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Winchester, KY Homes for Sale with Pool

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  • /101

    $1,290,000

    • 5 Beds
    • 5 Baths
    • 5,666 Sq Ft

    3760 Old Boonesboro Rd, Winchester, KY 40391

    Step through the striking red front doors and into a home where craftsmanship, character, and comfort come together. This beautifully maintained property sits on nearly 13 acres at the edge of Winchester, offering a peaceful retreat with the charm of a mid century floorplan and rich woodwork, tile, and hardwood floors throughout. The spacious kitchen and all three full baths feature high end

    Josh Wood Freedom Realty & Property Management

    3760 Old Boonesboro Rd, Winchester, KY 40391
  • /67

    $307,900

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft

    118 Windridge Dr, Winchester, KY 40391

    Enjoy rest, relaxation and all the outdoor activities you can dream up with this home. Cozy, 3-bedroom, 2-bathroom home ranch with attached one car garage in a well-established neighborhood. Home features new gas stove & range hood, new bathroom updates, hardwood floors, pocket doors, updated finishes, ventless gas fireplace, sunroom and professionally maintained in-ground pool with concrete

    Amber Hunt Whalen & Company

    118 Windridge Dr, Winchester, KY 40391
  • /54

    $749,900

    • 3 Beds
    • 3.5 Baths
    • 3,388 Sq Ft

    1480 Irvine Rd, Winchester, KY 40391

    Beautifully remodeled farmhouse on 10 fenced acres! This 3 bedroom, 3.5 bath home with a fully finished basement offers the perfect blend of modern upgrades and country living. Inside, you'll find refinished hardwood floors and fresh paint throughout. The custom kitchen is designed to impress with new cabinetry, granite countertops, glass subway tile backsplash, double ovens, two dishwashers, and

    Ivanna Barko National Real Estate

    1480 Irvine Rd, Winchester, KY 40391
  • /32

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    528 Estes Dr, Winchester, KY 40391

    Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

    Josh Wood Freedom Realty & Property Management

    528 Estes Dr, Winchester, KY 40391
  • /43

    $269,000

    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft

    564 Trapp-Goffs Corner Rd, Winchester, KY 40391

    Private 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet

    Felicia Mayes The Real Estate Co.

    564 Trapp-Goffs Corner Rd, 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
  • /49

    $350,000

    • 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
  • /55

    $679,500

    • 4 Beds
    • 3.5 Baths
    • 3,431 Sq Ft

    7919 Mount Sterling Rd, Winchester, KY 40391

    Don't let this stunning, 3,431sqft home featuring 4 bed rooms and 3 full baths, sitting on 3 acres, slip through your hands! Custom built brick home nestled in a serene, park like setting overlooking Stoner Creek. Step into to the dramatic two story entryway welcoming you with custom cabinetry and detailed finishes throughout. One of the most captivating features is the sunroom, overlooking the

    Hannah Toole Coldwell Banker McMahan

    7919 Mount Sterling Rd, 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
  • /100

    $1,789,000

    • 3 Beds
    • 2.5 Baths
    • 4,518 Sq Ft

    3166 Colby Rd, Winchester, KY 40391

    PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of

    Alyssa M Boley Coldwell Banker McMahan

    3166 Colby Rd, Winchester, KY 40391
  • /12

    $199,900

    • 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
  • /63

    $1,149,000

    • 3 Beds
    • 3.5 Baths
    • 3,672 Sq Ft

    2100 Irvine Rd Unit 40391, Winchester, KY 40391

    Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

    Mila Ensor Ensor Real Estate, LLC

    2100 Irvine Rd Unit 40391, Winchester, KY 40391

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$256,700
Median Single Family Sale Price
$260,500
Median Townhouse Sale Price
$194,000
Average Price Per Sq Ft
$163
Number of Homes for Sale
74
Last 12 months Home Sales
322
Months of Supply
2.80
Median List Price
$265,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
8%
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