Rachel M. Hess

Rachel M. Hess focuses her practice on representing national, regional and local residential and commercial developers, builders and management companies throughout the real estate transaction process.


1982, Maryland


University of Baltimore School of Law




Schedule a consultation

Rachel M. Hess focuses her practice on representing national, regional and local residential and commercial developers, builders and management companies throughout the real estate transaction process. Rachel’s new and existing clients routinely rely on her experience and intimate knowledge to determine the most feasible structure of the project to accomplish the client’s goals while reducing potential liability. She regularly advises and counsels clients relating to the structure and formation of all types of commercial, residential and mixed-use projects.

Her experience includes preparation and review of all documents necessary to implement the establishment of community associations, homeowners associations, land condominiums and building condominiums, including contracts, leases, declarations, bylaws, articles of incorporation, corporate documents, entity formation, deeds for the private transfer or public dedication of land, easement agreements, homeowners association depository statements, public offering statements, documents in compliance with the Interstate Land Sales Full Disclosure Act, disclosure statements, and attorney opinion letters for VA, FHA and FNMA project approvals.

For clients who wish to impose private utility charges against their property, Rachel routinely prepares and records the necessary instruments to establish these charges, including the declaration, disclosure statement and entity formation. Rachel also represents private utility companies in collection matters when homeowners are delinquent in their payments.

As part of her practice, Rachel provides legal advice to existing community associations concerning document interpretation and amendment of governing documents, collection of assessments, covenant and rule enforcement, architectural control issues and negotiation of contracts.

Rachel is well regarded by her peers and colleagues and considered a leading real estate attorney in Baltimore. She has written manuals (including Developing and Operating Planned Communities and Condominiums in Maryland, National Business Institute, 2006) and lectured on condominium law, testified before the Maryland legislature concerning then pending legislation, and served as an expert witness for cases involving condominium disputes.  Rachel also has lectured on the subject of the importance of covenants in the development process and how to address them at the the Maryland Building Industry Association of Maryland Land Development Council and The Land Use Institute seminar.

Rachel also serves as a Director of the Maryland Building Industry Association of Maryland Land Development Council. The Council offers services and special interest programs covering government relations and representation, educational opportunities, marketing exposure as well as the exchange of ideas to promote high standards within the development industry.

Rachel graduated from the University of Maryland, College Park, in 1979 with a Bachelor of Science degree in accounting and the University of Baltimore Law School in 1982. She is admitted to practice law in all of the courts of Maryland and is a member of the Maryland State Bar Association and Maryland Building Industry Association.

Over the past several decades, Rachel and the firm have been a crucial part of my success. Every deal starts with the contract and then all the supporting documents which follow, including HOA documents, amendments and more. With a proper foundation, all else is built on sturdy ground. Rachel has supported me in my business for decades, as well as personal matters including Will and Advanced Directive preparation. I have come to rely on Rachel’s vast knowledge and am truly grateful to her.

Alan K.

Even after 8 years I will never forget what Mr. Winegrad did for me. Took on my case and made sure he covered all areas diligently, professionally making sure I was able to after 10 years fighting to get a divorce and support for my child he made it happen in short time-span and ensured that I finally received a fair and just agreement so that I could move on! He went above and beyond and at that time I didn’t have much! Now my son is going to college with full scholarship! Thank You!

Martindale Review

Ms. Hess and her staff always provide the BEST services for a reasonable price. In addition, they have protected our properties in every way imaginable. We do not set up any new jobs without this law firm’s assistance. The very best in a complex, fluid world.

Martindale Review

No one ever wants to be in a position to need an attorney; however, life happens, and when it does, you want to be represented by the best. I have been with Stephen for over 10 years and he has never disappointed. He is honest and frank about the issues dealing with your case, he doesn’t sugarcoat anything, he’s honest. He studies the facts that you present, maps out a strategy and shares the good, the bad and the possibilities. He gives you the attention as if you are his only client.

Susan C.

We had an excellent experience working with Rory Parks, attorney with Winegrad, Hess & Heimlicher. He was knowledgeable, helpful, and reliable in guiding us through a complicated matter involving a tenant. We needed to appear in court, and he helped us feel confident and prepped. Rory is also personable, and helps bring a feeling of peace between people who might have difficulty speaking otherwise. We highly recommend Rory and his firm.

Burt and Rachel

Winegrad, Hess and Heimlicher is an absolute pleasure to work with in regards to any legal or collections related questions or concerns. Their responsiveness, attention to detail, record keeping and final resolutions are impeccable. I work with many attorney’s and the rate at which they resolve collection cases is by far one of the best around. I would highly recommend this law firm to anyone in the Property Management industry.

A Management Company
Stay up to date by
subscribing to our newsletter