Winchester, KY Homes

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  /33

  $400,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,741 Sq Ft

  113 Shala Mar Rue, Winchester, KY 40391

  Beautifully maintained brick ranch on a full basement, offering over 4,000 square feet under roof in a highly desirable location just minutes from Hamburg, I-64, Lexington, and Clark County Regional Hospital. This spacious home features 4 bedrooms, 3 full baths, and stunning hardwood floors. Two impressive floor-to-ceiling fireplaces add charm on both levels. The kitchen includes new stainless

  Rebakah Goodpaster Keller Williams Legacy Group

  113 Shala Mar Rue, Winchester, KY 40391
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  /30

  Est $460,473 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,092 Sq Ft

  2246 Becknerville Rd, Winchester, KY 40391

  2246 Becknerville Rd, Winchester, KY 40391
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  /3

  $225,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  412 Paisley Ct, Winchester, KY 40391

  Very nice 3 bedroom 2.1 bath townhome with walk out basement. Home was upgraded 2023 with new paint,carpet, granite countertops and stainless appliances. Only minutes from Winchester bypass.

  John Wilson Bluegrass Properties Group

  412 Paisley Ct, Winchester, KY 40391
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  /3

  Est $323,141 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,160 Sq Ft

  721 Wayland Dr, Winchester, KY 40391

  721 Wayland Dr, Winchester, KY 40391
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  /54

  $274,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  137 Sturbridge Ln, Winchester, KY 40391

  This lovely story and a half home is conveniently located close to Bypass road with easy access to everything Winchester has to offer. The main floor offers a comfortable living area that connects to the spacious eat-in kitchen, a convenient half bathroom, and the laundry room. Take a step out the back patio door to experience the generous, shaded, privacy fenced back yard perfect for kids or

  Josh Wood Freedom Realty & Property Mgt

  137 Sturbridge Ln, Winchester, KY 40391
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  /63

  Est $478,765 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 4,089 Sq Ft

  1389 Clintonville Rd, Winchester, KY 40391

  1389 Clintonville Rd, Winchester, KY 40391
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  /38

  $249,900 Pending

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

  313 Geronimo Ct, Winchester, KY 40391

  Welcome to 313 Geronimo Court in Winchester, KY well-maintained home nestled on a quiet cul-de-sac, offering comfortable living with a functional layout and great outdoor space. Inside, you will find water-resistant laminate wood-look flooring and tile throughout the main living areas, creating a clean and durable foundation. The kitchen includes refrigerator and stove with a cozy dining area

  Shari Frasure Keller Williams Commonwealth

  313 Geronimo Ct, Winchester, KY 40391
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  /19

  Est $250,085 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,107 Sq Ft

  641 Laura Dr, Winchester, KY 40391

  641 Laura Dr, Winchester, KY 40391
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  /32

  $349,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,111 Sq Ft

  275 Cross Brook Ct, Winchester, KY 40391

  Tucked away on a quiet corner cul-de-sac, this 3-bedroom, 2.5-bath home offers space, style, and versatility. Inside, you'll find updated flooring, large bedrooms, and an open layout perfect for everyday living and entertaining. The oversized walk-in pantry and 2-car garage add function and storage, while the huge additional building out back sets this property apart—ideal for a workshop, home

  Amanda Stewart Selling the South Realty

  275 Cross Brook Ct, Winchester, KY 40391
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  /91

  Est $816,365 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,125 Sq Ft

  645 Combs Ferry Rd, Winchester, KY 40391

  645 Combs Ferry Rd, Winchester, KY 40391
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  /21

  $289,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,696 Sq Ft

  219 Bartram Ct, Winchester, KY 40391

  This charming residence features a desirable first-floor primary bedroom and a spacious kitchen complete with a breakfast bar—perfect for everyday living and entertaining. Enjoy peace of mind with a brand-new roof and updated systems throughout. Located in a sought-after neighborhood close to everything you need. Don't miss the opportunity to make this home yours—schedule your showing today!

  Nora Williams Keller Williams Commonwealth

  219 Bartram Ct, Winchester, KY 40391
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  /65

  Est $1,012,789 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 4,258 Sq Ft

  485 Combs Ferry Rd, Winchester, KY 40391

  485 Combs Ferry Rd, Winchester, KY 40391
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  /30

  $250,000 Pending

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

  2721 Pretty Run Rd, Winchester, KY 40391

  Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer flexibility for family, guests, or work-from-home needs. Outside, the

  Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
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  /84

