Best Real Estate Agents in Chesapeake (city) County, VA• Updated
Explore the top-ranked real estate agents across Chesapeake (city) County, VA. Our 2026 rankings are built from closed transaction data, helping you compare agents by real performance — not just marketing.
Market Pulse: Balanced ⚖️
The Chesapeake (city) County, VA real estate market is currently a Balanced Market. Homes are retaining 99% of their value (Sale Price to List Price Ratio). With 370 active listings and 211 closed sales this month, inventory remains at 1.2 months of supply. Trends over the last half-year show median values moving down by 4%, while Average Days on Market holding steady. Listings in Chesapeake (city) are moving 17 days faster than the Virginia average.
Top Listing & Buyer's Agents in Chesapeake (city) County, VA
Detached Homes
Entry Level Detached Home Market Trends Median Price Market Trend The average price in the Entry Level Detached Home segment has risen by 14% over the last 6 months. Days On Market Avg. Market Trend Lower is better Days on market for Entry Level Detached Home is increasing, with homes now staying on market for 41 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Entry Level Detached Home market is shifting towards buyers, with the Sale Price to List Price Ratio now at 95%.
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Mid-Market Detached Home Market Trends Median Price Market Trend The average price in the Mid-Market Detached Home segment has softened by 6% over the last 6 months. Days On Market Avg. Market Trend Lower is better Days on market for Mid-Market Detached Home is decreasing, with homes now staying on market for 43 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Negotiation leverage in Mid-Market Detached Home has stabilized over the last 6 months, with sellers receiving 100%.
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High-End Detached Home Market Trends Median Price Market Trend The average price in the High-End Detached Home segment has risen by 3% over the last 6 months. Days On Market Avg. Market Trend Lower is better Days on market for High-End Detached Home is increasing, with homes now staying on market for 52 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Negotiation leverage in High-End Detached Home has stabilized over the last 6 months, with sellers receiving 100%.
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Ultra-Luxury Detached Home Market Trends Median Price Market Trend Prices in the Ultra-Luxury Detached Home tier have stabilized over the last 6 months. Days On Market Avg. Market Trend Lower is better Days on market for Ultra-Luxury Detached Home is increasing, with homes now staying on market for 55 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Ultra-Luxury Detached Home market is shifting towards buyers, with the Sale Price to List Price Ratio now at 97%.
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Condo/Co-op
Entry Level Condo/Co-op Market Trends Median Price Market Trend The average price in the Entry Level Condo/Co-op segment has softened by 14% over the last 6 months. Days On Market Avg. Market Trend Lower is better Days on market for Entry Level Condo/Co-op is increasing, with homes now staying on market for 53 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Entry Level Condo/Co-op market is shifting towards buyers, with the Sale Price to List Price Ratio now at 98%.
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Mid-Market Condo/Co-op Market Trends Median Price Market Trend The average price in the Mid-Market Condo/Co-op segment has risen by 3% over the last 6 months. Days On Market Avg. Market Trend Lower is better Days on market for Mid-Market Condo/Co-op is increasing, with homes now staying on market for 55 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Negotiation leverage in Mid-Market Condo/Co-op has stabilized over the last 6 months, with sellers receiving 100%.
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High-End Condo/Co-op Market Trends Median Price Market Trend The average price in the High-End Condo/Co-op segment has softened by 23% over the last 3 months. Days On Market Avg. Market Trend Lower is better Days on market for High-End Condo/Co-op is increasing, with homes now staying on market for 68 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the High-End Condo/Co-op market is shifting towards buyers, with the Sale Price to List Price Ratio now at 99%.
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Ultra-Luxury Condo/Co-op Market Trends Median Price Market Trend The Ultra-Luxury Condo/Co-op tier commands a price of $883K. Days On Market Avg. Market Trend Lower is better Condo/Co-op homes in the Ultra-Luxury range average 95 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Ultra-Luxury Condo/Co-op assets receive 98% of list price.
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Townhomes
Entry Level Townhome Market Trends Median Price Market Trend The average price in the Entry Level Townhome segment has softened by 8% over the last 6 months. Days On Market Avg. Market Trend Lower is better Days on market for Entry Level Townhome is increasing, with homes now staying on market for 51 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Entry Level Townhome market is shifting towards buyers, with the Sale Price to List Price Ratio now at 93%.
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Mid-Market Townhome Market Trends Median Price Market Trend The average price in the Mid-Market Townhome segment has risen by 4% over the last 6 months. Days On Market Avg. Market Trend Lower is better Days on market for Mid-Market Townhome is increasing, with homes now staying on market for 44 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Mid-Market Townhome market is shifting towards buyers, with the Sale Price to List Price Ratio now at 100%.
