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Homes for Sale in Clark County KY with 5-Bedrooms

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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.

    Agent Photo

    Philip 'PJ' Elder

    Omega Real Estate Brokerage LLC

    (859) 695-3879

    110 White Conkwright Rd, 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
  • /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
  • /13

    $246,400

    • 5 Beds
    • 3 Baths
    • 3,007 Sq Ft

    221 S Highland St, Winchester, KY 40391

    INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

    Joshua Lynch The Brokerage

    221 S Highland St, Winchester, KY 40391
  • /65

    $609,900

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

    6595 Mount Sterling Rd, Winchester, KY 40391

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

    Brooke Otis Mullins RO&CO Real Estate

    6595 Mount Sterling Rd, Winchester, KY 40391
  • /3

    $251,000

    • 6 Beds
    • 3 Baths
    • 2,302 Sq Ft

    133 S Highland St, Winchester, KY 40391

    16 Central Ave, Winchester, KY 40391Prime multi-family investment in a great Winchester location! This 2-story property features two spacious rental units, both offering strong income potential. The first unit includes 3 bedrooms and 2 bathrooms, while the second unit offers 3 bedrooms and 1 bathroom—ideal for accommodating a range of tenant needs. With an established rental history and close

    David Espinosa Bluegrass Realty Pros, Inc

    133 S Highland St, Winchester, KY 40391
  • /77

    $924,900

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

    7210 Ecton Rd, Winchester, KY 40391

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

    Megan McCoy Keller Williams Legacy Group

    7210 Ecton Rd, Winchester, KY 40391
  • /31

    $505,000

    • 8 Beds
    • 4 Baths
    • 5,058 Sq Ft

    265 S Highland St, Winchester, KY 40391

    Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

    J Corey Griffo RE/MAX Elite Lexington

    265 S Highland St, Winchester, KY 40391
  • /12

    $296,000

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

    55 Hillcrest Dr, Winchester, KY 40391

    All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving.

    Nina Vanetten RE/MAX Elite Lexington

    55 Hillcrest Dr, Winchester, KY 40391
  • /62

    $319,500

    • 8 Beds
    • 5 Baths
    • 3,637 Sq Ft

    144 Holly Ave, Winchester, KY 40391

    Excellent investment opportunity featuring two income-producing buildings on one lot, offered together as a package deal. This unique multifamily property includes a triplex and a separate duplex, making it ideal for investors looking to expand their portfolio with multiple units in one purchase. The triplex (Building A) consists of three units: Unit A-1: 2 bedrooms, 1 bathroom Unit A-2: 1

    Shane Underwood Keller Williams Commonwealth

    144 Holly Ave, Winchester, KY 40391
  • /37

    $1,595,000

    • 37 Beds
    • 19.5 Baths
    • 26,124 Sq Ft

    2 N Main St, Winchester, KY 40391

    Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule! The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

    Blanca Cheung Tsubaki Group, LLC

    2 N Main St, Winchester, KY 40391
  • /33

    $354,900

    • 5 Beds
    • 2 Baths
    • 1,952 Sq Ft

    1270 Sewell Shop Rd, Winchester, KY 40391

    Country Living with Convenience — 5 Fenced Acres in Winchester, KY Enjoy the perfect blend of peaceful country living and easy access to town with this well-maintained home on 5 fully fenced acres in Winchester, KY. Conveniently located just 30 minutes to Lexington, 5 miles to I-64, 10 minutes to Mt. Sterling, and 15 minutes to Winchester, this property offers country living without sacrificing

    Meggan Batey Keller Williams Legacy Group

    1270 Sewell Shop Rd, Winchester, KY 40391
  • /29

    $389,900

    • 8 Beds
    • 8 Baths
    • 4,000 Sq Ft

    17 W Lexington Ave, Winchester, KY 40391

    Investment Opportunity in the Heart of Downtown Winchester! Discover 17 W. Lexington Ave, a converted commercial building now featuring 8 studio/one-bedroom apartments. Each unit includes a full kitchen and private bath, offering the perfect blend of comfort and convenience for tenants. This multifamily property is ideally situated in historic downtown Winchester, within walking distance to

