“Hands down the best realtor I've ever worked with. Matt truly cares that his clients find what they're actually looking for, not just closing a sale. On the buying side, he was great at pointing out concerning items during showings, and he was especially valuable during our blue tape walkthrough on our new house. He was clearly on our side the whole time and helped keep communication with the builder clear and moving. He also did a fantastic job selling our previous home. Matt is professional, respectful, and genuinely easy to work with. I'd recommend him to anyone buying or selling, and we'll be calling him again next time.”
- 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 October 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
Jul 1, 2026 - Sep 30, 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 (Jul 2026 - Sep 2026).
Winterset’s rolling three-month snapshot shows inventory tightening while activity cools. Active listings are down nearly 10% from a year ago and homes sold have fallen by about 17%, with pending sales dropping at a similar pace.
On the pricing side, values have held up even as fewer deals are closing. The typical home value is up about 8% year over year, while the median list price is down roughly 9%, suggesting sellers are adjusting expectations to meet buyers.
Conditions have shifted toward a more balanced feel, even with the area still categorized as a seller’s market. Homes are taking longer to sell than a year ago, with median days on market rising to just over 50 and months of supply edging up to nearly four, so both buyers and sellers can benefit from an Agent Pronto–recommended agent who understands how to navigate this changing environment.
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.
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“I honestly couldn’t have asked for a better realtor. From the very beginning, I felt like I was working with someone who genuinely cared about me and what I was looking for—not just someone trying to close a deal. Isaiah was always there when I had questions, he kept me informed throughout the process, and made me feel comfortable even when things got stressful. I really appreciated his patience, honesty, and willingness to go the extra mile. Buying a home can be overwhelming, but having the right person by your side makes such a difference. I’m so grateful for all their help and for making the whole experience such a positive one. I would absolutely recommend Isaiah Thomas to anyone looking to buy or sell a home! 🏡❤️”
“Matt was excellent throughout the entire process of helping me buy my duplex. He made the transaction incredibly smooth, took the time to walk me through every step, and was always available to answer my questions. I always felt confident knowing he was there to guide me from start to finish. What impressed me most was that his commitment didn't end after closing. I initially hired a property management company to lease the duplex, but after several months they were unable to find tenants. I reached out to Matt, and he had the property leased within a week. That really showed me how knowledgeable, responsive, and dedicated he is. I highly recommend Matt to anyone looking to buy or sell real estate. He truly goes above and beyond for his clients, and I wouldn't hesitate to work with him again.”
“As a first time buyer, I was nervous of what to expect from a realtor. Rob absolutely exceeded my expectations of real estate agents— from the first day we met I could tell he genuinely cared about the state of the homes we looked at. He got me an awesome basket of gifts on closing day filled with home essentials. Thank you Rob! You’re excellent!”
“Amazing!! Highly recommend!! Went above and beyond and really took the time to help us from start to finish. If you're looking for someone to help you with buying or selling don't hesitate to contact Jordan!”
“Luann, is great to work with very friendly. She made me feel comfortable and helped with each step easy. If you need a house fast go with her as she knows Waterloo very well in what areas are the best to purchase. Her office space is beautiful as well and we closed at her office. She will make you feel like a friend of hers and wants what is best for you and your home. Reach out to her for any buying or purchasing needs.”
“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.”
“Kelsey went above and beyond for us in every way possible and was so consistent, informative, and kind throughout our whole first time buying process. You can tell she truly loves what she does and that made our experience so much more special. I couldn’t recommend her enough!”
“I work for a new construction builder in the Des Moines metro. Crossed paths with Kristina as her buyers were looking into a townhome in Altoona. We quickly had great conversation and she simply gave me the time of day. She made me feel heard and appreciated from day 1 all the way till closing on her buyers' home. She is knowledgeable, professional, outgoing and extremely personable. I would definitely recommend her to any unrepresented buyers or friends and family. We worked extremely well together. She was awesome!”
“I am particular with what I like and don’t like. John was very patient. Each time we would look at a house he would check to see if this is what we liked, could we see ourselves in the home. Any concerns I had, John was always prompt to follow up with me. I felt like at the time I was his only client.”
“Enjoyed working with Rich and his team. Our acreage sold quickly and we received multiple offers.”
“Toren was absolutely great with our home buying process. He is very knowledgeable when it comes to buying a new home. He was non-biased and gave us honest input, regardless of the condition of the home. He took our family into consideration, we have a one year old, and a small dog. Toren always kept that in mind when he was showing us a home. He was always flexible and found time for us, regardless of the situation. 10/10 would (and will) recommend him to any friend or family member that needs a realtor.”
“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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