Top Realtors and Real Estate Agents in Chesapeake, VA
Rankings based on verified MLS transaction data. Last updated August 2026. No pay-to-play.
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Top Agent
Top 0.13%
in Chesapeake, VA
$1.01B
All-Time Sales
$230K - $2.9M
Price Range
6%
Negotiated Off List
Top Agent
(182)
Megan Anderson
Keller Williams Town Center LLC
12 Years of experience
242+ Sales in the last 12 months
Top 0.26%
in Chesapeake, VA
$513.1M
All-Time Sales
$260K - $1.7M
Price Range
3%
Negotiated Off List
Top AgentTop 0.33%
in Chesapeake, VA
$511.2M
All-Time Sales
$250K - $2.7M
Price Range
5%
Negotiated Off List
Top Agent(116)
Barry Jenkins
Better Homes and Gardens Real Estate
24 Years of experience
3+ Sales in the last 12 months
Top 0.59%
in Chesapeake, VA
$152M
All-Time Sales
$170K - $1.2M
Price Range
Top AgentTop 0.72%
in Chesapeake, VA
$118.1M
All-Time Sales
$280K - $1.4M
Price Range
Top AgentTop 0.79%
in Chesapeake, VA
$343.6M
All-Time Sales
$270K - $1.4M
Price Range
3%
Negotiated Off List
Top Agent(9)
Charlene Wales
Better Homes and Gardens Real Estate
22 Years of experience
89+ Sales in the last 12 months
Top 1.12%
in Chesapeake, VA
$189.7M
All-Time Sales
$250K - $1.5M
Price Range
2%
Negotiated Off List
Top Agent$106.5M
All-Time Sales
$180K - $1.3M
Price Range
118
Sold in Chesapeake, VA
Top AgentTop 1.25%
in Chesapeake, VA
$175.6M
All-Time Sales
$260K - $1M
Price Range
3%
Negotiated Off List
Top AgentTop 1.38%
in Chesapeake, VA
$128.3M
All-Time Sales
$220K - $2.4M
Price Range
6%
Negotiated Off List
Top Agent$532M
All-Time Sales
$260K - $4.1M
Price Range
7%
Negotiated Off List
Top Agent(122)
CHERYL TALBOT
Berkshire Hathaway HomeServices RW Towne Realty
33 Years of experience
10+ Sales in the last 12 months
Top 1.64%
in Chesapeake, VA
$172.5M
All-Time Sales
$190K - $2.6M
Price Range
Top Agent(81)
John King
Berkshire Hathaway Home Services RW Towne Realty
13 Years of experience
40+ Sales in the last 12 months
Top 1.71%
in Chesapeake, VA
$144.2M
All-Time Sales
$270K - $1.1M
Price Range
Top AgentTop 1.84%
in Chesapeake, VA
$125.5M
All-Time Sales
$230K - $2.1M
Price Range
5%
Negotiated Off List
Top Agent(78)
Christine Cahoon
Keller Williams Coastal Virginia Chesapeake
20 Years of experience
7+ Sales in the last 12 months
Top 2.04%
in Chesapeake, VA
$169.7M
All-Time Sales
$260K - $1.8M
Price Range
4%
Negotiated Off List
Top AgentTop 2.1%
in Chesapeake, VA
$134.1M
All-Time Sales
$250K - $1.2M
Price Range
4%
Negotiated Off List
Top AgentTop 2.5%
in Chesapeake, VA
$86.6M
All-Time Sales
$240K - $2.1M
Price Range
4%
Negotiated Off List
Top AgentTop 2.56%
in Chesapeake, VA
$166M
All-Time Sales
$220K - $890K
Price Range
Top AgentTop 2.63%
in Chesapeake, VA
$111.5M
All-Time Sales
$250K - $890K
Price Range
Top AgentTop 2.82%
in Chesapeake, VA
$82.3M
All-Time Sales
$320K - $920K
Price Range
Top AgentTop 2.95%
in Chesapeake, VA
$87.8M
All-Time Sales
$200K - $1.9M
Price Range
Top Agent(53)
Richard Zapata
Keller Williams Coastal Virginia
8 Years of experience
66+ Sales in the last 12 months
Top 3.02%
in Chesapeake, VA
$76.8M
All-Time Sales
$270K - $1.3M
Price Range
Top AgentTop 3.41%
in Chesapeake, VA
$36.5M
All-Time Sales
$180K - $560K
Price Range
Top AgentTop 3.55%
in Chesapeake, VA
$98.3M
All-Time Sales
$290K - $1.5M
Price Range
3%
Negotiated Off List
Top AgentTop 3.61%
in Chesapeake, VA
$208.1M
All-Time Sales
$210K - $910K
Price Range
4%
Negotiated Off List
Chesapeake Housing Market Trends
Homes in Chesapeake take a median 28 days to sell, go for 100.22% of asking, prices are up 5.7% from a year ago. Verified MLS market data through August 2026.
