34

Clark County KY 2-Story Homes for Sale

Section Image Section Image Section Image
  • /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

    Agent Photo

    Brenda Rue

    Keller Williams Bluegrass Realty

    (859) 470-8131

    35 Cherokee Ct, Winchester, KY 40391
  • /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

    Agent Photo

    Heather Kuykendoll

    Bluegrass Properties Group

    (859) 535-9618

    538 S Maple St, 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
  • /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
  • /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
  • /31

    $204,900

    • 3 Beds
    • 1 Bath
    • 1,290 Sq Ft

    60 Hiawatha Trail, Winchester, KY 40391

    Updated, affordable, and ready for you! This 3-bedroom, 1-bath home offers approximately 1,300 square feet of comfortable living space with tasteful updates that make it easy to move right in. The layout provides a welcoming feel with bright living areas and an updated kitchen and bath. Downstairs you have a possible 4th bedroom or office space. Conveniently located in Winchester close to

    Christina Bucher Keller Williams Legacy Group

    60 Hiawatha Trail, Winchester, KY 40391
  • /33

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 1,608 Sq Ft

    740 Pilot Ridge Ln, Winchester, KY 40391

    Tucked away on 1.25 fully fenced acres, this custom-built home offers some of the most breathtaking views in Winchester. Designed with charm and comfort in mind, this 3-bedroom, 2.5-bath home blends modern convenience with timeless farmhouse style. Step inside to an open, inviting layout filled with natural light and warm finishes throughout. The spacious vaulted master suite is a true retreat,

    Holly Goeing The Agency

    740 Pilot Ridge Ln, Winchester, KY 40391
  • /52

    $339,900

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

    228 Holiday Rd, Winchester, KY 40391

    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 countertops, modern electrical and plumbing

    Caroline Mucci CENTURY 21 Commonwealth R E

    228 Holiday Rd, Winchester, KY 40391
  • /59

    $695,000

    • 3 Beds
    • 4 Baths
    • 4,008 Sq Ft

    1775 Irvine Rd, Winchester, KY 40391

    Absolutely fabulous all brick home with incredible views, one owner, what makes this home special is the feeling of elegance, a total renovation offers the ultimate in living, spacious lower level provides full bath, family room, firepalce, walk out door to a large patio, first level dining room, great room with firepalce, showcase kitchen, living room, upstairs with large master suite, side

    Mila Ensor Ensor Real Estate, LLC

    1775 Irvine Rd, Winchester, KY 40391
  • /52

    $275,000

    • 4 Beds
    • 2 Baths
    • 2,417 Sq Ft

    104 Jackson Ferry Rd, Winchester, KY 40391

    Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen

    Bob Sophiea eXp Realty, LLC

    104 Jackson Ferry Rd, 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
  • /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

    $297,000

    • 4 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    327 Newcastle Ln, Winchester, KY 40391

    Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase that overlooks the main floor. Upstairs are 3 additional bedrooms and a full bathroom. Fenced yard and covered patio to

    Huong Dunn Bluegrass Property Exchange

    327 Newcastle Ln, Winchester, KY 40391
  • /32

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,656 Sq Ft

    17 Euclid Ave, Winchester, KY 40391

    Welcome home to 17 Euclid Ave in beautiful College Park area of Winchester. This three bedroom two full bath home may be the one you are looking for. Beautiful Hardwood floors throughout most of the home. Two additional bedrooms are upstairs with a full bath. Fenced in back yard and a large deck for you summertime entertaining. Don't wait, let's take a look.

    Donna Thwaites Thwaites Realtors LLC

    17 Euclid Ave, Winchester, KY 40391
  • /25

    $254,900

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    1407 Ironworks Rd, Winchester, KY 40391

    Welcome to this beautifully remodeled 3 bedroom, 2 full bathroom home situated on a desirable corner lot. With 1,530 sq ft of living space, this home offers great combination of modern updates and comfortable living. Features Include 3 spacious bedrooms, 2 full bathrooms, Private master suite with ensuite bath, Fully remodeled interior, corner lot, Stainless appliances, full tiled showers and the

