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Homes for Sale in 40391

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  • /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
  • /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.

    Agent Photo

    Philip 'PJ' Elder

    Omega Real Estate Brokerage LLC

    (859) 695-3879

    110 White Conkwright Rd, Winchester, KY 40391
  • /71

    $749,999

    • 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

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 470-2071

    186 Chardonnay Ct, 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, new insulation and baffling, and

    Agent Photo

    Tyler Hurst

    Thwaites Realtors LLC

    (859) 927-8049

    128 Cherokee Dr, Winchester, KY 40391
  • /72

    $775,000

    • 5 Beds
    • 3 Baths
    • 4,437 Sq Ft

    465 Morris Rd, Winchester, KY 40391

    Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

    Agent Photo

    Brenda Leigh Walters

    United Real Estate Bluegrass

    (859) 459-0504

    465 Morris Rd, Winchester, KY 40391
  • /12

    $185,900 Open Mon 5PM - 7PM

    • 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

    Agent Photo

    Austina Bruton

    Re/Max Elite Realty - Hamburg

    (859) 695-6124

    41 7th 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
  • /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
  • /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
  • /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
  • /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

    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
  • /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
  • /92

    $1,650,000

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

    131 Wells Rd, Mount Sterling, KY 40353

    Less than 30 minutes from Lexington or 45 minutes from Keeneland, this 35-acre Clark County private sanctuary of Glass, Wood and Water is designed for flexibility, privacy, accessibility, multigenerational living and indoor-outdoor synergy. The home's crown jewel is a 1,200 sq. ft. four-season ***ATRIUM*** encircled by nearly every living space. Featuring a retractable ceiling, a cascading

    Terra Long Keller Williams Commonwealth

    131 Wells Rd, Mount Sterling, KY 40353
  • /60

    $269,000

    • 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

    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
  • /31

    $330,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 3 Baths
    • 2,624 Sq Ft

    28 Churchill Dr, Winchester, KY 40391

    Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being primary suites, one on the main level and one in the basement. This house is perfect for multigenerational living. New paint, floors, back splash, kitchen cabinets and granite counter tops. The fully finished basement has a newly added primary bedroom and bath. The updated bathroom has a double vanity with

    Libby VanMeter Marshall Lane Real Estate - Lexington

    28 Churchill Dr, 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 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
  • /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
  • /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
  • /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

    $479,900 Open Sun 2PM - 4PM

    • 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
  • /57

    $350,000

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

    443 S Maple St, Winchester, KY 40391

    Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make

    Terra Long Keller Williams Commonwealth

    443 S Maple St, 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

    $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
  • /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 with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391
  • /90

    $650,000

    • 6 Beds
    • 4 Baths
    • 4,351 Sq Ft

    142 Clubhouse Dr, Winchester, KY 40391

    Welcome to a lifestyle most only dream about — a stunning six-bedroom, four-bathroom residence perched along the lush fairways of Southwind Golf Course, complete with a lifetime membership for as long as you call this home. That's right, your morning coffee comes with panoramic views of manicured greens, and your evenings end with sunsets on the back porch. Inside, elegant double crown molding

    Timothy Saylor Threshold Real Estate Services

    142 Clubhouse Dr, Winchester, KY 40391
  • /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
  • /20

    $316,900

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

    200 Dubuy Dr, Winchester, KY 40391

    Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full

    Wayne Elkins RE/MAX Creative Realty

    200 Dubuy Dr, Winchester, KY 40391
  • /31

    $347,500

    • 4 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    110 Powe Dr, Winchester, KY 40391

    This 4 Bedroom, 3 Bath home is quietly nestled within the Greenfield subdivision. Prime location just off the Winchester Bypass. This property has so much to offer. Updates can be seen throughout. Large first floor primary bedroom with on-suite and walk in closet, spacious family room, large yard with mature trees as well as widened driveway for additional parking, above ground pool with duel

    Michael Hilario The Agency

    110 Powe Dr, Winchester, KY 40391
  • /23

    $326,900

    • 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
  • /49

    $345,000

    • 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

    $359,000

    • 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
  • /30

    $322,500

    • 3 Beds
    • 2.5 Baths
    • 2,648 Sq Ft

    412 Pueblo Ct, Winchester, KY 40391

    Welcome to this beautifully maintained 5-year-old home nestled on a quiet cul-de-sac in the desirable Ft. Estill area of Winchester. This charming property offers 3 bedrooms and 2.5 baths, a spacious and functional layout with comfortable living areas perfect for both everyday living and entertaining. Enjoy low-maintenance flooring throughout all the main living areas and plenty of natural light

    Lisa Dickens Rector Hayden Realtors

    412 Pueblo Ct, Winchester, KY 40391
  • /26

    $369,900 Open Sun 2PM - 4PM

    • 4 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    614 Colby Ridge Blvd, Winchester, KY 40391

    Welcome to this beautifully maintained 4 bed 2.5 bath home built in 2020 offering the perfect blend of modern design and everyday comfort. Open-concept once you step inside with lots of space. The kitchen and dining offers entertainment space along with the back deck. Check out this house. Located right behind Kroger close to everything and more.

    Stacey Dunaway HomeLand Real Estate Inc - Mt Sterling

    614 Colby Ridge Blvd, Winchester, KY 40391
  • /97

    $327,500

    • 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
  • /3

    $329,999

    • 3 Beds
    • 2.5 Baths
    • 2,607 Sq Ft

    414 Pueblo Ct, Winchester, KY 40391

    Turn-key and beautifully designed, this Craftsman-style 2-story home offers the perfect blend of style, space, and functionality. Featuring 3 spacious bedrooms, 2.5 baths, and a fully finished walk-out basement, this home is built for both everyday living and entertaining. The open-concept main level welcomes you with a seamless flow between the living area, entry, and the kitchen, complete with

    Walker Sabourin The Local Agents

    414 Pueblo Ct, Winchester, KY 40391
  • /66

    $325,000 Open Sun 1PM - 3PM

    • 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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