Winchester, KY Homes for Sale with Garage

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  /18

  $556,000

  • 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) 695-3879

  110 White Conkwright Rd, Winchester, KY 40391
• Explore Winchester

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  /71

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 7,058 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 470-2071

  186 Chardonnay Ct, Winchester, KY 40391
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  /41

  $343,900 New Construction

  • 3 - 5 Beds
  • 2 - 4 Baths
  • 1,424 Sq Ft

  Lucy Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Lucy floor plan, a versatile and thoughtfully designed new construction home that gives every member of the family the space they need to live, work, and thrive. Built by one of the most trusted home builders in Central Kentucky, the Lucy is a top choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want flexibility, comfort, and

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824256, Winchester, KY 40391
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  $378,900 New Construction

  • 3 - 5 Beds
  • 2.5 - 3.5 Baths
  • 2,098 Sq Ft

  Nancy Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Nancy floor plan, a masterfully designed two-story new construction home that blends smart functionality with open-concept living. Built by one of the most trusted home builders in Central Kentucky, the Nancy is an ideal choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want style, flexibility, and efficient use of space.From the

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824252, Winchester, KY 40391
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  /45

  $429,900 New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,722 Sq Ft

  Eleanor Plan at Boone's Crossing, Winchester, KY 40391

  Experience elevated living with the Eleanor floor plan, a thoughtfully designed new construction home available through one of the most trusted home builders in Central Kentucky. Created for today’s buyers seeking flexibility, luxury, and energy efficiency, the Eleanor blends timeless design with modern functionality for families looking for new construction homes in Lexington KY and surrounding

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824255, Winchester, KY 40391
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  /35

  $360,900 New Construction

  • 3 - 4 Beds
  • 2.5 - 3.5 Baths
  • 1,828 Sq Ft

  Grace Plan at Boone's Crossing, Winchester, KY 40391

  Discover the Grace floor plan, a thoughtfully designed new construction home that blends open-concept living with private, comfortable bedroom spaces. Built by one of the leading home builders in Central Kentucky, the Grace is a perfect fit for buyers searching for new construction homes in Lexington KY and nearby communities who want flexibility, style, and energy efficiency.From the moment you

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824257, Winchester, KY 40391
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  /46

  $347,900 New Construction

  • 3 - 6 Beds
  • 2 - 4 Baths
  • 1,580 Sq Ft

  Martha Plan at Boone's Crossing, Winchester, KY 40391

  The Martha floor plan is your canvas for creating a home that perfectly fits your lifestyle, offering unmatched flexibility, thoughtful design, and timeless appeal. Built by one of the leading home builders in Central Kentucky, the Martha is an excellent choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space that adapts to how they

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824258, Winchester, KY 40391
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  /28

  $363,900 New Construction

  • 4 - 5 Beds
  • 2.5 - 3.5 Baths
  • 2,100 Sq Ft

  Elizabeth Plan at Boone's Crossing, Winchester, KY 40391

  Experience the Elizabeth floor plan, a beautifully crafted new construction home designed for families who value open-concept living, thoughtful organization, and flexible bedroom space. Offered by one of the most trusted home builders in Central Kentucky, the Elizabeth is a standout option for buyers searching for new construction homes in Lexington KY and surrounding communities.From the moment

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824250, Winchester, KY 40391
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  /85

  $397,900 New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,263 Sq Ft

  Abigail Plan at Boone's Crossing, Winchester, KY 40391

  Step into the award-winning Abigail floor plan, a standout choice for buyers searching for new construction homes in Lexington, KY and Central Kentucky. Designed with today’s lifestyle in mind, this home offers the perfect blend of flexible floor plans, energy efficiency, and modern comfort—everything you expect from a trusted home builder in Lexington, KY.From the moment you arrive, the Abigail

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824251, Winchester, KY 40391
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  /52

