4,174

Winterset, IA Homes

Section Image
    • 2064 226th Ct, Winterset, IA 50273
      2064 226th Ct, Winterset, IA 50273
      2064 226th Ct, Winterset, IA 50273
      /35

      Est $638,309

      Not Listed For Sale

      2064 226th Ct, Winterset, IA 50273

      • 4 Beds
      • 3.5 Baths
      • 2,549 Sq Ft
      • Built 2006
      2064 226th Ct, Winterset, IA 50273

      Last Sold Summary

      • 136 Days On Market

  • 001 Rolling Green Ave, Winterset, IA 50273
    001 Rolling Green Ave, Winterset, IA 50273
    001 Rolling Green Ave, Winterset, IA 50273
    /7

    $165,000

    • Land
    • 7.68 Acres
    • $21,484 per Acre

    001 Rolling Green Ave, Winterset, IA 50273

    Build your dream home on 7.68 acres in scenic Madison County. Located just 20 minutes from West Des Moines and 2 miles south of Hwy 92, this beautiful building site offers rural water, electricity, and high-speed fiber internet at the road. Enjoy peaceful country living on a well-maintained gravel road with an easy commute to DSM.

    Jodi Broadbent Realty ONE Group Impact

    001 Rolling Green Ave, Winterset, IA 50273
  • Lot 1 114th Ct, Winterset, IA 50273
    Lot 1 114th Ct, Winterset, IA 50273
    Lot 1 114th Ct, Winterset, IA 50273
    /6

    $100,000

    Sold Aug 01, 2025

    Lot 1 114th Ct, Winterset, IA 50273

    • Land
    • 5.32 Acres
    • $18,797 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 269 Days On Market

    Last Listing Agent Julie Baudler RE/MAX Concepts

    Lot 1 114th Ct, Winterset, IA 50273
    • 2395 148th St, Winterset, IA 50273
      2395 148th St, Winterset, IA 50273
      2395 148th St, Winterset, IA 50273
      /35

      Est $533,111

      Not Listed For Sale

      2395 148th St, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 1,650 Sq Ft
      • Built 1998
      2395 148th St, Winterset, IA 50273

      Last Sold Summary

      • 6 Days On Market

  • 2237 Holliwell Valley Ct, Winterset, IA 50273
    2237 Holliwell Valley Ct, Winterset, IA 50273
    2237 Holliwell Valley Ct, Winterset, IA 50273
    /35

    $560,000

    $15K PRICE DROP Pending
    • 6 Beds
    • 4 Baths
    • 3,155 Sq Ft

    2237 Holliwell Valley Ct, Winterset, IA 50273

    If you are dreaming of countryside peace and quiet and need alot of living space, you will definately enjoy the beauty and freedom of a 4.3-acre homestead featuring 6 bedrooms, 4 baths, and multiple living areas. The elegant kitchen boasts a walk-in pantry, an abundance of countertop and cabinet space, and picturesque views of rolling hills and a neighboring pond. Step out from the dining area

    Sarah Cowman Homefront Real Estate, LLC

    2237 Holliwell Valley Ct, Winterset, IA 50273
  • 215 W Buchanan St, Winterset, IA 50273
    215 W Buchanan St, Winterset, IA 50273
    215 W Buchanan St, Winterset, IA 50273
    /28

    $350,000

    Sold Apr 17, 2026

    215 W Buchanan St, Winterset, IA 50273

    • 4 Beds
    • 2.5 Baths
    • 1,333 Sq Ft
    • Built 1900

    Last Sold Summary

    • 12% Below List Price
    • $263/SF
    • 203 Days On Market

    Current Estimated Value $309,012

    Last Listing Agent Elizabeth Gordon Realty ONE Group Impact

    215 W Buchanan St, Winterset, IA 50273
    • 906 N 14th Ave, Winterset, IA 50273
      906 N 14th Ave, Winterset, IA 50273
      906 N 14th Ave, Winterset, IA 50273
      /33

