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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: 3/1
MLS # 550269
Looking for a Ranch on large lot close to schools??? Here it is. Newly updated 3 BR RANCH. All new flooring, paint, landscaping and hardware. Kitchen and bath have been updated. A new deck has been added off the kitchen to enjoy the over side yard. The attached garage has that extra space you want for all the extra toys and tools. In the LL you will find a 370 sq ft family room. Call your agent to see this home.
Beds/Baths: 0/0
MLS # 552205
"EDGE OF HEAVEN" HISTORIC PIONEER FARMSTEAD PROVIDES SOME OF THE BEST VIEWS MADISON COUNTY HAS TO OFFER! Sizeable Hilltop parcel has gentle slopes; must-see 360 degree sunrise and sunset views. One of the relatively few larger undeveloped parcels in the area. No HOA fees; multiple building site options including for walk-outs. Water and Electric at road. Enjoy upscale Winterset charm with quick, easy Metro access. TERRIFIC LOCATION within a mile off Cumming HWY on gravel (approx 15 mins to WDM/Jordan Creek Mall, 8 mins to Winterset). Reasonable covenants (stick-built) protect your investment. Land is charmingly distinguished by tiny historic pioneer cemetery (scheduled to be restored in near future) located well back on the property, hence the “Edge of Heaven” nickname. Abundant wildlife; Horses OK.
Beds/Baths: 0/0
MLS # 513000
Build your dream home here on this very private building site with trees and great views of the scenic rolling Madison County countryside! Site located near pavement just south of Winterset. Covenants available online.
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 # 451751
Beautiful 10 ac. building lot. Heavily timbered and located just off the Cumming Hwy. Less than 20 min. to West Des Moines, no covenants.

View all Winterset houses for sale