Winchester, KY Homes for Sale with Garage

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  /18

  $574,000

  • 5 Beds
  • 3 Baths
  • 3,102 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  (859) 209-6934

  110 White Conkwright 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, own the most charming home atop a scenic hill at Blue Ridge Manor, a breathtaking 5.13 acre retreat where modern comfort meets classic elegance. As you drive up the long, private driveway, you'll feel like you're entering your own exclusive retreat, a sanctuary of peace and tranquility. Lovingly maintained by its original owner for the past 30 years, this

  

  Oxana Lopetegui-Pineda

  Lifstyl Real Estate

  (859) 659-6462

  1775 Irvine Rd, Winchester, KY 40391
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  /58

  $488,000

  • 4 Beds
  • 4 Baths
  • 4,448 Sq Ft

  150 Stone Crest Rd, Winchester, KY 40391

  IMMEDIATE OCCUPANCY! WELCOME HOME with Room to spread out in this SPACIOUS Home of over 4000 sq. ft. sitting on 5.5 Acres! Offering 4 Bedrooms, 4 Bathrooms, Living Room, Beautiful Kitchen with appliances and tons of cherry cabinets, Den, utility room and 2 Large Bonus Rooms in the Basement. one could be a bedroom. There is a 3-car Detached Garage, 2-car attached Garage, Large Carport, Huge Patio

  

  Brenda Murphy

  Murphy Realty Group

  (859) 374-8718

  150 Stone Crest 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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  /83

  $599,500

  • 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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  /39

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  600 Ferry Rd, Winchester, KY 40391

  Experience abundant wildlife with turkey and deer in your own hunting retreat, or simply enjoy the views from your backyard on this stunning 33-acre property. Conveniently located near the Kentucky River, with a boat ramp nearby, this home offers the perfect blend of nature and accessibility, making it ideal for nature lovers or those who enjoy fishing and hunting.Step inside to the foyer,

  Cathleen Gedeon CENTURY 21 Advantage Realty

  600 Ferry Rd, Winchester, KY 40391
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  /44

  $834,000

  • 5 Beds
  • 3.5 Baths
  • 3,384 Sq Ft

  150 Jones Nursery Rd, Winchester, KY 40391

  Experience the perfect blend of modern comfort and country charm in this stunning 4-bedroom, 3.5-bathroom Craftsman-style home, built in 2018. Nestled on 2.58 acres of scenic countryside, this property offers the serenity of rural living with convenient access to Lexington.Designed for both style and functionality, the spacious interior features a chef's kitchen with custom countertops, a

  Joshua Davis The Agency

  150 Jones Nursery Rd, Winchester, KY 40391
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  /114

  $649,000

  • 5 Beds
  • 4.5 Baths
  • 5,524 Sq Ft

  315 The Woods Ln, Winchester, KY 40391

  Beautiful 1.5-story brick home on a cul-de-sac with in-ground pool and walkout basement! The main level features hardwood floors, office, formal dining room, and spacious family room with gas fireplace. The kitchen includes stainless appliances (all convey), double oven, gas cooktop, island, eat-in area, and large pantry. Oversized mudroom/laundry adds great storage. First-floor primary suite

  Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
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  /52

  $555,000

  • 4 Beds
  • 2 Baths
  • 2,940 Sq Ft

  5515 Van Meter Rd, Winchester, KY 40391

  Welcome to your dream home, perfectly nestled in a highly desired location. This stunning property spans a generous 5 acres, offering an idyllic setting for homesteading. Experience the best of country living with the convenience of nearby amenities.The home boasts beautiful views that will take your breath away every morning. Imagine waking up to the serene beauty of nature, right at your

  Robyn Bradley Woods Realty Group

  5515 Van Meter Rd, Winchester, KY 40391
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  /67

  $549,000

  • 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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  /48

  $570,000

  • 5 Beds
  • 3 Baths
  • 3,489 Sq Ft

  594 Earlymeade Dr, Winchester, KY 40391

  This stunning 5BR,3BA brick home blends classic charm with modern comfort, all situated in a highly desirable neighborhood. The exterior features clean lime wash brick with contrasting painted trim and a crisp new black roof, new black 6mm gutters, exuding timeless curb appeal. A wide front porch with elegant columns welcomes you into the home, perfect for relaxing or greeting guest.Inside you

  Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391
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  /38

  $599,500

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft

  102 Bella Shae Way, Winchester, KY 40391

  Introducing the Stonewall plan—a stunning brick and stone ranch ideally positioned on a corner lot in Mallard Cove. This 4 bedroom, 2 full bath home with a side-entry garage offers timeless curb appeal and high-end features throughout. The thoughtfully designed layout includes a spacious living room with vaulted ceilings, arched and lighted built-ins, and a gas fireplace with a floor-to-ceiling

  Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
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  /69

  $650,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,927 Sq Ft

  2085 Hancock Valley Dr, Winchester, KY 40391

  Spacious 3-Bedroom Home on Nearly 5 Acres in Winchester, KY!Discover country living at its finest with this beautiful 3-bedroom, 3-bathroom home set on nearly 5 acres of picturesque land. Featuring beautiful hardwood floors, a finished basement, and plenty of space for entertaining and friends, this property is designed for comfort and social gatherings. Enjoy the in-ground pool, pole barn, and