    Joshua Lynch The Brokerage

    17 W Lexington Ave, Winchester, KY 40391
  • /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
  • /87

    $2,999,000

    • 6 Beds
    • 5 Baths
    • 3,693 Sq Ft

    3049 Ironworks Rd, Winchester, KY 40391

    Some properties are special simply because of the story behind them. This 150-acre farm in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function

    Zova Rothchild Keller Williams Legacy Group

    3049 Ironworks Rd, Winchester, KY 40391
  • /109

    $1,600,000

    • 5 Beds
    • 3 Baths
    • 7,172 Sq Ft

    351 Benton Rd, Mount Sterling, KY 40353

    Set on 27± fully fenced acres of pristine Kentucky countryside, this custom-built luxury home exudes sophistication from the moment you arrive. Every inch has been thoughtfully designed with premium materials, refined finishes, and an effortless sense of elegance, offering privacy, space, and an unmatched lifestyle. Inside, the split floor plan opens into an expansive main living area highlighted

    Courtney Mangold The Agency

    351 Benton Rd, Mount Sterling, KY 40353
  • /47

    $499,000

    • 5 Beds
    • 3.5 Baths
    • 3,823 Sq Ft

    595 Earlymeade Dr, Winchester, KY 40391

    Entertaining the idea of entertaining family and friends? Looking for space for living the good life in a fun house in a great neighborhood? Then look no further. This house is ready for you to make it your new home. Located in the desirable neighborhood of Earlymeade, this house is minutes from the Winchester Bypass, I- 64 corridor and the Hamburg area of Lexington. Along with 5 bedrooms and 3.5

    Craig Bridgewater Bridgewater Real Estate

    595 Earlymeade Dr, Winchester, KY 40391
  • /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
  • /15

    $600,000

    • 8 Beds
    • 4 Baths
    • 5,046 Sq Ft

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

    Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new

    Priya Patel-Rossetti Big Blue Realty

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
  • /68

    $2,450,000

    • 5 Beds
    • 5 Baths
    • 6,284 Sq Ft

    5039 Combs Ferry Rd, Ford, KY 40391

    This 5 Bedroom, 5 Bathroom home is quietly located in the highly desired Combs Ferry area of Clark County. Location is evident as you are approximately an 8-minute drive to Hamburg as well as 8-minute drive to downtown Winchester. This complete custom home was constructed in 2022. The 6284 sqft boasts custom features including built in appliances, in-ground oversized heated pool with outdoor

    Michael Hilario The Agency

    5039 Combs Ferry Rd, Ford, KY 40391
  • /103

    $3,500,000

    • 6 Beds
    • 5.5 Baths
    • 7,274 Sq Ft

    5045 Van Meter Rd, Winchester, KY 40391

    Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

    The Prather Team - Michael Prather Keller Williams Bluegrass Realty

    5045 Van Meter Rd, Winchester, KY 40391
  • /6

    $388,000

    • 5 Beds
    • 3 Baths
    • 2,762 Sq Ft

    101 E Lexington Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    101 E Lexington Ave, Winchester, KY 40391
  • /103

    $2,650,000

    • 6 Beds
    • 5.5 Baths
    • 7,274 Sq Ft

    5045 Van Meter Rd, Winchester, KY 40391

    Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

    The Prather Team - Michael Prather Keller Williams Bluegrass Realty

    5045 Van Meter Rd, Winchester, KY 40391
  • /60

    $899,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 2,842 Sq Ft

    1150 Craig Crossing, Winchester, KY 40391

    Stunning new construction offering 5 bedrooms, 3.5 bathrooms, sitting on roughly 2.5 serene acres. This home is surrounded by picturesque farmland and panoramic views. 4 bedrooms are located on the main level for ultimate convenience. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden

    Stephanie Hacker Kentucky Residential Real Estate, LLC

    1150 Craig Crossing, Winchester, KY 40391
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