4,174

Winterset, IA Homes

Section Image
  • 723 N 6th Avenue Cir, Winterset, IA 50273
    723 N 6th Avenue Cir, Winterset, IA 50273
    723 N 6th Avenue Cir, Winterset, IA 50273
    /21

    $197,000

    Sold Aug 01, 2025

    723 N 6th Avenue Cir, Winterset, IA 50273

    • 2 Beds
    • 2.5 Baths
    • 1,213 Sq Ft
    • Built 1996

    Last Sold Summary

    • 5% Below List Price
    • $162/SF
    • 157 Days On Market

    Current Estimated Value $212,789

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    723 N 6th Avenue Cir, Winterset, IA 50273
    • 306 S 4th St, Winterset, IA 50273
      306 S 4th St, Winterset, IA 50273
      306 S 4th St, Winterset, IA 50273
      /13

      Est $263,712

      Not Listed For Sale

      306 S 4th St, Winterset, IA 50273

      • 2 Beds
      • 1.5 Baths
      • 1,032 Sq Ft
      • Built 2004
      306 S 4th St, Winterset, IA 50273

      Last Sold Summary

      • 39 Days On Market

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

    $415,000

    Sold Apr 09, 2026

    204 W Washington St, Winterset, IA 50273

    • 5 Beds
    • 4 Baths
    • 3,520 Sq Ft
    • Built 1875

    Last Sold Summary

    • 13% Below List Price
    • $118/SF
    • 448 Days On Market

    Current Estimated Value $421,590

    Last Listing Agent Alyssa Tadlock Madison County Realty

    204 W Washington St, Winterset, IA 50273
    • 1234 Highway 169, Winterset, IA 50273
      1234 Highway 169, Winterset, IA 50273
      1234 Highway 169, Winterset, IA 50273
      /22

      Not Listed For Sale

      1234 Highway 169, Winterset, IA 50273

      1234 Highway 169, Winterset, IA 50273

      Last Sold Summary

      • 62 Days On Market

  • 1310 W Jefferson St, Winterset, IA 50273
    1310 W Jefferson St, Winterset, IA 50273
    1310 W Jefferson St, Winterset, IA 50273
    /12

    $269,900

    Sold Jul 17, 2025

    1310 W Jefferson St, Winterset, IA 50273

    • 4 Beds
    • 2.5 Baths
    • 1,388 Sq Ft
    • Built 1995

    Last Sold Summary

    • $194/SF
    • 12 Days On Market

    Current Estimated Value $287,595

    Last Listing Agent Jacob Ham Smart Avenue

    1310 W Jefferson St, Winterset, IA 50273
    • 123 Highway 169, Winterset, IA 50273
      123 Highway 169, Winterset, IA 50273
      123 Highway 169, Winterset, IA 50273
      /22

      Not Listed For Sale

      123 Highway 169, Winterset, IA 50273

      123 Highway 169, Winterset, IA 50273

      Last Sold Summary

      • 62 Days On Market

  • 2366 Holliwell Bridge Rd, Winterset, IA 50273
    2366 Holliwell Bridge Rd, Winterset, IA 50273
    /2

    $269,000

    Sold Dec 19, 2025

    2366 Holliwell Bridge Rd, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,996 Sq Ft
    • Built 1996

    Last Sold Summary

    • $135/SF
    • 10 Days On Market

    Last Listing Agent OUTSIDE AGENT OTHER

    2366 Holliwell Bridge Rd, Winterset, IA 50273
    • 2439 Settlers Trail, Winterset, IA 50273
      2439 Settlers Trail, Winterset, IA 50273
      2439 Settlers Trail, Winterset, IA 50273
      /24

      Not Listed For Sale

      2439 Settlers Trail, Winterset, IA 50273

      2439 Settlers Trail, Winterset, IA 50273

      Last Sold Summary

      • 9 Days On Market

  • 834 S 7th Ave, Winterset, IA 50273
    834 S 7th Ave, Winterset, IA 50273
    834 S 7th Ave, Winterset, IA 50273
    /23

    $185,000

    Sold Apr 16, 2026

    834 S 7th Ave, Winterset, IA 50273

    • 2 Beds
    • 1 Bath
    • 952 Sq Ft
    • Built 1903

    Last Sold Summary

    • $194/SF
    • 3 Days On Market

    Current Estimated Value $185,971

    Last Listing Agent Jennifer Stover Madison County Realty

    834 S 7th Ave, Winterset, IA 50273
    • 2320 Terrace Ave, Winterset, IA 50273
      2320 Terrace Ave, Winterset, IA 50273
      2320 Terrace Ave, Winterset, IA 50273
      /35

      Est $785,565

      Not Listed For Sale

      2320 Terrace Ave, Winterset, IA 50273

      • 4 Beds
      • 4 Baths
      • 2,009 Sq Ft
      • Built 2003
      2320 Terrace Ave, Winterset, IA 50273

