Explore Similar Homes Within 25 Miles of Winterset, IA

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Why Live in Winterset

Winterset, IA, is a small city with a rich historical backdrop and ties to Hollywood legends John Wayne and Clint Eastwood. Known for its welcoming community, Winterset attracts tourists year-round with the John Wayne Birthplace Museum and the renowned covered bridges of Madison County. The city hosts annual events like the John Wayne birthday celebration in May and the Covered Bridge Festival in October, featuring over 150 vendors, a parade, and a classic car show. Winterset’s housing options include historic homes with Colonial Revival and Victorian influences, contemporary models in subdivisions, and homes on larger plots north of town. The city’s architecture is complemented by walkable streets shaded by mature trees. City Park, listed on the National Register of Historic Places, offers attractions such as the Cutler-Donahue Covered Bridge, Clark Tower, and a hedge maze, along with recreational facilities like a soccer complex, softball fields, and a skate park. Downtown Winterset maintains an old-time, small-town vibe with boutique shops, vintage stores, and family businesses centered around the Madison County Courthouse square. Dining options are plentiful, particularly along John Wayne Drive. The Winterset Community School District includes four schools, with Winterset Junior High being the highest rated. Located about 35 miles from Des Moines, Winterset is accessible via U.S. Highway 169 and Iowa Highway 92, connecting to major interstates and the Des Moines International Airport.

Frequently Asked Questions

How much does it cost to rent a home in Winterset, IA?
The median rent for a home in Winterset, IA is $1,225 per month, though prices vary by neighborhood, size, and property type. As of May 2026, single-family homes tend to be the most affordable option while townhouses are currently more expensive.
How much do you need to make to afford rent in Winterset, IA?
To comfortably afford the median rent in Winterset, IA, a household needs to earn roughly $49,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,225 per month in Winterset, IA, renters typically need to show $3,675 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Winterset, IA?
In Winterset, IA, the price-to-rent ratio is 17.0, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Winterset, IA are best for renting a home?
The best neighborhood for renting in Winterset, IA depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include Drake and Downtown Des Moines, each with its own character and price range.

Rental Home Trends in Winterset, IA

Rental Home Trends

Median Rent
$1,225
Median Single Family Home Rent
$950
Median Townhouse Rent
$1,500
How to Rent a Home