      Est $392,450

      Not Listed For Sale

      906 N 14th Ave, Winterset, IA 50273

      • 3 Beds
      • 2.5 Baths
      • 1,682 Sq Ft
      • Built 2005
      906 N 14th Ave, Winterset, IA 50273

      Last Sold Summary

      • 3 Days On Market

  • 1624 W Summit St Unit 122, Winterset, IA 50273
    1624 W Summit St Unit 122, Winterset, IA 50273
    1624 W Summit St Unit 122, Winterset, IA 50273
    /7

    $45,900

    • 3 Beds
    • 2 Baths

    1624 W Summit St Unit 122, Winterset, IA 50273

    Welcome home to this refreshed 3 bedroom, 2 bathroom home! Fresh paint throughout gives the home a clean, modern feel while the spacious layout offers comfort and functionality. The primary bedroom features its own private en suite bathroom, creating the perfect retreat at the end of the day. Cozy up by the fireplace in the living room and enjoy the inviting atmosphere this home has to offer.

    Angie Standlee Covered Bridges MHP

    1624 W Summit St Unit 122, Winterset, IA 50273
  • 822 N 3rd Ave, Winterset, IA 50273
    822 N 3rd Ave, Winterset, IA 50273
    822 N 3rd Ave, Winterset, IA 50273
    /27

    $269,000

    Sold Oct 16, 2025

    822 N 3rd Ave, Winterset, IA 50273

    • 2 Beds
    • 2 Baths
    • 1,406 Sq Ft
    • Built 2005

    Last Sold Summary

    • $191/SF
    • 4 Days On Market

    Current Estimated Value $272,503

    Last Listing Agent Bruce Seymour RE/MAX Precision

    822 N 3rd Ave, Winterset, IA 50273
    • 807 N 15th Ave, Winterset, IA 50273
      807 N 15th Ave, Winterset, IA 50273
      807 N 15th Ave, Winterset, IA 50273
      /23

      Est $353,313

      Not Listed For Sale

      807 N 15th Ave, Winterset, IA 50273

      • 4 Beds
      • 3 Baths
      • 1,273 Sq Ft
      • Built 2007
      807 N 15th Ave, Winterset, IA 50273

      Last Sold Summary

      • 2 Days On Market

  • 204 S 8th Ave, Winterset, IA 50273
    204 S 8th Ave, Winterset, IA 50273
    204 S 8th Ave, Winterset, IA 50273
    /33

    $235,000

    • 5 Beds
    • 2 Baths
    • 1,701 Sq Ft

    204 S 8th Ave, Winterset, IA 50273

    Welcome home to this charming two-story home situated on a spacious corner lot! Offering 5 bedrooms and 2 bathrooms, there's plenty of room to spread out and make it your own. Inside, you'll find a comfortable blend of carpeting and laminate flooring that creates a warm and welcoming feel throughout. The attached garage offers space for two vehicles plus a dedicated workshop area, making it ideal

    Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

    204 S 8th Ave, Winterset, IA 50273
  • 0000 Hogback Bridge Rd, Winterset, IA 50273
    0000 Hogback Bridge Rd, Winterset, IA 50273
    0000 Hogback Bridge Rd, Winterset, IA 50273
    /23

    $270,000

    Sold Sep 18, 2025

    0000 Hogback Bridge Rd, Winterset, IA 50273

    • Land
    • 22.01 Acres
    • $12,267 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 4 Days On Market

    Last Listing Agent Dennis Williams Midwest Land Group LLC

    0000 Hogback Bridge Rd, Winterset, IA 50273
    • 905 N 15th Ave, Winterset, IA 50273
      905 N 15th Ave, Winterset, IA 50273
      905 N 15th Ave, Winterset, IA 50273
      /35

      Est $380,303

      Not Listed For Sale

      905 N 15th Ave, Winterset, IA 50273

      • 5 Beds
      • 2.5 Baths
      • 1,504 Sq Ft
      • Built 2005
      905 N 15th Ave, Winterset, IA 50273

      Last Sold Summary

      • 16 Days On Market

  • 1624 W Summit St Unit 138, Winterset, IA 50273
    1624 W Summit St Unit 138, Winterset, IA 50273
    1624 W Summit St Unit 138, Winterset, IA 50273
    /8

