Winchester, KY Homes for Sale

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  $320,000

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

  104 Teakwood Ct, Winchester, KY 40391

  PRICED BELOW RECENT APPRAISAL! 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

  

  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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  /36

  $319,900

  • 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

  (859) 681-9697

  128 Cherokee Dr, Winchester, KY 40391
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  /47

  $372,900

  • 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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  /14

  $312,975

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft

  1363 Clintonville Rd, Winchester, KY 40391

  Here's your chance to own a rare 5-acre property in Clark County, one of Central Kentucky's most desirable areas. Tucked just minutes from downtown Winchester, the Hamburg corridor, and Lexington, this property blends convenience with the peacefulness of country living. Whether you're dreaming of building a brand-new home, expanding into a mini farm, or investing in future growth, this land gives

  

  Rebakah Goodpaster

  Keller Williams Legacy Group

  (859) 659-6863

  1363 Clintonville Rd, Winchester, KY 40391
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  /67

  $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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  /23

  $498,900

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare find! Gorgeous 25 acres of gently rolling land with a barn and creek is perfect for building your dream home and creating your homestead! Don't miss this opportunity! This is farm is conveniently located 20 miles from Hamburg and 5 miles from the Winchester bypass. No city sewage. Deed restrictions apply. Relax and enjoy the spectacular views. Get ready to enjoy life! Land consists of 2

  Lura Justice Rector Hayden Realtors

  2996/3056 Irvine Rd, Winchester, KY 40391
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  /34

  $374,900

  • 4 Beds
  • 3 Baths
  • 2,516 Sq Ft

  110 Hampton Avenue Exd, Winchester, KY 40391

  Beautifully remodeled 4-bedroom, 3-full bath ranch nestled on a picturesque lot in one of Winchester's most desirable and well-established neighborhoods. Step inside to find a perfect blend of timeless charm and modern updates throughout. The main level offers a spacious and inviting layout with stunning finishes, featuring multiple fireplaces that create warmth and character in every living

  Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
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  /36

  $379,000

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  121 Fitch Ave, Winchester, KY 40391

  This beautifully updated 4-bedroom, 3-bath ranch home includes a private mother-in-law suite, offering flexible living options for guests or extended family. With 2,100 square feet of inviting living space and an attached two-car garage, this home perfectly combines timeless charm with thoughtful modern updates. Conveniently located just minutes from the interstate close to Lexington, it offers

  Ashley Spencer Keller Williams Commonwealth

  121 Fitch Ave, Winchester, KY 40391
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  /36

  $399,999 Open Sun 1PM - 3PM

  • 4 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  136 College St, Winchester, KY 40391

  Welcome to this exceptional, fully renovated home located in the heart of downtown Winchester. Meticulously redesigned with a thoughtful rear addition, this 4-bedroom, 4.5-bath residence offers the perfect blend of historic charm and modern luxury. Step inside to discover a bright and open floor plan featuring a spacious first-floor primary suite complete with a private en-suite bathroom,

  Ellie Hatton The Brokerage

  136 College St, Winchester, KY 40391
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  /104

  $359,900 Open Sun 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,520 Sq Ft

  145 Shanahan Ln, Winchester, KY 40391

  This 4-bedroom, 3-bath ranch on a basement offers over 2,500 sq ft of living space with modern updates, a welcoming layout and a safe neighborhood to live in. The large living room with cathedral ceilings flows into a well-appointed kitchen featuring ample counter space and newer appliances. New LVP flooring runs throughout the main level, while new patio doors open to a large deck—perfect for

  Josh Wood Freedom Realty & Property Management

  145 Shanahan Ln, Winchester, KY 40391
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  /35

  $350,000

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  130 Hibiscus Ln, Winchester, KY 40391

  This beautiful 4 bedroom, 2.5 bath home offers a spacious and thoughtful layout with the primary suite conveniently located on the main level. The open walkway overlooking the great room and vaulted ceilings create an airy, inviting feel, complemented by an electric fireplace for cozy evenings. The kitchen and living areas flow seamlessly for everyday comfort and entertaining. Enjoy the

  Ashley Barreto Indigo & Co

  130 Hibiscus Ln, 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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  /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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  /31

  $389,000

  • 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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  $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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  $339,000

