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Find the perfect real estate agent in Winterset, IA

We analyze top real estate agents in Winterset and across the country to find you the most proven local agents, for free.

Winterset, IA real estate

Compare the top real estate agents in Winterset

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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Home buyers and sellers love Agent Pronto.

We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent.

“Isaiah made the process of selling my home as stress free as possible. He was always available to go over anything that needed to be done or to answer any questions I had. He took time to schedule multiple open houses and coordinated with realtors selling other houses in my neighborhood to do a larger open house event. I would recommend Isaiah to anyone trying to buy and sell their home as he will push for the best deals and make what can be a confusing or stressful process as simple as possible.”

Kelsie Stone · Bondurant, IA

Photo of Isaiah Thomas
Century 21 Signature Real Estate
“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!”

Michael Pham · Des Moines, IA

Photo of Lacie Sibley
Iowa Realty
“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.”

Bob and Debbie · Ankeny, IA

Photo of Wendy Beal
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”

Karl Andrews · IA

Photo of Susan Peer
Berkshire Hathaway BHHS First Realty
“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.”

Audrey Mitchell · Des Moines, IA

Photo of Kristina Sharp
Iowa Realty
“Shane Campfield is the epitomy of professionalism. He is very good at his job. His communication and social skills are top knotch.”

Jim Pepper · Ames, IA

Photo of Shane Campfield
Century 21 Signature Real Estate
“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.”

D Gordon · Indianola, IA

Photo of Deanna Roth
Century 21 Signature Real Estate
“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!”

Scott Wilberg ·

Photo of Vi Salvato
Iowa Realty
“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!”

Annette · Ankeny, IA

Photo of Dakotah Reed
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.”

Steven Johnson · Ankeny, IA

Photo of Roger Severson
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!”

Jacob Olson · Adel, IA

Photo of Matt Fuelberth
Berkshire Hathaway Iowa Realty Mills Crossing
“Enjoyed working with Rich and his team. Our acreage sold quickly and we received multiple offers.”

Lois D. · Pleasantville, IA

Photo of Rich & Jeri Hudnut
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.”

Eric · Des Moines, IA

Photo of Campbell Team
Iowa Realty

Winterset real estate Market Report.

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 $288,750 for the month of July. June’s finalized data reported the typical value of a home in the city to be $260,000—up 5.69% over the previous 12 months. For comparison, county-level data pegged home values at $260,000 in Madison County for the most recent reporting period. That number is expected to float around $281,000 in July.

Winterset had 9 new listings and 13 listings that went under contract in June, decreasing the area’s total available inventory to 29—down 12.12% from the previous month. Inventory is projected to have further decreased in July.

Of those 29 active listings, 24.14% reduced their price in the month of June. The median listing price for homes in Winterset fell 23.57% from May to June, bringing the current median listing price to $214,000. Based on projected data for July, listing prices may continue to fall.

The number of days that homes have been on the market prior to going under contract fell sharply year-over-year. In June 2025, the median time for a listed property to go pending was 19 days, compared to 25 days in June 2024. However, in recent months the median number of days from listed to pending appears to be rising. That trend is predicted to have carried through to this July.

Winterset, IA real estate
22
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Winterset has to offer.

Winterset offers residents a charming blend of rich history, vibrant community events, and welcoming small-town hospitality.

Winterset presents a unique blend of small-town appeal, cultural richness, and scenic beauty, making it a delightful destination for current and future residents. The town charms with its remarkable history as the birthplace of John Wayne, celebrated at the John Wayne Birthplace & Museum, where visitors can explore a treasure trove of memorabilia and stories about the Hollywood icon. Winterset is renowned for its picturesque covered bridges, famously featured in "The Bridges of Madison County," including the Roseman Bridge and others scattered throughout the landscape.

Families appreciate the strong sense of community fostered by top-rated Winterset Community Schools, with committed teachers and a variety of programming that nurture academic and extracurricular growth. The town’s historic Madison County Courthouse stands as a centerpiece surrounded by boutique shops, cozy cafés, and venues like the Iowa Quilt Museum and Iowa Theater. Outdoor enthusiasts will find tranquility and adventure at Winterset City Park and Nearby Pammel State Park, ideal for hiking, picnicking, and exploring southern Iowa’s rolling hills.

Only a short drive from vibrant Des Moines, Winterset offers a peaceful retreat while keeping urban amenities within easy reach. Whether you’re browsing the celebrated Cedar Covered Bridge, enjoying local wineries, or exploring the thriving arts scene, life in Winterset is full of opportunities to create lifelong memories.

If you’re considering buying or selling a home in Winterset, Agent Pronto can help you find a knowledgeable real estate agent to make your move seamless and enjoyable.

Woman smiling

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!

Sarah W.

Take the guesswork out of finding an agent.

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.

Data analysis with a human touch.

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.

Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!


Frequently Asked Questions

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.