      Last Sold Summary

      • 32 Days On Market

  • TBD 176th Ct, Winterset, IA 50273
    TBD 176th Ct, Winterset, IA 50273
    TBD 176th Ct, Winterset, IA 50273
    /20

    $110,000

    Sold Mar 20, 2026

    TBD 176th Ct, Winterset, IA 50273

    • Land
    • 4.15 Acres
    • $26,506 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 204 Days On Market

    Last Listing Agent Colin Ortmeier Kiloterra

    TBD 176th Ct, Winterset, IA 50273
    • 623 E Green St, Winterset, IA 50273
      623 E Green St, Winterset, IA 50273
      623 E Green St, Winterset, IA 50273
      /19

      Est $119,342

      Not Listed For Sale

      623 E Green St, Winterset, IA 50273

      • 1 Bed
      • 1 Bath
      • 593 Sq Ft
      • Built 1880
      623 E Green St, Winterset, IA 50273

      Last Sold Summary

      • 66 Days On Market

  • 2055 170th Ct, Winterset, IA 50273
    2055 170th Ct, Winterset, IA 50273
    2055 170th Ct, Winterset, IA 50273
    /30

    $495,000

    Sold Apr 24, 2026

    2055 170th Ct, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2008

    Last Sold Summary

    • 1% Below List Price
    • $327/SF
    • 6 Days On Market

    Current Estimated Value $506,494

    Last Listing Agent Tiffany Ehler Boutique Real Estate

    2055 170th Ct, Winterset, IA 50273
    • 223 S E St, Winterset, IA 50273
      223 S E St, Winterset, IA 50273
      223 S E St, Winterset, IA 50273
      /25

      Est $221,323

      Not Listed For Sale

      223 S E St, Winterset, IA 50273

      • 2 Beds
      • 1.5 Baths
      • 990 Sq Ft
      • Built 1900
      223 S E St, Winterset, IA 50273

      Last Sold Summary

      • 6 Days On Market

  • 66 E High St, Winterset, IA 50273
    66 E High St, Winterset, IA 50273
    66 E High St, Winterset, IA 50273
    /30

    $199,000

    Sold Mar 06, 2026

    66 E High St, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,452 Sq Ft
    • Built 1870

    Last Sold Summary

    • 10% Below List Price
    • $137/SF
    • 202 Days On Market

    Current Estimated Value $205,123

    Last Listing Agent Cameron Campos RE/MAX Concepts

    66 E High St, Winterset, IA 50273
    • 0000 Burr Oak Ave, Winterset, IA 50273
      0000 Burr Oak Ave, Winterset, IA 50273
      0000 Burr Oak Ave, Winterset, IA 50273
      /11

      Not Listed For Sale

      0000 Burr Oak Ave, Winterset, IA 50273

      0000 Burr Oak Ave, Winterset, IA 50273

      Last Sold Summary

      • 14 Days On Market

  • 2228 Holliwell Valley Ct, Winterset, IA 50273
    2228 Holliwell Valley Ct, Winterset, IA 50273
    2228 Holliwell Valley Ct, Winterset, IA 50273
    /14

    $100,000

    Sold Jan 21, 2026

    2228 Holliwell Valley Ct, Winterset, IA 50273

    • Land
    • 3.67 Acres
    • $27,248 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 75 Days On Market

    Current Estimated Value $99,000

    Last Listing Agent Misty Darling BH&G Real Estate Innovations

    2228 Holliwell Valley Ct, Winterset, IA 50273
    • 1508 N 6th Ave, Winterset, IA 50273
      1508 N 6th Ave, Winterset, IA 50273
      1508 N 6th Ave, Winterset, IA 50273
      /4

      Est $347,755

      Not Listed For Sale

      1508 N 6th Ave, Winterset, IA 50273

      • 2 Beds
      • 2 Baths
      • 1,297 Sq Ft
      • Built 2024
      1508 N 6th Ave, Winterset, IA 50273

      Last Sold Summary

      • 59 Days On Market

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

    $406,604

    Sold Dec 12, 2025

    225 Maple Pointe, Winterset, IA 50273

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

    Last Sold Summary

    • 5% Above List Price
    • $290/SF
    • 4 Days On Market

    Last Listing Agent Robert D. Weeks Iowa Realty Waukee

    225 Maple Pointe, Winterset, IA 50273
    • Lot 12 114th Ct, Winterset, IA 50273
      Lot 12 114th Ct, Winterset, IA 50273
      Lot 12 114th Ct, Winterset, IA 50273
      /3

