Winchester, KY Homes for Sale with Garage

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  $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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  Explore Winchester

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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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  $330,000 Open Sat 12PM - 2PM

  • 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
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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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  $355,000

  • 3 Beds
  • 3 Baths
  • 2,166 Sq Ft

  115 Woodford Dr, Winchester, KY 40391

  Discover a perfect blend of comfort and elegance as you step inside this charming home. Sitting on a generous 1/4 acre lot, this property offers a peaceful retreat with space to relax and entertain both inside and out. The heart of the home is the airy and open kitchen, featuring an oversized island that is perfect for gathering and sharing a meal. A dedicated keeping room provides a cozy

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 251-8500

  115 Woodford Dr, 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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  $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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  /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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  $545,000

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft

  445 Lynnway Dr, Winchester, KY 40391

  For only the second time ever, this remarkable Colonial home is being offered for sale in the coveted Stoney Brook subdivision. From the moment you step into the welcoming entry hall, gleaming hardwood floors and timeless details set the stage for a home filled with warmth, tradition, and charm. The main level is designed for both everyday comfort and memorable gatherings. A gracious primary

  Janna Smith United Real Estate Bluegrass

  445 Lynnway Dr, Winchester, KY 40391
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  /43

  $524,900

  • 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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  $472,000

  • 3 Beds
  • 2 Baths
  • 2,727 Sq Ft

  865 Pretty Run Rd, Winchester, KY 40391

  Situated on 1.5 acres along a sought after country road, this one level home features a split bedroom layout with a primary suite that includes an en suite bath and walk in closet. The living room offers vaulted ceilings, hardwood floors, and a gas log fireplace, opening to a dining area and an eat in kitchen. A sunroom provides additional living space with skylights and views of the backyard.

  Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
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  $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 Keller Williams Commonwealth

  42 Mockingbird Valley Rd, Winchester, KY 40391
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  $429,000

  • 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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  $539,000

  • 4 Beds
  • 2.5 Baths
  • 3,989 Sq Ft

  415 David Ln, Winchester, KY 40391

  Location, location, location!! This house, 415 David Lane, is located in the most sought after neighborhood, Stoneybrook. It is approximately 20 minutes from the Hamburg area of Lexington and minutes from the I-75 corridor. Enter the house from the welcoming front porch to a entryway and notice immediately the gleaming hardwood floors and the stairway leading to the second floor. The primary

  Craig Bridgewater Bridgewater Real Estate

  415 David Ln, Winchester, KY 40391
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  $459,000

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

  129 Lana Ln, Winchester, KY 40391

  Open House -Sunday 1-3 p.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, bathrooms,

  Jo Gawthrop Keller Williams Bluegrass Realty

  129 Lana Ln, Winchester, KY 40391
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  $619,900

  • 4 Beds
  • 5 Baths
  • 4,374 Sq Ft

  600 Boone Ave, Winchester, KY 40391

  Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
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  /85

  $640,000

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft

  180 Casa Landa Way, Winchester, KY 40391

  This stately yet inviting residence in the highly desirable Stoney Brook subdivision offers the perfect blend of elegance and comfort. Thoughtfully designed for everyday living and entertaining, the home features generously sized rooms throughout.The main level includes formal living and dining spaces, a convenient half bath, and a beautifully appointed kitchen with granite countertops,

  Janna Smith United Real Estate Bluegrass

  180 Casa Landa Way, 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
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  /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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  $339,000 Open Sun 2PM - 4PM

  • 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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  $339,900

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

  322 S Burns Ave, Winchester, KY 40391

  This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining

  Nancy Hibbitts CENTURY 21 Advantage Realty

  322 S Burns Ave, Winchester, KY 40391
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  $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

  Tonya Skeens RE/MAX Elite Lexington

  213 Hood Ave, Winchester, KY 40391
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  $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

  Tonya Skeens RE/MAX Elite Lexington

  7300 Old Boonesboro Rd, Winchester, KY 40391
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  $325,000

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft

  398 Pine Ridge Rd, Winchester, KY 40391

  Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  $312,750

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  123 Strawberry Ln, Winchester, KY 40391

  Priced below recent appraisal this almost new 3 bed 2 bath open layout ranch. This split bedroom design places two bedrooms and the hall bath off the entry and the primary bedroom suite at the rear of the home. The central kitchen offers both a breakfast area and countertop dining at the island, and opens to the family room. Granite kitchen counter tops with stainless steel 50/50 under-mount sink