Market temperature
Seller's market
2.1 months of supply. Under 3 favors sellers, over 6 favors buyers.
What homes sell for
$446,704
median sale price
How fast they sell
28 days
median time on market
Supply and competition
2.1 months
of supply on the market
The numbers speak
for Chesapeake.
Every agent above earned their place with closed sales, not advertising. Tell us about your home and our algorithm picks the Chesapeake agents whose results fit it.
Chesapeake agents analyzed for these rankings
days faster: top-ranked agents sell in 15 days, the Chesapeake market in 28
median sale price in Chesapeake
Do Top Chesapeake Agents Sell Faster?
The 25 top-ranked agents on EffectiveAgents in Chesapeake sell in a median of 15 days, compared with the Chesapeake market median of 28 days on market.
About 13 days faster (46% quicker than the Chesapeake market)
Median days to sale reported by the top-ranked Chesapeake agents on EffectiveAgents, compared with the Chesapeake market median days on market. Agent figures reflect each agent's reported sales history.
When Is the Best Time to Sell a House in Chesapeake?
Based on the last 24 months of verified MLS market data, homes in Chesapeake sell fastest and closest to asking when they go under contract in May. To hit that window, plan to list around April.
Median days on market by month (shorter is faster)
May
Best month to sell
26 days
Typical time on market
100.4%
Of asking price
Seasonal averages from the last 24 months of Chesapeake, VA sales. Individual results vary with price, condition, and how the broader market moves. A local agent can pinpoint the right timing for your home.
Home Values by Neighborhood in Chesapeake
Median home values across Chesapeake, VA neighborhoods, with the change over the past five years.
Great Bridge
+29% over 5 years
$417K
Great Bridge East
+27% over 5 years
$409K
Deep Creek South
+31% over 5 years
$401K
Western Branch South
+30% over 5 years
$349K
Greenbrier East
+26% over 5 years
$339K
Western Branch North
+33% over 5 years
$301K
Greenbrier West
+28% over 5 years
$283K
Deep Creek North
+37% over 5 years
$269K
Indian River
+31% over 5 years
$244K
Median home values from verified market data; five-year change shown where available.
What These Numbers Mean for Chesapeake Buyers and Sellers
Chesapeake currently reads as a seller-tilted market, and the competitive indicators above the Housing Market Trends module explain why. With only 2.1 months of supply and 51.4% of homes leaving the market within two weeks, well-priced listings move quickly. The sale-to-list ratio sits at 100.22%, and 34.9% of homes closed above asking price, which tells buyers that lowball offers rarely succeed on desirable inventory. At the same time, 24.3% of active listings recorded a price reduction, a signal that overpriced or dated homes still stall regardless of the broader tempo.
For buyers, the practical takeaway is to separate the two segments. On fresh listings priced near $446,704 (roughly $225.12 per square foot), competitive terms and speed matter more than deep discounting. On homes that have logged a price drop, there is more room to negotiate. The median home sells in 28 days, so tracking how long a property has sat is one of the clearest leverage cues available.
For sellers, the data supports confident but realistic pricing. Homes that hit the market correctly are rewarded, but the 24.3% price-drop share shows that aspirational pricing invites the slower path. With 1,291 new listings and 1,078 pending sales monthly, the market is absorbing supply steadily rather than overheating. Chesapeake has 1,523 licensed agents, and skill in reading these segment-by-segment signals is what separates outcomes. The sections below explain how EffectiveAgents narrows that field to verified performers who understand local pricing dynamics.
What Chesapeake Home Prices Mean for You
Understanding the true cost of homeownership in Chesapeake goes beyond the listing price. These calculators break down what today's market conditions mean for your budget, your timeline, and your negotiating position.
| Median home price | $446,704 |
| Down payment (20%) | $89,341 |
| Loan amount | $357,363 |
| Monthly payment (PITI) | $3,069 |
Based on 28% debt-to-income ratio, 6.95% mortgage rate (as of September 17, 2026), 30-year fixed loan, 1.15% property tax rate, $275/mo insurance. Actual requirements vary by lender.
Based on $446,704 median home price with 20% down at 6.95% (as of September 17, 2026) for 30 years. Property tax estimated at 1.15% of home value.
Year-over-year data reflects the most recent rolling period from Chesapeake MLS records. Prior year values calculated from current figures and published YoY changes.