  • 2 Beds
  • 1 Bath
  • 1,055 Sq Ft

  1996 White Conkwright Rd, Winchester, KY 40391

  Discover peaceful country living on this charming 4.17-acre farmhouse retreat that has been meticulously maintained by the same loving family for 42 years. From the moment you arrive, the welcoming covered front porch invites you to slow down and take in the serene setting. The home features two bedrooms plus an additional room that could serve as a 3rd bedroom, one full bathroom, and an

  Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
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  $375,900

  • 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. Do you enjoy golfing, tennis, and swimming? Located less than a 5-minute walk to the Winchester Country Club. Great space with over 2200 square feet with plenty of storage space and a 2-car garage. Step inside and check out all the updates! New AC

  Vickie Skeens RE/MAX Elite Lexington

  213 Hood Ave, 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

  $429,000

  • 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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  $419,000 Open Sun 1PM - 3PM

  • 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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  /9

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft

  508 Boone Ave, Winchester, KY 40391

  3 bedroom, 2 1/2 bath brick home in Witherspoon Subdivision. New roof, new freeze resistant water lines, new heat and air, new appliances, and backsplash. Full basement with double space garage. Spacious formal living room and separate formal dining room. Great room includes breakfast area and sitting area, and fireplace. Large master ensuite includes closet with plenty of storage space.

  Donna C. Slone-Crumbie Wright Realty

  508 Boone Ave, Winchester, KY 40391
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  /36

  $355,000

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  208 Citation Ct, Winchester, KY 40391

  One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under. (see photos) Kitchen appliances include

  Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
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  /65

  $424,900

  • 4 Beds
  • 3 Baths
  • 2,111 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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  /13

  $340,000

  • 6 Beds
  • 4 Baths
  • 4,456 Sq Ft

  410 W Lexington Ave, Winchester, KY 40391

  Estate Sale. Selling 'AS IS', in 2024 new roof, walls repaired and freshly painted throughout.Great home for a growing family, covered front porch, 10-foot ceilings upstairs and down, handicap ramp, ample parking in rear. Motivated seller, call for your private showing today

  Melisa McDonald Wrenn Realty

  410 W Lexington Ave, Winchester, KY 40391
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  /34

  $339,999 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 1,776 Sq Ft

  213 Orchid Ct, Winchester, KY 40391

  Kasey McCarty 5.23 Real Estate

  213 Orchid Ct, Winchester, KY 40391
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  /4

  $369,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
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  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  270 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

  Rex Hall United Real Estate Bluegrass

  270 Evergreen 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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  /13

  $1,300,000

  345 Providence Ln, Winchester, KY 40391

  120 Acres of Scenic Farmland in Winchester, KY. Discover the beauty and tranquility of country living on this remarkable 120-acre farm nestled in the heart of Clark County, Kentucky. Featuring a picturesque mix of rolling pastureland, mature woodlands, and pond, this property offers endless possibilities for farming, livestock, recreation, or building your dream home. Conveniently located just

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
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  /42

  $330,000

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

  410 Corinne Ct, Winchester, KY 40391

  Charming Ranch-Style Home with Lots of Room- Step inside this 8 year old beautiful 1,604 sq. ft. ranch-style home featuring 9-foot ceilings and an open, inviting layout. With 3 comfortable bedrooms and a large, laundry room and back hallway, this home offers both style and functionality. The spacious living areas are enhanced by wood and tile flooring, adding a modern touch and easy maintenance.

  Shelly Sutton Kentucky Realty Group, LLC

  410 Corinne Ct, Winchester, KY 40391
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  /53

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  174 Hidden Grove Ln, Winchester, KY 40391

  Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway

  Kathryn Cheuvront Coldwell Banker McMahan

  174 Hidden Grove Ln, Winchester, KY 40391
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  /6

  $49,500

  • Land
  • 0.98 Acre
  • $50,510 per Acre

  204 Wigeon Ct, Winchester, KY 40391

  Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

  Jim Woodrum RE/MAX Creative, Winchester

  204 Wigeon Ct, Winchester, KY 40391
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  /20

  $299,900

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

  729 Wayland Dr, Winchester, KY 40391

  This charming 3-bedroom, 2-bath split level home offers the perfect blend of comfort and convenience-located just minutes from Lexington's popular Hamburg area with endless shopping, dining and entertainment options right at your fingertips! Step inside to find a beautifully updated kitchen featuring brand-new granite countertops and a stylish new island, perfect for family meals or

