4,090

Winterset, IA Homes

Section Image
    • 223 S 1st Ave, Winterset, IA 50273
      223 S 1st Ave, Winterset, IA 50273
      223 S 1st Ave, Winterset, IA 50273
      /35

      Est $267,396

      Not Listed For Sale

      223 S 1st Ave, Winterset, IA 50273

      • 3 Beds
      • 1.5 Baths
      • 1,058 Sq Ft
      • Built 1948
      223 S 1st Ave, Winterset, IA 50273

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Betsy Haas-Reineck LPT Realty, LLC

  • 302 W Court Ave, Winterset, IA 50273
    302 W Court Ave, Winterset, IA 50273
    302 W Court Ave, Winterset, IA 50273
    /34

    $365,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,396 Sq Ft

    302 W Court Ave, Winterset, IA 50273

    Timeless charm meets thoughtful updates in this classic 2-story home built in 1890, ideally located on historic Court Ave just one block from the town square. Offering 2,396 square feet, 3 bedrooms, and 2.5 baths, this beautifully maintained home blends original character with modern functionality in all the right ways. The showstopping custom-designed kitchen is truly the heart of the home,

    Jennifer Stover Madison County Realty

    302 W Court Ave, Winterset, IA 50273
  • 510 E Court Ave, Winterset, IA 50273
    510 E Court Ave, Winterset, IA 50273
    510 E Court Ave, Winterset, IA 50273
    /5

    $145,000

    Sold Jul 15, 2026

    510 E Court Ave, Winterset, IA 50273

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1972

    Last Sold Summary

    • 9% Below List Price
    • $126/SF
    • 29 Days On Market

    Current Estimated Value $160,836

    Last Listing Agent Rachel Eller Summerset Realty

    510 E Court Ave, Winterset, IA 50273
    • 215 S 2nd St, Winterset, IA 50273
      215 S 2nd St, Winterset, IA 50273
      215 S 2nd St, Winterset, IA 50273
      /21

      Est $153,036

      Not Listed For Sale

      215 S 2nd St, Winterset, IA 50273

      • 2 Beds
      • 1 Bath
      • 672 Sq Ft
      • Built 1947
      215 S 2nd St, Winterset, IA 50273

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Nicholas Scar Iowa Realty Mills Crossing

  • 1413 W Washington St, Winterset, IA 50273
    1413 W Washington St, Winterset, IA 50273
    1413 W Washington St, Winterset, IA 50273
    /17

    $229,900

    $10K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 1,270 Sq Ft

    1413 W Washington St, Winterset, IA 50273

    Beautifully maintained, this 4-bedroom ranch offers easy single-level living with an inviting open floor plan. A rare oversized 3-car garage with additional storage is a dream for car enthusiasts or hobbyists, and the deck off the kitchen provides the perfect backdrop for outdoor dining and entertaining!

    Sarah Cowman Homefront Real Estate, LLC

    1413 W Washington St, Winterset, IA 50273
  • 2378 Cumming Rd, Winterset, IA 50273
    2378 Cumming Rd, Winterset, IA 50273
    2378 Cumming Rd, Winterset, IA 50273
    /35

    $620,000

    Sold Jun 18, 2026

    2378 Cumming Rd, Winterset, IA 50273

    • 4 Beds
    • 3.5 Baths
    • 1,912 Sq Ft
    • Built 2017

    Last Sold Summary

    • 1% Below List Price
    • $324/SF
    • 10 Days On Market

    Current Estimated Value $618,633

    Last Listing Agent Abbey Robertson Century 21 Signature

    2378 Cumming Rd, Winterset, IA 50273
    • 323 E Jefferson St, Winterset, IA 50273
      323 E Jefferson St, Winterset, IA 50273
      323 E Jefferson St, Winterset, IA 50273
      /23

      Est $199,010

      Not Listed For Sale

      323 E Jefferson St, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 992 Sq Ft
      • Built 1947
      323 E Jefferson St, Winterset, IA 50273

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Deanna Roth Century 21 Signature

  • 1515 W Washington St, Winterset, IA 50273
    1515 W Washington St, Winterset, IA 50273
    1515 W Washington St, Winterset, IA 50273
    /35

