Jessica H. McConnell, Esquire

Attorney Jessica H. McConnell Headshot

Jessica H. McConnell


Prior to joining Chesapeake Wills & Trusts in 2022, Jessica was an experienced attorney, and had already spent 20+ years helping Marylanders resolve their legal matters.

Between owning her own small firm and working with Independent Disability Services, Jessica brings with her a wealth of knowledge, particularly about wills, trusts, and estates, but also in a number of other areas of the law.

Jessica grew up in Western Pennsylvania where she attended Chatham College in Pittsburgh. She was an Economics major with a minor in Psychology and graduated cum laude in 1998. After college, she moved to Baltimore and attended the University of Maryland School of Law.

Jessica hung out her shingle – opened her own private practice – in Elderburg, Maryland. She handled a wide range of legal matters, including bankruptcy, wills, probate, and domestic relations.

Afterward, Jessica began working for Independent Disability Services, where she helped people apply for and receive SSI and SSDI government benefits. She continued to work in probate on an as-needed basis, and, as a result, has a tremendous amount of estate planning and probate experience. Jessica is admitted to practice law in the state of Maryland and the Federal Court.

Jessica lives in Brooklyn Park, Maryland with her boyfriend and 2 children. In her spare time, Jessica enjoys photography, reading (especially psychological thrillers), and baking. Jessica is particularly famous for her baking at Christmas when she singlehandedly prepares over 10 different types of cookies, 3 varieties of fudge, and cheesecake. On Saturday afternoons, you’ll find her cheering for her son in a baseball game, helping her daughter search for the perfect university, or touring local wineries.

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