Top Realtors and Real Estate Agents in Chestertown, MD
Rankings based on verified MLS transaction data. Last updated September 2026. No pay-to-play.
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Top Agent
Top 0.4%
in Chestertown, MD
$1.05B
All-Time Sales
$200K - $2.9M
Price Range
Top Agent$65.6M
All-Time Sales
$350K - $5M
Price Range
6%
Negotiated Off List
Top AgentTop 4.8%
in Chestertown, MD
$277.6M
All-Time Sales
$310K - $1.5M
Price Range
4%
Negotiated Off List
Top AgentTop 5.2%
in Chestertown, MD
$162.1M
All-Time Sales
$270K - $2.4M
Price Range
5%
Negotiated Off List
Top Agent
(79)
Erin Anderson
Chesapeake Real Estate Associates LLC
9 Years of experience
41+ Sales in the last 12 months
Top 5.6%
in Chestertown, MD
$91.6M
All-Time Sales
$260K - $2.4M
Price Range
6%
Negotiated Off List
Top AgentTop 9.2%
in Chestertown, MD
$116.8M
All-Time Sales
$210K - $4M
Price Range
8%
Negotiated Off List
Top AgentTop 9.6%
in Chestertown, MD
$87.5M
All-Time Sales
$260K - $5.5M
Price Range
Top Agent(22)
Dee Dee Miller
Long and Foster Real Estate Inc
27 Years of experience
65+ Sales in the last 12 months
Top 12.4%
in Chestertown, MD
$311.6M
All-Time Sales
$400K - $5M
Price Range
6%
Negotiated Off List
Top Agent(807)
Robert Lucido
Keller Williams Lucido Agency
50 Years of experience
970+ Sales in the last 12 months
$4.82B
All-Time Sales
$390K - $14M
Price Range
5%
Negotiated Off List
Top Agent$111.7M
All-Time Sales
$270K - $1.4M
Price Range
3
Sold in Chestertown, MD
Top Agent(31)
Melissa Tippett
TTR Sotheby's International Realty
22 Years of experience
13+ Sales in the last 12 months
$81.1M
All-Time Sales
$310K - $2.1M
Price Range
7%
Negotiated Off List
Top Agent$204.8M
All-Time Sales
$160K - $1.5M
Price Range
2
Sold in Chestertown, MD
Top AgentTop 14%
in Chestertown, MD
$127.8M
All-Time Sales
$250K - $1.5M
Price Range
7%
Negotiated Off List
Top AgentTop 14.4%
in Chestertown, MD
$253.5M
All-Time Sales
$240K - $3.7M
Price Range
9%
Negotiated Off List
Top Agent(37)
Adam Murphy
ReMax Realty Centre - The Fox Team
10 Years of experience
48+ Sales in the last 12 months
Top 15.2%
in Chestertown, MD
$87.3M
All-Time Sales
$380K - $2.1M
Price Range
4%
Negotiated Off List
Top Agent$290.8M
All-Time Sales
$510K - $2.7M
Price Range
5%
Negotiated Off List
Top Agent$51.7M
All-Time Sales
$230K - $1.1M
Price Range
8%
Negotiated Off List
Top Agent$80.2M
All-Time Sales
$360K - $1.3M
Price Range
177
Total Number Of Homes Sold
Top Agent$67M
All-Time Sales
$240K - $1.2M
Price Range
221
Total Number Of Homes Sold
Top Agent$160.4M
All-Time Sales
$1.3M - $140M
Price Range
96
Total Number Of Homes Sold
Chestertown Housing Market Trends
Homes in Chestertown take a median 74 days to sell, go for 99.77% of asking, prices are up 6.8% from a year ago. Verified MLS market data through September 2026.
Market temperature
Balanced market
4.9 months of supply. Under 3 favors sellers, over 6 favors buyers.
What homes sell for
$323,846
median sale price
How fast they sell
74 days
median time on market
Supply and competition
4.9 months
of supply on the market
The numbers speak
for Chestertown.
Every agent above earned their place with closed sales, not advertising. Tell us about your home and our algorithm picks the Chestertown agents whose results fit it.
Chestertown agents analyzed for these rankings
days faster: top-ranked agents sell in 22 days, the Chestertown market in 74
median sale price in Chestertown
Do Top Chestertown Agents Sell Faster?
The 20 top-ranked agents on EffectiveAgents in Chestertown sell in a median of 22 days, compared with the Chestertown market median of 74 days on market.
About 52 days faster (70% quicker than the Chestertown market)
Median days to sale reported by the top-ranked Chestertown agents on EffectiveAgents, compared with the Chestertown market median days on market. Agent figures reflect each agent's reported sales history.
When Is the Best Time to Sell a House in Chestertown?
Based on the last 24 months of verified MLS market data, homes in Chestertown sell fastest and closest to asking when they go under contract in October. To hit that window, plan to list around September.
Median days on market by month (shorter is faster)
October
Best month to sell
44 days
Typical time on market
98.2%
Of asking price
Seasonal averages from the last 24 months of Chestertown, MD sales. Individual results vary with price, condition, and how the broader market moves. A local agent can pinpoint the right timing for your home.
How We Rank Chestertown 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 Chestertown 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.
250
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: September 2026
Chestertown Real Estate Agent FAQs
How were these Chestertown 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 Chestertown?
Our data covers 250 real estate agents serving the Chestertown area. The count represents agents with transaction activity recorded in our Chestertown market data, not simply everyone holding a license.
What does the median sale price in Chestertown mean for sellers?
Chestertown's median sale price is $323,846 as of September 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.
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 Chestertown 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 Chestertown 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 Chestertown 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 Chestertown realtor before hiring them?
Ask how many homes they have closed in Chestertown 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 Zip Code in Chestertown, MD
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