    $450,000

    • 3 Beds
    • 2 Baths
    • 2,484 Sq Ft

    1515 W Washington St, Winterset, IA 50273

    Imagine a home where you don't have to compromise on a single detail. Welcome to 1515 W Washington St in Winterset—a gorgeous brick home offering 2,484 finished sq ft on the main level alone! This 3-bed, 2-bath layout features an impressive flow centered around a dual-sided fireplace, creating the perfect gathering space. The chef's kitchen boasts sleek quartz countertops, extensive cabinet

    Ian Sparks Homefront Real Estate, LLC

    1515 W Washington St, Winterset, IA 50273
  • 114 S 14th Ave, Winterset, IA 50273
    114 S 14th Ave, Winterset, IA 50273
    114 S 14th Ave, Winterset, IA 50273
    /23

    $190,000

    Sold Mar 05, 2026

    114 S 14th Ave, Winterset, IA 50273

    • 4 Beds
    • 1.5 Baths
    • 1,344 Sq Ft
    • Built 1994

    Last Sold Summary

    • 17% Below List Price
    • $141/SF
    • 123 Days On Market

    Current Estimated Value $222,529

    Last Listing Agent Rachel Eller Summerset Realty

    114 S 14th Ave, Winterset, IA 50273
    • 2626 Fieldstone Ave, Winterset, IA 50273
      2626 Fieldstone Ave, Winterset, IA 50273
      2626 Fieldstone Ave, Winterset, IA 50273
      /20

      Est $346,919

      Not Listed For Sale

      2626 Fieldstone Ave, Winterset, IA 50273

      • 2 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 2006
      2626 Fieldstone Ave, Winterset, IA 50273

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Martha Aragon Platinum Realty LLC

  • 1706 W Summit St, Winterset, IA 50273
    1706 W Summit St, Winterset, IA 50273
    1706 W Summit St, Winterset, IA 50273
    /26

    $299,000

    $31K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,990 Sq Ft

    1706 W Summit St, Winterset, IA 50273

    This two-story brick home, built in 1923, has all of the character and charm that goes with a 1920s house. Original built-ins, woodwork, hardwood floors and glass doorknobs still remain in the house. With 1990 sf, 4 bedroom and 3 baths, there is plenty of room for everyone. The first floor features a large family room with beautiful built-ins surrounding the fireplace. French doors from the

    Larry Corkrean Madison County Realty

    1706 W Summit St, Winterset, IA 50273
  • 418 N 6th St, Winterset, IA 50273
    418 N 6th St, Winterset, IA 50273
    418 N 6th St, Winterset, IA 50273
    /18

    $285,000

    Sold Oct 24, 2025

    418 N 6th St, Winterset, IA 50273

    • Studio
    • 1 Bath
    • 995 Sq Ft
    • Built 1994

    Last Sold Summary

    • 8% Below List Price
    • $286/SF
    • 135 Days On Market

    Current Estimated Value $276,187

    Last Listing Agent Jennifer Stover Madison County Realty

    418 N 6th St, Winterset, IA 50273
    • 2364 Bittersweet Ave, Winterset, IA 50273
      2364 Bittersweet Ave, Winterset, IA 50273
      2364 Bittersweet Ave, Winterset, IA 50273
      /35

      Est $518,961

      Not Listed For Sale

      2364 Bittersweet Ave, Winterset, IA 50273

      • 3 Beds
      • 3 Baths
      • 1,312 Sq Ft
      • Built 2013
      2364 Bittersweet Ave, Winterset, IA 50273

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Jeffrey Longman RE/MAX Precision

  • 304 Maple Pointe, Winterset, IA 50273
    304 Maple Pointe, Winterset, IA 50273
    /2

    $383,000

    Sold Oct 09, 2025

    304 Maple Pointe, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $274/SF
    • 113 Days On Market

    Last Listing Agent Robert D. Weeks Iowa Realty Waukee

    304 Maple Pointe, Winterset, IA 50273
    • 1181 230th St, Winterset, IA 50273
      1181 230th St, Winterset, IA 50273
      1181 230th St, Winterset, IA 50273
      /25

      Est $474,251

      Not Listed For Sale

      1181 230th St, Winterset, IA 50273

      • 2 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1996
      1181 230th St, Winterset, IA 50273

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Rachel Eller Summerset Realty

  • 301 N 15th Ave, Winterset, IA 50273
    301 N 15th Ave, Winterset, IA 50273
    301 N 15th Ave, Winterset, IA 50273
    /19

    $300,000

    Sold Jun 04, 2026

    301 N 15th Ave, Winterset, IA 50273

    • 4 Beds
    • 3 Baths
    • 1,087 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Above List Price
    • $276/SF
    • 4 Days On Market

