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Chessie Calloway

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

Recent Sales

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  • $325,000
    2 bd2 ba1,186 sqft Ocean View, DE
    2 bd2 ba1,186 sqft
    Ocean View, DE
    Sold 3 months ago
    Buyer
    30224 Driftwood Ct UNIT 7502, Ocean View, DE, 19970
  • $338,000
    3 bd2 ba1,224 sqft Georgetown, DE
    3 bd2 ba1,224 sqft
    Georgetown, DE
    Sold 3 months ago
    Buyer
    24989 Baker Ln, Georgetown, DE, 19947
  • $380,000
    4 bd3 ba2,460 sqft Millington, MD
    4 bd3 ba2,460 sqft
    Millington, MD
    Sold 3 months ago
    Buyer
    303 Carville Dr, Millington, MD, 21651
  • $202,500
    2 bd1 ba775 sqft Delaware City, DE
    2 bd1 ba775 sqft
    Delaware City, DE
    Sold 1 year ago
    Seller
    307 5th St, Delaware City, DE, 19706
  • $260,000
    3 bd2 ba1,075 sqft Middletown, DE
    3 bd2 ba1,075 sqft
    Middletown, DE
    Sold 1 year ago
    Buyer
    58 Cole Blvd, Middletown, DE, 19709
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3
Sales last 12 months
8
Total sales
$45K-$584K
Price range
$316K
Average price

Get to know Chessie Calloway

Real Estate Agent/Salesperson

Specialties
Buyer's AgentListing Agent
5 Years of experience

Chessie Calloway's listings & sales (9)

For Sale
For Rent
Sold
This map can show the most recent 100 listings and 100 sales. Review all listings and sales below.

For Sale (1)

Sold (8)

Address
Sold date
Closing price
Represented
Flag Sale
5/16/2025$325,000Buyer
5/9/2025$338,000Buyer
4/30/2025$380,000Buyer
7/19/2024$202,500Seller
7/15/2024$260,000Buyer

Chessie Calloway's reviews (15)

Write a review
  • Highly likely to recommend5.05.0

    7/31/2025 - Huskydoggie2
    Bought a Single Family home in 2025 in Cambridge, MD.

    Local knowledge
    Process expertise
    Responsiveness
    Negotiation skills
    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 was always available to answer our questions.
  • Highly likely to recommend5.05.0

    11/20/2024 - ncalloway1010
    Bought a Single Family home in 2024 in Denton, MD.

    Local knowledge
    Process expertise
    Responsiveness
    Negotiation skills
    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. Chessie is outgoing, ambitious, and the kindest person you will ever meet. Couldn’t im...
  • Highly likely to recommend5.05.0

    11/14/2024 - kdmclm
    Bought a Townhouse home in 2024 in Denton, MD.

    Local knowledge
    Process expertise
    Responsiveness
    Negotiation skills
    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 professionalism, her responsiveness, her advocacy/negotiation on our behalf, and n...
  • Highly likely to recommend5.05.0

    6/25/2024 - jesswantz
    Bought a Single Family home in 2024 in Church hill, MD.

    Local knowledge
    Process expertise
    Responsiveness
    Negotiation skills
    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!! I highly recommend reaching out to her if you're on the house hunt!
  • Highly likely to recommend5.05.0

    2/27/2024 - devdelange9
    Consulted me on buying or selling a home in Chestertown, MD.

    Local knowledge
    Process expertise
    Responsiveness
    Negotiation skills
    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 any challenge with a smile. She is a pleasure to be around, and a great person ...

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    Chessie Calloway

    (She/Her/Hers)
    Smith & Co with RE/MAX Executive
    3sales last 12 months
    8total sales
    $45K-$584Kprice range
    $316Kaverage price
    5years of experience