$273,836Average Value$189Average Price per Sq Ft34Homes For Sale
Winterset is a charming Iowa city with ties to Hollywood royalty
Winterset is the south-central Iowa city where John Wayne learned to walk and Clint Eastwood fell in love. This rural destination of about 5,400 is the birthplace of “The Duke,” who went on to Hollywood superstardom. “The Bridges of Madison County,” directed by and starring Eastwood, was filmed here. The John Wayne Birthplace Museum and Madison County’s world-renowned covered bridges are highlights of a community that blends history and small-town charm. “Winterset is friendly and welcoming,” says Marcia Munger of Keller Williams Realty, who grew up there and still regularly returns for visits with friends and family. “It’s a community with a lot of warmth and character.”
Visitors to Winterset's John Wayne Birthplace Museum will learn about his extensive connections to the state of Iowa.
The Madison County Courthouse is the literal center of Winterset and the county.
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John Wayne museum, covered bridge fest are major tourist attractions
Winterset’s economy is boosted year-round by tourist dollars. “I don’t think I’ve ever gone back home and there isn’t someone taking a picture in front of the John Wayne statue,” says Munger of the iconic attraction at the corner of Washington Street and John Wayne Drive. The museum hosts an annual birthday celebration for its most famous resident every year in May. The community also hosts the two-day Covered Bridge Festival every year on the second full weekend in October. More than 150 vendors set up shop downtown, and the festivities include a parade and a classic car show. Madison County Regional Hospital in Winterset, and the Winterset Community School District are other top employers.
John Wayne was born in Winterset in 1907, and his childhood home is an international attraction.
Winterset and surrounding Madison County are home to several covered bridges, like the Cedar Covered Bridge.
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Historic architecture stands out among housing options
Winterset’s residential settings are typical of a small town in the 21st century. Most homes are older, with some built as far back as the 19th century. Colonial Revival and Victorian influences stand out among the older homes, which come in a variety of shapes and sizes and radiate out from the center of the community. Many historic homes have been renovated, adding curb appeal to walkable streets shaded by mature trees. “It’s a great place to grow up,” Munger says. “Kids will go off to college and work, then they have kids and will come back to raise a family.” Newer homes are contemporary models with driveways and attached garages in subdivision settings, primarily on the west side of the community. Homes on several acres or more can be found north of town. A small collection of townhouses can also be found. Prices range from under $100,000 to $500,000-plus. The median sales price is about $250,000.
Original homes updated with bold colors are commonplace in the neighborhoods of Winterset.
New homes are popping up on the outskirts of Winterset.
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Early winters forced a name change
Residents can expect summers to be hot and humid and winters to be cold and snowy. In fact, the community was originally named Summerset, until winter rolled around. Officials then changed the name. The community’s resilience was on display in the wake of a deadly tornado that swept through the Winterset area in 2022. “If a tragedy happens, everyone is there to help,” Munger says.
Covered bridge, tower featured attractions at historic City Park
City Park is filled with historical attractions, including Cutler-Donahue Covered Bridge and Clark Tower, a “castle” dedicated to the community’s early settlers. The walkable green space, which also includes a hedge maze, was placed on the National Register of Historic Places in 2021. Parts of the park were renovated after the 2022 tornado, and an all-inclusive playground was added in 2024. The community also boasts a soccer complex, a softball complex, youth baseball fields and a skate park. There’s even a pocket park dedicated to George Washington Carver. Boaters and anglers can take advantage of the recreational opportunities on nearby Cedar Lake. Lakeview Country Club offers 9 holes of golf along the lakefront.
Winterset City Park's expansive grounds provide something for everyone.
A view of the river valley and rolling hills south of Winterset await visitors willing to climb to the top of Clark Tower.
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Downtown still has an "old-time, small-town vibe"
Boutique shops, vintage stores and family businesses are concentrated near the Madison County Courthouse square in the heart of downtown. “It has an old-time, small-town vibe,” Munger says. “Montross Pharmacy is still just like it was when I was in high school in the ‘70s.” Restaurants, bars and cafes are also concentrated downtown, with several along the John Wayne Drive corridor. More shopping and dining options, including a pair of grocery stores, can be found north of downtown.
Beautiful brick buildings occupy the entire square in downtown Winterset.
Sitting right on the downtown square, China Café is a local favorite offering Chinese and Vietnamese classics.
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Four schools make up the local school district
Winterset Junior High, which earns a B from Niche, is the highest rated of four local schools. The junior high shares a campus with C-plus-rated Winterset Senior High, and nearby Winterset Middle has a B-minus. Winterset Elementary has a C-plus. Winterset High School offers dual-enrollment classes in English, math, science and social studies.
Winterset Huskie pride runs strong throughout the community.
Winterset Middle School serves students in grades 4-6.
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Easy access to Des Moines via nearby interstates
U.S. Highway 169 and Iowa Highway 92 intersect just north of downtown, providing convenient access to major interstates. Highway 169 connects directly to I-80, while Iowa 92 connects directly to Interstate 35. Both lead to the capital city of Des Moines, about 35 miles away. Winterset has a municipal airport, but Des Moines International is the closest commercial airport.
Written By
Matt Pallister
Photography Contributed By
Drew Davis
Video By
Joshua Kassabian
Interested in learning more about homes in this area?
Reach out to
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an experienced agent in this area.
On average, homes in Winterset, IA sell after 62 days on the market compared to the national average of 56 days. The median sale price for homes in Winterset, IA over the last 12 months is $226,000, down 5% from the median home sale price over the previous 12 months.