    Current Estimated Value $296,859

    Last Listing Agent Kate Anderson RE/MAX Concepts

    301 N 15th Ave, Winterset, IA 50273
    • 2567 Clark Tower Rd, Winterset, IA 50273
      2567 Clark Tower Rd, Winterset, IA 50273
      2567 Clark Tower Rd, Winterset, IA 50273
      /26

      Est $480,475

      Not Listed For Sale

      2567 Clark Tower Rd, Winterset, IA 50273

      • 4 Beds
      • 2 Baths
      • 2,883 Sq Ft
      • Built 2000
      2567 Clark Tower Rd, Winterset, IA 50273

      Last Sold Summary

      • 128 Days On Market

      Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  • 621 W Jefferson St, Winterset, IA 50273
    621 W Jefferson St, Winterset, IA 50273
    621 W Jefferson St, Winterset, IA 50273
    /35

    $337,000

    Sold Jun 18, 2026

    621 W Jefferson St, Winterset, IA 50273

    • 5 Beds
    • 2.5 Baths
    • 2,217 Sq Ft
    • Built 1903

    Last Sold Summary

    • 1% Below List Price
    • $152/SF
    • 46 Days On Market

    Current Estimated Value $334,174

    Last Listing Agent Jennifer Stover Madison County Realty

    621 W Jefferson St, Winterset, IA 50273
    • 2325 Carver Rd, Winterset, IA 50273
      2325 Carver Rd, Winterset, IA 50273
      2325 Carver Rd, Winterset, IA 50273
      /33

      Est $544,277

      Not Listed For Sale

      2325 Carver Rd, Winterset, IA 50273

      • 3 Beds
      • 2.5 Baths
      • 1,842 Sq Ft
      • Built 2022
      2325 Carver Rd, Winterset, IA 50273

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Kyle Kuhns RE/MAX Revolution

  • Lot 24 112th Ct, Winterset, IA 50273
    Lot 24 112th Ct, Winterset, IA 50273
    Lot 24 112th Ct, Winterset, IA 50273
    /7

    $190,000

    Sold Jun 04, 2026

    Lot 24 112th Ct, Winterset, IA 50273

    • Land
    • 2.96 Acres
    • $64,189 per Acre

    Last Sold Summary

    • 1% Above List Price
    • 553 Days On Market

    Last Listing Agent Julie Baudler RE/MAX Concepts

    Lot 24 112th Ct, Winterset, IA 50273
    • 1849 Fox Trail, Winterset, IA 50273
      1849 Fox Trail, Winterset, IA 50273
      1849 Fox Trail, Winterset, IA 50273
      /34

      Est $677,495

      Not Listed For Sale

      1849 Fox Trail, Winterset, IA 50273

      • 3 Beds
      • 3.5 Baths
      • 1,826 Sq Ft
      • Built 2002
      1849 Fox Trail, Winterset, IA 50273

      Last Sold Summary

      • 150 Days On Market

      Last Listing Agent Timothy Schutte EXIT Realty & Associates

  • 900 E Filmore St, Winterset, IA 50273
    900 E Filmore St, Winterset, IA 50273
    /2

    $325,000

    Sold Aug 26, 2026

    900 E Filmore St, Winterset, IA 50273

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2008

    Last Sold Summary

    • $242/SF
    • 70 Days On Market

    Current Estimated Value $316,375

    Last Listing Agent Larry Corkrean Madison County Realty

    900 E Filmore St, Winterset, IA 50273
    • 2078 226th Ct, Winterset, IA 50273
      2078 226th Ct, Winterset, IA 50273
      2078 226th Ct, Winterset, IA 50273
      /35

      Est $634,578

      Not Listed For Sale

      2078 226th Ct, Winterset, IA 50273

      • 5 Beds
      • 4 Baths
      • 2,117 Sq Ft
      • Built 2005
      2078 226th Ct, Winterset, IA 50273

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  • 2089 270th St, Winterset, IA 50273
    2089 270th St, Winterset, IA 50273
    2089 270th St, Winterset, IA 50273
    /29

