$273,664Average Value$189Average Price per Sq Ft35Homes 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 74 days on the market compared to the national average of 58 days. The median sale price for homes in Winterset, IA over the last 12 months is $260,000, up 11% from the median home sale price over the previous 12 months.
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.
Welcoming 1 1⁄2 story brick home on Winterset West side. Recent remodel, galley kitchen, main floor bedroom and full bath. Living room open to dining area. Handy drop zone near rear door from detached garage. Full unfinished basement with included washer and dryer and 1⁄2 bath with a bonus laundry sink and workshop area. Three bedrooms on the second level hardwood floors and full bath upstairs.
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
Luxury Executive Acreage on Pavement | 18.64 Acres Just South of Winterset, Iowa Presenting a premier 18.64-acre executive acreage opportunity located just three miles south of Winterset on paved Clark Tower Road. Opportunities of this caliber in Madison County are increasingly difficult to find, offering the perfect combination of scenic beauty, privacy, usable land, and convenient access to the
57.36 Acres with Log Home, Livestock Facilities & Equipment – Earlham School District Located just 3 miles north of Highway 92 and approximately 2 miles east of Earlham Road, this 57.36 gross acre property offers a great combination of rural living, pasture ground, and functional farm improvements. The property features a 2-story log cabin style home built in 1996 offering approximately 2,282
Located in scenic Madison County this newly built home and buildings offers peace and quiet with close commute to Winterset and West Des Moines. Located on hard surface road 8.5 miles south of Winterset. The home offers 2 bedrooms and 2 baths. The main floor offers an open concept with a nice main living and dining area. The upstairs offers the opportunity to expand to increase finished square
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.
If you are dreaming of countryside peace and quiet and need alot of living space, you will definately enjoy the beauty and freedom of a 4.3-acre homestead featuring 6 bedrooms, 4 baths, and multiple living areas. The elegant kitchen boasts a walk-in pantry, an abundance of countertop and cabinet space, and picturesque views of rolling hills and a neighboring pond. Step out from the dining area
Perfect acreage alert! This exceptional walkout ranch is ready for new owners to move in and enjoy the breathtaking sunsets over the valley. All of the big ticket items have been upgraded: roof, HVAC, windows, deck - radon mitigation installed - nothing to worry about here! Situated on over 4.5 acres of stunning Iowa countryside, the home features more than 3,000 square feet of beautifully
Welcome to modern acreage living at its finest! Set on 5.32 picturesque acres in gorgeous Madison County and located in the highly desirable Adel school district, this stunning home offers the perfect blend of peaceful country living with everyday convenience. Just 13 minutes from Grand Prairie Parkway, you’ll enjoy an easy drive on all blacktop roads—no gravel! Inside, discover 4,593 sq ft of
3.45 Acres – Bring Your Own Builder!LAKE LOT available in Covered Bridge Estates, a welcoming community with paved roads. Enjoy the feel of peaceful country living while still having quick, convenient access to the Des Moines metro. All information obtained from seller and public records.
Step into timeless character with this stately 19th-century home, showcasing stunning original woodwork and rich architectural charm throughout. Set on an expansive lot, the property features a 4-car attached garage, a welcoming wrap around porch, and plenty of parking space. Inside, you’ll find a beautiful open floor plan designed for both everyday living and entertaining. The spacious living
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
This spacious, south facing newly renovated 2-bedroom, 2-bath condo offers modern comfort and upscale finishes throughout. The open-concept layout features a stylish kitchen with an island, high-end appliances, and ample cabinetry—perfect for entertaining or everyday living. Cozy up by the fireplace in the inviting living area, or enjoy the convenience of elevator access and secure underground
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
Duplex apartment available in Winterset featuring 1 bedroom and 1 bathroom. This unit offers on-site laundry and basement access for additional storage and convenience. Rent is $800 per month with an $800 security deposit required. A $50 background check is required with the application. Contact for more details or to schedule a showing. 1 Bedroom, 1 bathroom townhome. This unit has stairs to
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