Recently updated ranch style home with 4 bedrooms and 2 baths. Interior includes three BR’s on the main floor, living room, and kitchen just off attached one car garage. One bedroom on the main level would also make a perfect office space and was previously used as a sewing room. All bedrooms have generous sized closets. Updated kitchen with bright over the sink window facing south, included
Hard to find home on this parcel just N of Winterset 4-way intersection of Hwy 92 & 169. This home has 3BR's & 3 baths sitting proudly on nearly 1 acre. Kitchen has had a complete remodel including adding a convenient island & farm sink. Master/BR on 1st floor has large walk-in closet, & tiled walk-in shower. Main floor laundry off the kitchen. Other features on the 1st level include a formal
Corner lot three-bedroom, one bath ranch with attached garage on Winterset West side. Home has fenced yard, great fire pit area for outdoor entertaining, contained decorative garden/flower beds and a row of new trees. Other new yard features include landscaping rock and creative oval garden landscaping mound. Updates include fully encapsulated deep crawl space with warranty and new sump pump.
Story and 1/2, 3BR 1.5 bath affordable home located in Winterset. Large eat-in kitchen, huge living room with staircase on one end. Staircase leads to 3 bedrooms on the second floor with 1/2 bath. Main floor laundry. Bath on second floor can be entered from the hall or access through SW bedroom. Enclosed rear porch off kitchen attached one car garage with entrance on both ends totals 544 sq feet.
Charm with economy! That's what this 5BR, 1 bath, 1.5 story home offers! Great natural light from the large east-facing picture window in the living room. There are 3 bedrooms on the main level, along with the full bath. The open carpeted stairway will lead you to the 2 non-conforming bedrooms (no closets) on the 2nd level. Easy-to-clean laminate flooring throughout main level. The main floor
Well loved and cared for 4 bed 3 bath ranch home is ready for a new owner! You will love the curb appeal with the classy brick front of the home! Inside you will be suprised with the large entryway leading into the living room with gas fireplace. There is a formal dining room as well as an eating area adjacent to the kitchen - perfect for large gatherings! The kitchen is sure to impress with tons
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.
Discover peaceful country living just steps from Winterset’s city limits with this beautifully updated acreage. The property is exceptionally neat and well-kept, offering the perfect blend of rural charm and modern convenience.The home features several modern upgrades. Inside, enjoy a a beautiful kitchen with farmhouse charm, quaint dining & living areas, 4 bedrooms and 2 baths.The barn is
Want to own a slice of Heaven?! This is it! Fully renovated acreage just off pavement about 3 miles north of charming and growing Winterset and about 7 miles south of DeSoto and I80. Spacious ranch alongside the North River with stunning finishings. Open concept at its finest with vaulted ceilings and daylight everywhere you look! Incredible kitchen that you'll want to show off as you host all
5-bedroom, 2-bath home located at 325 W Hutchings St. in Winterset. Offering 1,280 sq ft plus a large basement, this property provides plenty of space for living, storage, or future finishing. Conveniently situated just one block from the hospital and a few blocks from local schools, making daily routines easy. Hard-to-find 5-bedroom layout offers flexibility for families, guests, or home office
Tucked at the end of a quiet street, this 4-bedroom home sits on an oversized lot in a welcoming neighborhood. You'll love the fully fenced yard, wooden fencing, and large deck, perfect for enjoying the outdoors.Inside, the main level offers a functional layout with a drop zone at the front entry, a dedicated office/study, and a spacious living area with a cozy fireplace. The kitchen features
Ashlee & Kyle KnickerbockerKeller Williams Realty GDM
If the "Wow Factor" is what you are hoping for in a home, this one is a must-see! This home was gutted down to the studs and completely rebuilt, so it is just like brand new! Walk in the front door, and you will love all the natural light as you enter the living room with a cozy gas fireplace. The large dining area adjoins the gorgeous kitchen with tons of cabinets and countertop space. There is
Nestled in the heart of the Winterset historic area is this classic American Foursquare with early Craftsman accents. A wonderful example of historic charm and contemporary finish, this home has been expertly maintained and superbly updated to reflect modern design tastes. The living room and dining area are warm and inviting gathering places. The completely remodeled kitchen has abundant
Available immediately is a large sunny apartment located on the square in Winterset, above the US Cellular store. The best part of this quiet unit is the stunning view of the Madison County Courthouse out of the two large front windows. There is an extra-large eat-in kitchen with a pantry, large bathroom and a huge storage closet. The beautiful hardwood floors and the unique antique pocket doors
Property Id: 1608183In this adorable home you will find peace and privacy while still reaping all the benefits of small-town life! Located in a quiet neighborhood, this property's southern border runs along the fence of a neighboring horse pasture; and there is space for a garden in the beautiful back yard. The house has original hard wood floors, and new carpet in the two
Rent is based on income if rental assistance is available. Section 8 accepted.12 Month Lease$400 DepositStove & Fridge provided. Coin operated laundry on site. This institution is an equal opportunity provider.* Prices and availability subject to change without notice.* Square footage definitions vary. Displayed square footage is
Rent is based on income if rental assistance is available. Section 8 accepted.12 Month Lease$400 DepositStove & Fridge provided. Coin operated laundry on site. This institution is an equal opportunity provider.* Prices and availability subject to change without notice.* Square footage definitions vary. Displayed square footage is
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