    $53,900

    • 3 Beds
    • 2 Baths

    1624 W Summit St Unit 138, Winterset, IA 50273

    Lot 138 is an updated 3-bedroom, 2-bathroom home! Featuring all new LVP flooring throughout, this home offers a modern and low-maintenance living space perfect for everyday comfort. The kitchen is open concept with brand new countertops, along with a new stove and refrigerator to be installed! Fresh paint throughout the home adds a bright, clean feel in every room. The second bathroom has been

    Angie Standlee Covered Bridges MHP

    1624 W Summit St Unit 138, Winterset, IA 50273
  • 1426 W Court Ave, Winterset, IA 50273
    1426 W Court Ave, Winterset, IA 50273
    1426 W Court Ave, Winterset, IA 50273
    /26

    $370,000

    Sold May 13, 2026

    1426 W Court Ave, Winterset, IA 50273

    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft
    • Built 2000

    Last Sold Summary

    • 3% Below List Price
    • $206/SF
    • 3 Days On Market

    Current Estimated Value $371,777

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    1426 W Court Ave, Winterset, IA 50273
    • 909 N 9th Ave, Winterset, IA 50273
      909 N 9th Ave, Winterset, IA 50273
      909 N 9th Ave, Winterset, IA 50273
      /35

      Est $536,220

      Not Listed For Sale

      909 N 9th Ave, Winterset, IA 50273

      • 4 Beds
      • 3 Baths
      • 2,692 Sq Ft
      • Built 2006
      909 N 9th Ave, Winterset, IA 50273

      Last Sold Summary

      • 244 Days On Market

  • 2188 114th Ct, Winterset, IA 50072
    2188 114th Ct, Winterset, IA 50072
    2188 114th Ct, Winterset, IA 50072
    /34

    $1,225,000

    Pending
    • 5 Beds
    • 5 Baths
    • 2,434 Sq Ft

    2188 114th Ct, Winterset, IA 50072

    Welcome to modern acreage living at its finest! Set on 5.32 picturesque acres in gorgeous Madison County and located in the highly desirable Adel school district, this stunning home offers the perfect blend of peaceful country living with everyday convenience. Just 13 minutes from Grand Prairie Parkway, you’ll enjoy an easy drive on all blacktop roads—no gravel! Inside, discover 4,593 sq ft of

    Julie Baudler RE/MAX Concepts

    2188 114th Ct, Winterset, IA 50072
  • 103 S 3rd St, Winterset, IA 50273
    103 S 3rd St, Winterset, IA 50273
    103 S 3rd St, Winterset, IA 50273
    /22

    $125,000

    Sold Oct 07, 2025

    103 S 3rd St, Winterset, IA 50273

    • 2 Beds
    • 2 Baths
    • 1,093 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Below List Price
    • $114/SF
    • 82 Days On Market

    Current Estimated Value $146,234

    Last Listing Agent Zineta Imamovic Realty ONE Group Impact

    103 S 3rd St, Winterset, IA 50273
    • 809 W Mills St, Winterset, IA 50273
      809 W Mills St, Winterset, IA 50273
      809 W Mills St, Winterset, IA 50273
      /17

      Est $296,701

      Not Listed For Sale

      809 W Mills St, Winterset, IA 50273

      • 3 Beds
      • 3 Baths
      • 1,344 Sq Ft
      • Built 2004
      809 W Mills St, Winterset, IA 50273

      Last Sold Summary

      • 1 Day On Market

  • 2318 Saint Charles Rd, Winterset, IA 50273
    2318 Saint Charles Rd, Winterset, IA 50273
    2318 Saint Charles Rd, Winterset, IA 50273
    /35

    $969,000

    • 3 Beds
    • 2 Baths
    • 1,982 Sq Ft

    2318 Saint Charles Rd, Winterset, IA 50273

    Escape to your own peaceful slice of heaven with this stunning acreage offering over 45 scenic acres of rolling countryside, abundant wildlife, and endless possibilities. Approximately 18 acres are enrolled in a tax-deferred forestry program, while additional acreage provides excellent hay ground potential and beautiful pasture areas ideal for horses or hobby farming. A large outbuilding offers

