4,174

Winterset, IA Homes

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  • /7

    $160,000

    • Land
    • 3.32 Acres
    • $48,193 per Acre

    2211 Cedar Bridge Rd, Winterset, IA 50273

    Introducing Five Iron Farms - Madison County's newest acreage subdivision. Five Iron Farms offers the best of both world: located in the city limits with city services, but also situated on 3+acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview Country Club. Bring your own builder. A good reference address to use

    Jennifer Stover Madison County Realty

    2211 Cedar Bridge Rd, Winterset, IA 50273
  • /25

    $288,000

    Sold Nov 14, 2025

    722 W Mills St, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft
    • Built 1993

    Last Sold Summary

    • 4% Below List Price
    • $230/SF
    • 24 Days On Market

    Current Estimated Value $273,404

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    722 W Mills St, Winterset, IA 50273
    • /24

      Est $324,810

      Not Listed For Sale

      225 N 14th Ave, Winterset, IA 50273

      • 4 Beds
      • 3 Baths
      • 1,415 Sq Ft
      • Built 2000
      225 N 14th Ave, Winterset, IA 50273

      Last Sold Summary

      • 42 Days On Market

  • /32

    $335,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,912 Sq Ft

    59 E Benton St, Winterset, IA 50273

    Step inside this well-loved home that blends timeless character with modern updates—ready for its next owner to make it their own. The home’s original woodwork, in excellent condition, adds warmth and charm throughout. Enjoy relaxing mornings with coffee or peaceful evenings with dinner on the inviting front porch. Inside, you’ll find a spacious living room that flows seamlessly into a formal

    Sarah Cowman Homefront Real Estate, LLC

    59 E Benton St, Winterset, IA 50273
  • /35

    $300,000

    Sold Nov 03, 2025

    2385 Holliwell Bridge Rd, Winterset, IA 50273

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1933

    Last Sold Summary

    • 6% Below List Price
    • $222/SF
    • 73 Days On Market

    Current Estimated Value $275,621

    Last Listing Agent Misty Darling BH&G Real Estate Innovations

    2385 Holliwell Bridge Rd, Winterset, IA 50273
    • /17

      Est $297,261

      Not Listed For Sale

      802 N 4th Ave, Winterset, IA 50273

      • 4 Beds
      • 2 Baths
      • 1,008 Sq Ft
      • Built 1960
      802 N 4th Ave, Winterset, IA 50273

      Last Sold Summary

      • 71 Days On Market

  • /7

    $160,000

    • Land
    • 3.27 Acres
    • $48,930 per Acre

    2323 Cedar Bridge Rd, Winterset, IA 50273

    Introducing Five Iron Farms - Madison County's newest acreage subdivision. Five Iron Farms offers the best of both world: located in the city limits with city services, but also situated on 3+acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview Country Club. Bring your own builder. A good reference address to use

    Jennifer Stover Madison County Realty

    2323 Cedar Bridge Rd, Winterset, IA 50273
  • /31

    $245,000

    Sold Jun 11, 2026

    317 E Washington St, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,498 Sq Ft
    • Built 1880

    Last Sold Summary

    • 6% Below List Price
    • $164/SF
    • 5 Days On Market

    Current Estimated Value $258,191

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    317 E Washington St, Winterset, IA 50273
    • /35

      Est $452,286

      Not Listed For Sale

      1410 W Washington St, Winterset, IA 50273

      • 5 Beds
      • 4.5 Baths
      • 2,000 Sq Ft
      • Built 1979
      1410 W Washington St, Winterset, IA 50273

      Last Sold Summary

      • 317 Days On Market

  • /35

    $849,900

    $200K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,660 Sq Ft

    2230 260th St, Winterset, IA 50273

    Set on 19.5 acres just outside Winterset, this property offers a rare combination of scale, function and lifestyle. With nearly 4,800 finished square feet, geothermal heating and cooling, a 36x54 outbuilding and approximately 13 acres of productive row crop, this is a well-rounded acreage package that is difficult to replicate.The 1.5-story home features a warm, timeless interior with vaulted

