I’m Timothy Guinee Sr., a Massachusetts-licensed attorney, criminal defense lawyer, and military pilot. After college, I joined the Air Force and became a pilot, learning firsthand the value of precision, leadership, and staying calm under pressure. I went on to earn my Juris Doctor from Massachusetts School of Law and now represent clients in criminal cases while also helping families with estate planning and guiding veterans and individuals through VA and Social Security disability claims. My career is built on integrity, discipline, and a commitment to protecting what matters most for the people I serve.
By combining military discipline, aviation expertise, and courtroom-tested legal experience, I provide clear, personalized guidance across criminal defense, estate planning, and disability law. I am committed to protecting what matters most to my clients, helping them navigate complex systems, and ensuring peace of mind with integrity and precision.
Orchard Hill Law was founded on the belief that every client deserves guidance, protection, and peace of mind in navigating life’s most challenging legal issues. Drawing on years of experience as a criminal defense attorney and military pilot, Timothy Guinee Sr. built the firm to provide not just legal representation, but clarity and confidence in complex situations. At Orchard Hill Law, we understand that legal challenges are deeply personal. Whether it’s defending your rights in court, helping secure VA or Social Security disability benefits, or guiding you through estate planning to protect your family and legacy, we approach each case with integrity, discipline, and a steadfast commitment to our clients. Our goal is to make the legal process clear and manageable, so you can focus on what matters most while knowing your affairs are in capable, trusted hands.
Contact UsAt Orchard Hill Law, we provide strong and disciplined representation in criminal defense cases. With extensive courtroom experience, we fight to protect your rights at every stage, ensuring fairness and integrity in the process.
Orchard Hill Law helps families safeguard their future through thoughtful estate planning. From Wills and Trusts to Powers of Attorney and Health Care Proxies, we provide clear guidance to protect your assets and ensure your loved ones are cared for.
Drawing on unique military experience, Orchard Hill Law proudly assists veterans in navigating the VA system. We advocate for service members and veterans to secure the disability benefits they have earned through their dedication and sacrifice.
At Orchard Hill Law PC, we help individuals overcome the challenges of securing Social Security Disability benefits. Our team provides the support and advocacy needed to pursue the financial stability you deserve.
Facing a legal challenge or planning for the future? At Orchard Hill Law, we’re here to guide you with clarity, discipline, and integrity. Share your details below and our team will reach out promptly.
© 2025 Orchard Hill Law. All Rights Reserved.