We analyze top real estate agents in Winterset and across the country to find you the most proven local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for August 2025. *
* 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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“Isaiah was extremely helpful and always willing to show us houses when they popped up last minute. Even though it took us 3 years before we found the house for us, Isaiah was super patient with us and made sure we were able to check a majority of our boxes.”
“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!”
“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”
“Kristina Sharp worked hard to make sure I was happy with the property and was with me the whole way since I had not purchased a home before. She made me feel comfortable and went through everything so I could understand the home buying proceedures. I have and will continue to recomend Kristina and a person who cares about the people she is trying to assist when buying a home.”
“Shane Campfield is the epitomy of professionalism. He is very good at his job. His communication and social skills are top knotch.”
“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.”
“To whom it my concern, It is our immense pleasure to recommend Viola Salvato as a real estate agent for any individual or family searching for the ideal home. Viola had an initial meeting with us regarding our specific needs in a home as well as our budgetary limits. She is highly talented and immediately found us numerous listings of homes. She did not waste our time with homes that were not in line with our needs. Viola is a master with contract negotiation she came up with a deal that was good for us as well as making the seller happy. She knows the area like the back of her hand and there is nothing that escapes her attention when it comes to properties for sale in this area. We found Viola to be a highly attentive agent, almost as if we were her only customers, although we know that was not the case. She returned all phone calls and emails the same day. We never felt neglected or unimportant. She also is highly personable with an engaging personality. She is hands down the best!”
“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.”
Information and statistics on the latest trends in the Winterset real estate market, updated for August 2025. *
The typical home value in Winterset is projected to be $267,500 for the month of August. July’s finalized data reported the typical value of a home in the city to be $265,000—down 6.53% over the previous 12 months. For comparison, county-level data pegged home values at $270,000 in Madison County for the most recent reporting period. That number is expected to float around $275,000 in August.
Winterset had 11 new listings and 7 listings that went under contract in July, increasing the area’s total available inventory to 32—up 18.52% from the previous month. Inventory is projected to have further increased in August.
Of those 32 active listings, 34.38% reduced their price in the month of July. The median listing price for homes in Winterset grew 35.68% from June to July, bringing the current median listing price to $289,000. Based on projected data for August, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In July 2025, the median time for a listed property to go pending was 21 days, compared to 2 days in July 2024. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this August.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Winterset offers residents a welcoming, active community with strong schools, abundant parks and outdoor recreation, and a rich sense of hometown pride.
Winterset greets you with a handsome courthouse square, indie shops, and a calendar that celebrates community year-round. Set amid the scenic rolling hills of Madison County, it’s renowned for the famed covered bridges and the annual Covered Bridge Festival, where music, arts, and heritage take center stage. History buffs will appreciate the globally known John Wayne Birthplace & Museum and the stitch-by-stitch storytelling at the Iowa Quilt Museum, both right downtown.
Outdoor time is easy to find. Wander to City Park for Clark Tower views or pack a picnic for Pammel Park’s trails and river bends. Local wineries, seasonal farmers markets, and eateries add flavor to weekends, while a quick drive connects you to big-city amenities in Des Moines. Day trips to neighboring communities such as Indianola and Adel expand dining, recreation, and festival options without sacrificing small-town ease.
Families will find strong academics and spirited extracurriculars in the Winterset Community School District, known for engaged teachers, competitive athletics, and arts programs that punch above their weight. Housing spans historic homes near the square to newer builds on quiet streets, and commutes are straightforward thanks to major routes nearby.
Whether you’re relocating for quiet mornings and starry nights or planning a move to be closer to work and weekend fun, Agent Pronto can connect you with a top local real estate pro to buy with confidence or sell for the best result.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Winterset to qualify the best agents for your specific needs.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Winterset. But we don’t stop there.
Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.
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Tips and market insights to make your Winterset real estate journey a success.
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. 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.
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.
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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