Top Real Estate Agents in Chesapeake, VA – December 2025
Find the best real estate agents in Chesapeake, VA. See who's closing the most deals, selling fastest, and dominating the market—backed by 12 months of MLS data.
We analyzed 1,555 MLS transactions across 883 agents in Chesapeake over the last 12 months to find who's actually moving property. Here's what the data says.
Key Market Stats
- Median Home Price: $450K
- Avg Days on Market: 60 days
- #1 Agent: Deana Renn (46 transactions, $39.4M volume)
Chesapeake Housing Market Snapshot
Understanding the current market conditions helps you set realistic expectations and negotiate effectively.
| Metric | Value |
|---|---|
| Median Home Price | $450K |
| Avg Days on Market | 60 days |
| Listings Selling Under 30 Days | 42% |
| Listings on Market 90+ Days | 21% |
| Price Trend (vs Prior Quarter) | -10.5% |
Balanced Market
How to Choose the Right Real Estate Agent in Chesapeake
Finding the right agent is about more than just transaction volume. Here's what to look for:
Ask these before signing with any Chesapeake agent:
- How many homes have you sold in Chesapeake in the past 12 months?
- How often will you update me, and through what channels?
- How do you determine list price? What's your sale-to-list ratio?
- What specific tactics will you use to market my property?
- Can you provide contact info for 3 recent clients?
Walk away if you see these warning signs:
- No recent local deals — They may not know the current market.
- Vague marketing — "We'll put it on the MLS" isn't a strategy.
- Pressure tactics — Good agents educate, not push.
Which structure fits your needs?
| Team | Solo Agent | |
|---|---|---|
| Availability | More coverage | Single point of contact |
| Specialization | Dedicated roles | Generalist approach |
| Communication | May vary by team member | Consistent relationship |
| Best for | High-volume, fast markets | Personalized attention |
Chesapeake Agent Rankings
| Rank | Agent | Brokerage | Transactions | Total Volume | Cohort |
|---|---|---|---|---|---|
| 1 | Deana Renn | Atcoastal Realty | 46 | $39.4M | Top 1% |
| 2 | Lori Cutrell | — | 21 | $13.4M | Top 5% |
| 3 | Steve Freeman | — | 19 | $10.5M | Top 5% |
| 4 | Jennifer Lovell | — | 19 | $12.5M | Top 5% |
| 5 | Monique Darling | — | 18 | $10.9M | Top 5% |
| 6 | Carmon Pizzanello | Berkshire Hathaway Homeservices Rw Towne Realty | 17 | $10.6M | Top 10% |
| 7 | Ron Sawyer | Re/Max Prime - Broker | 17 | $7.8M | Top 10% |
| 8 | Heide Mahr | Pointe East Realty INC - Broker | 16 | $12.1M | Top 10% |
| 9 | Christian Ramirez | — | 15 | $8.8M | Top 25% |
| 10 | Gina Allen | Howard Hanna Real Estate - Broker | 15 | $10.7M | Top 25% |
Rankings based on MLS transaction data. Cohort percentile calculated against all agents in the market.
Top Agents by Transaction Volume
Speed to Sale: Agent vs Market Average
Agents highlighted in orange sell faster than the Chesapeake market average of 60 days.
Total Sales Volume
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Methodology
Data Collection
We analyzed 1,555 MLS listings in Chesapeake, VA from the last 12 months, sourced from our proprietary database of 21M+ nationwide transactions.
Ranking Calculation
Agents are ranked by transaction count with a minimum of 3 transactions required. Cohort percentiles compare each agent against all agents in the market.
Performance Metrics
We calculate days on market, total volume, and average sale price to provide a complete performance picture.
Frequently Asked Questions
How We Keep This List Updated
This ranking of top real estate agents in Chesapeake is updated monthly using the latest MLS transaction data. Our automated pipeline processes millions of records to identify agents with consistent, verifiable performance.
What triggers ranking changes:
- New transactions closing in the MLS
- Shifts in agent volume relative to market peers
- Updated brokerage affiliations
Last updated: 12-30-2025
About This Data
Rankings are based solely on MLS transaction data. Tab Tab Labs does not accept payment for placement. Past performance does not guarantee future results. Always interview multiple agents before making a decision.
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