    Helen Turner Iowa Realty Mills Crossing

    2318 Saint Charles Rd, Winterset, IA 50273
  • 2223 Holliwell Valley Ct, Winterset, IA 50273
    2223 Holliwell Valley Ct, Winterset, IA 50273
    2223 Holliwell Valley Ct, Winterset, IA 50273
    /35

    $640,000

    Sold Jul 02, 2026

    2223 Holliwell Valley Ct, Winterset, IA 50273

    • 4 Beds
    • 3.5 Baths
    • 1,972 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $325/SF
    • 14 Days On Market

    Current Estimated Value $649,950

    Last Listing Agent Melissa Hatchitt Realty ONE Group Impact

    2223 Holliwell Valley Ct, Winterset, IA 50273
    • 829 W Fremont St, Winterset, IA 50273
      829 W Fremont St, Winterset, IA 50273
      829 W Fremont St, Winterset, IA 50273
      /28

      Est $223,437

      Not Listed For Sale

      829 W Fremont St, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 1,213 Sq Ft
      • Built 2001
      829 W Fremont St, Winterset, IA 50273

      Last Sold Summary

      • 30 Days On Market

  • 36 St, Winterset, IA 50273
    36 St, Winterset, IA 50273
    /2

    $69,000

    $6K PRICE DROP
    • Land
    • 3.45 Acres
    • $20,000 per Acre

    36 St, Winterset, IA 50273

    3.45 Acres – Bring Your Own Builder!LAKE LOT available in Covered Bridge Estates, a welcoming community with paved roads. Enjoy the feel of peaceful country living while still having quick, convenient access to the Des Moines metro. All information obtained from seller and public records.

    Rachel Eller Summerset Realty

    36 St, Winterset, IA 50273
  • 324 S 10th Ave, Winterset, IA 50273
    324 S 10th Ave, Winterset, IA 50273
    324 S 10th Ave, Winterset, IA 50273
    /35

    $217,000

    Sold Jan 15, 2026

    324 S 10th Ave, Winterset, IA 50273

    • 1 Bed
    • 2.5 Baths
    • 1,213 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $179/SF
    • 27 Days On Market

    Current Estimated Value $221,229

    Last Listing Agent Toni Tindle Covered Bridge Realty

    324 S 10th Ave, Winterset, IA 50273
    • 1303 N 7th St, Winterset, IA 50273
      1303 N 7th St, Winterset, IA 50273
      1303 N 7th St, Winterset, IA 50273
      /35

      Est $366,332

      Not Listed For Sale

      1303 N 7th St, Winterset, IA 50273

      • 5 Beds
      • 3 Baths
      • 1,411 Sq Ft
      • Built 2002
      1303 N 7th St, Winterset, IA 50273

      Last Sold Summary

      • 12 Days On Market

  • 505 E Court Ave, Winterset, IA 50273
    505 E Court Ave, Winterset, IA 50273
    505 E Court Ave, Winterset, IA 50273
    /34

    $549,999

    $45K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,200 Sq Ft

    505 E Court Ave, Winterset, IA 50273

    Step into timeless character with this stately 19th-century home, showcasing stunning original woodwork and rich architectural charm throughout. Set on an expansive lot, the property features a 4-car attached garage, a welcoming wrap around porch, and plenty of parking space. Inside, you’ll find a beautiful open floor plan designed for both everyday living and entertaining. The spacious living

    Sarah Cowman Homefront Real Estate, LLC

    505 E Court Ave, Winterset, IA 50273
  • 2075 Hogback Bridge Rd, Winterset, IA 50273
    2075 Hogback Bridge Rd, Winterset, IA 50273
    2075 Hogback Bridge Rd, Winterset, IA 50273
    /35

    $450,000

    Sold Jun 04, 2026

    2075 Hogback Bridge Rd, Winterset, IA 50273

    • 3 Beds
    • 3 Baths
    • 2,568 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Below List Price
    • $175/SF
    • 23 Days On Market

