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Winchester, KY Homes for Sale with Basement

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  • /12

    $279,000

    $26K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,214 Sq Ft

    55 Hillcrest Dr, Winchester, KY 40391

    Open house 05/10 2-*4 pm **Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (6 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming

    Nina Vanetten RE/MAX Elite Lexington

    55 Hillcrest Dr, Winchester, KY 40391
  • /14

    $189,999

    • 3 Beds
    • 1 Bath
    • 950 Sq Ft

    41 Hiawatha Trail, Winchester, KY 40391

    Investor Special with Charm & Potential! Don't miss this opportunity to bring new life to this adorable brick home full of character and promise! Featuring beautiful hardwood floors, timeless curb appeal, and a layout ready to shine again, this property is the perfect canvas for your next project. Whether you're an investor, flipper, or buyer looking to build equity, this home offers classic

    Hannah Toole Coldwell Banker McMahan

    41 Hiawatha Trail, Winchester, KY 40391
  • /118

    $675,000

    Open House 6/07
    • 3 Beds
    • 3 Baths
    • 2,765 Sq Ft

    5865 Van Meter Rd, Winchester, KY 40391

    Experience the perfect balance of peaceful country living and modern comfort at 5865 Van Meter Road. Situated on 5.05 scenic acres with breathtaking farmland views, this spacious ranch-style home offers more than 2,700 square feet of thoughtfully designed living space with privacy, versatility, and charm throughout. A brand-new roof installed in May 2026 adds even more value and peace of mind.

    Laura Hayes Carpenter Keller Williams Commonwealth

    5865 Van Meter Rd, Winchester, KY 40391
  • /3

    $700,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    415 Alexis Way, Winchester, KY 40391

    Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

    Shane Underwood Keller Williams Commonwealth

    415 Alexis Way, Winchester, KY 40391
  • /90

    $269,900

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    115 Watercrest Cir, Winchester, KY 40391

    Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? This standout

    Darrell Tackett Dream Maker Realty, LLC

    115 Watercrest Cir, Winchester, KY 40391
  • /65

    $759,000

    $66K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,361 Sq Ft

    455 Davis Ln, Winchester, KY 40391

    Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

    Dale Hatton Dream Maker Realty, LLC

    455 Davis Ln, Winchester, KY 40391
  • /30

    $312,000

    $11K PRICE DROP
    • 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
  • /43

    $319,900

    • 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
  • /12

    $199,900

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,484 Sq Ft

    605 College St, Winchester, KY 40391

    Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

    Steve Adams Steven D Adams Real Estate Services, LLC

    605 College St, Winchester, KY 40391
  • /97

    $315,000

    $25K PRICE DROP
    • 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
  • /33

    $309,999

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,648 Sq Ft

    414 Pueblo Ct, Winchester, KY 40391

    PRICE DROP and a MOTIVATED SELLER!! Turn-key, dialed-in, and ready to impress! This Craftsman-style stunner delivers the space, flow, and finishes today's buyers are chasing. With 3 oversized bedrooms, 2.5 baths, and a fully finished walk-out basement, this home lives large and shows even better. The main level hits immediately with an open, airy layout that connects living, dining, and kitchen

    Walker Sabourin The Local Agents

    414 Pueblo Ct, Winchester, KY 40391
  • /92

    $849,900

    • 3 Beds
    • 3 Baths
    • 3,336 Sq Ft

    6356 Van Meter Rd, Winchester, KY 40391

    Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington, Winchester, Paris, and all of Central Kentucky. Enjoy wide-open spaces, scenic

    Josh Wood Freedom Realty & Property Management

    6356 Van Meter Rd, Winchester, KY 40391
  • /22

    $230,000

    • 4 Beds
    • 2 Baths
    • 2,106 Sq Ft

    108 Spruce Ct, Winchester, KY 40391

    Charming home located on a quiet cul-de-sac in Winchester. This 4-bedroom, 2-bath home offers great potential for homeowners and investors alike. Featuring a functional layout and spacious yard, this property is ready for your personal touch. The kitchen includes a stainless steel refrigerator, with an additional refrigerator located in the basement. Enjoy a bar area in the basement, perfect for

    Tierra Newkirk Keller Williams Commonwealth

    108 Spruce Ct, Winchester, KY 40391

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