What to Look for in a Chesapeake Realtor
Choosing an agent on name recognition alone overlooks what actually drives results: verified transaction history and negotiation outcomes. In a market where 34.9% of homes close above list and the sale-to-list ratio holds at 100.22%, an agent's ability to structure a competitive offer or defend a list price carries measurable weight. Among the 1,523 licensed agents in Chesapeake, EffectiveAgents has ranked 152 based on analyzed performance data. The top-ranked agent, Brian Wurst at A Better Way Realty, has closed 3,366 transactions with $968.4M in all-time sales volume, experience that spans neighborhoods from Great Bridge and Greenbrier East to South Norfolk. That depth matters because pricing dynamics in Western Branch North differ from those in Deep Creek South, and an agent who has worked across them reads leverage more accurately. Beyond raw volume, review patterns provide context: 525 reviews across a long track record indicate consistency rather than a handful of standout closings, a signal worth weighing alongside transaction counts when you compare candidates.
How We Rank Chesapeake Real Estate Agents
Our rankings are built from verified MLS transaction data, not advertising spend. For every agent we analyze more than fifteen performance signals, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results (how far above or below list price an agent's clients actually close), price-point fit, and verified reviews. The agents shown first are those whose verified results put them at the top of the Chesapeake market today.
Agents cannot pay for placement in these rankings. The underlying data refreshes as new closed transactions are reported, so rankings shift with real market performance. Learn how we rank agents.
1,523
agents analyzed
15+
performance signals
$0
paid for placement
Rankings reviewed by Kevin Stuteville, Licensed Florida Real Estate Broker (License BK3068131), Founder of EffectiveAgents.
Data last updated: August 2026
Chesapeake Real Estate Agent FAQs
Who is the best real estate agent in Chesapeake, VA?
The top-ranked agent in Chesapeake, VA is Brian Wurst at A Better Way Realty, with 3,366 closed transactions, 525 reviews, and $968.4M in all-time sales volume. EffectiveAgents identifies leading agents through a data-driven methodology that analyzes verified transaction history, closing performance, and client review patterns rather than advertising spend. Of 1,523 licensed agents locally, only 152 meet the ranking criteria. The best fit depends on your neighborhood and price point, so comparing several ranked agents is the recommended approach.
How were these Chesapeake real estate agents ranked?
Rankings are built from verified MLS transaction data. We analyze more than fifteen performance signals for every agent, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results, price-point fit, and verified reviews. Agents cannot pay for placement.
How many real estate agents are in Chesapeake?
Our data covers 1,523 real estate agents serving the Chesapeake area. The count represents agents with transaction activity recorded in our Chesapeake market data, not simply everyone holding a license.
What does the median sale price in Chesapeake mean for sellers?
Chesapeake's median sale price is $446,704 as of August 2026. Half of recent sales closed above that figure and half below. It is a useful baseline for understanding the market, but an experienced local agent will price your home against comparable recent sales in your neighborhood, not the citywide median.
How long does it take to sell a house in Chesapeake?
The median home in Chesapeake sells in about 28 days, and that timeline has held roughly steady with a +1 day change year over year. Actual time to sell depends on pricing accuracy, condition, and location, since 51.4% of homes go under contract within two weeks while 24.3% of listings require a price reduction first. Homes priced correctly against comparable sales and prepared for market tend to move fastest, while aspirational pricing extends the timeline considerably.
Does it cost anything to use EffectiveAgents?
No. EffectiveAgents is free for home buyers and sellers, with no obligation to work with any agent we match you with.
Do agents pay to be ranked or featured?
No. Agents cannot pay for placement anywhere in these rankings. Positions are earned from verified transaction performance only.
What commission do Chesapeake realtors charge?
Commissions are negotiable and vary by agent, service level, and transaction. There is no set rate, and recent industry changes have made commission structures more flexible than ever. Discuss the structure directly with your agent before signing a listing or buyer agreement.
Should I use a local Chesapeake agent or a national brand?
The individual agent matters more than the brand on the sign. Offices within the same national franchise vary widely in performance, and the agent you hire, not the logo, prices your home, negotiates your contract, and manages your closing. A strong local agent brings firsthand knowledge of Chesapeake neighborhoods, pricing patterns, and buyer activity. Compare agents on verified local results such as recent sales, days on market, and negotiation outcomes rather than name recognition.
What questions should I ask a Chesapeake realtor before hiring them?
Ask how many homes they have closed in Chesapeake in the past year, what their average sale-to-list ratio is, and how much of their business is in your neighborhood and price range. Ask how they will market your home or find you listings, and how often they will communicate. Strong agents answer with specifics. Verified transaction data is the fastest way to confirm what you hear.
Top Realtors by Neighborhood in Chesapeake, VA
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