  $369,900 New Construction

  • 3 - 6 Beds
  • 2 Baths
  • 1,770 Sq Ft

  Barbara Plan at Boone's Crossing, Winchester, KY 40391

  Experience the true essence of homecoming with the Barbara floor plan, a beautifully designed new construction home available through one of the most trusted home builders in Central Kentucky. Thoughtfully crafted for modern living, this plan blends timeless exterior charm with a warm, open interior designed for comfort, flexibility, and everyday functionality.Step onto the inviting covered front

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824253, Winchester, KY 40391
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  /47

  $235,000

  • 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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  /101

  $1,290,000

  • 5 Beds
  • 5 Baths
  • 5,666 Sq Ft

  3760 Old Boonesboro Rd, Winchester, KY 40391

  Step through the striking red front doors and into a home where craftsmanship, character, and comfort come together. This beautifully maintained property sits on nearly 13 acres at the edge of Winchester, offering a peaceful retreat with the charm of a mid century floorplan and rich woodwork, tile, and hardwood floors throughout. The spacious kitchen and all three full baths feature high end

  Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
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  /67

  $307,900

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft

  118 Windridge Dr, Winchester, KY 40391

  Enjoy rest, relaxation and all the outdoor activities you can dream up with this home. Cozy, 3-bedroom, 2-bathroom home ranch with attached one car garage in a well-established neighborhood. Home features new gas stove & range hood, new bathroom updates, hardwood floors, pocket doors, updated finishes, ventless gas fireplace, sunroom and professionally maintained in-ground pool with concrete

  Amber Hunt Whalen & Company

  118 Windridge Dr, Winchester, KY 40391
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  /54

  $749,900

  • 3 Beds
  • 3.5 Baths
  • 3,388 Sq Ft

  1480 Irvine Rd, Winchester, KY 40391

  Beautifully remodeled farmhouse on 10 fenced acres! This 3 bedroom, 3.5 bath home with a fully finished basement offers the perfect blend of modern upgrades and country living. Inside, you'll find refinished hardwood floors and fresh paint throughout. The custom kitchen is designed to impress with new cabinetry, granite countertops, glass subway tile backsplash, double ovens, two dishwashers, and

  Ivanna Barko National Real Estate

  1480 Irvine Rd, Winchester, KY 40391
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  /32

  $265,000

  • 4 Beds
  • 2 Baths
  • 1,739 Sq Ft

  504 Harvard Dr, Winchester, KY 40391

  A spacious Ranch style home with many recent updates. With 4 bedrooms and 2 bath you'll find plenty of space for the everyone. With new laminate flooring, several new doors, and new paint throughout; this home is move in ready! Other updates include a new shower in the master bath, new microwave, new tile in the Utility room, new island top, new shelving in the walk in closet, and new gutters.

  Justin Lee JL Realty Group, LLC

  504 Harvard Dr, Winchester, KY 40391
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  /36

  $435,000

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft

  3886 Jackson Ferry Rd, Winchester, KY 40391

  Take in the scenery, enjoy the quite county life, sitting on 5 acres, this brick ranch home offers easy living and peaceful country life. Four Bedrooms 2 full updated baths, Primary Suite with walk in closet, hardwood floors, beautiful brick fireplace in Living Room with Vaulted ceiling and built in shelving, Dining Room, Kitchen with breakfast area granite counter tops and all appliances (range,

  Whitney Ensor Ensor Real Estate, LLC

  3886 Jackson Ferry Rd, Winchester, KY 40391
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  /16

  $179,900

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

  47 Buckner St, Winchester, KY 40391

  This 3-bedroom, 2 full bath home is nestled in a convenient location and ready for new owners. Updates can be admired throughout. Property boats spacious bedrooms including primary bedroom with on-suite, large back yard with garage and so much more. Schedule your showing today!