  Est $426,175 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 3,149 Sq Ft

  2845 Schollsville Rd, Winchester, KY 40391

  2845 Schollsville Rd, Winchester, KY 40391
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  /75

  $289,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft

  126 Ashley Dr, Winchester, KY 40391

  Don't miss out on this Beautiful RANCH Style home w/Private, new and Fully Fenced Yard. This Move-in Ready 3 Bed / 2 Bath is immaculate with many updates. Completely remodeled Bathroom with walk-in shower, Fresh Paint, Spacious living room w/ Vaulted Ceiling. Carpet all replaced with gorgeous, matching hardwood thru out. Granite Countertops, new can lighting and kitchen floor replaced with

  Jennifer Guyton White Realty, LLC

  126 Ashley Dr, Winchester, KY 40391
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  /17

  Est $177,589 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,530 Sq Ft

  121 Lindberg Ave, Winchester, KY 40391

  121 Lindberg Ave, Winchester, KY 40391
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  /39

  $258,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  172 Ryans Mill Rd, Winchester, KY 40391

  This nicely maintained 3-bedroom, 2-bath ranch offers the perfect blend of comfort and convenience. Enjoy abundant natural light throughout the open floor plan, creating a bright and inviting atmosphere. The spacious kitchen and living areas are perfect for both daily living and entertaining. Step outside to a generous, fully fenced backyard, ideal for pets, play, or outdoor gatherings. Located

  Elizabeth Herrington Bluegrass Sotheby's International Realty

  172 Ryans Mill Rd, Winchester, KY 40391
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  /14

  Est $153,367 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,250 Sq Ft

  109 4th St, Winchester, KY 40391

  109 4th St, Winchester, KY 40391
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  /34

  $332,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,162 Sq Ft

  366 Hanover Dr, Winchester, KY 40391

  Gorgeous 2 Story Home, Offering 4 Bedrooms, 3 Baths, Oversized Bonus Room, First Floor Primary, With Large Walk-In Closet, And En-Suite, Separate Dining, Attached Garage, First Floor Laundry & Mud Room.... You Need To Schedule! Centrally Located To All Main Shopping, Hospitals And Schools, This Home Has Everything! Choose From Two Covered Porches For Morning Coffee Or An Evening Tea. Or Spend

  Melissa Thompson Keller Williams Legacy Group

  366 Hanover Dr, Winchester, KY 40391
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  /3

  Est $360,626 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,478 Sq Ft

  146 Gibson Way, Winchester, KY 40391

  146 Gibson Way, Winchester, KY 40391
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  /32

  $350,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  418 Skylark Dr, Winchester, KY 40391

  There's a certain kind of comfort you feel the moment you pull up, a classic brick home, shaded by mature trees, in a quiet neighborhood where kids still ride bikes and neighbors wave from their driveways. Inside, the layout just works. The kitchen has the kind of space that makes everyday life easier, granite counters, shaker cabinets, and an island that's seen everything from cereal mornings to

  Kymberly Clem EXP Realty, LLC

  418 Skylark Dr, Winchester, KY 40391
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  /28

  Est $198,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,245 Sq Ft

  125 Lindberg Ave, Winchester, KY 40391

  125 Lindberg Ave, Winchester, KY 40391
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  /28

  $359,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  210 Jett Dr, Winchester, KY 40391

  Open House, Sunday, June 22, 2025, 1-3Don't miss out on this wonderful ranch floor plan, New Construction, 3 bedrooms, 2 baths, covered porch, great location, Call today.Size of home may vary from plan, spec home,all specifics have already been ordered. This information will follow within a few weeks and posted on line.

  Mila Ensor Ensor Real Estate LLC

  210 Jett Dr, Winchester, KY 40391
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  /49

  Est $555,240 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,016 Sq Ft

  147 Hawthorne Dr, Winchester, KY 40391

  147 Hawthorne Dr, Winchester, KY 40391
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  /81

  $599,500 Pending

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

  2615 Crowe Ridge Rd, Winchester, KY 40391

  This one-owner, custom-built home sits on approximately 8 acres of beautiful Bluegrass land and offers space, comfort, and thoughtful design throughout. The open-concept great room and kitchen feature exposed beam ceilings and custom-stained concrete floors. The kitchen is a dream for cooks,with abundant counter space, storage, a large island, and window overlooking the backyard and pool. Just

  ROBIN TRIMBLE HomeFirst Real Estate

  2615 Crowe Ridge Rd, Winchester, KY 40391
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  /27

  Est $324,024 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,794 Sq Ft

  107 Bella Ct, Winchester, KY 40391

  107 Bella Ct, Winchester, KY 40391
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  /43

  $129,900 Pending

  • 2 Beds
  • 1 Bath
  • 858 Sq Ft

  44 Watts Rd, Winchester, KY 40391

  Tucked away on a peaceful dead-end street with minimal traffic, this inviting 2-bedroom, 1-bath home offers comfort, convenience, and character. Step inside to find beautiful hardwood floors throughout, a spacious living room full of natural light, and a cozy eat-in kitchen perfect for casual meals and morning coffee.Enjoy the privacy of a fenced backyard—ideal for relaxing, gardening, or

