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

The data indicates a active environment in Chesapeake, VA. Inventory is at 3.1 months, meaning a balanced environment with steady turnover. Inventory is balanced but lean, requiring buyers to be decisive.

Currently, $442,000 represents the median entry point in Chesapeake, VA. Over the past half-year, home values in Chesapeake have moved upward by approximately 6% based on regional transaction data.

Sellers hold significant leverage in Chesapeake, VA, with a Sale Price to List Price Ratio of 100.4%. On average, properties in Chesapeake are transitioning from active to sold status in 46 days.

Based on closed transaction data, Amy Holloway ranks at the top of our Chesapeake leaderboard — with 2 completed transactions on record earning an algorithm performance score of 150. 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 Amy Holloway 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 transaction-level analysis puts Erin Ward at the top for Mid-Market Detached Home listings in Chesapeake, VA. Erin Ward has consistently held closer to asking price than the typical Mid-Market Detached Home agent in Chesapeake, VA. For sellers prioritizing their final number, that's the metric that matters most.

If you're hunting for a Entry Level Detached Home in Chesapeake, VA, Aaron Cano's track record speaks for itself. For buyers competing in the Entry Level Detached Home market in Chesapeake, VA, their track record indicates speed and negotiating strength that outperforms the segment baseline on both counts.

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.

Sudan Weng has a strong showing as a buyer's agent in Chesapeake's Entry Level Townhome market. Across their deals in the Entry Level Townhome category, Sudan Weng has consistently achieved better-than-average terms relative to asking price in Chesapeake, VA. That kind of negotiating edge compounds over a transaction.

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

In the High-End Detached Home category, few agents in Chesapeake, VA can match the track record of Kathy Nelms. They've built a consistent track record in the High-End Detached Home category specifically — not just broad volume, but demonstrated results in this exact niche in Chesapeake, VA.

Angela McCaskill has helped buyers close on Mid-Market Condo/Co-op properties in Chesapeake, VA — and the data shows it. Our algorithm surfaces Angela McCaskill based on actual closed buyer deals in the Mid-Market Condo/Co-op market. That's the kind of specific, verifiable track record buyers should look for in an agent.