Best Real Estate Agents in Winterset, IA• Updated Aug 2026

The data indicates a active environment in Winterset, IA. Inventory is at 2.8 months, meaning a balanced environment with steady turnover. Inventory is balanced but lean, requiring buyers to be decisive.

Currently, $377,000 represents the median entry point in Winterset, IA. Over the past half-year, home values in Winterset have moved upward by approximately 33% based on regional transaction data.

Buyers have room for negotiation in Winterset, IA, with a Sale Price to List Price Ratio of 99.2%. On average, properties in Winterset are transitioning from active to sold status in 71 days.

Based on closed transaction data, Robert D Weeks ranks at the top of our Winterset leaderboard — with 3 completed transactions on record earning an algorithm performance score of 63. Agent Algo's rankings are built entirely from real deal outcomes — not reviews or paid placements — so this reflects actual results in the local market.

Winterset, IA maintains a distinct profile within the broader Madison region. Median home values are currently 29% higher than the regional average, reflecting the unique demand and inventory dynamics of Winterset.

Buyers targeting Mid-Market Detached Home homes in Winterset, IA may want to work with Sarah Cowman. Their buyer transactions in this segment close faster than the local norm and at sale-to-list ratios that are more favorable than typical — meaning they move quickly and negotiate effectively for the buyers they represent.

Our data flags Jennifer Stover as a top buyer's advocate for Entry Level Detached Home properties in Winterset, IA. The data shows a consistent pattern across their deals here: shorter time to close than the segment average, and acquisition terms that tend to land below-average relative to list price. Two things buyers care about most.

Among agents with recent closings in the Mid-Market Detached Home space, Robert D Weeks has the strongest performance metrics in Winterset, IA. In a category where leaving money on the table is easy, their sale-to-list performance in this segment stands above the local benchmark — reflecting an ability to negotiate and price effectively.

Among agents actively helping buyers in the Entry Level Condo/Co-op space, Jennifer Stover stands out in Winterset, IA. Their buyer transactions in the Entry Level Condo/Co-op category in Winterset, IA reflect genuine niche experience — a meaningful advantage over agents working this segment only occasionally.

Jennifer Stover has a strong showing as a buyer's agent in Winterset's Mid-Market Condo/Co-op market. Across their deals in the Mid-Market Condo/Co-op category, Jennifer Stover has consistently achieved better-than-average terms relative to asking price in Winterset, IA. That kind of negotiating edge compounds over a transaction.

Sellers of Entry Level Detached Home homes in Winterset, IA have found a reliable partner in Misty Darling, based on closed deal data. Speed and price retention together are the hardest combination to find in a single agent. Their track record in the Entry Level Detached Home category in Winterset, IA reflects both.

In the Mid-Market Condo/Co-op category, few agents in Winterset, IA can match the track record of Jennifer Stover. Their listings in this segment consistently close faster than the local pace — a meaningful edge when carrying costs and market timing matter to sellers.

Sarah Cowman specializes in High-End Detached Home properties and has built a measurable edge in Winterset's market. Our algorithm ranks them based on closed transaction outcomes in the High-End Detached Home segment, not self-reported volume or marketing activity. The ranking reflects actual local performance.