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Winterset, IA Homes for Sale — Page 2 | Realty.com
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3 bedsNew construction
45 listings
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With a pool

Homes for Sale in Winterset, IA

Homes for Sale in Winterset, IA

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21 of 45 Listings
Map

Homes for Sale in Winterset, IA

21 of 45 Listings

Your local brokerage

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Thomas O'Leary

Realty.com

Lic. #B64731100

Call Thomas
  1. 423 E Jefferson Street — photoPrice Reduced30Active

    $309,500

    3 bd · 2 ba · 1,913 sqft

    423 E Jefferson Street, Winterset, IA

    Jennifer Stover · Madison County Realty

  2. 1524 260th Street — photo35Active

    $949,900

    3 bd · 3 ba · 3,210 sqft

    1524 260th Street, Winterset, IA

    Betsy Breeding · Realty ONE Group Impact

  3. 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

  4. 2444 Quail Ridge Avenue — photoPrice Reduced13Active

    $389,000

    2 bd · 2 ba · 979 sqft

    2444 Quail Ridge Avenue, Winterset, IA

    Rachel Eller · Summerset Realty

  5. 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

  6. 519 W Filmore Street — photo29Active

    $299,000

    2 bd · 2 ba · 1,476 sqft

    519 W Filmore Street, Winterset, IA

    Kurt Clements · ListWithFreedom.com

  7. 2318 Saint Charles Road — photoPrice Reduced35Active

    $898,000

    3 bd · 2 ba · 1,982 sqft

    2318 Saint Charles Road, Winterset, IA

    Helen Turner · Iowa Realty Mills Crossing

  8. 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

  9. 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

  10. 302 W Court Avenue — photoPrice Reduced34Active

    $365,000

    3 bd · 3 ba · 2,396 sqft

    302 W Court Avenue, Winterset, IA

    Jennifer Stover · Madison County Realty

  11. 1405 W Jefferson Street — photoPrice Reduced35Active

    $315,000

    4 bd · 3 ba · 1,470 sqft

    1405 W Jefferson Street, Winterset, IA

    Matt Law · RE/MAX Precision

  12. 505 E Court Avenue — photoPrice Reduced34Active

    $549,999

    5 bd · 4 ba · 4,200 sqft

    505 E Court Avenue, Winterset, IA

    Sarah Cowman · Homefront Real Estate, LLC

  13. 719 E Washington Street — photoPrice Reduced34Active

    $579,900

    3 bd · 3 ba · 2,432 sqft

    719 E Washington Street, Winterset, IA

    Sarah Cowman · Homefront Real Estate, LLC

  14. 117 E North Street — photoPrice Reduced35Active

    $329,900

    6 bd · 3 ba · 1,800 sqft

    117 E North Street, Winterset, IA

    Lisa Davis · RE/MAX Precision

  15. 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

  16. 407 W Madison Street — photoPrice Reduced12Active

    $206,000

    2 bd · 1 ba · 1,031 sqft

    407 W Madison Street, Winterset, IA

    Alyssa Tadlock · Madison County Realty

  17. 409 W Madison Street — photoPrice Reduced11Active

    $210,000

    2 bd · 1 ba · 1,031 sqft

    409 W Madison Street, Winterset, IA

    Alyssa Tadlock · Madison County Realty

  18. 118 N 5th Street — photo31Active

    $169,000

    3 bd · 1 ba · 1,523 sqft

    118 N 5th Street, Winterset, IA

    Toni Tindle · Covered Bridge Realty

  19. 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

  20. 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

  21. 1913 N 1st Street — photoPrice Reduced35Active

    $375,000

    3 bd · 3 ba · 2,389 sqft

    1913 N 1st Street, Winterset, IA

    Toni Tindle · Covered Bridge Realty

12

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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: 2026-09-22 20:24:13 UTC
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    Thomas O'Leary

    Realty.com

    Lic. #B64731100

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    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

    August 2026 · This period is still settling

    Winterset 12-month median sale price trend

    Homes that sold · County records, as of Aug 27, 2026

    Median sale price
    $247,250$177,781–$351,750 typical range
    Price per sq. ft.
    $182
    Sales
    14
    Paid in cash
    21.4%

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

    Median list price
    $315,000
    Homes for sale
    44

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

    Year-over-year
    14.8%

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

    Median home size
    1,513 sq. ft.

    Nearby areas

    ZIP codes

    • 50263 (357)
    • 50266 (239)
    • 50323 (181)
    • 50211 (176)
    • 50265 (148)
    • 50322 (122)
    • 50310 (109)
    • 50131 (101)

    Cities

    • Des Moines (552)
    • West Des Moines (396)
    • Urbandale (335)
    • Waukee (332)
    • Norwalk (177)
    • Johnston (101)
    • Clive (93)
    • Adel (68)