  Michael Hilario The Agency

  47 Buckner St, Winchester, KY 40391
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  /59

  $695,000

  • 3 Beds
  • 4 Baths
  • 4,008 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Absolutely fabulous all brick home with incredible views, one owner, what makes this home special is the feeling of elegance, a total renovation offers the ultimate in living, spacious lower level provides full bath, family room, firepalce, walk out door to a large patio, first level dining room, great room with firepalce, showcase kitchen, living room, upstairs with large master suite, side

  Mila Ensor Ensor Real Estate, LLC

  1775 Irvine Rd, Winchester, KY 40391
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  /30

  $200,000

  • 3 Beds
  • 2 Baths
  • 1,289 Sq Ft

  128 Bay Hill Dr, Winchester, KY 40391

  Opportunity knocks in Royal Oaks Village—be part of Winchester's next chapter. Located within the expanding Deerlawn development, this single-story ranch townhome offers incredible upside in an area poised for growth. With future plans bringing hundreds of new homes, townhomes, and duplexes nearby, this is your chance to get in early and build equity. Inside, you'll find a spacious and functional

  Melia Hord Keller Williams Legacy Group

  128 Bay Hill Dr, Winchester, KY 40391
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  /24

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft

  201 Prescott Ln, Winchester, KY 40391

  This Is The One You Have Been Waiting For!!! Perfect Location, Flat Fully Fenced Backyard And A Large Rear Covered Patio. This 1 1/2 Story 3 Bedroom 2 Bath Home Has Vaulted Ceilings; Lots Of Cabinets; Stainless ' Steel Appliances; Good Size Primary Bedroom With En Suite; Walk In Closet; 2 More Generous Sized Bedrooms And So Much More!

  Patrick Arvin Keller Williams Commonwealth

  201 Prescott Ln, Winchester, KY 40391
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  /52

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,417 Sq Ft

  104 Jackson Ferry Rd, Winchester, KY 40391

  Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen

  Bob Sophiea eXp Realty, LLC

  104 Jackson Ferry Rd, Winchester, KY 40391
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  /29

  $224,900

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  11 Shelley Dr, Winchester, KY 40391

  SELLER is motivated to offers! Welcoming you to this lovely updated throughout 3 bedroom, 2 full bath ranch! As you step into the home with its cozy feeling, and spacious space in every room, including a full unfinished basement wonderful for storage or to finish that into living square footage, great size back yard with large back patio perfect for the family gatherings, also a partial fenced in

  Nichole Bingham CENTURY 21 Advantage Realty

  11 Shelley Dr, Winchester, KY 40391
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  /63

  $460,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Enjoy peaceful country living on 17 beautiful acres in Clark County! This 3-bedroom, 2-bath ranch home sits on a scenic stretch of Trapp-Goffs Corner Road and offers the perfect blend of privacy, space, and convenience just minutes from Winchester and an easy drive to Lexington. The home features comfortable main-level living with a functional layout and a partially finished basement that

  Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /43

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Private 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet

  Felicia Mayes The Real Estate Co.

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /65

  $609,900

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

  6595 Mount Sterling Rd, Winchester, KY 40391

  Sellers have current accepted offer in place with a 48-hour kick-out clause.

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
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  /36

  $369,000

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

  133 Shala-Mar Rue, Winchester, KY 40391

  Welcome to your next home in one of Clark County's most sought after communities—Shala Mar Estates. This beautifully updated 3-bedroom, 2-bathroom residence offers the perfect blend of comfort, style, and modern convenience. The expansive primary suite is a true retreat, featuring a stunning ensuite bathroom with a brand new soaking tub and a separate tiled shower. Two additional bedrooms provide

  Nena Honaker Tom Goebel & Company

  133 Shala-Mar Rue, Winchester, KY 40391
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  /12

  $299,900

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
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  /77

  $924,900

  • 5 Beds
  • 4.5 Baths
  • 6,314 Sq Ft

  7210 Ecton Rd, Winchester, KY 40391

  Welcome to 7210 Ecton Road a stunning 5 bedroom, 4.5 bathroom home situated on 7+/- acres (awaiting final survey) of gently rolling Kentucky countryside. This property offers the perfect balance of modern comfort, privacy, and wide-open space, just minutes from downtown Winchester. Step inside to discover a spacious and well-designed floor plan featuring: 5 generously sized bedrooms including a

