“We met with Isaiah early in our home search at an open house while visiting from out of town. He was very knowledgeable and patient answering our numerous questions and it felt like the right fit for us. He helped us immensely every step of the way, providing his expert opinion when asked, helping us better understand the market so we could adjust our expectations accordingly, and quickly and efficiently organizing open houses and private showings for the homes that fit our criteria. He was not pushy and did not rush the process which we both appreciated as first time home buyers. We were unfamiliar with the area and received recommendations from him for multiple mortgage brokers, inspection companies, and more providing us options for trusted people to work with without feeling pressured. When we landed on our home, he walked us through each step and advocated for us when unexpected issues arose. Our home buying process went more smoothly with Isaiah's guidance!”
- Agent Pronto
- Iowa
- Winterset
The best way to find top real estate agents in Winterset, IA
We analyze thousands of real estate agents in Winterset and nationwide to find you proven local professionals, for free.
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 July 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. *
Latest Rolling 3-Month Snapshot
Mar 1, 2026 - May 31, 2026
Quarterly Pricing Trends for Winterset
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Winterset
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Winterset
Rolling three-month data ending on quarter boundaries when available.
Quarterly Inventory and Sales Activity for Winterset
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Winterset
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Winterset
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Winterset’s rolling three-month snapshot shows more homes cycling through the market but with slower overall throughput than a year ago. Active listings are up to 69 even as homes sold in this period are down sharply year over year, and pending sales are also lower than last year, signaling cooler contract activity despite more choices for shoppers.
Pricing has moved upward over the past year, with the typical home value around $272,000 and nearly 25% higher than a year earlier. At the same time, the median list price is only modestly higher year over year, suggesting sellers are not pushing asking prices as aggressively as the gains in closed-sale values might suggest.
Market pace and balance have shifted notably, with months of supply rising to about 5.3 compared with much leaner conditions a year ago. Homes still go under contract reasonably often, with roughly 41% leaving the market within two weeks and an average sale-to-list ratio near 96%, but virtually none are closing above asking price now. Buyers weighing these mixed signals and sellers setting expectations in this changing environment can both benefit from Agent Pronto’s help in finding an agent who understands the latest Winterset trends.
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!”
“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!!!”
“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.”
“She did go really far out of her way to show a house and had really good input on things we didn't notice”
“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.”
“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!”
“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.”
“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!”
“Enjoyed working with Rich and his team. Our acreage sold quickly and we received multiple offers.”
“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.”
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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