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

The data indicates a stable environment in Winterset, IA. Inventory is at 7.3 months, meaning a balanced environment with steady turnover. Inventory levels provide a healthy range of options for prospective buyers.

Currently, $274,000 represents the median entry point in Winterset, IA. Over the past half-year, home values in Winterset have moved upward by approximately 8% based on regional transaction data.

Buyers have room for negotiation in Winterset, IA, with a Sale Price to List Price Ratio of 98.8%. On average, properties in Winterset are transitioning from active to sold status in 67 days.

Based on closed transaction data, Robert D Weeks ranks at the top of our Winterset leaderboard — with 2 completed transactions on record earning an algorithm performance score of 19. 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 7% 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 Mid-Market Condo/Co-op properties in Winterset, IA. 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.

If you're hunting for a Entry Level Detached Home in Winterset, IA, Hannah Woods's track record speaks for itself. Buying effectively in this segment means knowing when and how hard to push. Their track record here shows they regularly outperform the local sale-to-list benchmark — in the buyer's favor.

Among agents actively helping buyers in the High-End Detached Home space, Jennifer Stover stands out in Winterset, IA. Their buyer closings in this segment show a sale-to-list ratio that's more favorable than the local average — a signal of effective negotiation that keeps final purchase prices competitive for buyers.

When looking specifically at High-End Detached Home transactions, Robert D Weeks consistently surfaces as a top performer in Winterset, IA. Robert D Weeks has consistently held closer to asking price than the typical High-End Detached Home agent in Winterset, IA. For sellers prioritizing their final number, that's the metric that matters most.

Sellers of Entry Level Detached Home homes in Winterset, IA have found a reliable partner in Sarah Cowman, based on closed deal data. 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.

In the Mid-Market Detached Home category, few agents in Winterset, IA can match the track record of Rachel Eller. Their listings in this segment have consistently closed faster than the local average while achieving above-average sale-to-list ratios — a rare combination that directly benefits sellers on both time and final price.

Jennifer Stover specializes in Mid-Market Condo/Co-op properties and has built a measurable edge in Winterset's market. Jennifer Stover has consistently held closer to asking price than the typical Mid-Market Condo/Co-op agent in Winterset, IA. For sellers prioritizing their final number, that's the metric that matters most.