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Multi-Family (2-4 Unit)
Entry Level Multi-Family (2-4 Unit) Market Trends Median Price Market Trend The average price in the Entry Level Multi-Family (2-4 Unit) segment has softened by 18% over the last 2 months. Days On Market Avg. Market Trend Lower is better Days on market for Entry Level Multi-Family (2-4 Unit) is decreasing, with homes now staying on market for 29 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Entry Level Multi-Family (2-4 Unit) market is shifting towards buyers, with the Sale Price to List Price Ratio now at 81%.
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Mid-Market Multi-Family (2-4 Unit) Market Trends Median Price Market Trend Prices in the Mid-Market Multi-Family (2-4 Unit) tier have stabilized over the last 4 months. Days On Market Avg. Market Trend Lower is better Days on market for Mid-Market Multi-Family (2-4 Unit) is decreasing, with homes now staying on market for 16 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Mid-Market Multi-Family (2-4 Unit) market is strengthening, with the Sale Price to List Price Ratio now at 104%.
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High-End Multi-Family (2-4 Unit) Market Trends Median Price Market Trend The High-End Multi-Family (2-4 Unit) tier commands a price of $395K. Days On Market Avg. Market Trend Lower is better Multi-Family (2-4 Unit) homes in the High-End range average 129 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of High-End Multi-Family (2-4 Unit) assets receive 100% of list price.
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Chesapeake (city) Real Estate Market Trends October 2026
Inventory Breakdown by Segment
| Property Type | Entry Level | High-End | Mid-Market | Ultra-Luxury | Total |
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| Condo/Co-op | 10 | 9 | 59 | — | 78 |
| Detached Home | 9 | 101 | 147 | 17 | 274 |
| Townhome | 5 | — | 13 | — | 18 |
Market Insights & FAQ
How is the real estate market in Chesapeake (city) County, VA performing right now?
The data indicates a high-intensity environment in Chesapeake (city) County, 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.
What are the current pricing trends for Chesapeake (city) County, VA real estate?
Currently, $410,000 represents the median entry point in Chesapeake (city) County, VA. Over the past half-year, home values in Chesapeake (city) have moved downward by approximately 4% based on regional transaction data.
Are sellers in Chesapeake (city) County, VA getting their full asking price?
Buyers have room for negotiation in Chesapeake (city) County, VA, with a Sale Price to List Price Ratio of 99.2%. On average, properties in Chesapeake (city) are transitioning from active to sold status in 45 days.
Who is the best agent to sell my home in Chesapeake (city)?
Based on closed transaction data, Shawn Burr ranks at the top of our Chesapeake (city) 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.
How does the Chesapeake (city) County, VA market compare to Virginia trends?
Chesapeake (city) County, VA maintains a distinct profile within the broader Virginia region. Median home values are currently 0% lower than the regional average, reflecting the unique demand and inventory dynamics of Chesapeake (city).
Who is a top listing agent for Entry Level Detached Home homes in Chesapeake (city) County, VA?
If you're selling a Entry Level Detached Home in Chesapeake (city) County, 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.
Which agent is best for buying a Entry Level Detached Home in Chesapeake (city) County, VA?
Our data flags Aaron Cano as a top buyer's advocate for Entry Level Detached Home properties in Chesapeake (city) County, 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.
Who is a top listing agent for Mid-Market Detached Home homes in Chesapeake (city) County, VA?
Among agents with recent closings in the Mid-Market Detached Home space, Jenny Lovell has the strongest performance metrics in Chesapeake (city) County, 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.
Who is a top listing agent for Mid-Market Condo/Co-op homes in Chesapeake (city) County, VA?
Beth Wiegan has been particularly active in Chesapeake (city)'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.
Which agent is best for buying a Mid-Market Townhome in Chesapeake (city) County, VA?
Conner Walters has a strong showing as a buyer's agent in Chesapeake (city)'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.
Which agent is best for buying a High-End Detached Home in Chesapeake (city) County, VA?
For those looking to purchase a High-End Detached Home in Chesapeake (city) County, VA, Matthew Salway has the deal history to support the choice. For buyers competing in the High-End Detached Home market in Chesapeake (city) County, VA, their track record indicates speed and negotiating strength that outperforms the segment baseline on both counts.
Which agent is best for buying a Mid-Market Detached Home in Chesapeake (city) County, VA?
Navigating Chesapeake (city)'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.
Who is a top listing agent for High-End Detached Home homes in Chesapeake (city) County, VA?
Emily Berry specializes in High-End Detached Home properties and has built a measurable edge in Chesapeake (city)'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.