Performance indicators for the Winterset short-term rental market based on reliable data.
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Reliable / Active
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Middle-Earners Gross Yield
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Middle-Earners Revenue
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Middle-Earners Occupancy
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Median Home Sale Price
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Top-Earners Revenue
The highest-performing listings in Winterset.
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Generally Investor friendly
Short-term rentals are explicitly permitted and must register annually ($10) plus undergo inspections ($50 + $15 per unit) every 2–3 years (annual if multiple re-inspections), which is a known, relatively low-cost compliance pathway. The city’s framework is supportive and lacks caps or zoning bans, making investment feasible though not frictionless. Non-compliance can trigger municipal infractions, so diligent compliance is essential.
Local STR Agent
STR specialist · Winterset, IA
Winterset is a city in and the county seat of Madison County, Iowa. The population was 5,353 at the time of the 2020 census.Winterset is part of the Des Moines metropolitan area. It is the birthplace of actor John Wayne.