    Current Estimated Value $452,798

    Last Listing Agent Ian Sparks Homefront Real Estate, LLC

    2075 Hogback Bridge Rd, Winterset, IA 50273
    • 911 N 6th Avenue Cir, Winterset, IA 50273
      911 N 6th Avenue Cir, Winterset, IA 50273
      911 N 6th Avenue Cir, Winterset, IA 50273
      /23

      Est $216,918

      Not Listed For Sale

      911 N 6th Avenue Cir, Winterset, IA 50273

      • 2 Beds
      • 2.5 Baths
      • 1,213 Sq Ft
      • Built 2000
      911 N 6th Avenue Cir, Winterset, IA 50273

      Last Sold Summary

      • 20 Days On Market

  • 420 W Mills St, Winterset, IA 50273
    420 W Mills St, Winterset, IA 50273
    420 W Mills St, Winterset, IA 50273
    /26

    $250,000

    • 4 Beds
    • 2 Baths
    • 1,432 Sq Ft

    420 W Mills St, Winterset, IA 50273

    This well-maintained home offers a ton of space and a sprawling floor plan that sets it apart from your traditional split-level layout. A major highlight is the large, completely finished master suite situated privately above the garage. In total, the home features 4 bedrooms, 2 full bathrooms, and one half bathroom, along with its own dedicated laundry room. The kitchen includes a convenient bar

    Ian Sparks Homefront Real Estate, LLC

    420 W Mills St, Winterset, IA 50273
  • 520 W Benton St, Winterset, IA 50273
    520 W Benton St, Winterset, IA 50273
    520 W Benton St, Winterset, IA 50273
    /34

    $250,000

    Sold Sep 22, 2025

    520 W Benton St, Winterset, IA 50273

    • 4 Beds
    • 2 Baths
    • 1,451 Sq Ft
    • Built 1966

    Last Sold Summary

    • $172/SF
    • 19 Days On Market

    Current Estimated Value $244,897

    Last Listing Agent Misty Darling BH&G Real Estate Innovations

    520 W Benton St, Winterset, IA 50273
    • 1210 W Jefferson St, Winterset, IA 50273
      1210 W Jefferson St, Winterset, IA 50273
      1210 W Jefferson St, Winterset, IA 50273
      /28

      Est $320,455

      Not Listed For Sale

      1210 W Jefferson St, Winterset, IA 50273

      • 3 Beds
      • 2.5 Baths
      • 1,464 Sq Ft
      • Built 1992
      1210 W Jefferson St, Winterset, IA 50273

      Last Sold Summary

      • 6 Days On Market

  • 619 N 10th St, Winterset, IA 50273
    619 N 10th St, Winterset, IA 50273
    619 N 10th St, Winterset, IA 50273
    /27

    $225,000

    $15K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,095 Sq Ft

    619 N 10th St, Winterset, IA 50273

    Adorable and thoughtfully updated 1 1/2 story home in historic Winterset, featuring a 2006 lift with a full poured-concrete basement. The main level offers a bright eat-in kitchen with all appliances included, whih opens to a deck - perfect for grilling. Off the kitchen is a full bathroom with laundry! There is a main floor bedroom that could also be used as a living room or flex space. Upstairs

    Sarah Cowman Homefront Real Estate, LLC

    619 N 10th St, Winterset, IA 50273
  • 317 W Jefferson St, Winterset, IA 50273
    317 W Jefferson St, Winterset, IA 50273
    317 W Jefferson St, Winterset, IA 50273
    /16

    $160,000

    Sold Jun 02, 2026

    317 W Jefferson St, Winterset, IA 50273

    • 2 Beds
    • 1.5 Baths
    • 1,620 Sq Ft
    • Built 1900

    Last Sold Summary

    • 19% Above List Price
    • $99/SF
    • 13 Days On Market

    Current Estimated Value $169,333

    Last Listing Agent Ted Weaver RE/MAX Concepts

    317 W Jefferson St, Winterset, IA 50273
    • 221 N 15th Ave, Winterset, IA 50273
      221 N 15th Ave, Winterset, IA 50273
      221 N 15th Ave, Winterset, IA 50273
      /31

