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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 # 550910
This charming move-in ready bungalow has 2 bedrooms on the main level and one in the lower level, plenty of cabinets, an eat-in kitchen, & beautiful old woodwork. The assessor's site does not show the finish in the lower level. The home was built in 1890 but moved to its current location in approximately 1953. The home has recently gone through many updates: new carpet, vinyl flooring, windows, siding, & sump pump with pop-up valve in 2017, A/C 2011, wiring & water lines 2005, sewer line to street replaced in 2011. The oversized 2 car garage is 30x36 with insulated walls, a gas heater, 200V outlet, a 1/2 bath, and pull-down ladder to storage above. There is also a shed with a wooden floor on the property. This is a great move-in ready home!
Beds/Baths: 0/0
MLS # 419363
Covered Bridge Estates- One of Madison County's premiere Developments 3 ac. lots. Choose a variety of walk-outs, day lights and standard lots. Covered Bridge Estates offers the best of both worlds, country living and easy access to the Des Moines metro. Located on Hwy 169 and the roads in the development are paved. Stunning views all around! Bring your own builder. Contract Available.
Beds/Baths: 0/0
MLS # 527162
Wonderful building lots in Winterset! Cul-De-Sac home sites available with a great price!
Beds/Baths: 0/0
MLS # 546201
Commercial building lot in prime location. High increases in traffic count along highway. Area is home to new commercial construction that includes: retail store, hotel, bank, grocery store & office building. Great access to lot from public frontage road -- just west of Highway 169/92.
Beds/Baths: 0/0
MLS # 433438
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.

View all Winterset houses for sale