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Homes Under $700K in Winchester, KY
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3 bedsNew constructionWith a pool

Homes Under $700K in Winchester, KY

Homes Under $700K in Winchester, KY

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24 of 106 Listings
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Homes Under $700K in Winchester, KY

24 of 106 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas
  1. 5 S Burns Avenue — photoNew29Active

    $150,000

    3 bd · 1 ba · 1,842 sqft

    5 S Burns Avenue, Winchester, KY

    Tirza Howard · The Howard Realty Co

  2. 135 E Broadway Street — photoNew19Active

    $350,000

    3 bd · 3 ba · 2,592 sqft

    135 E Broadway Street, Winchester, KY

    Dale Hatton · Dream Maker Realty, LLC

  3. 4305 Old Boonesboro Road — photo31Active

    $315,000

    3 bd · 2 ba · 1,512 sqft

    4305 Old Boonesboro Road, Winchester, KY

    Brenda H Sipes · WEICHERT REALTORS - ABG Properties

  4. 209 E Washington Street — photoNew25Active

    $165,000

    3 bd · 1 ba · 1,249 sqft

    209 E Washington Street, Winchester, KY

    Michelle R Blackburn · RE/MAX Creative, Winchester

  5. 225 Buffalo Trace — photo24Active

    $199,900

    3 bd · 2 ba · 915 sqft

    225 Buffalo Trace, Winchester, KY

    Tyler I Back · The Brokerage

  6. 11 Stoney Brook Drive 1 — photoPrice Reduced18Active

    $359,000

    3 bd · 2 ba · 1,990 sqft

    11 Stoney Brook Drive 1, Winchester, KY

    Garry H Milton · Milton and Associates Real Estate

  7. 119 Tower Lane — photo60Active

    $235,000

    3 bd · 1 ba · 1,272 sqft

    119 Tower Lane, Winchester, KY

    Shawna Wever · Wever Realty LLC

  8. 215 Robyn Drive — photo50Active

    $249,900

    3 bd · 1 ba · 1,250 sqft

    215 Robyn Drive, Winchester, KY

    Joshua Wood · Freedom Realty & Property Management

  9. 522 Acadia Way — photo23Active

    $225,000

    4 bd · 2 ba · 1,400 sqft

    522 Acadia Way, Winchester, KY

    Tyler I Back · The Brokerage

  10. 330 Vanover Way — photo30Active

    $249,900

    3 bd · 3 ba · 1,416 sqft

    330 Vanover Way, Winchester, KY

    Darrell Tackett · Dream Maker Realty, LLC

  11. 54 Locust Drive — photo40Active

    $244,000

    3 bd · 2 ba · 1,692 sqft

    54 Locust Drive, Winchester, KY

    Natalie Avant · Berkshire Hathaway HomeServices Foster Realtors

  12. 3208 Ford Hampton Road — photo21Active

    $135,000

    2 bd · 1 ba · 807 sqft

    3208 Ford Hampton Road, Winchester, KY

    Bob Sophiea · eXp Realty, LLC

  13. 104 Teal Lane — photo50Active

    $639,000

    5 bd · 4 ba · 5,011 sqft

    104 Teal Lane, Winchester, KY

    Jenny B Ray · RE/MAX Elite Lexington

  14. 682 Athens Boonesboro Road — photo38Active

    $275,000

    2 bd · 1 ba · 1,231 sqft

    682 Athens Boonesboro Road, Winchester, KY

    Robin Owens · Kirkpatrick & Company

  15. 528 Estes Drive — photo26Active

    $234,900

    3 bd · 2 ba · 1,904 sqft

    528 Estes Drive, Winchester, KY

    Joshua Wood · Freedom Realty & Property Management

  16. 198 Hilltop Drive — photoPrice Reduced27Active

    $280,000

    4 bd · 2 ba · 1,752 sqft

    198 Hilltop Drive, Winchester, KY

    Stephanie Hacker · Kentucky Residential Real Estate, LLC

  17. 15 Moundale Avenue — photo65Active

    $359,900

    3 bd · 2 ba · 2,269 sqft

    15 Moundale Avenue, Winchester, KY

    Joshua Wood · Freedom Realty & Property Management

  18. 125 Kittison Drive — photoPrice Reduced24Active

    $229,900

    3 bd · 1 ba · 1,100 sqft

    125 Kittison Drive, Winchester, KY

    Kathryn M Cheuvront · Coldwell Banker McMahan

  19. 59 Hillcrest Drive — photoPrice Reduced12Active

    $256,000

    4 bd · 2 ba · 1,996 sqft

    59 Hillcrest Drive, Winchester, KY

    Dylan Langdon · The Agency

  20. 148 Hidden Grove Lane — photo46Active

    $174,900

    2 bd · 2 ba · 1,100 sqft

    148 Hidden Grove Lane, Winchester, KY

    Kathryn M Cheuvront · Coldwell Banker McMahan

  21. 410 Fairholme Way — photo47Active

    $484,900

    4 bd · 3 ba · 2,381 sqft

    410 Fairholme Way, Winchester, KY

    Morgan Withrow · The Brokerage

  22. 204 Jett Drive — photo7Active

    $365,900

    3 bd · 2 ba · 1,558 sqft

    204 Jett Drive, Winchester, KY

    Mila J Ensor · Ensor Real Estate, LLC

  23. 3 Nunnelly Court — photo23Active

    $225,000

    3 bd · 2 ba · 1,319 sqft

    3 Nunnelly Court, Winchester, KY

    Yasir Ahmed · Black Mountain Realty

  24. 206 Jett Drive — photo24Active

    $365,900

    3 bd · 2 ba · 1,635 sqft

    206 Jett Drive, Winchester, KY

    Mila J Ensor · Ensor Real Estate, LLC

12…5

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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

July 2026 · This period is still settling

Winchester 12-month median sale price trend

Selling at 99.6% of asking price

Sales here are closing essentially at asking. MLS · 50 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 14, 2026

Median sale price
$241,250$196,175–$368,750 typical range
Price per sq. ft.
$160
Sales
28
Paid in cash
57.1%

Homes on the market · MLS, as of Jul 21, 2026

Median list price
$319,900
Homes for sale
113

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

Year-over-year
-3.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size
1,544 sq. ft.
  • By feature

    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #221881

    Call Thomas