Homes for Sale in 40391

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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
• 

  

  

  /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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  /29

  $70,000

  • 3 Beds
  • 2 Baths
  • 750 Sq Ft

  113 Mimosa Dr, Winchester, KY 40391

  Discover the perfect balance between home ownership, affordability, and rural tranquility in this charming 3-bedroom two bath home. Conveniently located near shopping areas and interstates providing easy access to Lexington, Winchester and many central Kentucky cities. The interior features freshly updated flooring, offering a cohesive feel to living spaces. The true highlight of this property is

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 328-1402

  113 Mimosa Dr, 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 including a brand new furnace installed in February of 2026, and exceptional curb appeal and charm,

  

  Tyler Hurst

  Thwaites Realtors LLC

  (859) 927-8049

  128 Cherokee Dr, Winchester, KY 40391
• 

  

  

  /22

  $139,000

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  3208 Ford Hampton Rd, Winchester, KY 40391

  Escape to a lifestyle defined by the peace and natural beauty of this delightful two bedroom property just steps away from the majestic Kentucky River, this home isn't just a place to iive, it is a dedicated sanctuary whether you are seeking a cozy year round residence or a recreational retreat. One of the standout features is the exceptioal connection to the outdoors with generous porches on

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 765-6889

  3208 Ford Hampton Rd, Winchester, KY 40391
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  /32

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  4305 Old Boonesboro Rd, Winchester, KY 40391

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3072

  4305 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /22

  $255,000

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft

  35 Cherokee Ct, Winchester, KY 40391

  Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more

  

  Brenda Rue

  Keller Williams Bluegrass Realty

  (859) 470-8131

  35 Cherokee Ct, Winchester, KY 40391
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  /32

  $349,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,628 Sq Ft

  538 S Maple St, Winchester, KY 40391

  Be the first to call this stunning new construction home! Perfectly situated in the heart of Winchester, this two-story residence offers a fresh, modern feel with convenience at your doorstep. Step inside to discover a bright and airy open-concept main level, featuring durable and stylish Luxury Vinyl Plank (LVP) flooring throughout. The kitchen is a true showstopper, boasting crisp white

  

  Heather Kuykendoll

  Bluegrass Properties Group

  (859) 535-9618

  538 S Maple St, Winchester, KY 40391
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  /37

  $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

  Step into the Nancy plan, a masterful fusion of form and function that optimizes every square foot. This two-story gem offers the best of both worlds: an open-concept haven on the first floor and a serene retreat on the second, all wrapped in your choice of a Farmhouse, French Country, or Cottage facade, ensuring your home is a reflection of your distinct style.As you enter, a versatile flex room

  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

  Unlock a world of possibilities with the Eleanor plan – an exquisite home designed for those seeking the luxury of a first-floor owner's suite while yearning for additional bedrooms and flexible spaces on the second floor. The Eleanor plan offers not just a home but a canvas for your vision, where the exterior can be customized with a choice of a Farmhouse, French Country, or Cottage facade,

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824255, Winchester, KY 40391
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  /92

  $1,750,000

  • 8 Beds
  • 9 Baths
  • 10,825 Sq Ft

  131 Wells Rd, Mount Sterling, KY 40353

  A rare opportunity to own an architecturally stunning custom estate on approximately 35 acres with two private entrances. Designed for beauty, function, privacy, and accessibility, this one of a kind residence offers craftsmanship and scale rarely seen in today's market. At the heart of the home is a breathtaking approximately 1,200 square foot central atrium surrounded by nearly every living

  Terra Long Keller Williams Commonwealth

  131 Wells Rd, Mount Sterling, KY 40353
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  /59

  $289,000

  • 3 Beds
  • 1 Bath
  • 1,273 Sq Ft

  119 Tower Ln, Winchester, KY 40391

  A rare and refined retreat set on five unrestricted acres in Winchester. Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh designer paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The

  Shawna Wever Wever Realty LLC

  119 Tower Ln, 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

  Welcome to the Grace plan, where the art of harmonious living comes to life, striking the perfect balance between spacious living areas on the first floor and cozy bedrooms on the second. As you approach, take in the captivating exterior options, where you have the power to choose between a Farmhouse, French Country, or Cottage facade, ensuring your home is a reflection of your unique style.Upon

  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 plan is your canvas for crafting the ideal home that suits your unique lifestyle and needs. This versatile layout is a true chameleon, offering three distinct configurations: a welcoming ranch, an expansive ranch with a basement for extra space, or an impressive two-story design featuring additional rooms (bedrooms or a loft) and an extra bath on the second floor.As you step through

  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

  Step into the exquisite Elizabeth, a home that caters to families who cherish open-concept living on the first floor while seeking ample bedroom space on the second floor. As you approach, a gracious front porch welcomes your guests into a grand and inviting foyer that sets the tone for what's to come.Upon crossing the threshold and passing the convenient powder room and elegant stairs, you'll be

  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 world of the award-winning Abigail plan, where possibilities for flexible living, working, and relaxation abound. This exceptional design offers you the opportunity to tailor your exterior with a choice of a Farmhouse, French Country, or Cottage facade, ensuring your home reflects your unique style and taste.As you enter, you'll be captivated by a generous flex room that opens up

