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Chessie Calloway

(She/Her/Hers)
Smith & Co with RE/MAX Executive
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Recent Sales

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  • $286,990
    3 bd2 ba1,219 sqft Greensboro, MD
    3 bd2 ba1,219 sqft
    Greensboro, MD
    Sold 4 days ago
    Buyer
    133 Hobbs St, Greensboro, MD, 21639
  • $435,000
    3 bd2 ba2,040 sqft Bridgeville, DE
    3 bd2 ba2,040 sqft
    Bridgeville, DE
    Sold 2 months ago
    Buyer
    5215 Hartzell Rd, Bridgeville, DE, 19933
  • $191,000
    2 bd1 ba1,269 sqft Chestertown, MD
    2 bd1 ba1,269 sqft
    Chestertown, MD
    Sold 4 months ago
    Buyer
    21317 Persimmon Dr, Chestertown, MD, 21620
  • $325,000
    4 bd3 ba2,040 sqft Cambridge, MD
    4 bd3 ba2,040 sqft
    Cambridge, MD
    Sold 7 months ago
    Buyer
    1638 Terrapin Cir, Cambridge, MD, 21613
  • $325,000
    2 bd2 ba1,186 sqft Ocean View, DE
    2 bd2 ba1,186 sqft
    Ocean View, DE
    Sold 9 months ago
    Buyer
    30224 Driftwood Ct Unit 7502, Ocean View, DE, 19970
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7
Sales last 12 months
27
Total sales
$191K-$584K
Price range
$338K
Average price

Get to know Chessie Calloway

Real Estate Agent/Salesperson

Specialties
Buyer's AgentListing Agent
6 Years of experience

Chessie Calloway's listings & sales (27)

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For Rent
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Sold (27)

Chessie Calloway's reviews (16)

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  • 5.0
    • 12/30/2025
    • Nolan Adams

    Bought and sold a Single Family home in 2025 in Hurlock, MD.

    Chessie did an excellent job assisting us with both transactions, sale/purchase of our old and new house. She is very responsive, and available to her clients for showing...
    Chessie did an excellent job assisting us with both transactions, sale/purchase of our old and new house. She is very responsive, ...
    5.0
    • 7/31/2025
    • Huskydoggie2

    Bought a Single Family home in 2025 in Cambridge, MD.

    Chessie did an an outstanding job helping us find our home. We moved from another state which can be challenging but Chessie was there every step of the way with us and w...
    Chessie did an an outstanding job helping us find our home. We moved from another state which can be challenging but Chessie was t...
  • 5.0
    • 11/20/2024
    • Natalie Calloway

    Bought a Single Family home in 2024 in Denton, MD.

    Chessie absolutely understood everything we were looking for in a home and helped us to find it! Once we found it, she did everything in her power to make it ours. Chessi...
    Chessie absolutely understood everything we were looking for in a home and helped us to find it! Once we found it, she did everyth...
    5.0
    • 11/14/2024
    • kdmclm

    Bought a Townhouse home in 2024 in Denton, MD.

    Chessie has been with us not only through a rental process, but also buying a home. Both times we have worked with Chessie, we have been nothing but impressed with her pr...
    Chessie has been with us not only through a rental process, but also buying a home. Both times we have worked with Chessie, we hav...
  • 5.0
    • 6/25/2024
    • jesswantz

    Bought a Single Family home in 2024 in Church hill, MD.

    Chessie is the sweetest human on the planet and was so wonderful to work with through this journey. She made the entire process from search to closing completely seamless...
    Chessie is the sweetest human on the planet and was so wonderful to work with through this journey. She made the entire process fr...
    5.0
    • 2/27/2024
    • devdelange9

    Consulted me on buying or selling a home in Chestertown, MD.

    Chessie is an amazing advocate. She is prepared and knowledgeable about the local area, and always willing to find out more if needed. She is detail oriented and takes on...
    Chessie is an amazing advocate. She is prepared and knowledgeable about the local area, and always willing to find out more if nee...
  • 5.0
    • 11/2/2023
    • clalone2013

    Bought a Single Family home in 2023 in Sudlersville, MD.

    Chessie was very helpful during the home searching and home buying process. Was always able to answer questions and would ask her team if she couldn’t answer the question...
    Chessie was very helpful during the home searching and home buying process. Was always able to answer questions and would ask her ...
    5.0
    • 11/2/2023
    • user2251093

    Bought a Single Family home in 2023 in Chestertown, MD.

    Great communication and very professional! Very accommodating to my changing schedule. Very knowledgeable about the home buying process and patient with me, took her ti...
    Great communication and very professional! Very accommodating to my changing schedule. Very knowledgeable about the home buying ...
  • 5.0
    • 9/25/2023
    • Christiansheilds1996

    Bought a home in 2023.

    As first home buyers who had previous negative experiences trying to purchase a home in the past, we were very cautious of who we were going to enter the process with thi...
    As first home buyers who had previous negative experiences trying to purchase a home in the past, we were very cautious of who we ...
    5.0
    • 5/11/2023
    • user1372030

    Bought a home in 2023.

    Chessie made the process of buying my new home throughout the entire process from the beginning to the end, even the financial piece by communicating timely with my lende...
    Chessie made the process of buying my new home throughout the entire process from the beginning to the end, even the financial pie...
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    Chessie Calloway

    (She/Her/Hers)
    Smith & Co with RE/MAX Executive
    7sales last 12 months
    27total sales
    $191K-$584Kprice range
    $338Kaverage price
    6years of experience