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Winterset, IA real estate

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

Median sale price
$272K
+24% from Q1 '26
Median list price
$273K
-4.3% from Q1 '26
Active listings
69
+19% from Q1 '26
Homes sold
20
+67% from Q1 '26
New pendings
31
+41% from Q1 '26
New listings
43
+59% from Q1 '26

Quarterly Pricing Trends for Winterset

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Winterset Q2 '21 Q2 '22 Q2 '23 Q2 '24 Q2 '25 Q1 '26 Median sale price in Apr 2021 - Jun 2021: $200K Median sale price in Jul 2021 - Sep 2021: $180K Median sale price in Oct 2021 - Dec 2021: $194K Median sale price in Jan 2022 - Mar 2022: $214K Median sale price in Apr 2022 - Jun 2022: $207K Median sale price in Jul 2022 - Sep 2022: $184K Median sale price in Oct 2022 - Dec 2022: $212K Median sale price in Jan 2023 - Mar 2023: $179K Median sale price in Apr 2023 - Jun 2023: $229K Median sale price in Jul 2023 - Sep 2023: $240K Median sale price in Oct 2023 - Dec 2023: $269K Median sale price in Jan 2024 - Mar 2024: $228K Median sale price in Apr 2024 - Jun 2024: $226K Median sale price in Jul 2024 - Sep 2024: $249K Median sale price in Oct 2024 - Dec 2024: $210K Median sale price in Jan 2025 - Mar 2025: $229K Median sale price in Apr 2025 - Jun 2025: $222K Median sale price in Jul 2025 - Sep 2025: $260K Median sale price in Oct 2025 - Dec 2025: $213K Median sale price in Jan 2026 - Mar 2026: $219K Median list price in Apr 2021 - Jun 2021: $203K Median list price in Jul 2021 - Sep 2021: $180K Median list price in Oct 2021 - Dec 2021: $219K Median list price in Jan 2022 - Mar 2022: $210K Median list price in Apr 2022 - Jun 2022: $200K Median list price in Jul 2022 - Sep 2022: $230K Median list price in Oct 2022 - Dec 2022: $199K Median list price in Jan 2023 - Mar 2023: $225K Median list price in Apr 2023 - Jun 2023: $240K Median list price in Jul 2023 - Sep 2023: $250K Median list price in Oct 2023 - Dec 2023: $260K Median list price in Jan 2024 - Mar 2024: $225K Median list price in Apr 2024 - Jun 2024: $239K Median list price in Jul 2024 - Sep 2024: $230K Median list price in Oct 2024 - Dec 2024: $221K Median list price in Jan 2025 - Mar 2025: $252K Median list price in Apr 2025 - Jun 2025: $263K Median list price in Jul 2025 - Sep 2025: $269K Median list price in Oct 2025 - Dec 2025: $210K Median list price in Jan 2026 - Mar 2026: $285K Apr 2021 - Jun 2021 Median sale price $200K Median list price $203K Jul 2021 - Sep 2021 Median sale price $180K Median list price $180K Oct 2021 - Dec 2021 Median sale price $194K Median list price $219K Jan 2022 - Mar 2022 Median sale price $214K Median list price $210K Apr 2022 - Jun 2022 Median sale price $207K Median list price $200K Jul 2022 - Sep 2022 Median sale price $184K Median list price $230K Oct 2022 - Dec 2022 Median sale price $212K Median list price $199K Jan 2023 - Mar 2023 Median sale price $179K Median list price $225K Apr 2023 - Jun 2023 Median sale price $229K Median list price $240K Jul 2023 - Sep 2023 Median sale price $240K Median list price $250K Oct 2023 - Dec 2023 Median sale price $269K Median list price $260K Jan 2024 - Mar 2024 Median sale price $228K Median list price $225K Apr 2024 - Jun 2024 Median sale price $226K Median list price $239K Jul 2024 - Sep 2024 Median sale price $249K Median list price $230K Oct 2024 - Dec 2024 Median sale price $210K Median list price $221K Jan 2025 - Mar 2025 Median sale price $229K Median list price $252K Apr 2025 - Jun 2025 Median sale price $222K Median list price $263K Jul 2025 - Sep 2025 Median sale price $260K Median list price $269K Oct 2025 - Dec 2025 Median sale price $213K Median list price $210K Jan 2026 - Mar 2026 Median sale price $219K Median list price $285K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
22
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

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.

Find your Winterset real estate agent today →


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.

“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!”

Evans Family · Grimes, 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
“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!!!”

Tammie Illg · Diagonal, IA

Photo of Presley Sparks
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.”

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
“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
“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

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 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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