$273,598Average Value$193Average Price per Sq Ft40Homes 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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On average, homes in Winterset, IA sell after 75 days on the market compared to the national average of 55 days. The median sale price for homes in Winterset, IA over the last 12 months is $260,000, up 10% from the median home sale price over the previous 12 months.
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
Proudly sitting on a corner lot with many all-new features in 2026. It's a perfect blend of the past and present Be the first to live in this newly remodeled home with all new light fixtures, a larger kitchen, added bedroom closet storage, fresh paint, new hardware, smart siding, metal roof and more. Four-bedroom home with one BR on the main floor and 3 bedrooms on the second level. Large living
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
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.
Just listed: Winterset modestly priced ranch-style home.This property features two bedrooms, one full bathroom, and a partial bath located off the laundry room. The home offers easy entry through an enclosed front porch with a closet.The interior includes a large open kitchen and dining area. All kitchen appliances are included. For outdoor living and dining, sliders from the kitchen lead
Located northeast of Macksburg and southwest of Winterset, this 68.86-acre m/l Madison County farm offers an excellent combination of CRP income, mature timber, wildlife habitat, and recreation. The property includes 46.71 acres enrolled in CRP, generating $11,052 annually through September 30, 2033. The balance of the farm features substantial timber and wooded cover, creating outstanding
Garret ArmstrongWhitetail Properties Real Estate, LLC
Discover the possibilities with this 13.88 +/- acre property in Madison County, offering a desirable mix of open pasture and mature timber. With multiple potential building sites, this property provides the flexibility to create your ideal country home or recreational retreat.The property is conveniently located on pavement, with water and power available at the road, making it
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
Peoples Company is proud to present the Hogback Farm, an exceptional 451 acre m/l recreational and income-producing property located in the heart of Madison County, Iowa, just a short drive from the Des Moines metro. Tucked into a highly desirable corridor between the vibrant and growing communities of Winterset and Adel, less than one mile from paved US Highway 169, this property offers a rare
DREAMS DO COME TRUE! Take a look at this exquisite 2 story home on 15ac in beautiful MADISON COUNTY. As soon as you walk in the door you will see what makes this home stand out. The CRAFTSMANSHIP is amazing, from the CUSTOM CABINETS, DOORS and COMMERCIAL EXHAUST VENT, all made on site, to the CUSTOM STEEL BACKSPLASH and BARN BOARDS from the old Homestead that was located on this acreage. The
Located northeast of Macksburg and southwest of Winterset, this 77.34-acre m/l Madison County property offers an attractive combination of income, recreation, wildlife habitat, and potential building opportunities. The farm is enrolled in the Conservation Reserve Program (CRP), providing an annual payment of $10,647.00 while maintaining established grassland habitat. The CRP cover, combined with
Garret ArmstrongWhitetail Properties Real Estate, LLC
Well kept and adorable 2 bed 1 bath ranch home. You will love the character in this sweet easy one level living home just blocks from the historic Winterset square. original hardwood floors and trim throughout with all the essentials renovated including a new metal roof in 2025. The covered front porch greets you and is the perfect spot for morning coffee. The bedrooms are generous sized and have
This comfortable property features three bedrooms, one full bath, and a laundry room with washer and dryer hook-ups. A one car garage is attached to the property for convenience and direct access to your kitchen. This property is located in Winterset and we have other properties with the same floor plan in Stuart, Indianola, & Osceola. Most communities are within walking distance to schools,
Rental Option, or For Sale on Contract for the right candidate! This 2 bedroom, 1 bathroom home is a comfy, with an eat in kitchen with an island. This home has a NEW roof, plenty of windows, with newer blinds, that provides the home with natural light. The living room is very spacious in this home. The bathroom is conveniently located between both bedrooms for great efficiency.
Nice 2 Bedroom 1 Bath apartment with coin laundry in each building. New Oak kitchen. Stove refrigerator and dishwasher included. Landlord pays heat water and trash. Tenant pays electric. Each unit has a through the wall AC for those warm summer days. Great small town near enough to Des Moines to enjoy perks of big city if desired. We require: Each adult to apply with $40 fee, Verifiable
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