    Julie Egli RE/MAX Precision

    2230 260th St, Winterset, IA 50273
  • /35

    $725,000

    Sold Oct 15, 2025

    1813 Maple Ct, Winterset, IA 50273

    • 3 Beds
    • 3 Baths
    • 1,740 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Below List Price
    • $417/SF
    • 22 Days On Market

    Current Estimated Value $735,742

    Last Listing Agent Amy Lucht Century 21 Signature

    1813 Maple Ct, Winterset, IA 50273
    • /29

      Est $443,643

      Not Listed For Sale

      1515 W Washington St, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 2,484 Sq Ft
      • Built 1978
      1515 W Washington St, Winterset, IA 50273

      Last Sold Summary

      • 23 Days On Market

  • /7

    $170,000

    $45K PRICE DROP
    • Land
    • 3.76 Acres
    • $45,213 per Acre

    Lot 27 114th Ct, Winterset, IA 50273

    Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a

    Julie Baudler RE/MAX Concepts

    Lot 27 114th Ct, Winterset, IA 50273
  • /6

    $125,000

    Sold Nov 21, 2025

    Lot 5 114th Ct, Winterset, IA 50273

    • Land
    • 2.9 Acres
    • $43,103 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 363 Days On Market

    Last Listing Agent Julie Baudler RE/MAX Concepts

    Lot 5 114th Ct, Winterset, IA 50273
    • /29

      Est $313,584

      Not Listed For Sale

      1233 W Washington St, Winterset, IA 50273

      • 3 Beds
      • 2.5 Baths
      • 2,106 Sq Ft
      • Built 1976
      1233 W Washington St, Winterset, IA 50273

      Last Sold Summary

      • 293 Days On Market

  • /15

    $215,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,180 Sq Ft

    1110 W South St, Winterset, IA 50273

    Well-maintained 3-bedroom, 2-bath ranch home in a desirable Winterset location! This move-in ready home has been tastefully updated and offers comfortable one-level living. The fenced backyard provides a great space for kids, pets, or entertaining. Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this property offers a wonderful combination of

    Rachel Eller Summerset Realty

    1110 W South St, Winterset, IA 50273
  • /35

    $365,000

    Sold Jul 28, 2025

    2981 214th Trail, Winterset, IA 50273

    • 2 Beds
    • 2 Baths
    • 1,031 Sq Ft
    • Built 1890

    Last Sold Summary

    • 3% Below List Price
    • $354/SF
    • 109 Days On Market

    Current Estimated Value $378,741

    Last Listing Agent Connie Brown Iowa Realty Ankeny

    2981 214th Trail, Winterset, IA 50273
    • /32

      Est $472,648

      Not Listed For Sale

      924 Husky Dr, Winterset, IA 50273

      • 5 Beds
      • 3 Baths
      • 2,051 Sq Ft
      • Built 2004
      924 Husky Dr, Winterset, IA 50273

      Last Sold Summary

      • 537 Days On Market

  • /35

    $949,900

    • 3 Beds
    • 2.5 Baths
    • 3,210 Sq Ft

    1524 260th St, Winterset, IA 50273

    DREAMS DO COME TRUE! Take a look at this exquisite 2 story home on 15ac in beautiful MADISON COUNTY. The CRAFTSMANSHIP of this home is amazing, from the CUSTOM CABINETS, DOORS and COMMERCIAL EXHAUST VENT, all made on site, to the CUSTOM STEEL BACKSPLASH and BARN BOARDS from the old Homestead that was located on this acreage. The LARGE GRANITE BAR has a built-in beverage frig and seating for 8.