      Not Listed For Sale

      Lot 12 114th Ct, Winterset, IA 50273

      Lot 12 114th Ct, Winterset, IA 50273

      Last Sold Summary

      • 76 Days On Market

  • Lot 11 114th Ct, Winterset, IA 50273
    Lot 11 114th Ct, Winterset, IA 50273
    Lot 11 114th Ct, Winterset, IA 50273
    /7

    $190,000

    Sold Dec 04, 2025

    Lot 11 114th Ct, Winterset, IA 50273

    • Land
    • 3.09 Acres
    • $61,489 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 336 Days On Market

    Last Listing Agent Julie Baudler RE/MAX Concepts

    Lot 11 114th Ct, Winterset, IA 50273
    • Lot 39 114th Ct, Winterset, IA 50273
      Lot 39 114th Ct, Winterset, IA 50273
      Lot 39 114th Ct, Winterset, IA 50273
      /5

      Not Listed For Sale

      Lot 39 114th Ct, Winterset, IA 50273

      Lot 39 114th Ct, Winterset, IA 50273

      Last Sold Summary

      • 166 Days On Market

  • TBD Carver Rd, Winterset, IA 50273
    TBD Carver Rd, Winterset, IA 50273
    /2

    $100,000

    Sold Nov 24, 2025

    TBD Carver Rd, Winterset, IA 50273

    • Land
    • 5 Acres
    • $20,000 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent OUTSIDE AGENT OTHER

    TBD Carver Rd, Winterset, IA 50273
    • Lot 37 Limestone Ct, Winterset, IA 50273
      Lot 37 Limestone Ct, Winterset, IA 50273
      Lot 37 Limestone Ct, Winterset, IA 50273
      /5

      Not Listed For Sale

      Lot 37 Limestone Ct, Winterset, IA 50273

      Lot 37 Limestone Ct, Winterset, IA 50273

      Last Sold Summary

      • 113 Days On Market

  • 222 Oak Tree Dr, Winterset, IA 50273
    222 Oak Tree Dr, Winterset, IA 50273
    222 Oak Tree Dr, Winterset, IA 50273
    /34

    $372,500

    Sold Jul 06, 2026

    222 Oak Tree Dr, Winterset, IA 50273

    • 3 Beds
    • 2.5 Baths
    • 1,574 Sq Ft
    • Built 2007

    Last Sold Summary

    • 7% Below List Price
    • $237/SF
    • 74 Days On Market

    Current Estimated Value $390,893

    Last Listing Agent Amber Stemler Iowa Realty Mills Crossing

    222 Oak Tree Dr, Winterset, IA 50273
    • Lot 33 Limestone Ct, Winterset, IA 50273
      Lot 33 Limestone Ct, Winterset, IA 50273
      Lot 33 Limestone Ct, Winterset, IA 50273
      /5

      Not Listed For Sale

      Lot 33 Limestone Ct, Winterset, IA 50273

      Lot 33 Limestone Ct, Winterset, IA 50273

      Last Sold Summary

      • 183 Days On Market

  • 1427 W Washington St, Winterset, IA 50273
    1427 W Washington St, Winterset, IA 50273
    1427 W Washington St, Winterset, IA 50273
    /28

    $325,000

    Sold Aug 15, 2025

    1427 W Washington St, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft
    • Built 1991

    Last Sold Summary

    • $230/SF
    • 61 Days On Market

    Current Estimated Value $332,063

    Last Listing Agent Alyssa Tadlock Madison County Realty

    1427 W Washington St, Winterset, IA 50273
    • Lot 19 112th Ct, Winterset, IA 50273
      Lot 19 112th Ct, Winterset, IA 50273
      Lot 19 112th Ct, Winterset, IA 50273
      /5

      Not Listed For Sale

      Lot 19 112th Ct, Winterset, IA 50273

      Lot 19 112th Ct, Winterset, IA 50273

      Last Sold Summary

      • 114 Days On Market

  • 1706 Mueller Ct, Winterset, IA 50273
    1706 Mueller Ct, Winterset, IA 50273
    1706 Mueller Ct, Winterset, IA 50273
    /35

    $650,000

    Sold Mar 31, 2026

    1706 Mueller Ct, Winterset, IA 50273

    • 3 Beds
    • 3 Baths
    • 2,064 Sq Ft
    • Built 2000

    Last Sold Summary

    • $315/SF
    • 70 Days On Market

    Current Estimated Value $655,688

    Last Listing Agent Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

    1706 Mueller Ct, Winterset, IA 50273
    • Lot 6 114th Ct, Winterset, IA 50273
      Lot 6 114th Ct, Winterset, IA 50273
      Lot 6 114th Ct, Winterset, IA 50273
      /5

      Not Listed For Sale

      Lot 6 114th Ct, Winterset, IA 50273

      Lot 6 114th Ct, Winterset, IA 50273

      Last Sold Summary

      • 238 Days On Market

  • 115 W North St, Winterset, IA 50273
    115 W North St, Winterset, IA 50273
    115 W North St, Winterset, IA 50273
    /26

