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Homes for Sale in 40391

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  • /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
  • /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

    $550,000

    • 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
  • /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

    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
  • /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
  • /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

    $320,000 Open Sun 11AM - 1PM

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

    28 Churchill Dr, Winchester, KY 40391

    ***Motivated Sellers*** 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

    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
  • /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

    $257,000

    • 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
  • /19

    $209,000

    • Land
    • 41.69 Acres
    • $5,014 per Acre

    2697 Pine Ridge Rd, Winchester, KY 40391

    Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and

    Derek Blankenship Keller Williams Commonwealth

    2697 Pine Ridge 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
  • /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
  • /38

    $329,900

    • 4 Beds
    • 1 Bath
    • 2,327 Sq Ft

    162 French Ave, Winchester, KY 40391

    Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready

    Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

    162 French Ave, 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
  • /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
  • /17

    $415,000

    • 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
  • /63

    $460,000

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

    1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

    Property is under contract with a 72 hour kickout clause. 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

    Cheri Shaffer Lifstyl Real Estate

    1911 Trapp-Goffs Corner Rd, 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
  • /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
  • /52

    $339,900

    • 4 Beds
    • 2 Baths
    • 1,843 Sq Ft

    228 Holiday Rd, Winchester, KY 40391

    Back on the market at no fault of the sellers. Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and

    Caroline Mucci CENTURY 21 Commonwealth R E

    228 Holiday Rd, Winchester, KY 40391
  • /20

    $312,000

    • 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

    $339,900

    • 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

    $324,900

    • 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 Open Sun 1PM - 3PM

    • 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
  • /38

    $296,900

    • 4 Beds
    • 2 Baths
    • 2,116 Sq Ft

    618 Westmeade Dr, Winchester, KY 40391

    Conveniently located, this charming well kept home features a functional floorplan offering space that can be tailored for those who love to entertain or the growing family. On the main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living

    Kristi Donaldson United Real Estate Bluegrass

    618 Westmeade Dr, Winchester, KY 40391
  • /40

    $299,000 Open Sun 1PM - 3PM

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

    54 Locust Dr, Winchester, KY 40391

    Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a

    Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

    54 Locust Dr, 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

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