  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 plan. This impeccably crafted design effortlessly blends the allure of its exterior and interior, promising a sense of belonging and comfort like no other.Step onto the scene and be captivated by the charm of covered porches gracing both the front and back of the home, inviting you to savor the joys of outdoor living. Inside, the Barbara

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824253, 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

  The new Lucy plan offers every member of your family the space they need to live, work, and thrive. This exceptional design empowers you with the freedom to extend both your living room and rear porch, creating additional havens for relaxation and enjoyment, both inside and out.The Lucy plan is your canvas for crafting the home of your dreams. Choose from three extraordinary configurations: a

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824256, Winchester, KY 40391
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  /19

  $499,000

  • Land
  • 36.94 Acres
  • $13,508 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
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  /45

  $489,900 Open House 4/26

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Welcome to Fairholme Estates—where luxury meets comfort! This brand-new ranch-style home offers 4 bedrooms, 3 full baths, and 9' ceilings throughout for a spacious, airy feel. The designer kitchen features a huge island, beautiful finishes, and flows seamlessly into the vaulted great room filled with natural light from large windows. A Jack and Jill bath with separate sinks provides convenience,

  Kristin Ray Lifstyl Real Estate

  414 Fairholme Way, Winchester, KY 40391
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  /84

  $343,000

  • 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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  /24

  $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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  /10

  $550,000 New Construction

  • 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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  /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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  /22

  $665,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  414 Alexis Way, Winchester, KY 40391

  Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

  Shane Underwood Keller Williams Commonwealth

  414 Alexis Way, Winchester, KY 40391
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  /72

  $406,900 New Construction

  • 3 - 6 Beds
  • 2.5 - 5.5 Baths
  • 2,570 Sq Ft

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

  Unleash your creativity and make your mark with the Jackie plan – a home that empowers you to design your ideal living and lounging spaces. Step into a world of endless possibilities, where the exterior can be personalized with your choice of a Farmhouse, French Country, or Cottage facade, setting the stage for your one-of-a-kind dream home.As you enter, you'll be greeted by a generously sized

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824254, 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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  /5

  $369,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
• 

  

  /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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  /44

  $360,000

  • 4 Beds
  • 3 Baths
  • 3,440 Sq Ft

  221 W Hickman St, Winchester, KY 40391

  Step into a home where history and beauty meet in the most charming way. This stunning, fully remodeled historic home offers over 3,400 square feet of thoughtfully renewed living space, blending timeless character with elegant modern updates. From the moment you walk inside, you'll feel the warmth and romance of a home that has been lovingly restored while still honoring its original charm.

  Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
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  /49

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 2,628 Sq Ft

  221 Moundale Ave, Winchester, KY 40391

  Step back in time as you walk up the stone steps into this beautiful 3 bed 2.5 bath house. This house has been very well maintained and offers many updates. You get the best of both worlds the craftsmanship of an older home with all the newer amenities. Hardwood, tile and brick floors throughout the house with Granite countertops, This house sits on a lot and a half. The owners have recently

  Andrew Fugitt Coldwell Banker McMahan

  221 Moundale Ave, 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
• 

  

  /55

  $334,900

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  1291 Muddy Creek Rd, Winchester, KY 40391

  Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides

  Terri McGraw FC Tucker Bluegrass

  1291 Muddy Creek Rd, 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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  /56

  $399,900

  • 5 Beds
  • 3 Baths
  • 3,718 Sq Ft

  1503 Schollsville Rd, Winchester, KY 40391

  Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft

  Keith Wilson Coldwell Banker McMahan

  1503 Schollsville Rd, 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
• 

  

  /32

  $349,900

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

  8720 Wades Mill Rd, Mount Sterling, KY 40353

  Spacious inside and out, this 4-bedroom, 2-bath brick and vinyl split-foyer home sits on a beautiful 1.65-acre lot along desirable Wades Mill Rd and offers the space and features you've been searching for. The main level includes a large living room, a spacious kitchen with updated tile flooring and painted cabinetry, a dining area, primary bedroom and bath, plus an additional bedroom. The lower

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  8720 Wades Mill Rd, Mount Sterling, KY 40353
• 

  

  /51

  $775,000

  • 5 Beds
  • 3.5 Baths
  • 2,904 Sq Ft

  1783 Gay Evans Rd, Winchester, KY 40391

  Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring

  Lucy Martin Jenkins United Real Estate Bluegrass

  1783 Gay Evans Rd, Winchester, KY 40391
• 

  

  /100

  $1,789,000

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
• 

  

  /20

  $175,000

  • Land
  • 11.36 Acres
  • $15,402 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of convenience and countryside charm with this beautiful 11+ acre tract located just outside of Winchester in Clark County. Offering gently rolling terrain and multiple potential building sites, this property provides an ideal setting for your dream home, mini-farm, or private retreat.Enjoy the peace and privacy of rural living without sacrificing accessibility and just

  Christa Joynt Keller Williams Commonwealth

  2996 Irvine Rd, Winchester, KY 40391

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