  Josh Wood Freedom Realty & Property Mgt

  44 Watts Rd, Winchester, KY 40391
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  /19

  Est $245,727 Not Listed For Sale

  7055 Bybee Rd, Winchester, KY 40391

  7055 Bybee Rd, Winchester, KY 40391
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  /91

  $394,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  101 Dorset Ln, Winchester, KY 40391

  ***Click on the Virtual Tour section to see the video walk through!*** Welcome to your perfect home retreat! This beautifully updated ranch home features a 2-car garage, spacious open layout, and large bedrooms. The backyard is a showstopper — relax under the covered patio or take a dip in the heated in-ground pool, newly installed in 2022 and surrounded by a sleek concrete patio. Inside, enjoy

  Josh Wood Freedom Realty & Property Mgt

  101 Dorset Ln, Winchester, KY 40391
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  /9

  Est $186,016 Not Listed For Sale

  1200 Craig Crossing Rd, Winchester, KY 40391

  1200 Craig Crossing Rd, Winchester, KY 40391
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  /60

  $175,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  265 Cunningham Ln, Winchester, KY 40391

  Country Living at Its Finest Y'all! Pack the U-Haul and get excited because this nearly new single wide home is awaiting its new owners! It has a split bedroom floor plan, fully equipped kitchen and handy laundry/mud room that leads to the back yard. With 1.429 acres, you have room to roam all while being located only minutes from the Mountain Parkway.

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  265 Cunningham Ln, Winchester, KY 40391
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  /9

  Est $273,765 Not Listed For Sale

  1055 Craig Crossing Rd Unit Lot 33, Winchester, KY 40391

  1055 Craig Crossing Rd Unit Lot 33, Winchester, KY 40391
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  /82

  $425,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,679 Sq Ft

  102 Camelot Dr, Winchester, KY 40391

  This one-of-a-kind stunner in the back of Winchester's beloved Hampton Manor neighborhood has only had one owner since being built in 1987 and includes everything you could ask for in a forever home! Gorgeous hardwood floors welcome you in the front door where you'll find the first of two living rooms and the connected dining room. Down the hallway the oversized first floor primary suite has a

  Scott Fryar Keller Williams Bluegrass Realty

  102 Camelot Dr, Winchester, KY 40391
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  /9

  Est $174,054 Not Listed For Sale

  1135 Craig Crossing Rd, Winchester, KY 40391

  1135 Craig Crossing Rd, Winchester, KY 40391
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  /23

  $349,500 Pending

  • 4 Beds
  • 3 Baths
  • 2,936 Sq Ft

  413 Lyon Dr, Winchester, KY 40391

  Well maintained in an established neighborhood on a large corner lot. Nice hardwood floors in the dining area. Dental crown molding and chair rail in the living room and kitchen/dining area. Book shelves and wood stove in the den. Room in the basement could be an additional bedroom. Large basement garage with cabinets. Front brick porch, rear 10'x16' all season room, rear court yard and deck

  Ray Rush Rush Real Estate

  413 Lyon Dr, Winchester, KY 40391
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  /9

  Est $170,722 Not Listed For Sale

  611 Craig Crossing Rd, Winchester, KY 40391

  611 Craig Crossing Rd, Winchester, KY 40391
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  /28

  $399,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,078 Sq Ft

  220 Spring Valley Dr, Winchester, KY 40391

  This beautiful 5 acre property is a rare find! Located on a quiet cul-de-sac just minutes from I-64, Winchester and Bourbon County, this home offers the perfect blend of tranquility and convenience. The home includes 4 bedrooms, 2.5 baths with a mostly finished basement providing additional living space and storage. There are 2 wood burning fireplaces, perfect for cozy evenings. Additionally,

  Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
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  /9

  Est $205,024 Not Listed For Sale

  870 Craig Crossing Rd, Winchester, KY 40391

  870 Craig Crossing Rd, Winchester, KY 40391
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  /36

  $179,000 Pending

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

  218 Buffalo Trace, Winchester, KY 40391

  Must see this nice home located in Buffalo Trace! Ranch with fenced in back yard, covered porch/patio, storage area, concrete drive, and nice yard with landscaping. Vinyl siding and metal roof. Features: Open floor plan, Living room, dining area, kitchen is fully applianced, and laundry area with washer and dryer included. Vaulted ceilings. Primary bedroom has large full bath. Two guest

  Sandy Statom ERA Team Realtors

  218 Buffalo Trace, Winchester, KY 40391
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  /9

  Est $250,019 Not Listed For Sale

  1095 Craig Crossing Rd, Winchester, KY 40391

  1095 Craig Crossing Rd, Winchester, KY 40391

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