Winterset, IA Homes

• 

  

  

  /25

  $575,000

  Sold Nov 20, 2025

  2283 Pioneer Ave, Winterset, IA 50273

  • 5 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $277/SF
  • 40 Days On Market

  Current Estimated Value $516,558

  Last Listing Agent Bryan Curtis Attain RE

  2283 Pioneer Ave, Winterset, IA 50273
• 

  

  

  /35

  Est $558,694

  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

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  

  

  /33

  $999,500

  $251K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 2,282 Sq Ft

  1826 Green Ln, Winterset, IA 50273

  Rare opportunity to own 57.36 gross acres featuring a charming 2-story log home, quality livestock facilities, productive pasture, and North River frontage in the desirable Earlham School District. Located just 3 miles north of Highway 92 and approximately 2 miles east of Earlham Road, this well-maintained farm offers the ideal combination of country living and functional agricultural

  Shane Spyksma Kiloterra

  1826 Green Ln, 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 $308,707

  Last Listing Agent Elizabeth Gordon Realty ONE Group Impact

  215 W Buchanan St, Winterset, IA 50273
• 

  

  

  /17

  Est $291,496

  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

  Last Listing Agent Alyssa Tadlock Madison County Realty
• 

  

  /18

  $194,000

  Pending

  • Land
  • 13.88 Acres
  • $13,977 per Acre

  000 Clark Tower Rd, Winterset, IA 50273

  Discover the possibilities with this 13.88 +/- acre property in Madison County, offering a desirable mix of open pasture and mature timber. With multiple potential building sites, this property provides the flexibility to create your ideal country home or recreational retreat.The property is conveniently located on a pavement, with water and power available at the road, making it well-suited

  Aaron Creger Midwest Land Group LLC

  000 Clark Tower Rd, 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
• 

  

  /28

  Est $220,686

  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

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /47

  $537,513

  • Land
  • 77.34 Acres
  • $6,950 per Acre

  1474 280th St, Winterset, IA 50273

  Located northeast of Macksburg and southwest of Winterset, this 77.34-acre m/l Madison County property offers an attractive combination of income, recreation, wildlife habitat, and potential building opportunities. The farm is enrolled in the Conservation Reserve Program (CRP), providing an annual payment of $10,647.00 while maintaining established grassland habitat. The CRP cover, combined with

  Garret Armstrong Whitetail Properties Real Estate, LLC

  1474 280th St, Winterset, IA 50273
• 

  

  /35

  $530,000

  Sold Jul 10, 2026

  2237 Holliwell Valley Ct, Winterset, IA 50273

  • 6 Beds
  • 4 Baths
  • 3,155 Sq Ft
  • Built 2017

  Last Sold Summary

  • 8% Below List Price
  • $168/SF
  • 151 Days On Market

  Current Estimated Value $573,699

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  2237 Holliwell Valley Ct, Winterset, IA 50273
• 

  

  /35

  Est $378,634

  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

  Last Listing Agent Rachel Eller Summerset Realty
• 

  

  /35

  $395,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,576 Sq Ft

  1473 280th St, Winterset, IA 50273

  Sitting on 4.96± acres in the countryside of Madison County, this Amish-built home offers the perfect opportunity to create your dream rural retreat. Built in 2018, the 2,576 sq. ft. home features 4 bedrooms, 3 bathrooms, vaulted ceilings, and a unique natural tree centerpiece. The home offers a durable metal exterior and roof, spray-foam insulation, rural water, plumbing, propane, hot water

  Will Cooper Midwest Land Group LLC

  1473 280th St, 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
• 

  

  /24

  Est $350,795

  Not Listed For Sale

  701 E Madison St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2018

  701 E Madison St, Winterset, IA 50273

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /30

  $205,000

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft

  306 E Buchanan St, Winterset, IA 50273

  Well kept and adorable 2 bed 1 bath ranch home. You will love the character in this sweet easy one level living home just blocks from the historic Winterset square. original hardwood floors and trim throughout with all the essentials renovated including a new metal roof in 2025. The covered front porch greets you and is the perfect spot for morning coffee. The bedrooms are generous sized and have

  Sarah Cowman Homefront Real Estate, LLC

  306 E Buchanan St, 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
• 

  