  Joseph Smallwood Christies International Real Estate Bluegrass

  123 Strawberry Ln, Winchester, KY 40391
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  $359,000

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  356 Boone Ave, Winchester, KY 40391

  **Step into timeless elegance in the heart of downtown Winchester!** This stunning 4-bedroom, 3-full-bath home on historic Boone Avenue has been *completely renovated* while thoughtfully preserving its historic charm. High ceilings, original woodwork, and classic architectural details blend seamlessly with modern updates, offering the best of both worlds. The spacious floor plan features a

  Elizabeth Hodge Lifstyl Real Estate

  356 Boone 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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  $849,900 Open Sun 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 4,345 Sq Ft

  1701 Gay Evans Rd, Winchester, KY 40391

  BACK ON MARKET AT NO FAULT TO SELLERS!!! 4bds with 2 BONUS ROOMS!! Your dream country retreat awaits! Nestled on 8+ scenic acres, this stunning brick ranch offers the perfect blend of modern efficiency, functional living space, and peaceful country charm. A brand-new geothermal heating and cooling system ensures year-round comfort and energy savings, giving you confidence in your home's

  Nora Williams Keller Williams Commonwealth

  1701 Gay Evans Rd, Winchester, KY 40391
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  /25

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,438 Sq Ft

  231 Leslie Dr, Winchester, KY 40391

  This adorable three-bedroom, two-bath home is ready for it's new owner to love! The open floor plan makes this home feel spacious and bright. The yard is perfect for family fun or entertaining.

  Destiny Darby Keller Williams Commonwealth

  231 Leslie Dr, Winchester, KY 40391
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  $235,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
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  /26

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,295 Sq Ft

  175 Waterworks Rd, Winchester, KY 40391

  The country house you have been looking for! 3 bed, 2 bath with an amazing front porch where you can sit and view the small stream in the front yard! Sitting on 3.17 acres with approximately 735 feet of road frontage which should allow for division for a second lot / home. 565 sq ft all metal detached garage, a livestock barn with 3 stalls, and a back deck with farm views. High speed internet

  Jason Townsend Kentucky Residential Real Estate, LLC

  175 Waterworks Rd, Winchester, KY 40391
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  $199,900

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft

  27 Ashland Ave, Winchester, KY 40391

  Move right in and enjoy this well-maintained 3 bed, 2 bath ranch in the heart of Massie Addition! Thoughtfully updated with a recent roof on home and garage, new hot water heater (2025), and a modern, fresh interior paint palette, this home is ready for you. The generous ~half-acre lot offers room to garden, play, or relax under the trees, while the detached 2-car garage adds excellent storage

  Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
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  /31

  $245,000

  • 3 Beds
  • 2.5 Baths
  • 1,935 Sq Ft

  203 Inverness Ln, Winchester, KY 40391

  At 203 Inverness Lane, life feels a little easier. Set on a corner lot at the entry of a quiet street, this townhome welcomes you in with beautiful hardwood floors and natural light pouring through the windows. The layout flows effortlessly. Picture laughter in the living room drifting into the dining space as dinner simmers in the kitchen, or doors opening to the deck where summer evenings are

  Kymberly McCreary EXP Realty, LLC

  203 Inverness Ln, Winchester, KY 40391
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  /26

  $215,000

  • 3 Beds
  • 2.5 Baths
  • 1,224 Sq Ft

  388 Colby Ridge Blvd, Winchester, KY 40391

  Need to see inside of this one! Seller bought in May 2021. Remodeled kitchen. Removed one wall between kitchen and living room. Installed a granite bar/island and countertops. Installed all new kitchen cabinets. Installed all new stainless steel appliances (including a top-of-the-line Kitchen Aid dishwasher). Put in deep sink and garbage disposal. Pantry cabinet beside refrigerator.

  Joyce Ratliff Tom Goebel & Company

  388 Colby Ridge Blvd, Winchester, KY 40391
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  /36

  $275,000

  • 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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  /98

  $789,900

  • 6 Beds
  • 5 Baths
  • 4,843 Sq Ft

  3900 Mount Sterling Rd, Winchester, KY 40391

  More pictures coming! This extraordinary home located on 8.4 acres and nestled back from the main road, offers spectacular views from both the front and rear and those views can be enjoyed from the expansive covered front porch or the extra-large covered back porch. As you arrive, the meticulous care taken to maintain the property is apparent. Inside, discover a beautifully updated kitchen, five

  Teresa Richmond Freedom Realty & Property Management

  3900 Mount Sterling Rd, Winchester, KY 40391
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  /9

  $365,000

  • 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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