Winchester, KY Homes for Sale

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  $330,000

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

  104 Teakwood Ct, Winchester, KY 40391

  This immaculate, all brick two-story home in the desirable Royal Oaks Plantation subdivision offers 4 bedrooms and 2.5 bathrooms with exceptional detail throughout. The main level features beautiful custom crown molding and exquisite hardwood flooring. Step out from the massive kitchen with island onto the coveted screened-in porch to enjoy peaceful views of the lake and the beautifully

  

  Jessica Noto

  Century 21 Advantage Realty - Georgetown

  (859) 365-5976

  104 Teakwood Ct, Winchester, KY 40391
• Explore Winchester

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  /71

  $799,999

  • 4 Beds
  • 2.5 Baths
  • 5,290 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 813-4308

  186 Chardonnay Ct, Winchester, KY 40391
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  /47

  $379,900

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft

  114 Mallard Ln, Winchester, KY 40391

  Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a

  

  Robin Jones

  Keller Williams Legacy Group

  (859) 809-3100

  114 Mallard Ln, Winchester, KY 40391
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  $699,000

  • 3 Beds
  • 4 Baths
  • 4,123 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Just 12 minutes from Lexington, this charming home rests atop 5 acres of breathtaking rolling hills, offering a perfect mix of privacy, elegance, and convenience. The long private driveway may seem steep at first glance, but after a few trips, you'll find it feels completely natural, and the elevated vantage point rewards you with sweeping countryside views and unmatched tranquility, exactly the

  

  Oxana Lopetegui-Pineda

  Lifstyl Real Estate

  (859) 659-6462

  1775 Irvine Rd, Winchester, KY 40391
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  /117

  $3,175,000

  • 8 Beds
  • 7.5 Baths
  • 12,702 Sq Ft

  4664 Lexington Rd, Winchester, KY 40391

  Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot

  Zach Davis Kirkpatrick & Company

  4664 Lexington Rd, Winchester, KY 40391
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  /65

  $599,900

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft

  6595 Mount Sterling Rd, Winchester, KY 40391

  INCREDIBLE! This custom-built home sits on 2.3 acres in a prime location—just minutes from I-64 and perfectly positioned between Winchester and Mount Sterling. The main level features a grand formal dining room, a family room with a vaulted coffered ceiling, and an eat-in kitchen open to the living area for easy entertaining. You'll also find the first primary suite plus two additional bedrooms

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
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  $524,000

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft

  160 Agawam Rd, Winchester, KY 40391

  Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-acre fenced lot. This versatile property offers the perfect blend of comfort, functionality, and rural charm - ideal for families, hobby farmers, or equestrian enthusiasts. Inside, you'll find 3 bedrooms and 3 bathrooms with a fully finished basement that offers ample space for additional bedrooms, a home gym,

  Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
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  /46

  $619,000

  • 3 Beds
  • 3.5 Baths
  • 2,900 Sq Ft

  433 Fairholme Way, Winchester, KY 40391

  This elegant ranch on a basement offers refined main-level living with upscale finishes throughout. The chef's kitchen is a standout featuring double ovens, custom soft-close cabintry, granite countertops, a large island with seating, a spacious walk-in pantry for entertaining and everyday ease. Primary bedroom has Amish cutom built closet. Enjoy quiet evenings on the covered front porch with

  Kathryn Cheuvront Coldwell Banker McMahan

  433 Fairholme Way, Winchester, KY 40391
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  /31

  $409,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  133 Shala-Mar Rue, Winchester, KY 40391

  Charming 3 Bedroom, 2 Bath Ranch Near Hamburg - Fully Renovated! Don't miss this beautifully updated 3-bedroom, 2-bath ranch-style home located just minutes from Hamburg! This move-in ready gem features brand new windows, siding, gutters, roof, and exterior doors, ensuring both curb appeal and peace of mind. Step inside to a spacious, light-filled living room—perfect for entertaining. The

  Nena Honaker Tom Goebel & Company

  133 Shala-Mar Rue, Winchester, KY 40391
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  /78

  $674,500

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft

  420 Alexis Way, Winchester, KY 40391

  Check out 420 Alexis Way in Winchester! This stunning home features a beautiful great room, fully equipped kitchen, extra garage and an inground pool. The primary suite is a luxurious retreat with a spa-like bathroom. With three additional bedrooms and a bonus room, there is plenty of space. The outdoor area is perfect for relaxing by the heated pool. Extra touches include crown molding and

  Edwin Burden McCormick Realty Inc.

