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3 beds
119 listings

Homes for Sale in Winchester, KY

Homes for Sale in Winchester, KY

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24 of 119 Listings
Map

Homes for Sale in Winchester, KY

24 of 119 Listings

  1. 7440 Bybee Road — photoNew38
Active

$519,900

5 bd · 3 ba · 2,200 sqft

7440 Bybee Road, Winchester, KY

Jessica Pelfrey · WEICHERT REALTORS - Ford Brothers

  • 128 Cherokee Drive — photoPrice Reduced35Active

    $299,900

    5 bd · 2 ba · 2,082 sqft

    128 Cherokee Drive, Winchester, KY

    Tyler A Hurst · Oak & Acre

  • 127 Lindberg Avenue — photoNew22Active

    $280,000

    4 bd · 3 ba · 1,967 sqft

    127 Lindberg Avenue, Winchester, KY

    Wayne Elkins · RE/MAX Creative Realty

  • 119 Winterberry Circle — photoNew64Active

    $439,900

    3 bd · 2 ba · 2,276 sqft

    119 Winterberry Circle, Winchester, KY

    Courtney Ann Mangold · The Agency

  • 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

  • Price ReducedActive

    $155,900

    1 bd · 2 ba · 1,056 sqft

    101 Alabama Street, Winchester, KY

    A. Rebecca Woods · Woods Realty Group

  • 410 Fairholme Way — photo58Active

    $484,900

    4 bd · 3 ba · 2,381 sqft

    410 Fairholme Way, Winchester, KY

    Morgan Withrow · The Brokerage

  • 230 Evergreen Drive — photo6Active

    $462,738

    3 bd · 2 ba · 1,806 sqft

    230 Evergreen Drive, Winchester, KY

    Rex Hall · United Real Estate Bluegrass

  • 200 Evergreen Drive — photo6Active

    $457,900

    4 bd · 3 ba · 1,986 sqft

    200 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

  • 285 Rose Drive — photo34Active

    $434,000

    3 bd · 2 ba · 1,928 sqft

    285 Rose Drive, Winchester, KY

    Tracey Goebel · Tom Goebel & Company

  • 131 Teal Lane — photo22Active

    $617,000

    3 bd · 4 ba · 4,848 sqft

    131 Teal Lane, Winchester, KY

    Rony Jo Ballou · Power House Realty

  • 323 Skylark Drive — photo38Active

    $424,500

    5 bd · 4 ba · 3,674 sqft

    323 Skylark Drive, Winchester, KY

    Tracey Goebel · Tom Goebel & Company

  • Price ReducedActive

    $325,000

    4 bd · 2 ba · 3,261 sqft

    443 S Maple Street, Winchester, KY

    Terra Long · Keller Williams Commonwealth

  • 25 W Hickman Street — photo46Active

    $325,000

    5 bd · 3 ba · 3,378 sqft

    25 W Hickman Street, Winchester, KY

    Christina Bucher · Keller Williams Legacy Group

  • 563 Constitution Drive — photoPrice Reduced21Active

    $99,500

    2 bd · 2 ba · 924 sqft

    563 Constitution Drive, Winchester, KY

    Jason Townsend · Kentucky Residential Real Estate, LLC

  • 121 Bay Hill Drive — photoOpen house Sun, Oct 25 · 2:00 PM45Active

    $279,900

    3 bd · 3 ba · 2,779 sqft

    121 Bay Hill Drive, Winchester, KY

    Kimberly C Dice · eXp Realty, LLC

  • 26 Holiday Road — photo60Active

    $255,000

    3 bd · 1 ba · 1,135 sqft

    26 Holiday Road, Winchester, KY

    Joshua Wood · Freedom Realty & Property Management

  • 106 Quail Ridge Road — photo29Active

    $221,000

    3 bd · 2 ba · 1,665 sqft

    106 Quail Ridge Road, Winchester, KY

    Mila J Ensor · Ensor Real Estate, LLC

  • 214 Center Drive — photo23Active

    $199,500

    3 bd · 1 ba · 1,193 sqft

    214 Center Drive, Winchester, KY

    Lukas Owens · The Brokerage

  • 12…5

    Explore Winchester homes

    By price

    • Homes Under $300K
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    Nearby areas

    ZIP codes

    • 40475 (293)
    • 40509 (149)
    • 40356 (144)
    • 40324 (143)
    • 40391 (119)
    • 40515 (109)
    • 40511 (84)
    • 40353 (83)

    Cities

    • Lexington (809)
    • Richmond (293)
    • Nicholasville (144)
    • Georgetown (143)
    • Mount Sterling
    (82)
  • Paris (55)
  • Irvine (30)
  • Carlisle (29)
  • 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.
    Winchester, KY Homes for Sale | Realty.com