Imagine Your Home
  • Buy
  • Rent
  • Commercial
  • Find a REALTOR®
  • Our Association
    Price range
    $
    $
    Bedrooms
    Bathrooms
    Property type
    Square feet
    Lot size
    Heating
    Cooling
    Parking spots
    Garage
    Basement
    Year built
    Max HOA
    Tours
    View
    More amenities
    277 homes

    40391 Real Estate and Homes for Sale

    277 homes available
    Contingent
    227 Cross Brook Lane, Winchester, KY 40391
    $284,900
    3beds
    2bath
    1,508sqft
    0.2acres
    House for Sale

    227 Cross Brook Lane, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    Contingent
    44 5th Street, Winchester, KY 40391
    $170,000
    3beds
    1bath
    1,270sqft
    0.25acres
    House for Sale

    44 5th Street, Winchester, KY 40391

    Listing by: The Howard Realty Co
    1363 Clintonville Road, Winchester, KY 40391
    $312,975
    2beds
    1bath
    1,116sqft
    5acres
    House for Sale

    1363 Clintonville Road, Winchester, KY 40391

    Listing by: Keller Williams Legacy Group
    313 Snowden Drive, Winchester, KY 40391
    $239,900
    3beds
    1bath
    1,232sqft
    0.19acres
    House for Sale

    313 Snowden Drive, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    Pending
    58 Fitch Avenue, Winchester, KY 40391
    $269,000
    4beds
    2.5bath
    1,736sqft
    0.29acres
    House for Sale

    58 Fitch Avenue, Winchester, KY 40391

    Listing by: Lifstyl Real Estate
    420 Alexis Way, Winchester, KY 40391
    $674,500
    4beds
    2.5bath
    2,770sqft
    0.38acres
    House for Sale

    420 Alexis Way, Winchester, KY 40391

    Listing by: McCormick Realty Inc.
    308 Duclair Drive, Winchester, KY 40391
    $50,000
    0.41acres
    Land for Sale

    308 Duclair Drive, Winchester, KY 40391

    Listing by: Keller Williams Commonwealth
    200 Tartan Court, Winchester, KY 40391
    $59,000
    1.69acres
    Land for Sale

    200 Tartan Court, Winchester, KY 40391

    Listing by: Rector Hayden Realtors
    Price Reduced $25,000 Sep 16
    205 Chardonnay Court, Winchester, KY 40391
    $350,000
    4beds
    2.5bath
    2,179sqft
    0.29acres
    House for Sale

    205 Chardonnay Court, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    Virtual TourPrice Reduced $20,000 Sep 16
    2509 Mount Sterling Road, Winchester, KY 40391
    $879,900
    4beds
    3.5bath
    4,922sqft
    10.17acres
    House for Sale

    2509 Mount Sterling Road, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    37 Lynnway Drive, Winchester, KY 40391
    $300,000
    3beds
    2.5bath
    3,220sqft
    0.48acres
    House for Sale

    37 Lynnway Drive, Winchester, KY 40391

    Listing by: Thwaites Realtors LLC
    115 Woodford Drive, Winchester, KY 40391
    $355,000
    3beds
    3bath
    2,166sqft
    0.4acres
    House for Sale

    115 Woodford Drive, Winchester, KY 40391

    Listing by: WEICHERT REALTORS - ABG Properties
    Pending
    497 Goose Creek Road, Winchester, KY 40391
    $496,900
    4beds
    3.5bath
    2,972sqft
    2.52acres
    House for Sale

    497 Goose Creek Road, Winchester, KY 40391

    Listing by: Threshold Real Estate Services
    Pending
    510 Kimberly Drive, Winchester, KY 40391
    $324,900
    4beds
    2bath
    2,430sqft
    0.17acres
    House for Sale

    510 Kimberly Drive, Winchester, KY 40391

    Listing by: Indigo & Co
    ContingentVirtual Tour
    5620 Ironworks Road, Winchester, KY 40391
    $225,000
    3beds
    2bath
    1,699sqft
    1.08acres
    House for Sale

    5620 Ironworks Road, Winchester, KY 40391

    Listing by: RE/MAX Creative, Winchester
    5705 Mount Sterling Road, Winchester, KY 40391
    $399,000
    4beds
    2.5bath
    2,980sqft
    3.01acres
    House for Sale

    5705 Mount Sterling Road, Winchester, KY 40391

    Listing by: Dream Maker Realty, LLC
    Pending
    946 Pine Ridge Road, Winchester, KY 40391
    $500,000
    4beds
    2 full, 2 halfbath
    3,523sqft
    8.07acres
    House for Sale

    946 Pine Ridge Road, Winchester, KY 40391

    Listing by: Kentucky Residential Real Estate, LLC
    Pending
    816 Stratton Lane, Winchester, KY 40391
    $250,000
    4beds
    2.5bath
    3,024sqft
    0.27acres
    House for Sale

