,884 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft

  204 Arbor Ct, Winchester, KY 40391

  204 Arbor Ct, Winchester, KY 40391
• 

  

  /99

  $749,000 Pending

  • 4 Beds
  • 4 Baths
  • 4,644 Sq Ft

  110 Camelot Dr, Winchester, KY 40391

  Don't miss this rare opportunity to abide in one of Winchester's finest locations, Camelot Drive. A hidden gem tucked away in the back of Hampton Manor, this home boasts space and privacy on an idyllic cul-de-sac just off Boone Avenue. Details such as crown molding, built-in cabinetry, high ceilings, 2 fireplaces, transom windows, and hardwood floors fill this home with character and charm.

  Joyce Ratliff Tom Goebel & Company

  110 Camelot Dr, Winchester, KY 40391
• 

  

  /17

  Est $131,913 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 781 Sq Ft

  334 Oxford Dr, Winchester, KY 40391

  334 Oxford Dr, Winchester, KY 40391
• 

  

  /32

  $199,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft

  116 Linden Ave, Winchester, KY 40391

  Welcome to 116 Linden Avenue located minutes from Winchester's charming downtown. This move in ready 3-bedroom, 2-bath home is complete with fresh paint and a great layout that offers both comfort and functionality. Enjoy the convenience of a first-floor primary bedroom and the bonus of a spacious yard, perfect for outdoor entertaining, gardening, or relaxing. Whether you're looking for your next

  Robert Bratton Bluegrass Sotheby's International Realty

  116 Linden Ave, Winchester, KY 40391
• 

  

  /17

  Est $304,249 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft

  203 Lamond Ruelle, Winchester, KY 40391

  203 Lamond Ruelle, Winchester, KY 40391
• 

  

  /41

  $279,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft

  225 Prescott Ln, Winchester, KY 40391

  What are your thoughts on a residence featuring a prime location, within walking distance to several schools? Now that I've got your interest, the primary bedroom is situated on the main level. How do three or possibly four bedrooms, accompanied by 2.5 bathrooms, sound? This residence is located in the Oakmont subdivision and has been under the same ownership for over 15 years. Don't miss your

  Teresa Richmond Freedom Realty & Property Mgt

  225 Prescott Ln, Winchester, KY 40391
• 

  

  /34

  Est $341,441 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,643 Sq Ft

  115 Shala Mar Rue, Winchester, KY 40391

  115 Shala Mar Rue, Winchester, KY 40391
• 

  

  /23

  $225,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  26 Stefanie Ct, Winchester, KY 40391

  Welcome to this charming 3BR-1BA brick ranch nestled in a quiet court in Winchester. The home features classic hardwood flooring throughout, offering timeless style and easy maintenance. Outback you will enjoy a fenced in yard and a detached 1 car garage. Don't miss the opportunity to own a move-in-ready gem. Call today for your showing.

  Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
• 

  

  /35

  Est $284,573 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft

  130 Woodford Dr, Winchester, KY 40391

  130 Woodford Dr, Winchester, KY 40391

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