    Michael Hilario The Agency

    1407 Ironworks Rd, Winchester, KY 40391
  • /19

    $265,000

    • 4 Beds
    • 3 Baths
    • 2,445 Sq Ft

    130 E Broadway St, Winchester, KY 40391

    Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income

    Sarah May Mayca Property Solutions

    130 E Broadway St, Winchester, KY 40391
  • /12

    $259,900

    • 4 Beds
    • 1 Bath
    • 1,610 Sq Ft

    120 Windsor Dr, Winchester, KY 40391

    Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester, KY! This inviting 4 bedroom, 1 bath home offers comfortable living with a warm electric fireplace perfect for relaxing evenings. The spacious layout provides flexibility for family, guests, or a home office. Step outside to a fully fenced backyard ideal for pets, play, or enjoying quiet mornings with your

    Team Farthing - Mitch Farthing Southern Legacy Realty

    120 Windsor Dr, Winchester, KY 40391
  • /26

    $184,000

    • 2 Beds
    • 1.5 Baths
    • 1,102 Sq Ft

    356 Colby Ridge Blvd, Winchester, KY 40391

    This cozy 2-bedroom, 1.5-bath home is the perfect fit for first-time buyers or anyone looking to expand their investment portfolio. The inviting living room features a propane-operated fireplace that provides a reliable backup heat source. The spacious primary bedroom includes his-and-her closets, and both bedrooms are equipped with additional split units for personalized comfort. A full

    Nena Honaker Tom Goebel & Company

    356 Colby Ridge Blvd, Winchester, KY 40391
  • /23

    $270,000

    • 4 Beds
    • 2 Baths
    • 1,984 Sq Ft

    108 Ashley Dr, Winchester, KY 40391

    Be among the first to discover this exceptional property! This is a brand new listing, presenting a unique opportunity to own a home in a highly sought-after location. Imagine living in a neighborhood where everything you need is just a stone's throw away. This fabulous property boasts not only a full basement, offering endless possibilities for recreation, storage, or a home office, but also an

    A. Rebecca Woods Woods Realty Group

    108 Ashley Dr, Winchester, KY 40391
  • /12

    $299,900

    • 4 Beds
    • 4 Baths
    • 2,072 Sq Ft

    1128 Dale Dr, Winchester, KY 40391

    Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

    Brian Hatfield Coldwell Banker McMahan

    1128 Dale Dr, 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
  • /47

    $452,500

    • 3 Beds
    • 2.5 Baths
    • 2,961 Sq Ft

    42 Mockingbird Valley Rd, Winchester, KY 40391

    This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

    Markus Cross McCallie Real Estate

    42 Mockingbird Valley Rd, Winchester, KY 40391
  • /30

    $229,900

    • 4 Beds
    • 2 Baths
    • 2,683 Sq Ft

    217 S Highland St, Winchester, KY 40391

    This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

    Michael Hilario The Agency

    217 S Highland St, 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
  • /58

    $515,000

    • 2 Beds
    • 1.5 Baths
    • 5,054 Sq Ft

    808 Bypass Rd, Winchester, KY 40391

    Unique Mixed-Use Opportunity! This versatile property offers prime potential for a restaurant, café, or retail space in a high-visibility location. The commercial space is turn key for a culinary venture or boutique business. Attached is a separate rental unit with private entrance, offering additional income or an ideal live/work setup. Additional space available for potential 2nd Apartment.

    Diana C Brooker Lifstyl Real Estate

    808 Bypass Rd, 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
  • /94

    $795,000

    • 4 Beds
    • 3.5 Baths
    • 4,584 Sq Ft

    4040 Muddy Creek Rd, Winchester, KY 40391

    A Farmhouse Retreat with Timeless Craftsmanship on 13.6 Acres Nestled on 13.6 rolling acres in Clark County, this custom built farmhouse captivates with soaring tongue-and-groove ceilings, rich woodwork, and thoughtful craftsmanship that sets this home apart. Oversized doors, custom cabinetry, and detailed finishes showcase the quality throughout, while two wood-burning fireplaces with homemade

    Julie Wiggington RE/MAX Creative, Winchester

    4040 Muddy Creek 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
  • /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
  • /3

    $645,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,526 Sq Ft

    106 Bella Shae Way, Winchester, KY 40391

    Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

    Shane Underwood Keller Williams Commonwealth

    106 Bella Shae Way, Winchester, KY 40391
How to Buy a Home How to Finance a Home How to Sell a Home