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New construction
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40 listings

Homes for Sale in Winterset, IA

Homes for Sale in Winterset, IA

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24 of 40 Listings
Map

Homes for Sale in Winterset, IA

24 of 40 Listings

  1. 2381 Highway 169 None — photo35Active

$990,000

4 bd · 5 ba · 3,076 sqft

2381 Highway 169 None, Winterset, IA

Jeff Longman · RE/MAX Precision

  • 624 W Summit Street — photo11Active

    $75,000

    1 bd · 1 ba · 576 sqft

    624 W Summit Street, Winterset, IA

    Randall Henry · Madison County Realty

  • 401 E Benton Street — photo28Active

    $310,000

    4 bd · 2 ba · 1,032 sqft

    401 E Benton Street, Winterset, IA

    Jennifer Stover · Madison County Realty

  • 703 E Filmore Street — photo35Active

    $254,000

    4 bd · 1 ba · 1,338 sqft

    703 E Filmore Street, Winterset, IA

    Toni Tindle · Covered Bridge Realty

  • 816 E Washington Street — photoPrice Reduced23Active

    $234,900

    3 bd · 2 ba · 1,241 sqft

    816 E Washington Street, Winterset, IA

    Laurel Pangman · Keller Williams Realty GDM

  • 110 N 10th Avenue — photoPrice Reduced29Active

    $210,000

    3 bd · 2 ba · 964 sqft

    110 N 10th Avenue, Winterset, IA

    Kyle Kuhns · RE/MAX Revolution

  • 310 W Washington Street — photo35Active

    $349,000

    4 bd · 2 ba · 2,430 sqft

    310 W Washington Street, Winterset, IA

    Sarah Cowman · Homefront Real Estate, LLC

  • 305 Magnolia Point — photoPrice Reduced34Active

    $469,900

    4 bd · 4 ba · 1,807 sqft

    305 Magnolia Point, Winterset, IA

    Rachel Wallace · RE/MAX Precision

  • 602 N 1st Avenue — photo34Active

    $280,000

    4 bd · 3 ba · 2,146 sqft

    602 N 1st Avenue, Winterset, IA

    Kate Carlson · Realty ONE Group Impact

  • 1515 W Washington Street — photo35Active

    $450,000

    3 bd · 2 ba · 2,484 sqft

    1515 W Washington Street, Winterset, IA

    Ian Sparks · Homefront Real Estate, LLC

  • 313 E North Street — photo14Active

    $69,900

    3 bd · 1 ba · 1,221 sqft

    313 E North Street, Winterset, IA

    Roger Queck · Pro Team Realty

  • 306 E Buchanan Street — photoPrice Reduced29Active

    $205,000

    2 bd · 1 ba · 986 sqft

    306 E Buchanan Street, Winterset, IA

    Sarah Cowman · Homefront Real Estate, LLC

  • 715 N 5th Street — photo30Active

    $185,000

    3 bd · 2 ba · 1,456 sqft

    715 N 5th Street, Winterset, IA

    Kenny Kauzlarich · RE/MAX Precision

  • 1818 Patricia Acres Court — photo33Active

    $474,000

    3 bd · 3 ba · 2,616 sqft

    1818 Patricia Acres Court, Winterset, IA

    Betsy Breeding · Realty ONE Group Impact

  • 121 E Benton Street — photoPrice Reduced18Active

    $215,000

    2 bd · 1 ba · 848 sqft

    121 E Benton Street, Winterset, IA

    Larry Corkrean · Madison County Realty

  • 5219 Cherrywood Lane — photoPrice Reduced34Active

    $559,000

    4 bd · 3 ba · 1,506 sqft

    5219 Cherrywood Lane, Winterset, IA

    Jonny Lee · RE/MAX Precision

  • 204 S 8th Avenue — photoPrice Reduced33Active

    $225,000

    5 bd · 2 ba · 1,701 sqft

    204 S 8th Avenue, Winterset, IA

    Ashlee Knickerbocker · Keller Williams Realty GDM

  • 423 E Jefferson Street — photoPrice Reduced30Active

    $324,900

    3 bd · 2 ba · 1,913 sqft

    423 E Jefferson Street, Winterset, IA

    Jennifer Stover · Madison County Realty

  • 1524 260th Street — photo35Active

    $949,900

    3 bd · 3 ba · 3,210 sqft

    1524 260th Street, Winterset, IA

    Betsy Breeding · Realty ONE Group Impact

  • 715 N 3rd Avenue — photoPrice Reduced32Active

    $265,000

    4 bd · 2 ba · 866 sqft

    715 N 3rd Avenue, Winterset, IA

    Alyssa Tadlock · Madison County Realty

  • 2444 Quail Ridge Avenue — photoPrice Reduced13Active

    $389,000

    2 bd · 2 ba · 979 sqft

    2444 Quail Ridge Avenue, Winterset, IA

    Rachel Eller · Summerset Realty

  • 215 E Filmore Street E — photoPrice Reduced31Active

    $215,000

    2 bd · 2 ba · 1,148 sqft

    215 E Filmore Street E, Winterset, IA

    Toni Tindle · Covered Bridge Realty

  • 519 W Filmore Street — photo29Active

    $299,000

    2 bd · 2 ba · 1,476 sqft

    519 W Filmore Street, Winterset, IA

    Kurt Clements · ListWithFreedom.com

  • 2318 Saint Charles Road — photoPrice Reduced35Active

    $900,000

    3 bd · 2 ba · 1,982 sqft

    2318 Saint Charles Road, Winterset, IA

    Helen Turner · Iowa Realty Mills Crossing

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    Nearby areas

    ZIP codes

    • 50263 (348)
    • 50266 (241)
    • 50323 (176)
    • 50211 (158)
    • 50265 (139)
    • 50322 (117)
    • 50131 (93)
    • 50315 (93)

    Cities

    • Des Moines (550)
    • West Des Moines (388)
    • Waukee (327)
    • Urbandale (320)
    • Norwalk (159)
  • Johnston (93)
  • Clive (92)
  • Adel (63)
  • Listing data & MLS disclosures

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    IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect participants and/or the MLS from liability.
    Listing information ©2026 Des Moines Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-09-02 15:51:16 UTC

    Winterset, IA community profile

    Population
    5,469
    Median income
    $69,177
    Housing units
    2,581
    People per sq. mi.
    27.1
    Area
    201.8 sq. mi.

    Source: HJN community data

    Winterset housing market

    July 2026

    Winterset 12-month median sale price trend

    Selling at 96.8% of asking price

    Buyers here are paying below asking. MLS · 14 sales · as of Jul 31, 2026

    Homes that sold · County records, as of Jul 31, 2026

    Median sale price
    $298,000$158,500–$545,500 typical range
    Price per sq. ft.
    $187
    Sales
    22
    Paid in cash
    45.5%

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

    Median list price
    $344,950
    Homes for sale
    42

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

    Year-over-year
    2.1%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

    Median home size
    1,513 sq. ft.
    Winterset, IA Homes for Sale | Realty.com