    Betsy Breeding Realty ONE Group Impact

    1524 260th St, Winterset, IA 50273
  • /25

    $205,500

    Sold Oct 28, 2025

    417 S 2nd St, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft
    • Built 1921

    Last Sold Summary

    • 4% Below List Price
    • $135/SF
    • 91 Days On Market

    Current Estimated Value $202,260

    Last Listing Agent Sue Monroe Spire Real Estate

    417 S 2nd St, Winterset, IA 50273
    • /26

      Est $289,363

      Not Listed For Sale

      803 S 3rd St, Winterset, IA 50273

      • 4 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1961
      803 S 3rd St, Winterset, IA 50273

      Last Sold Summary

      • 212 Days On Market

  • /29

    $299,000

    • 2 Beds
    • 1.5 Baths
    • 1,476 Sq Ft

    519 W Filmore St, Winterset, IA 50273

    Old-world charm meets modern living in this beautifully maintained and renovated two story home, situated on a corner lot with landscaped grounds. Rich original woodwork, abundant natural light, and timeless character create a warm and inviting atmosphere throughout.The fully renovated kitchen and bathroom blend classic style with modern luxury, featuring custom cabinetry, premium Café

    Kurt Clements ListWithFreedom.com Inc

    519 W Filmore St, Winterset, IA 50273
  • /19

    $298,000

    Sold Aug 29, 2025

    103 W Lane St, Winterset, IA 50273

    • 4 Beds
    • 2.5 Baths
    • 2,696 Sq Ft
    • Built 1908

    Last Sold Summary

    • $111/SF
    • 20 Days On Market

    Current Estimated Value $320,564

    Last Listing Agent Amanda Poganski Realty ONE Group Impact

    103 W Lane St, Winterset, IA 50273
    • /19

      Est $288,645

      Not Listed For Sale

      1018 N 3rd Ave, Winterset, IA 50273

      • 2 Beds
      • 2 Baths
      • 1,426 Sq Ft
      • Built 2007
      1018 N 3rd Ave, Winterset, IA 50273

      Last Sold Summary

      • 24 Days On Market

  • /7

    $230,000

    • Land
    • 2.9 Acres
    • $79,310 per Acre

    Lot 30 Limestone Ct, Winterset, IA 50273

    Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a

    Julie Baudler RE/MAX Concepts

    Lot 30 Limestone Ct, Winterset, IA 50273
  • /12

    $140,000

    Sold Jul 29, 2025

    2331 Clark Tower Rd, Winterset, IA 50273

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1965

    Last Sold Summary

    • 20% Below List Price
    • $154/SF
    • 278 Days On Market

    Current Estimated Value $146,441

    Last Listing Agent Randall Henry Madison County Realty

    2331 Clark Tower Rd, Winterset, IA 50273
    • /21

      Est $287,101

      Not Listed For Sale

      926 N 3rd Ave, Winterset, IA 50273

      • 2 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2005
      926 N 3rd Ave, Winterset, IA 50273

      Last Sold Summary

      • 5 Days On Market

  • /7

    $194,000

    $5K PRICE INCREASE
    • Land
    • 2.88 Acres
    • $67,361 per Acre

    Lot 25 114th Ct, Winterset, IA 50273

    Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a

    Julie Baudler RE/MAX Concepts

    Lot 25 114th Ct, Winterset, IA 50273
  • /17

    $84,000

    Sold Dec 19, 2025

    315 N 4th Ave, Winterset, IA 50273

    • 3 Beds
    • 1 Bath
    • 1,075 Sq Ft
    • Built 1888

    Last Sold Summary

    • 20% Below List Price
    • $78/SF
    • 176 Days On Market

    Current Estimated Value $109,514

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    315 N 4th Ave, Winterset, IA 50273
    • /34

      Est $431,538

      Not Listed For Sale

      1145 W Summit St, Winterset, IA 50273

      • 4 Beds
      • 4.5 Baths
      • 2,532 Sq Ft
      • Built 1867
      1145 W Summit St, Winterset, IA 50273

      Last Sold Summary

      • 237 Days On Market

  • /17

    $174,900

    $5K PRICE DROP Pending
    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    402 N 9th St, Winterset, IA 50273

    Well maintained ranch on a corner lot. Open floor plan with 1,152 sf, 3 bedroom, 1 full bath. 1st floor laundry room. Spacious kitchen and dining area. Gas fireplace in living room. Large covered patio space - perfect for grilling all year and relaxing in the summer. Parking pad for 2 cars. Newer roof.

