We Meet You Where You Are

Who We Are

A multi-generational law firm located in Winchester, Massachusetts, we’ve upheld our reputation for excellence in legal representation for over 30 years. 

At O’Leary Law, our family values influence how we practice law. We meet our clients where they’re at, proudly utilizing our extensive legal expertise to provide hardworking people with practical advice that will resolve their legal worries. We pride ourselves in providing the legal expertise you deserve.

Katie and Bill Oleary

Practice Areas


Have you been in a car accident? From navigating insurance coverage to settling claims, we provide representation for motor vehicle cases.


We represent both individuals and businesses facing civil contractual disputes and related matters in the district and superior courts.


Have you been in an accident, suffered a slip and fall, or been injured by a defective product? We can help you settle your claim efficiently and effectively.


From lease management to disputes and evictions, we guide landlords through the wide range of legal matters that arise with property management.

Estate Planning & Probate

Let us help you protect your interests and wishes for future generations.

Real Estate

Whether you're buying or selling a home, we can represent you through the entire process.


Facing criminal charges? We provide consultation and representation on district court criminal matters for cases ranging from misdemeanors to felonies.


If you have been injured at work and need representation we can help.


Should you have legal issues that arise outside the scope of our practice, we can refer you to a top-notch attorney within our network.

What Our Clients Say