    $243,000

    Sold Oct 31, 2025

    2089 270th St, Winterset, IA 50273

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Built 1891

    Last Sold Summary

    • 12% Below List Price
    • $304/SF
    • 9 Days On Market

    Current Estimated Value $299,525

    Last Listing Agent Dan Rozga RE/MAX Concepts

    2089 270th St, Winterset, IA 50273
    • 2589 Saint Charles Rd, Winterset, IA 50273
      2589 Saint Charles Rd, Winterset, IA 50273
      2589 Saint Charles Rd, Winterset, IA 50273
      /35

      Est $760,333

      Not Listed For Sale

      2589 Saint Charles Rd, Winterset, IA 50273

      • 3 Beds
      • 2.5 Baths
      • 2,508 Sq Ft
      • Built 2000
      2589 Saint Charles Rd, Winterset, IA 50273

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Jennifer Stover Madison County Realty

  • 1021 W South St, Winterset, IA 50273
    1021 W South St, Winterset, IA 50273
    1021 W South St, Winterset, IA 50273
    /14

    $225,000

    Sold Dec 23, 2025

    1021 W South St, Winterset, IA 50273

    • 3 Beds
    • 1.5 Baths
    • 912 Sq Ft
    • Built 1962

    Last Sold Summary

    • 6% Below List Price
    • $247/SF
    • 133 Days On Market

    Current Estimated Value $228,941

    Last Listing Agent Jenna Carney Keller Williams Realty GDM

    1021 W South St, Winterset, IA 50273
    • 2331 Clark Tower Rd, Winterset, IA 50273
      2331 Clark Tower Rd, Winterset, IA 50273
      2331 Clark Tower Rd, Winterset, IA 50273
      /12

      Est $147,984

      Not Listed For Sale

      2331 Clark Tower Rd, Winterset, IA 50273

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1965
      2331 Clark Tower Rd, Winterset, IA 50273

      Last Sold Summary

      • 278 Days On Market

      Last Listing Agent Randall Henry Madison County Realty

  • 2369 Saint Charles Rd, Winterset, IA 50273
    2369 Saint Charles Rd, Winterset, IA 50273
    2369 Saint Charles Rd, Winterset, IA 50273
    /23

    $367,500

    Sold Dec 01, 2025

    2369 Saint Charles Rd, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Built 2007

    Last Sold Summary

    • 26% Below List Price
    • $223/SF
    • 160 Days On Market

    Current Estimated Value $388,874

    Last Listing Agent Betsy Breeding Realty ONE Group Impact

    2369 Saint Charles Rd, Winterset, IA 50273
    • 2238 Rustic Ave, Winterset, IA 50273
      2238 Rustic Ave, Winterset, IA 50273
      2238 Rustic Ave, Winterset, IA 50273
      /18

      Est $496,569

      Not Listed For Sale

      2238 Rustic Ave, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 1,402 Sq Ft
      • Built 2004
      2238 Rustic Ave, Winterset, IA 50273

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Rachel Eller Summerset Realty

  • 912 N 6th Avenue Cir, Winterset, IA 50273
    912 N 6th Avenue Cir, Winterset, IA 50273
    912 N 6th Avenue Cir, Winterset, IA 50273
    /24

    $225,000

    Sold Mar 16, 2026

    912 N 6th Avenue Cir, Winterset, IA 50273

    • 2 Beds
    • 2.5 Baths
    • 1,213 Sq Ft
    • Built 1995

    Last Sold Summary

    • 2% Below List Price
    • $185/SF
    • 11 Days On Market

    Current Estimated Value $223,017

    Last Listing Agent Jennifer Stover Madison County Realty

    912 N 6th Avenue Cir, Winterset, IA 50273
    • 2981 214th Trail, Winterset, IA 50273
      2981 214th Trail, Winterset, IA 50273
      2981 214th Trail, Winterset, IA 50273
      /35

      Est $389,385

      Not Listed For Sale

      2981 214th Trail, Winterset, IA 50273

      • 2 Beds
      • 2 Baths
      • 1,031 Sq Ft
      • Built 1890
      2981 214th Trail, Winterset, IA 50273

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Connie Brown Iowa Realty Ankeny

  • 802 N 10th Ave, Winterset, IA 50273
    802 N 10th Ave, Winterset, IA 50273
    802 N 10th Ave, Winterset, IA 50273
    /28