  Terry Billiter Premier Property Consultants

  2085 Hancock Valley Dr, Winchester, KY 40391
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  /52

  $530,000

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

  1778 Elkin Rd, Winchester, KY 40391

  Peaceful Living on 8.83 acres of gently rolling hills in the heart of Kentucky. Breathtaking countryside features a newer custom-built home that offers peace, privacy and serene surroundings. Wake up to birdsong, watch deer wander at dusk and soak in the golden sunsets from your own front porch. Highlights include: spacious open concept kitchen with white custom cabinetry, beautiful engineered

  Vicki VanWinkle Pacesetters Real Estate

  1778 Elkin Rd, Winchester, KY 40391
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  /10

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, Winchester, KY 40391
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  /46

  $455,000

  • 3 Beds
  • 2.5 Baths
  • 3,261 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  Beautiful Hampton Manor home offers easy access to all Winchester has to offer! Located right off Boone Ave, this home boasts tons of updates including an Entertaiment Kitchen with granite countertops, Bosch appliances and great storage, refinished hardwoods, new windows, Updated bathroom showers, a pool, covered front porch back porch and separate covered area outback to enjoy all summer long. 3

  Whitney Ensor Ensor Real Estate LLC

  42 Mockingbird Valley Rd, Winchester, KY 40391
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  /37

  $1,249,500

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

  700 Nick Ln, Winchester, KY 40391

  🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you

  Darrell Tackett Dream Maker Realty, LLC

  700 Nick Ln, Winchester, KY 40391
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  /56

  $274,900

  • 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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  /21

  $289,000

  • 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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  /33

  $400,000 Open Sun 2PM - 4PM

  • 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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  /33

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  1831 Kiddville Rd, Winchester, KY 40391

  Offering a perfect blend of modern comfort, energy efficiency, and country charm. Conveniently located just 1.3 miles from Exit 10 off the Bert T. Combs Mountain Parkway, this property provides easy access to both natural beauty and city amenities, with Downtown Winchester only 15 miles away and Natural Bridge State Park just 27 miles down the road. The living area features a cozy vent-free gas

  Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
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  /20

  $207,500

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  111 Quail Ridge Rd, Winchester, KY 40391

  Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and kitchen

  Kim Dice EXP Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
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  /21

  $205,000

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  109 Quail Ridge Rd, Winchester, KY 40391

  Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and kitchen

  Kim Dice EXP Realty, LLC

  109 Quail Ridge Rd, Winchester, KY 40391
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  /23

  $229,000

  • 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 — 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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  /3

  $380,000

  • 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 and a

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 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 ensuite

  Rex Hall United Real Estate Bluegrass

  265 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,885 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 ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
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  /3

  $380,000

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

  230 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.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  230 Evergreen Dr, Winchester, KY 40391
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  /3

  $345,000

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

  225 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.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  225 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,935 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 ensuite

  Rex Hall United Real Estate Bluegrass

  220 Evergreen Dr, Winchester, KY 40391
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  /2

  $345,000

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

  215 Evergreen Dr, Winchester, KY 40391

  Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  215 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $380,000

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

  200 Evergreen Dr, Winchester, KY 40391

  Introducing the Run For The Roses - 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. The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite bathroom. The kitchen

  Rex Hall United Real Estate Bluegrass

  200 Evergreen Dr, Winchester, KY 40391
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  /103

  $2,995,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /32

  $350,000

  • 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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  /35

  $315,000

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

  607 Colby Ridge Blvd, Winchester, KY 40391

  Built by Kessinger Construction, this open floor plan home offers plenty of layout and entertaining options. The durable luxury vinyl tile flooring is through the first floor, utility room and bathrooms. The first floor also features 9' ceilings. The kitchen offers an island ideal for bar stools and there is a spacious dining area. A door leads to a covered porch with a ceiling fan overlooking a

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  607 Colby Ridge Blvd, Winchester, KY 40391
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  /92

  $1,200,000

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft

  6237 Bybee Rd, Winchester, KY 40391

  Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /31

  $100,000

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  15 Sycamore St, Winchester, KY 40391

  3 bedroom 1 bath house. Older home that needs some updates. This house is being sold online at . Selling as/is, must close within 30 days from close of auction. 10% Buyers Premium, 10% down night of sell. Rony Jo Ballou Auctioneer 859-595-6808

  Rony Jo Ballou Power House Realty

  15 Sycamore St, Winchester, KY 40391
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  /42

  $265,500

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft

  9 Apache Trail, Winchester, KY 40391

  Beautiful remodeled move-in ready four bedroom, 2 full bath split foyer. Here are some of the updates: New LVP floors throughout entire home. New carpet on the stairs. New paint throughout home. New fan with remote in living room. Range dishwasher, & new refrigerator stay. New mirrors and lights above them in both baths. New garage door and garage door opener (with 2-year warranty). One side of

  Joyce Ratliff Tom Goebel & Company

  9 Apache Trail, Winchester, KY 40391
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  /19

  $325,000

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

  220 Mcdowell Dr, Winchester, KY 40391

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

  Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
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  /25

  $285,000

  • 4 Beds
  • 2.5 Baths
  • 3,024 Sq Ft

  816 Stratton Ln, Winchester, KY 40391

  Welcome to your dream home! Nestled in an excellent location in Winchester, KY, this charming 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort and convenience. Enjoy the backyard, ideal for outdoor entertainment and relaxation, as well as the inviting front deck, perfect for sipping your morning coffee or watching the sunset. The above ground pool stays with the home and will be a

  Haley Rollins Dream Maker Realty, LLC

  816 Stratton Ln, Winchester, KY 40391

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