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3 beds
3 Bedroom Homes in Winchester, KY
70 listings

3 Bedroom Homes in Winchester, KY

3 Bedroom Homes in Winchester, KY

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24 of 70 Listings
Map

3 Bedroom Homes in Winchester, KY

24 of 70 Listings

  1. 107 Kittison Drive — photoPrice Reduced48

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas
Active

$179,000

3 bd · 2 ba · 1,725 sqft

107 Kittison Drive, Winchester, KY

Kelli Hunt · Berkshire Hathaway HomeServices Foster Realtors

  • 702 Princeton Drive — photo17Active

    $125,000

    3 bd · 3 ba · 2,051 sqft

    702 Princeton Drive, Winchester, KY

    Dennis Woodrum · Bluegrass Realty & Investments

  • 735 Schollsville Road — photoNew47Active

    $365,000

    3 bd · 3 ba · 2,554 sqft

    735 Schollsville Road, Winchester, KY

    Edgar Saborit · Lifstyl Real Estate

  • 42 Mockingbird Valley Road — photoNew58Active

    $439,500

    3 bd · 3 ba · 2,961 sqft

    42 Mockingbird Valley Road, Winchester, KY

    Markus Cross · FC Tucker Bluegrass

  • 13 Long Avenue — photoNew34Active

    $219,000

    3 bd · 2 ba · 1,297 sqft

    13 Long Avenue, Winchester, KY

    Kathryn M Cheuvront · Coldwell Banker McMahan

  • 14 Cook Avenue — photoPrice Reduced37Active

    $209,000

    3 bd · 2 ba · 1,261 sqft

    14 Cook Avenue, Winchester, KY

    Janna L Smith · United Real Estate Bluegrass

  • 317 Vanover Way — photo26Active

    $249,900

    3 bd · 2 ba · 1,492 sqft

    317 Vanover Way, Winchester, KY

    Austina Bruton · Rector Hayden Realtors

  • 31 Casa Landa Way — photo50Active

    $380,000

    3 bd · 2 ba · 1,922 sqft

    31 Casa Landa Way, Winchester, KY

    Christine E McDonald · FC Tucker Bluegrass

  • 1515 Sewell Shop Road — photoPrice Reduced40Active

    $560,000

    3 bd · 2 ba · 1,878 sqft

    1515 Sewell Shop Road, Winchester, KY

    Jason Townsend · Kentucky Residential Real Estate, LLC

  • 103 Southern Court — photo27Active

    $260,000

    3 bd · 2 ba · 1,500 sqft

    103 Southern Court, Winchester, KY

    Michelle R Blackburn · RE/MAX Creative, Winchester

  • 520 College Street — photoPrice Reduced13Active

    $192,400

    3 bd · 1 ba · 1,272 sqft

    520 College Street, Winchester, KY

    Chelsea Morguson · McCallie Real Estate

  • 117 Colonial Park Drive — photo29Active

    $209,000

    3 bd · 1 ba · 1,075 sqft

    117 Colonial Park Drive, Winchester, KY

    Roger Browning · Four Seasons Realty

  • Active

    $299,900

    3 bd · 2 ba · 1,444 sqft

    8 Monroe Avenue, Winchester, KY

    Robyn R Bradley · Woods Realty Group

  • 307 McDowell Drive — photoOpen house Sun, Nov 8 · 1:00 PM41Active

    $285,000

    3 bd · 2 ba · 1,737 sqft

    307 McDowell Drive, Winchester, KY

    Jason R Scolf · The Brokerage

  • 121 Ralston Lane — photo18Active

    $56,700

    3 bd · 1 ba · 1,052 sqft

    121 Ralston Lane, Winchester, KY

    Kathy B Burton · Coldwell Banker McMahan

  • 528 Estes Drive — photoPrice Reduced25Active

    $219,900

    3 bd · 2 ba · 1,904 sqft

    528 Estes Drive, Winchester, KY

    Joshua Wood · Freedom Realty & Property Management

  • 314 Botts Court — photo38Active

    $299,900

    3 bd · 2 ba · 1,648 sqft

    314 Botts Court, Winchester, KY

    Edgar Saborit · Lifstyl Real Estate

  • Price ReducedActive

    $255,000

    3 bd · 3 ba · 2,260 sqft

    209 Boone Avenue, Winchester, KY

    Todd Hyatt · Lois Ann Disponett Real Est

  • 230 Evergreen Drive — photo6Active

    $462,738

    3 bd · 2 ba · 1,806 sqft

    230 Evergreen Drive, Winchester, KY

    Rex Hall · United Real Estate Bluegrass

  • 225 Evergreen Drive — photo6Active

    $469,925

    3 bd · 2 ba · 1,855 sqft

    225 Evergreen Drive, Winchester, KY

    Rex Hall · United Real Estate Bluegrass

  • 13 Euclid Avenue — photo54Active

    $250,000

    3 bd · 2 ba · 1,893 sqft

    13 Euclid Avenue, Winchester, KY

    Robin S Jones · Keller Williams Legacy Group

  • 220 Evergreen Drive — photo6Active

    $513,600

    3 bd · 2 ba · 2,268 sqft

    220 Evergreen Drive, Winchester, KY

    Rex Hall · United Real Estate Bluegrass

  • 131 Teal Lane — photo29Active

    $617,000

    3 bd · 4 ba · 4,848 sqft

    131 Teal Lane, Winchester, KY

    Rony Jo Ballou · Power House Realty

  • 121 Bay Hill Drive — photoOpen house Sun, Nov 8 · 2:00 PM45Active

    $279,900

    3 bd · 3 ba · 2,779 sqft

    121 Bay Hill Drive, Winchester, KY

    Kimberly C Dice · eXp Realty, LLC

  • 123

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #221881

    Call Thomas

    Listing data & MLS disclosures

    Imagine MLS (Bluegrass REALTORS)
    The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.

    Winchester, KY community profile

    Population
    19,583
    Median income
    $57,052
    Housing units
    9,262
    People per sq. mi.
    81.2
    Area
    241.2 sq. mi.

    Source: HJN community data

    Winchester housing market

    August 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 98.2% of asking price

    Buyers here are paying below asking. MLS · 32 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 19, 2026

    Median sale price
    $315,000$218,000–$595,000 typical range
    Price per sq. ft.
    $173
    Sales
    37
    Paid in cash
    32.4%

    Homes on the market · MLS, as of Aug 30, 2026

    Median list price
    $319,900
    Homes for sale
    111

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    14.0%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,544 sq. ft.