    $432,250

    Sold Jul 10, 2026

    802 N 10th Ave, Winterset, IA 50273

    • 4 Beds
    • 3 Baths
    • 1,555 Sq Ft
    • Built 2019

    Last Sold Summary

    • 5% Below List Price
    • $278/SF
    • 39 Days On Market

    Current Estimated Value $458,487

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    802 N 10th Ave, Winterset, IA 50273
    • 2990 214th Trail, Winterset, IA 50273
      2990 214th Trail, Winterset, IA 50273
      2990 214th Trail, Winterset, IA 50273
      /31

      Est $766,555

      Not Listed For Sale

      2990 214th Trail, Winterset, IA 50273

      • 4 Beds
      • 3 Baths
      • 1,704 Sq Ft
      • Built 2002
      2990 214th Trail, Winterset, IA 50273

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Julianna Cullen RE/MAX Precision

  • Lot 13 114th Ct, Winterset, IA 50273
    Lot 13 114th Ct, Winterset, IA 50273
    Lot 13 114th Ct, Winterset, IA 50273
    /7

    $195,000

    Sold Nov 14, 2025

    Lot 13 114th Ct, Winterset, IA 50273

    • Land
    • 3.08 Acres
    • $63,312 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 355 Days On Market

    Last Listing Agent Julie Baudler RE/MAX Concepts

    Lot 13 114th Ct, Winterset, IA 50273
    • 1948 Nature Trail, Winterset, IA 50273
      1948 Nature Trail, Winterset, IA 50273
      1948 Nature Trail, Winterset, IA 50273
      /32

      Not Listed For Sale

      1948 Nature Trail, Winterset, IA 50273

      • 4 Beds
      • 2.5 Baths
      • 2,532 Sq Ft
      • Built 1974
      1948 Nature Trail, Winterset, IA 50273

      Last Sold Summary

      • 132 Days On Market

      Last Listing Agent Dorrance Brezina Developers Realty Group LLC

  • 1903 Quail Ridge Ave, Winterset, IA 50273
    1903 Quail Ridge Ave, Winterset, IA 50273
    /2

    $558,500

    Sold May 07, 2026

    1903 Quail Ridge Ave, Winterset, IA 50273

    • 4 Beds
    • 3 Baths
    • 1,664 Sq Ft
    • Built 1948

    Last Sold Summary

    • 7% Below List Price
    • $336/SF
    • 0 Days On Market

    Current Estimated Value $567,831

    Last Listing Agent OUTSIDE AGENT OTHER

    1903 Quail Ridge Ave, Winterset, IA 50273
    • 1671 McBride Ridge Ct, Winterset, IA 50273
      1671 McBride Ridge Ct, Winterset, IA 50273
      1671 McBride Ridge Ct, Winterset, IA 50273
      /35

      Est $682,251

      Not Listed For Sale

      1671 McBride Ridge Ct, Winterset, IA 50273

      • 4 Beds
      • 3 Baths
      • 1,804 Sq Ft
      • Built 2002
      1671 McBride Ridge Ct, Winterset, IA 50273

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent Misty Darling BH&G Real Estate Innovations

  • 400 N 14th Ave, Winterset, IA 50273
    400 N 14th Ave, Winterset, IA 50273
    400 N 14th Ave, Winterset, IA 50273
    /30

    $480,000

    Sold Jun 06, 2026

    400 N 14th Ave, Winterset, IA 50273

    • 4 Beds
    • 3 Baths
    • 1,540 Sq Ft
    • Built 2013

    Last Sold Summary

    • 4% Below List Price
    • $312/SF
    • 200 Days On Market

    Current Estimated Value $453,404

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    400 N 14th Ave, Winterset, IA 50273
    • 2331 152nd St, Winterset, IA 50273
      2331 152nd St, Winterset, IA 50273
      2331 152nd St, Winterset, IA 50273
      /21

      Est $427,184

      Not Listed For Sale

      2331 152nd St, Winterset, IA 50273

      • 3 Beds
      • 1.5 Baths
      • 1,196 Sq Ft
      • Built 1981
      2331 152nd St, Winterset, IA 50273

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Jennifer Stover Madison County Realty

  • 00 N River Trail, Winterset, IA 50273
    00 N River Trail, Winterset, IA 50273
    00 N River Trail, Winterset, IA 50273
    /32

    $1,645,000

    Sold Oct 30, 2025

    00 N River Trail, Winterset, IA 50273

    • Land
    • 141.79 Acres
    • $11,602 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 21 Days On Market

    Last Listing Agent Eric Lonnevik Peoples Company

    00 N River Trail, Winterset, IA 50273

Showing Results 321 - 360, Page 9 of 18

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