  Megan McCoy Keller Williams Legacy Group

  7210 Ecton Rd, Winchester, KY 40391
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  /12

  $185,900

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street. This brick ranch offers 3 bedrooms, 2 full baths, and hardwood floors throughout the living room, hallway, and bedrooms, ready to be refreshed with a re-sand and polish. The layout provides a foundation for a buyer looking to add personal updates and make it their own. Located at the end of the street, the home offers added privacy along with peaceful farm views behind

  Austina Bruton Re/Max Elite Realty - Hamburg

  41 7th St, Winchester, KY 40391
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  /12

  $297,000

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft

  327 Newcastle Ln, Winchester, KY 40391

  Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase that overlooks the main floor. Upstairs are 3 additional bedrooms and a full bathroom. Fenced yard and covered patio to

  Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, Winchester, KY 40391
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  /100

  $429,900

  • 4 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  240 Athens Boonesboro Rd, Winchester, KY 40391

  Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your

  Darrell Tackett Dream Maker Realty, LLC

  240 Athens Boonesboro Rd, Winchester, KY 40391
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  /58

  $89,900

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  1860 Ford Rd, Winchester, KY 40391

  Freshly cleaned and ready for its next owner, this property offers exceptional potential. The spacious 1,800 sq. ft. block garage provides a solid foundation for countless uses — from a workshop or storage facility to a future business or hobby space. An older trailer is also located on the property. It will require a full renovation or removal, giving you the freedom to redesign the space

  Darrell Tackett Dream Maker Realty, LLC

  1860 Ford Rd, Winchester, KY 40391
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  /17

  $425,000

  • 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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  /55

  $679,500

  • 4 Beds
  • 3.5 Baths
  • 3,431 Sq Ft

  7919 Mount Sterling Rd, Winchester, KY 40391

  Don't let this stunning, 3,431sqft home featuring 4 bed rooms and 3 full baths, sitting on 3 acres, slip through your hands! Custom built brick home nestled in a serene, park like setting overlooking Stoner Creek. Step into to the dramatic two story entryway welcoming you with custom cabinetry and detailed finishes throughout. One of the most captivating features is the sunroom, overlooking the

  Hannah Toole Coldwell Banker McMahan

  7919 Mount Sterling Rd, Winchester, KY 40391
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  /29

  $344,900

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  23 Windridge Dr, Winchester, KY 40391

  Welcome home!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The

  Holly Goeing The Agency

  23 Windridge Dr, Winchester, KY 40391
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  /12

  $289,000

  • 5 Beds
  • 2 Baths
  • 2,214 Sq Ft

  55 Hillcrest Dr, Winchester, KY 40391

  **New roof (6 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence .** All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an

  Nina Vanetten RE/MAX Elite Lexington

  55 Hillcrest Dr, Winchester, KY 40391
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  /97

  $335,000

  • 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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  /23

  $329,000

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

  225 Plantations Dr, Winchester, KY 40391

  Welcome to 225 Plantations Drive, a beautifully maintained home in the desirable Royal Oaks Subdivision. This charming three-bedroom, two-and-a-half-bath residence is in wonderful condition and move-in ready! This is home comes with a wonderful floorplan that has a primary bedroom with built-in's on the first floor, Kitchen with granite and stainless appliances and deck has been updated with Trex

  John Wilson Bluegrass Properties Group

  225 Plantations Dr, Winchester, KY 40391
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  /67

  $325,000

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
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  /84

  $340,000

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  215 Old Log Lick Rd, Winchester, KY 40391

  Enjoy where you live! Zen like grounds will bring inner peace in this 1,450 sq foot home on over 3 private acres. Covered front and back porches span the width of the house. Get off the grid with the solar panels on the roof (25 yr warranty), six raised garden beds, and fenced chicken coop! Average utility bill $50 in 2025 and $35 in 2024! (Solar panels paid for by Seller). No worries for fast

  Kerry Ball Local First Realty, LLC

  215 Old Log Lick Rd, Winchester, KY 40391

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