  Brittany Beer EXP Realty, LLC

  729 Wayland Dr, Winchester, KY 40391
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  /8

  $25,000

  • Land
  • 0.1 Acre
  • $250,000 per Acre

  61 Melbourne St, Winchester, KY 40391

  Opportunity is knocking to build your dream home or investment property on this 0.1035 -acre residential lot at 61 Melbourne St, located in the North Park neighborhood right cross the street from the park and easy access to local amenities, schools, and roadways. With public utilities available, this lot offers endless possibilities for new construction or future development, providing a great

  Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
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  /25

  $209,900

  • 2 Beds
  • 1 Bath
  • 1,557 Sq Ft

  23 Hillcrest Dr, Winchester, KY 40391

  Bedford stone ranch ideally located in Winchester; just minutes from Richmond and Lexington. This 2-bedroom, 1-bath home offers a flexible bonus room that can easily function as a third bedroom, home office, or hobby space. Sitting on a spacious corner lot, the home features a walk-out unfinished basement with a 1-car garage, providing plenty of storage or room to expand. Outdoor living is a

  Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
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  /14

  $134,800

  • Land
  • 2.3 Acres
  • $58,609 per Acre

  110 Knox Ct, Winchester, KY 40391

  The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

  Amanda Thomas The Agency

  110 Knox Ct, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 5

Why Live in Winchester

Winchester, KY, the largest city in Clark County, is known for its vibrant community and unique local flavors, including the birthplace of beer cheese and Ale-8-One soda. Main Street is the hub for dining, featuring popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail, which includes around 15 restaurants with signature beer cheese recipes. The city offers practical amenities with nearby grocery stores like Kroger and Walmart Supercenter, and retail options such as TJ Maxx and Lowe’s. Housing in Winchester includes Victorian-era inspired homes and newer subdivisions, with properties often featuring gravel driveways and spacious lawns suitable for gardens. Clark County Public Schools provide strong academic programs, including AP and dual enrollment courses at George Rogers Clark High School. For outdoor activities, residents enjoy Legacy Grove Park, College Park, and Lykins Park, which offer facilities for basketball, tennis, hiking, and disc golf. Winchester hosts annual events like the Beer Cheese Festival and the Daniel Boone Pioneer Festival, attracting visitors with arts, crafts, and food. The Bluegrass Heritage Museum showcases the history of Central Kentucky. Commuting is convenient with Winchester located 16 miles from Lexington and 20 miles from Richmond. The city has a cooperative community spirit, bolstered by investments from younger residents and a thriving local economy.

Learn more about living in Winchester

Frequently Asked Questions

What is the average home price in Winchester, KY?

Homes for sale in Winchester, KY have an average home price of $325,136.

How many homes have sold over the last 12 months in Winchester, KY?

318 homes have sold in Winchester, KY over the last 12 months.

Is Winchester, KY a safe city?

In general, the safest neighborhood in Winchester, KY with lower crime scores is Becknerville.

What are the most popular zip codes in Winchester, KY?

The most popular zip codes in Winchester, KY include 40391, 40361, 40353, 40516 and 40475.

What are the most popular neighborhoods in Winchester, KY?

The most popular neighborhoods in Winchester, KY with the most homes for sale are Old Pine Grove, Becknerville and Wyandotte.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $260,000. If you put a 20% down payment of $52,000 and had a 30-year fixed mortgage with an interest rate of 6.19%, your estimated principal and interest payment would be $1,270 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $54K a year to afford the median home price in Winchester.

How are the schools in Winchester, KY?

Winchester, KY has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are George Rogers Clark High School, Strode Station Elementary School and Baker Intermediate School. The neighborhoods in Winchester with the highest rated schools are Old Pine Grove, Becknerville and Wyandotte. Browse all the schools in Winchester, KY to learn more.

Home Trends in Winchester, KY

On average, homes in Winchester, KY sell after 30 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, KY over the last 12 months is $244,500, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$244,500

Median Single Family Sale Price

$259,950

Median Townhouse Sale Price

$189,500

Average Price Per Sq Ft

$161

Number of Homes for Sale

89

Last 12 months Home Sales

318

Months of Supply

3.40

Median List Price

$260,000

Median Change From 1st List Price

3%

Median Home Sale Price YoY Change

3%