    Randall Henry Madison County Realty

    402 N 9th St, Winterset, IA 50273
  • /32

    $485,000

    Sold Nov 03, 2025

    301 Magnolia Point, Winterset, IA 50273

    • 6 Beds
    • 3.5 Baths
    • 2,351 Sq Ft
    • Built 2020

    Last Sold Summary

    • 9% Below List Price
    • $206/SF
    • 146 Days On Market

    Current Estimated Value $478,256

    Last Listing Agent Rachel Eller Summerset Realty

    301 Magnolia Point, Winterset, IA 50273
    • /33

      Est $320,365

      Not Listed For Sale

      1169 W Summit St, Winterset, IA 50273

      • 4 Beds
      • 1.5 Baths
      • 2,102 Sq Ft
      • Built 1915
      1169 W Summit St, Winterset, IA 50273

      Last Sold Summary

      • 7 Days On Market

  • /23

    $299,900

    Pending
    • 3 Beds
    • 2 Baths
    • 838 Sq Ft

    521 W Hutchings St, Winterset, IA 50273

    Walk out ranch home with huge yard! This is a must see property! You will appreciate the updated inside featuring a bright eat in kitchen (the kitchen appliances are all included!). The living room has a cozy electric fireplace and nice big windows overlooking the huge back yard. There are 2 bedrooms and a full bath upstairs. The basement is a bright sunny walk out with a large family room,

    Sarah Cowman Homefront Real Estate, LLC

    521 W Hutchings St, Winterset, IA 50273
  • /23

    $200,000

    Sold Aug 01, 2025

    324 W Filmore St, Winterset, IA 50273

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1956

    Last Sold Summary

    • 7% Below List Price
    • $198/SF
    • 29 Days On Market

    Current Estimated Value $203,543

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    324 W Filmore St, Winterset, IA 50273
    • /17

      Est $255,515

      Not Listed For Sale

      818 W Jefferson St, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 1,785 Sq Ft
      • Built 1950
      818 W Jefferson St, Winterset, IA 50273

      Last Sold Summary

      • 85 Days On Market

  • /7

    $225,000

    $35K PRICE DROP
    • Land
    • 3.14 Acres
    • $71,656 per Acre

    Lot 14 114th Ct, Winterset, IA 50273

    Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a

    Julie Baudler RE/MAX Concepts

    Lot 14 114th Ct, Winterset, IA 50273
  • /13

    $210,000

    Sold Jun 24, 2026

    411 W Madison St, Winterset, IA 50273

    • 2 Beds
    • 1 Bath
    • 1,031 Sq Ft
    • Built 2025

    Last Sold Summary

    • 5% Below List Price
    • $204/SF
    • 188 Days On Market

    Last Listing Agent Alyssa Tadlock Madison County Realty

    411 W Madison St, Winterset, IA 50273
    • /35

      Est $397,734

      Not Listed For Sale

      924 W Jefferson St, Winterset, IA 50273

      • 3 Beds
      • 3.5 Baths
      • 1,664 Sq Ft
      • Built 1956
      924 W Jefferson St, Winterset, IA 50273

      Last Sold Summary

      • 2 Days On Market

  • /30

    $399,990

    $199K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 2,286 Sq Ft

    1024 W Summit St, Winterset, IA 50273

    In town acreage opportunity. 3-bedroom, 1-bath home on 9.88 m/l acres located just outside the Winterset city limits. The home offers 2,286 sq ft of living area with main-level and upper-level bedrooms, and a partial basement. A detached 1-car garage and a 1,620 sq ft pole building provides additional storage and workspace. The acreage features open ground with level to rolling terrain and treed

    Jerold Steenhoek Iowa Realty Waukee

    1024 W Summit St, Winterset, IA 50273

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