Top Realtors and Real Estate Agents in Chestertown, MD

    Rankings based on verified MLS transaction data. No pay-to-play.

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    Michael Rosendale profile picture
    BadgeTop Agent

    (7)

    Michael Rosendale

    Rosendale Realty

    36 Years of experience

    10+ Sales in the last 12 months

    Top 0.8%

    in Chestertown, MD

    $1.05B

    All-Time Sales

    $200K - $2.9M

    Price Range

    Miles Norris profile picture
    BadgeTop Agent

    (24)

    Miles Norris

    Select Land And Homes Inc

    10 Years of experience

    1+ Sales in the last 12 months

    Top 1.2%

    in Chestertown, MD

    $65.6M

    All-Time Sales

    $350K - $5M

    Price Range

    6%

    Negotiated Off List

    Crystal Smith profile picture
    BadgeTop Agent

    (30)

    Crystal Smith

    RE/MAX Executive

    21 Years of experience

    107+ Sales in the last 12 months

    Top 4.8%

    in Chestertown, MD

    $266.5M

    All-Time Sales

    $310K - $1.5M

    Price Range

    4%

    Negotiated Off List

    Erin Anderson profile picture
    BadgeTop Agent

    (77)

    Erin Anderson

    Chesapeake Real Estate Associates LLC

    9 Years of experience

    34+ Sales in the last 12 months

    Top 5.2%

    in Chestertown, MD

    $85.2M

    All-Time Sales

    $260K - $2.3M

    Price Range

    6%

    Negotiated Off List

    Dale Hunter Jr profile picture
    BadgeTop Agent

    (47)

    Dale Hunter Jr

    Bayside Realty

    31 Years of experience

    56+ Sales in the last 12 months

    Top 8.4%

    in Chestertown, MD

    $109.7M

    All-Time Sales

    $210K - $4M

    Price Range

    8%

    Negotiated Off List

    Joseph A Zang III profile picture
    BadgeTop Agent

    (20)

    Joseph A Zang III

    RE/MAX Chesapeake

    20 Years of experience

    21+ Sales in the last 12 months

    Top 8.8%

    in Chestertown, MD

    $86.2M

    All-Time Sales

    $260K - $5.5M

    Price Range

    Laura Anderson profile picture
    BadgeTop Agent

    (148)

    Laura Anderson

    Coldwell Banker Realty

    13 Years of experience

    20+ Sales in the last 12 months

    Top 11.2%

    in Chestertown, MD

    $110.2M

    All-Time Sales

    $270K - $1.4M

    Price Range

    Gary Bright profile picture
    BadgeTop Agent

    (24)

    Gary Bright

    Tesla Realty Group

    14 Years of experience

    15+ Sales in the last 12 months

    $50.6M

    All-Time Sales

    $230K - $1.1M

    Price Range

    8%

    Negotiated Off List

    Richard Harrington profile picture
    BadgeTop Agent

    (43)

    Richard Harrington

    RE/MAX

    46 Years of experience

    4+ Sales in the last 12 months

    $66.4M

    All-Time Sales

    $240K - $1.2M

    Price Range

    219

    Total Number Of Homes Sold

    Retha Arrabal profile picture

    (35)

    Retha Arrabal

    Doug Ashley Realtors Llc

    Top 0.4%

    in Chestertown, MD

    192

    Sold in Chestertown, MD

    1

    Sold in last 18 months

    Michele Palmer profile picture

    (28)

    Michele Palmer

    Doug Ashley Realtors Llc

    Top 1.6%

    in Chestertown, MD

    75

    Sold in Chestertown, MD

    3

    Sold in last 18 months

    Mary Carlisle profile picture

    (13)

    Mary Carlisle

    Coldwell Banker Chesapeake Rea

    Top 2%

    in Chestertown, MD

    59

    Sold in Chestertown, MD

    Jody Baker profile picture

    (26)

    Jody Baker

    Cross Street Realtors Llc

    Top 2.4%

    in Chestertown, MD

    58

    Sold in Chestertown, MD

    2

    Sold in last 18 months

    Liddy Campbell profile picture

    (11)

    Liddy Campbell

    Ttr Sotheby\'s International Realty

    Top 2.8%

    in Chestertown, MD

    54

    Sold in Chestertown, MD

    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.

    Rankings reviewed by Kevin Stuteville, Licensed Florida Real Estate Broker (License BK3068131), Founder of EffectiveAgents.

    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.

    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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