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Nestled in the picturesque rolling terrain, Winterset, Iowa is famous as the birthplace of actor John Wayne and the world-famous covered bridges that were popularized by Robert James Waller’s novel, “The Bridges of Madison County.”

Winterset is a fascinating and fun place to visit, explore and live, with a rich history, enticing shopping and dining, welcoming lodgings, a thriving business community and a responsive economic development group. During the summer, Winterset and Madison County host a whole calendar’s worth of great community events such as live music at the Madison County Winery, Two Saints Winery and Covered Bridge Winery. You can also catch a summer concert series featuring the Winterset Community Band and local artists in Winterset’s town square, a monthly classic car show, see a movie at the Art Matinee Theater, shop at the weekly farmers market and attend local bike nights for both bicycle and motorcycle lovers!

Winterset also hosts a multitude of events throughout the year that provide the community with fun, food and everything in between. The city celebrates local celebrity John Wayne during his annual birthday celebration in May and the United States’ birthday during the annual Independence Day celebration in July. The Madison County Fair brings together animals, food and competitions of all types at the end of July. In August, community members get active at the annual Cannonball Pump and Run, which combines weight lifting, running and a post-party in to one family fun event and come back together mere days later for delicious barbeque at the Madison County BBQ Shootout. In October, you can enjoy the literary side of the community at the annual Covered Bridges Festival which features food, entertainment, the famous covered bridges and beautiful fall colors.

When you want to get away for the weekend the Des Moines Metro area is just a 30 minute drive to popular events and attractions like the Blank Park Zoo, the Iowa Cubs, the Science Center of Iowa, the Des Moines Arts Festival and the Des Moines Farmers Market. For additional information, check out the Catch Des Moines website which includes events and entertainment the Des Moines Metro area. 

If you're interested in visiting and living in Winterset, visit the Madison County website which includes community information, as well as information about the above events and more!

Wanting to move to this picturesque community nestled in the heart of Madison County?  Then check out the most current list of available Winterset homes for sale and find the home and community of your dreams.


Winterset Homes for Sale:

Beds/Baths: 3/2
MLS # 546531
Take a look at this 3 bedroom, 1.5 bath home on two lots! Home features a large family room with fireplace, convenient eat-in kitchen and a two car attached garage. Basement offers possibility of a 4th bedroom or office. Enjoy your shaded lots with mature trees while sitting on your deck. Call for showing!
Beds/Baths: 0/0
MLS # 545547
Approx 30A m/l near one of scenic Madison County's covered bridges. This would be a great place to build your dream home .. lots of trees, peace and quiet and wildlife. Please Note: There will be a deed restriction: No development will be allowed on the northern half of the listed parcel. The assessor's page shows 40A m/l, but included in that acreage amount is the owner's own home and land around it.
Beds/Baths: 0/0
MLS # 433437
If you're seeking the benefits of country living but appreciate the convenience of city services, Cedar Woods offers a remarkable setting you won't find anywhere else! With its beautiful acreage lots, wooded walk-outs, ponds, rain gardens & abundant wildlife, you'll be surrounded by the beauty of nature in this low-impact community. Located on Cumming Hwy, road in development is asphalt; NO association dues; City of Winterset maintains the roads in the development. Ask about the City sewer services.
Beds/Baths: 0/0
MLS # 527167
Wonderful building lots in Winterset! Cul-De-Sac home sites available with a great price!
Beds/Baths: 0/0
MLS # 550175
Offering 232 acres of highly productive Madison County farmland to be sold in four tracts at public auction on December 5, 2017 at Earlham Community Center in Earlham. Please continue scrolling for detailed information about the auction and each individual tract. Madison County Land Auction 232 Acres M/L Offered in Four Tracts Tuesday, December 5th, 2017 10:00 A.M. Location: Earlham Community Center 150 E 1st Street Earlham, IA 50072 Bidder Registration: All prospective bidders must register with Peoples Company and receive a bidder number to bid at the auction.

View all Winterset houses for sale