  /23

  Est $211,334

  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

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /25

  $414,900

  $15K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,077 Sq Ft

  2607 Quail Ridge Trail, Winterset, IA 50273

  Set on 3 peaceful acres in Madison County, this charming 1.5-story farmhouse offers the perfect blend of country character, privacy and everyday function. With 2,077 square feet, the home features a warm farmhouse style throughout, including a farmhouse kitchen, inviting living spaces, 2 bathrooms, one bedroom on the main level, and three additional bedrooms upstairs.The sunroom overlooks the

  Julie Egli RE/MAX Precision

  2607 Quail Ridge Trail, 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 $150,123

  Last Listing Agent Zineta Imamovic Realty ONE Group Impact

  103 S 3rd St, Winterset, IA 50273
• 

  

  /21

  Est $213,408

  Not Listed For Sale

  723 N 6th Avenue Cir, Winterset, IA 50273

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

  723 N 6th Avenue Cir, Winterset, IA 50273

  Last Sold Summary

  • 157 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /29

  $260,000

  $10K PRICE DROP

  • Land
  • 10.23 Acres
  • $25,415 per Acre

  2212 Deer Run Ave, Winterset, IA 50273

  Have you been looking for the perfect country spot to build your dream home? This 10 acre lot has all of the infrastructure already in place. It is build-ready! $50,000 has been invested in the property for a building pad, water and electric brought from the road to the build site, new driveway, etc. A future barndominium or walkout home will enjoy rolling countryside views for miles.

  Jeffrey Longman RE/MAX Precision

  2212 Deer Run Ave, 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 $643,618

  Last Listing Agent Melissa Hatchitt Realty ONE Group Impact

  2223 Holliwell Valley Ct, Winterset, IA 50273
• 

  

  /12

  Est $309,090

  Not Listed For Sale

  1310 W Jefferson St, Winterset, IA 50273

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

  1310 W Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Jacob Ham Smart Avenue
• 

  

  /7

  $165,000

  • Land
  • 7.26 Acres
  • $22,727 per Acre

  001 Rolling Green Ave, Winterset, IA 50273

  Build your dream home on 7.26 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
• 

  

  /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 $222,739

  Last Listing Agent Toni Tindle Covered Bridge Realty

  324 S 10th Ave, Winterset, IA 50273
• 

  

  /28

  Est $338,428

  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

  Last Listing Agent Ou Meksay RE/MAX Concepts
• 

  

  /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.

  Mahayla Claiser Covered Bridges MHP

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

  

  /34

  $1,165,850

  Sold Aug 12, 2026

  2188 114th Ct, Winterset, IA 50072

  • 5 Beds
  • 5 Baths
  • 2,434 Sq Ft
  • Built 2026

  Last Sold Summary

  • 5% Below List Price
  • $479/SF
  • 124 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  2188 114th Ct, Winterset, IA 50072
• 

  

  /23

  Est $277,646

  Not Listed For Sale

  322 N 15th Ave, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,438 Sq Ft
  • Built 2003

  322 N 15th Ave, Winterset, IA 50273

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /33

  $225,000

  $10K PRICE DROP

  • 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
• 

  /2

  $360,000

  Sold Jul 31, 2026

  315 N 14th Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Below List Price
  • $288/SF
  • 42 Days On Market

  Current Estimated Value $334,144

  Last Listing Agent OUTSIDE AGENT OTHER

  315 N 14th Ave, Winterset, IA 50273
• 

  

  /31

  Est $339,052

  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

  Last Listing Agent Danielle Burnight RE/MAX Concepts
• 

  

  /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

  Mahayla Claiser Covered Bridges MHP

  1624 W Summit St Unit 138, 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 $440,574

  Last Listing Agent Ian Sparks Homefront Real Estate, LLC

  2075 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  /33

  Est $327,752

  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

  Last Listing Agent Tobi Greene RE/MAX Precision
• 

  

  /30

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  715 N 5th St, Winterset, IA 50273

  Welcome home to 715 N 5th Street! Nestled on the peaceful north edge of town, this home offers the perfect blend of affordable living and small town charm! You will love the spacious design, featuring oversized closets in every bedroom, including a private primary suite complete with a relaxing garden tub. Situated right in the heart of convenience, you're just minutes from all the local

  Kenneth Kauzlarich RE/MAX Precision

  715 N 5th 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 $252,106

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  520 W Benton St, Winterset, IA 50273
• 

  

  /25

  Est $338,757

  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

  Last Listing Agent Cy Phillips Space Simply
• 

  

  /35

  $900,000

  $69K PRICE DROP

  • 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
• 

  

  /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 $170,000

  Last Listing Agent Ted Weaver RE/MAX Concepts

  317 W Jefferson St, Winterset, IA 50273

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