  420 Alexis Way, Winchester, KY 40391
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  /36

  $449,500

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft

  134 Fontaine Blvd, Winchester, KY 40391

  Some homes are just houses—but this one was built for connection, creativity, and meaningful moments. Located in the desirable Oak Hill neighborhood, just minutes from GRC High School, this meticulously maintained 4-bedroom, 2.5-bath home offers the space and flexibility today's families are looking for. Formerly home to the beloved "2 Momma's Cooking for You," the property features a fully

  Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
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  /43

  $524,900 Open Sun 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,647 Sq Ft

  5199 Schollsville Rd, Winchester, KY 40391

  Welcome to 5199 Schollsville Road, a picturesque 16-acre farm that feels like home the moment you arrive. You can picture yourself watching the sun rise from the front porch and winding down the day with a quiet evening on the spacious back porch overlooking the land. Inside, the kitchen has been beautifully updated and the thoughtful floor plan offers two en suite bedrooms upstairs, along with

  Brooke Martin RO&CO Real Estate

  5199 Schollsville Rd, Winchester, KY 40391
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  /14

  $394,999

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  408 Corinne Ct, Winchester, KY 40391

  Come see this immaculate 3 bedroom, 2 bath single-story ranch with an open-concept split bedroom layout and 1,604 square feet of living space. This home has been beautifully maintained and is ready for its next owner. Inside you will find laminate and tile floors and stainless steel appliances that make daily living easy and stylish. The spacious design flows seamlessly, creating a bright and

  Caleb Gonzalez The Brokerage

  408 Corinne Ct, Winchester, KY 40391
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  /64

  $440,000

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  1857 Ironworks Rd, Winchester, KY 40391

  Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acres in Clark County. Dreaming of the country life? This is it, originally built in 1865 this timeless home has been completely updated and seamlessly blended the history with modern elegant design and livability. Classic farmhouse style with tons of natural light that bring the outside in. Spacious great room

  Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
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  /58

  $457,900

  • 3 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  The term 'Move In Ready' really and truly applies here at 42 Mockingbird Valley Road! Versatility, Family Friendly, Well Constructed and Maintained, Mature Landscaping and Quiet Location are among the many attributes you'll find. This beautiful one level home on a full basement is ready for your personal touches.Sparking hardwood floors throughout will highlight and set off your furniture

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, Winchester, KY 40391
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  $429,000 Open Sat 4PM - 6PM

  • 4 Beds
  • 3.5 Baths
  • 2,637 Sq Ft

  397 Calmes Blvd, Winchester, KY 40391

  This stunning, renovated home is move-in ready and packed with upgrades that make it an absolute must-see! Step inside and enjoy the fresh, modern feel of the newly painted interior, with updated flooring throughout—including brand-new flooring in the basement, kitchen, and upstairs hall, along with plush new carpet on the upper level. The two remodeled bathrooms feature sleek finishes that add a

  Omar Shalash Tru Life Real Estate

  397 Calmes Blvd, Winchester, KY 40391
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  /53

  $459,000

  • 4 Beds
  • 3 Baths
  • 2,844 Sq Ft

  129 Lana Ln, Winchester, KY 40391

  Open House Sunday 10/5-1p.m.-3:00p.m. Stunning renovated 4-BR,3BA brick ranch with walkout basement, in-ground pool & pool house! This home has undergone extensive remodeling to improve traffic flow while preserving distinct living spaces. These updates create a seamless and intuitive flow through, enhancing both functionality and style! Recent Improvements and Updates-fully remodeled kitchen,

  Jo Gawthrop Keller Williams Bluegrass Realty

  129 Lana Ln, Winchester, KY 40391
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  /65

  $469,900

  • 8 Beds
  • 5 Baths
  • 3,845 Sq Ft

  1731 Ford Hampton Rd, Winchester, KY 40391

  *NEW PAINT and FLOORING* This spacious property offers exceptional value and strong potential in a sought-after area.The main house has been freshly painted and brand new flooring throughout. Versatile Home on 5.47 Acres with Horse Barn & Multi-Unit Living.Welcome to your private hilltop retreat with panoramic mountain views. This property blends flexibility, privacy, and income

  Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
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  /17

  $439,000

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  104 Colby Hills Dr, Winchester, KY 40391

  (Reducted 50,000) for fast sell. Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  104 Colby Hills Dr, Winchester, KY 40391
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  /3

  $430,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  265 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, walkout unfinished basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

  Rex Hall United Real Estate Bluegrass

  265 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $430,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  220 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

  Rex Hall United Real Estate Bluegrass

  220 Evergreen Dr, Winchester, KY 40391
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  /79

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  1410 Dry Fork Creek Rd, Winchester, KY 40391

  This breathtaking 92.3 +/- acre turnkey property is a nature lover's dream, offering endless opportunities for recreation, relaxation, and country living at its finest. Enjoy gently rolling terrain with a perfect blend of pasture, woods, and scenic trails, along with approximately one mile of road and creek frontage in a peaceful, private setting. Roughly 25 acres of hay field provide excellent

  Skyler Lewis Dream Maker Realty, LLC

  1410 Dry Fork Creek Rd, Winchester, KY 40391
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  /25

  $229,900

  • 4 Beds
  • 2 Baths
  • 1,636 Sq Ft

  204 Crawford Ct, Winchester, KY 40391

  Move right in and fall in love with this fully renovated 4-bedroom, 2-bath beauty! The open floor plan, neutral tones, and modern finishes create a bright and welcoming feel. The updated kitchen shines with granite countertops, stainless steel appliances, and plenty of space to gather. Fresh flooring, updated baths, and stylish details throughout make this home truly turnkey!

  Tisha Monte Bluegrass Properties Group

  204 Crawford Ct, Winchester, KY 40391
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  /26

  $265,000 Open Sat 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,132 Sq Ft

  102 Ashley Dr, Winchester, KY 40391

  This cute 3 bedroom and 2 bath home is waiting for you in the quiet neighborhood of Holiday Hills. You will enjoy the convenience to all the things Winchester has to offer as well as easy access to I64 for commuting to Mount Sterling and Lexington. The inside is waiting for you to add your personal touches and the yard is only waiting for those pets or kids to come play. The easy maintenance and

  Kimberli Fister Kentucky Land and Home

  102 Ashley Dr, Winchester, KY 40391
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  /34

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  23 Kittison Dr, Winchester, KY 40391

  ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.

  Teresa Richmond Freedom Realty & Property Management

  23 Kittison Dr, Winchester, KY 40391
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  /53

  $279,500

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

  724 Terry Dr, Winchester, KY 40391

  Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-bedroom, 2 full bath split-level home featuring a cozy finished basement perfect for relaxing or entertaining. Enjoy both front and rear porches, ideal for morning coffee or evening gatherings. The spacious, fenced-in backyard offers privacy and room to play, garden, or unwind. Nestled in a quiet

  Darrell Tackett Dream Maker Realty, LLC

  724 Terry Dr, Winchester, KY 40391
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  /28

  $239,000

  • 3 Beds
  • 2.5 Baths
  • 1,430 Sq Ft

  204 Moss Ct, Winchester, KY 40391

  This beautiful 3-bedroom, 2.5-bath home offers over 1,400 sq. ft. of living space and sits just steps from a quiet cul-de-sac — perfect for kids to play safely and enjoy the neighborhood. Inside, you'll find new LVP flooring in the entryway, kitchen, and downstairs bathrooms, along with a spacious bonus living area that's ideal for family gatherings or a cozy movie night. Major updates provide

  Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
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  /23

  $226,000

  • 3 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  363 Silverton Way, Winchester, KY 40391

  Unique Setting... Unlike Any Other! Wake up to the beauty of the surrounding countryside a€" every single day. This 3-bedroom, 2.5-bath townhome is nestled in the desirable Royal Oaks Village, just one mile from I-64, making it a perfect location for both homeowners and renters alike. This low-maintenance property features tile flooring in the foyer, kitchen, and baths. The kitchen comes fully

  Kim Dice EXP Realty, LLC

  363 Silverton Way, Winchester, KY 40391
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  /32

  $249,900

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

  528 Estes Dr, Winchester, KY 40391

  Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
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  $270,000