      Est $324,850

      Not Listed For Sale

      221 N 15th Ave, Winterset, IA 50273

      • 5 Beds
      • 2.5 Baths
      • 1,415 Sq Ft
      • Built 2002
      221 N 15th Ave, Winterset, IA 50273

      Last Sold Summary

      • 54 Days On Market

  • 117 E North St, Winterset, IA 50273
    117 E North St, Winterset, IA 50273
    117 E North St, Winterset, IA 50273
    /35

    $339,900

    $10K PRICE DROP Pending
    • 6 Beds
    • 3 Baths
    • 1,800 Sq Ft

    117 E North St, Winterset, IA 50273

    Welcome to timeless Americana charm in the heart of beautiful Winterset. Nestled on a quiet, tree lined street just moments from the beloved historic square, this spacious 2 sty offers warmth, character and a sense of community that make Winterset such a special place to call home. With 6 bedrooms and 3 baths, this home offers remarkable flexibility and room to grow. 4 bedrooms are on 2nd level

    Lisa Davis RE/MAX Precision

    117 E North St, Winterset, IA 50273
  • 701 W Buchanan St, Winterset, IA 50273
    701 W Buchanan St, Winterset, IA 50273
    701 W Buchanan St, Winterset, IA 50273
    /30

    $285,000

    Sold Oct 31, 2025

    701 W Buchanan St, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,823 Sq Ft
    • Built 1950

    Last Sold Summary

    • 1% Below List Price
    • $156/SF
    • 58 Days On Market

    Current Estimated Value $268,742

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    701 W Buchanan St, Winterset, IA 50273
    • 215 N 15th Ave, Winterset, IA 50273
      215 N 15th Ave, Winterset, IA 50273
      215 N 15th Ave, Winterset, IA 50273
      /33

      Est $320,252

      Not Listed For Sale

      215 N 15th Ave, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 2,060 Sq Ft
      • Built 2001
      215 N 15th Ave, Winterset, IA 50273

      Last Sold Summary

      • 26 Days On Market

  • 423 E Jefferson St, Winterset, IA 50273
    423 E Jefferson St, Winterset, IA 50273
    423 E Jefferson St, Winterset, IA 50273
    /30

    $340,000

    • 3 Beds
    • 2 Baths
    • 1,913 Sq Ft

    423 E Jefferson St, Winterset, IA 50273

    Welcome home to this adorable 3-bedroom, 2-bath Arts & Crafts bungalow built in 1920, offering 1,913 sq ft of timeless charm and thoughtful updates. From the inviting covered porch and fenced front yard to the beautiful original details throughout, this home perfectly blends historic character with today’s conveniences. Step inside to find a warm and welcoming family room featuring wood beams, a

    Jennifer Stover Madison County Realty

    423 E Jefferson St, Winterset, IA 50273
  • 507 W Madison St, Winterset, IA 50273
    507 W Madison St, Winterset, IA 50273
    507 W Madison St, Winterset, IA 50273
    /25

    $185,000

    Sold Aug 25, 2025

    507 W Madison St, Winterset, IA 50273

    • 2 Beds
    • 1 Bath
    • 1,030 Sq Ft
    • Built 2021

    Last Sold Summary

    • 12% Below List Price
    • $180/SF
    • 83 Days On Market

    Current Estimated Value $201,103

    Last Listing Agent Toni Tindle Covered Bridge Realty

    507 W Madison St, Winterset, IA 50273
    • 307 N 14th Ave, Winterset, IA 50273
      307 N 14th Ave, Winterset, IA 50273
      307 N 14th Ave, Winterset, IA 50273
      /25

      Est $331,038

      Not Listed For Sale

      307 N 14th Ave, Winterset, IA 50273

      • 4 Beds
      • 2 Baths
      • 1,172 Sq Ft
      • Built 2008
      307 N 14th Ave, Winterset, IA 50273

      Last Sold Summary

      • 49 Days On Market

Showing Results 41 - 80, Page 2 of 18

Iowa Madison County Winterset

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