Best Real Estate Agents in Chesapeake, VA• Updated Oct 2026

The data indicates a high-intensity environment in Chesapeake, VA. Inventory is at 1.2 months, meaning a fast-paced market where inventory is limited. Inventory is critically low, meaning well-priced homes move rapidly often with multiple offers.

Currently, $410,000 represents the median entry point in Chesapeake, VA. Over the past half-year, home values in Chesapeake have moved downward by approximately 4% based on regional transaction data.

Buyers have room for negotiation in Chesapeake, VA, with a Sale Price to List Price Ratio of 99.2%. On average, properties in Chesapeake are transitioning from active to sold status in 45 days.

Based on closed transaction data, Shawn Burr ranks at the top of our Chesapeake leaderboard — with 3 completed transactions on record earning an algorithm performance score of 157. 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.

Chesapeake, VA maintains a distinct profile within the broader Chesapeake (city) region. Median home values are currently 0% lower than the regional average, reflecting the unique demand and inventory dynamics of Chesapeake.

If you're selling a Entry Level Detached Home in Chesapeake, VA, the data points to Shawn Burr as a standout choice. 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.

Our data flags Aaron Cano as a top buyer's advocate for Entry Level Detached Home properties in Chesapeake, VA. 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, Jenny Lovell has the strongest performance metrics in Chesapeake, VA. 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.

Beth Wiegan has been particularly active in Chesapeake's Mid-Market Condo/Co-op segment, and the numbers back it up. 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.

Conner Walters has a strong showing as a buyer's agent in Chesapeake's Mid-Market Townhome market. 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.

For those looking to purchase a High-End Detached Home in Chesapeake, VA, Matthew Salway has the deal history to support the choice. For buyers competing in the High-End Detached Home market in Chesapeake, VA, their track record indicates speed and negotiating strength that outperforms the segment baseline on both counts.

Navigating Chesapeake's Mid-Market Detached Home market as a buyer? Debbie Woolard is among the most effective agents in this niche. 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.

Emily Berry specializes in High-End Detached Home properties and has built a measurable edge in Chesapeake's market. The data points to a dual edge here: shorter time on market than is typical for this segment, and sale prices that hold closer to — or above — the asking price compared to local norms.