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

  130 Village Ct, Winchester, KY 40391

  Here's that hard to find RANCH with a full unfinished basement. Needs a little TLC. Just under 2,000 square feet of living space on the first floor. The basement with a one car garage is about the same. The home has 4 bedrooms and 2 full bathrooms on the first level. It also has a half bath in with the laundry in the basement. Kitchen and 2 full bathrooms have been updated. The windows have been

  Joyce Ratliff Tom Goebel & Company

  130 Village Ct, Winchester, KY 40391
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  /24

  $369,000

  • 4 Beds
  • 2.5 Baths
  • 2,811 Sq Ft

  446 Tremont Ln, Winchester, KY 40391

  Agent is Seller. 2800 square feet with four bedrooms and 2-1/2 baths. A large corner lot with side entry 2 car garage. Walkout patio, remodeled front porch, fully privacy fenced back yard, upgraded hot-water heaters, Upgraded fully insulated garage with steel back insulated door, walk in master closet, two story entry, and gas fireplace are just a few of the features in this home. Call today

  Dylan Langdon The Agency

  446 Tremont Ln, Winchester, KY 40391
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  $225,000

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft

  363 S Main St, Winchester, KY 40391

  Built in the 1940s, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. Enjoy original wood floors, a spiral staircase, a gorgeous fireplace, and an updated kitchen with ample storage. Flexible nooks, a huge master closet, and mudroom add convenience. Outdoor living shines with a covered front porch, oversized back deck, and private backyard. Walk to downtown shops,

  Zachary Otis HomeLand Real Estate Inc

  363 S Main St, Winchester, KY 40391
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  /27

  $190,000 Open House 10/22

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft

  6 Monroe Ave, Winchester, KY 40391

  Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional.

  Lindsey Bivens Berkshire Hathaway de Movellan Properties

  6 Monroe Ave, Winchester, KY 40391
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  /79

  $225,000

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft

  133 S Burns Ave, Winchester, KY 40391

  Beautiful, Old-World style in the heart of Winchester! From the red, domed porch roof to the arched doorways and multiple fireplaces, this home is full of character and class. Being sold as-is, but with many renovations and updates already done to maintain and restore the charm of this old beauty including a new shingle roof (2024), replaced porch boards, and a fresh coat of interior paint. The

  Josh Wood Freedom Realty & Property Management

  133 S Burns Ave, Winchester, KY 40391
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  /36

  $324,900

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

  128 Cherokee Dr, Winchester, KY 40391

  Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022, and exceptional curb appeal and charm, this home is just waiting for its new owner!

  Tyler Hurst Thwaites Realtors LLC

  128 Cherokee Dr, Winchester, KY 40391
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  /30

  $240,000

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

  2721 Pretty Run Rd, Winchester, KY 40391

  Back on market due to buyer financing, no fault of the seller! 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

  Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
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  /8

  $159,000

  • 2 Beds
  • 3 Baths
  • 1,056 Sq Ft

  175 Chatham Place Unit 135-2, Winchester, KY 40391

  (Why rent ) when you can own this Townhome it has 2 bedrooms,3 bathroms (one full bath and 2 half baths) living room,kitchen, locted near schools and shopping,just behind Lowes.Owner/Broker

  Garry Milton Milton and Associates Real Estate

  175 Chatham Place Unit 135-2, Winchester, KY 40391
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  /37

  $384,000

  • 4 Beds
  • 2.5 Baths
  • 2,244 Sq Ft

  213 Hood Ave, Winchester, KY 40391

  This newly updated 4-bedroom home with lots of character sits in an established neighborhood on just under a half-acre lot in the heart of Winchester. Located less than a 5-minute walk to the Winchester Country Club. Great space with over 2200 square feet with lots of storage space and a 2-car garage. Step inside and check out all the updates! New HVAC system, new concrete front porch, updated

  Vickie Skeens RE/MAX Elite Lexington

  213 Hood Ave, Winchester, KY 40391
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  /50

  $850,000

  • 4 Beds
  • 3 Baths
  • 3,311 Sq Ft

  7300 Old Boonesboro Rd, Winchester, KY 40391

  This beautiful home sits on over 7 acres of peaceful countryside. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of

  Vickie Skeens RE/MAX Elite Lexington

  7300 Old Boonesboro Rd, Winchester, KY 40391

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