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Homes for Sale in 40391

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  • /22

    $260,000

    • 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

    Agent Photo

    Brenda Rue

    Keller Williams Bluegrass Realty

    (859) 470-8131

    35 Cherokee Ct, Winchester, KY 40391
  • /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

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 328-1402

    113 Mimosa Dr, Winchester, KY 40391
  • /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,

    Agent Photo

    Tyler Hurst

    Thwaites Realtors LLC

    (859) 927-8049

    128 Cherokee Dr, Winchester, KY 40391
  • /37

    $219,000

    • 3 Beds
    • 1 Bath
    • 1,188 Sq Ft

    314 E Broadway St, Winchester, KY 40391

    Welcome to this beautifully maintained 3-bedroom, 1-bath ranch offering 1,188 sqft of classic charm on a spacious 0.26-acre lot! This home blends timeless character with thoughtful updates, featuring an inviting single-level layout, bright living areas, well-sized bedrooms, and an updated kitchen with an added pantry for extra storage. Out back, enjoy an attached and enclosed sunroom perfect for

    Agent Photo

    Ashley Spencer

    Keller Williams Commonwealth

    (859) 208-2608

    314 E Broadway St, 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

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 765-6889

    3208 Ford Hampton Rd, Winchester, KY 40391
  • /32

    $375,000

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

    4305 Old Boonesboro Rd, Winchester, KY 40391

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 549-3072

    4305 Old Boonesboro Rd, Winchester, KY 40391
  • /32

    $354,900 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

    Agent Photo

    Heather Kuykendoll

    Bluegrass Properties Group

    (859) 535-9618

    538 S Maple St, Winchester, KY 40391
  • /32

    $254,900

    • 3 Beds
    • 2 Baths
    • 1,251 Sq Ft

    414 Wellington Way, Winchester, KY 40391

    Charming, Move-In Ready Ranch with Updates & Fenced Yard! Welcome home to this super cute and well-maintained 3-bedroom, 2-bath ranch offering easy one-level living and a smart, functional layout. Close to shopping and the interstate for easy commutes. Recent improvements include a brand-new roof, fresh interior paint throughout, a new garage door and opener, and a new stainless-steel appliance

    Amy Diamond ERA Select Real Estate

    414 Wellington Way, Winchester, KY 40391
  • /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
  • /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
  • /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
  • /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
  • /59

    $294,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /23

    $475,000

    2996/3056 Irvine Rd, Winchester, KY 40391

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

    Lura Justice Rector Hayden Realtors

    2996/3056 Irvine Rd, Winchester, KY 40391
  • /18

    $260,000

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft

    280 Pine Ridge Rd, Winchester, KY 40391

    Bring your vision to life on 12+ beautiful acres in Winchester! This 3-bedroom, 1-bath home offers the charm of a 1964 build and the opportunity to create your own private retreat. With plenty of room for gardens, animals, workshops, or expansion, this property is perfect for those dreaming of country living. Renovate the existing home or reimagine the space to fit your needs — the possibilities

    Derek Blankenship Keller Williams Commonwealth

    280 Pine Ridge Rd, Winchester, KY 40391
  • /44

    $250,000

    • Land
    • 6.56 Acres
    • $38,110 per Acre

    8674 Wades Mill Rd, Winchester, KY 40391

    Properties like this rarely come on the market in such a sought-after area. From the moment you pull up to the impressive stone pillar entrance along the paved county road, its clear this land was meant for something special. A black farm fence outlines the property, framing beautifully manicured grass and giving the entire setting the feel of a private estate. Rows of planted pines create a

    Cory Meade Whitetail Properties Real Estate

    8674 Wades Mill Rd, Winchester, KY 40391
  • /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
  • /45

    $489,900 New Construction

    • 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
  • /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
  • /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
  • /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
  • /29

    $359,900

    • 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
  • /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
  • /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
  • /17

    $429,000

    • 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
  • /6

    $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
  • /3

    $670,000 New Construction

    • 3 Beds
    • 2 Baths
    • 2,261 Sq Ft

    113 Bella Shae Way, Winchester, KY 40391

    Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

    Shane Underwood Keller Williams Commonwealth

    113 Bella Shae Way, Winchester, KY 40391
  • /23

    $332,700

    • 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
  • /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
  • /49

    $355,000

    • 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
  • /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

    $339,900

    • 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
  • /97

    $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
  • /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

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