“Isaiah was such an asset to us while selling our home and helping us find a new one. He was punctual, always available, and was 100% in our corner on every step of the way.”
Century 21 Signature Real Estate
- Agent Pronto
- Iowa
- Winterset
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Compare top Winterset real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for May 2026. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
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Winterset real estate Market Report.
Information and statistics on the latest trends in the Winterset real estate market, updated for May 2026. *
Inventory in Winterset has expanded, with 31 homes for sale in March 2026, up about 24% from the prior month and roughly 41% year over year, while new listings held steady at 17 compared with last year. Contract activity has slowed, with only 9 pending sales and a drop of about 53% from a year ago, creating a mix of more options for buyers but fewer deals moving toward closing.
Pricing is adjusting to this softer contract flow, as the typical home value sits near $201,375, down about 1.8% from last year and over 18% month over month. Sellers are also facing a longer selling journey, with homes spending a median of 93 days on the market, though that is nearly 10% faster than a year ago, and about 29% of listings seeing a price cut before finding a buyer.
Compared with Madison County overall, where the typical value is around $209,375 and still up about 2.1% annually, Winterset’s values are a bit lower and under more downward pressure, with projections pointing to a typical value of about $178,662 and a median list price near $297,602 next month alongside an expected 34 active listings. Even with these shifts, Winterset is still labeled a seller’s market with a gauge reading of 34 and an average sale-to-list ratio close to 0.95, so both buyers and sellers can benefit from an Agent Pronto–recommended agent who understands how to navigate these conditions.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Winterset has to offer.
Winterset offers residents a welcoming, family‑friendly community with strong schools, abundant parks and trails, and a vibrant slate of local events that make everyday life engaging and rewarding.
Winterset is a small, well connected county seat that combines historic character with practical everyday convenience. Located within commuting distance of the Des Moines metro, it offers a slower pace while keeping larger city jobs, shopping, and healthcare within reach.
Residents enjoy an active town square anchored by the Madison County Courthouse, local shops, and regular community events. Everyday errands are simple, with grocery options, medical clinics, and services close at hand. Families appreciate local schools within the Winterset Community School District and opportunities for youth activities through the Winterset Parks and Recreation department.
Outdoor amenities are a major draw. The iconic Madison County Covered Bridges and Winterset City Park provide walking paths, playgrounds, and open green space, while nearby destinations in Madison County expand your options for weekend exploration. Cultural life includes the John Wayne Birthplace & Museum and events at the Iowa Theater, giving residents small town scale with a surprising range of experiences.
Whether you are weighing a move from Des Moines or relocating within Winterset, the right agent can explain neighborhood nuances, school zones, and commute patterns. By matching you with a professional who knows Winterset inside and out, Agent Pronto helps both buyers and sellers make confident decisions and reduce the stress of every step in the process.
Trusted by over 500,000 buyers and sellers.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Lacie was amazing throughout the whole buying experience as a first-time home owner. She made every effort to keep me informed during our buying process and shown her expertise when any questions arose. When there were some questions she couldn't answer she was able to defer me to the appriorate subject-matter expert whether it was an electrician for electrical questions/work to inspection questions. She was absolutely fantastic to work with and would highly recommend her to friends and family that are looking to buy/sell now and later! Thank you Lacie Shelby for working with my partner and I. Thank you even more for making our first home purchase worth it!”
Iowa Realty
“Presley went out of her way to provide us with the best service possible. Very respectful and considerate. I would highly recommend Presley to anyone looking for property within her location to anyone. She is amazing! Cares for her clients and it shows!!!”
Iowa Realty Indianola
“Wendy Beal was knowledgeable and very proffesional. Her familiarity of the Ankeny market and current trends were of great help in setting the strategy for selling our home. We would highly recommend Wendy Beal for anybody looking to buy or sell in central Iowa.”
Iowa Realty
“She did go really far out of her way to show a house and had really good input on things we didn't notice”
Berkshire Hathaway BHHS First Realty
“Deanna was amazing! She listened to me & understood my goals. She answered all questions & was respectful of my wants & needs. She was quick with responses & was there for me every step of the process.”
Century 21 Signature Real Estate
“Dakotah was amazing to work with! Dakotah was referred to us by someone and we will continue to refer him to others. Knowledgeable about the Des Moines area and homes in the area. Always felt that Dakotah was looking out for us as first time home buyers and helped us explain the home buying process in great detail. When we do decide to sell our incredible home, we will surely work with Dakotah again!”
Iowa Realty
“Roger was very responsive to our house selling & buying needs. He also presented to us additional options on other properties to consider besides the ones we found of interest to your.”
Iowa Realty
“Matt cares deeply about his clients and is as trustworthy as they come. He was a fantastic guide and advisor through our home buying process. We ran into a number of snafus and hiccups but he navigated us through them to secure a good deal. Highly recommend Matt!”
Berkshire Hathaway Iowa Realty Mills Crossing
“Enjoyed working with Rich and his team. Our acreage sold quickly and we received multiple offers.”
RE/MAX Concepts
“Julie really knows how to market a property and obtain a ton of exposure. She was extremely helpful and insightful in selling my house. She also really cares for her clients.”
Iowa Realty
Frequently Asked Questions
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There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Winterset. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Winterset Realtor® or real estate agent today.
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