    816 Stratton Lane, Winchester, KY 40391

    Listing by: Dream Maker Realty, LLC
    Pending
    3431 Colby Road, Winchester, KY 40391
    $330,000
    4beds
    2bath
    sqft
    3.12acres
    House for Sale

    3431 Colby Road, Winchester, KY 40391

    Listing by: The Agency
    1395 Two Mile Road, Winchester, KY 40391
    $519,500
    20.78acres
    Land for Sale

    1395 Two Mile Road, Winchester, KY 40391

    Listing by: Tom Goebel & Company
    1395 Two Mile Road, Winchester, KY 40391
    $2,500,000
    148acres
    Land for Sale

    1395 Two Mile Road, Winchester, KY 40391

    Listing by: Tom Goebel & Company
    1395 Two Mile Road, Winchester, KY 40391
    $603,750
    24.15acres
    Land for Sale

    1395 Two Mile Road, Winchester, KY 40391

    Listing by: Tom Goebel & Company
    1395 Two Mile Road, Winchester, KY 40391
    $2,500,000
    148acres
    Land for Sale

    1395 Two Mile Road, Winchester, KY 40391

    Listing by: Tom Goebel & Company
    175 Chatham Place, Winchester, KY 40391
    $5,646,000
    2beds
    1 full, 2 halfbath
    37,192sqft
    2.62acres
    House for Sale

    175 Chatham Place, Winchester, KY 40391

    Listing by: Milton and Associates Real Estate
    2 N Main Street, Winchester, KY 40391
    $1,595,000
    37beds
    19.5bath
    26,124sqft
    0.22acres
    House for Sale

    2 N Main Street, Winchester, KY 40391

    Listing by: Tsubaki Group, LLC
    102 W Hickman Street, Winchester, KY 40391
    $171,000
    2beds
    1bath
    870sqft
    0.1acres
    House for Sale

    102 W Hickman Street, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    5045 Van Meter Road, Winchester, KY 40391
    $3,330,000
    6beds
    5.5bath
    7,274sqft
    78acres
    House for Sale

    5045 Van Meter Road, Winchester, KY 40391

    Listing by: Keller Williams Bluegrass Realty
    208 Citation Court, Winchester, KY 40391
    $360,000
    2beds
    2bath
    1,568sqft
    0.15acres
    House for Sale

    208 Citation Court, Winchester, KY 40391

    Listing by: Tom Goebel & Company
    ContingentVirtual Tour
    213 Honeysuckle Lane, Winchester, KY 40391
    $398,000
    4beds
    2 full, 2 halfbath
    3,087sqft
    0.21acres
    House for Sale

    213 Honeysuckle Lane, Winchester, KY 40391

    Listing by: Keller Williams Commonwealth
    $325,000
    3beds
    2bath
    1,617sqft
    0.23acres
    House for Sale

    118 Windridge Drive, Winchester, KY 40391

    Listing by: RE/MAX Creative, Winchester
    Price Reduced $30,900 Sep 14
    3056 Irvine Road, Winchester, KY 40391
    $299,000
    14.51acres
    Land for Sale

    3056 Irvine Road, Winchester, KY 40391

    Listing by: Rector Hayden Realtors
    Price Reduced $30,900 Sep 14
    2996/3056 Irvine Road, Winchester, KY 40391
    $498,900
    25.87acres
    Land for Sale

    2996/3056 Irvine Road, Winchester, KY 40391

    Listing by: Rector Hayden Realtors
    2996 Irvine Road, Winchester, KY 40391
    $199,900
    11.36acres
    Land for Sale

    2996 Irvine Road, Winchester, KY 40391

    Listing by: Rector Hayden Realtors
    521 Acadia Way, Winchester, KY 40391
    $225,000
    4beds
    2bath
    1,370sqft
    0.24acres
    House for Sale

    521 Acadia Way, Winchester, KY 40391

    Listing by: The Brokerage
    3614 Stamper Drive, Winchester, KY 40391
    $269,950
    3beds
    2bath
    1,247sqft
    0.13acres
    House for Sale

    3614 Stamper Drive, Winchester, KY 40391

    Listing by: Dream Maker Realty, LLC
    Contingent
    511 Acadia Way, Winchester, KY 40391
    $225,000
    4beds
    2bath
    1,400sqft
    0.21acres
    House for Sale

    511 Acadia Way, Winchester, KY 40391

    Listing by: The Brokerage
    Contingent
    9711 Ironworks Road, Winchester, KY 40391
    $225,000
    beds
    sqft
    18.38acres
    Farm for Sale

    9711 Ironworks Road, Winchester, KY 40391

    Listing by: Denniston Realty
    81 - 120 of 277 results

    40391

    Median Sale Price

    $ 244,850

    2.0 % year-over-year

    # of Homes Sold

    382

    -17.7 % year-over-year

    Median Days On Market

    26

    -30.8 % year-over-year

    © 2025 Imagine MLS
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Equal opportunity
    Membio