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4 Bedroom Homes in Winterset, IA
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3 bedsNew constructionWith a pool

4 Bedroom Homes in Winterset, IA

4 Bedroom Homes in Winterset, IA

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15 Listings
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4 Bedroom Homes in Winterset, IA

15 Listings

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Thomas O'Leary

Realty.com

Lic. #B64731100

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  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

  2. 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

  3. 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

  4. 1582 N River Trail — photo35Active

    $1,500,000

    4 bd · 3 ba · 1,884 sqft

    1582 N River Trail, Winterset, IA

    Heather Helland · RE/MAX Precision

  5. 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

  6. 305 Magnolia Point — photoPrice Reduced34Active

    $464,900

    4 bd · 4 ba · 1,807 sqft

    305 Magnolia Point, Winterset, IA

    Rachel Wallace · RE/MAX Precision

  7. 602 N 1st Avenue — photoPrice Reduced34Active

    $275,000

    4 bd · 3 ba · 2,146 sqft

    602 N 1st Avenue, Winterset, IA

    Kate Carlson · Realty ONE Group Impact

  8. 5219 Cherrywood Lane — photoPrice Reduced34Active

    $559,000

    4 bd · 3 ba · 1,506 sqft

    5219 Cherrywood Lane, Winterset, IA

    Jonny Lee · RE/MAX Precision

  9. 715 N 3rd Avenue — photoPrice Reduced34Active

    $249,900

    4 bd · 2 ba · 866 sqft

    715 N 3rd Avenue, Winterset, IA

    Alyssa Tadlock · Madison County Realty

  10. 511 W Washington Street — photoPrice Reduced27Active

    $320,000

    4 bd · 3 ba · 1,540 sqft

    511 W Washington Street, Winterset, IA

    Toni Tindle · Covered Bridge Realty

  11. 2607 Quail Ridge Trail — photoPrice Reduced25Active

    $414,900

    4 bd · 2 ba · 2,077 sqft

    2607 Quail Ridge Trail, Winterset, IA

    Julie Egli · RE/MAX Precision

  12. 1405 W Jefferson Street — photoPrice Reduced35Active

    $325,000

    4 bd · 3 ba · 1,470 sqft

    1405 W Jefferson Street, Winterset, IA

    Matt Law · RE/MAX Precision

  13. 1706 W Summit Street — photoPrice Reduced26Active

    $299,000

    4 bd · 3 ba · 1,990 sqft

    1706 W Summit Street, Winterset, IA

    Larry Corkrean · Madison County Realty

  14. 615 N 1st Avenue — photoPrice Reduced35Active

    $350,000

    4 bd · 2 ba · 2,724 sqft

    615 N 1st Avenue, Winterset, IA

    Sarah Cowman · Homefront Real Estate, LLC

  15. 804 N 4th Avenue — photoPrice Reduced31Active

    $249,999

    4 bd · 2 ba · 1,880 sqft

    804 N 4th Avenue, Winterset, IA

    Sarah Cowman · Homefront Real Estate, LLC

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Des Moines Area Association of REALTORS
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: 2026-09-12 15:32:50 UTC
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #B64731100

    Call Thomas

    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
    $295,500$150,000–$540,500 typical range
    Price per sq. ft.
    $180
    Sales
    23
    Paid in cash
    43.5%

    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.