    $335,000

    Sold Jul 28, 2025

    115 W North St, Winterset, IA 50273

    • 4 Beds
    • 3 Baths
    • 1,497 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $224/SF
    • 88 Days On Market

    Current Estimated Value $340,739

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    115 W North St, Winterset, IA 50273
    • 2381 Adair- Madison Ave, Winterset, IA 50273
      2381 Adair- Madison Ave, Winterset, IA 50273
      2381 Adair- Madison Ave, Winterset, IA 50273
      /32

      Est $304,945

      Not Listed For Sale

      2381 Adair- Madison Ave, Winterset, IA 50273

      • 3 Beds
      • 1 Bath
      • 1,200 Sq Ft
      • Built 1925
      2381 Adair- Madison Ave, Winterset, IA 50273

      Last Sold Summary

      • 32 Days On Market

  • 2202 Ash Tree Dr, Winterset, IA 50074
    2202 Ash Tree Dr, Winterset, IA 50074
    2202 Ash Tree Dr, Winterset, IA 50074
    /27

    $485,000

    Sold Mar 26, 2026

    2202 Ash Tree Dr, Winterset, IA 50074

    • 3 Beds
    • 3 Baths
    • 1,502 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $323/SF
    • 85 Days On Market

    Last Listing Agent Austin Sullivan RE/MAX Concepts

    2202 Ash Tree Dr, Winterset, IA 50074
    • 0000 290th St, Winterset, IA 50273
      0000 290th St, Winterset, IA 50273
      0000 290th St, Winterset, IA 50273
      /17

      Not Listed For Sale

      0000 290th St, Winterset, IA 50273

      0000 290th St, Winterset, IA 50273

      Last Sold Summary

      • 79 Days On Market

  • 1804 Millstream Ct, Winterset, IA 50273
    1804 Millstream Ct, Winterset, IA 50273
    1804 Millstream Ct, Winterset, IA 50273
    /11

    $130,000

    Sold Sep 12, 2025

    1804 Millstream Ct, Winterset, IA 50273

    • Land
    • 6.02 Acres
    • $21,595 per Acre

    Last Sold Summary

    • 35% Below List Price
    • 104 Days On Market

    Current Estimated Value $134,209

    Last Listing Agent Lindsay Range EXIT Realty & Associates

    1804 Millstream Ct, Winterset, IA 50273
    • 2196 198th Ct, Winterset, IA 50273
      2196 198th Ct, Winterset, IA 50273
      2196 198th Ct, Winterset, IA 50273
      /35

      Est $542,018

      Not Listed For Sale

      2196 198th Ct, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 1,899 Sq Ft
      • Built 2019
      2196 198th Ct, Winterset, IA 50273

      Last Sold Summary

      • 64 Days On Market

  • 604 W Jefferson St, Winterset, IA 50273
    604 W Jefferson St, Winterset, IA 50273
    604 W Jefferson St, Winterset, IA 50273
    /34

    $308,900

    Sold Sep 26, 2025

    604 W Jefferson St, Winterset, IA 50273

    • 3 Beds
    • 4 Baths
    • 1,694 Sq Ft
    • Built 1913

    Last Sold Summary

    • $182/SF
    • 8 Days On Market

    Current Estimated Value $300,452

    Last Listing Agent Rene Soldwisch Realty ONE Group Impact

    604 W Jefferson St, Winterset, IA 50273
    • 215 W Green St, Winterset, IA 50273
      215 W Green St, Winterset, IA 50273
      215 W Green St, Winterset, IA 50273
      /17

      Est $186,476

      Not Listed For Sale

      215 W Green St, Winterset, IA 50273

      • 4 Beds
      • 1 Bath
      • 1,209 Sq Ft
      • Built 1880
      215 W Green St, Winterset, IA 50273

      Last Sold Summary

      • 8 Days On Market

  • 000 S 2nd St, Winterset, IA 50273
    000 S 2nd St, Winterset, IA 50273
    /2

    $15,000

    Sold Feb 13, 2026

    000 S 2nd St, Winterset, IA 50273

    • Land
    • 7,405 Sq Ft
    • $88,235 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Kyle Kuhns RE/MAX Revolution

    000 S 2nd St, Winterset, IA 50273
    • 225th 130th St, Winterset, IA 50273
      225th 130th St, Winterset, IA 50273
      225th 130th St, Winterset, IA 50273
      /17

      Not Listed For Sale

      225th 130th St, Winterset, IA 50273

      225th 130th St, Winterset, IA 50273

      Last Sold Summary

      • 12 Days On Market

Showing Results 361 - 400, Page 10 of 18

Iowa Madison County Winterset

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group