About Jason Piccirillo
Realtor® | Legacy Homes – Mark Tavares Realty
Rooted in Connecticut. Committed to Community
Meet Jason
I was born and raised in Milford, Connecticut, and currently live in Cheshire with my wife, Heather, and our four amazing children: William, Giuliana, James, and Grace. Growing up in a family deeply rooted in the construction industry, I was introduced early on to the value of hard work, craftsmanship, and attention to detail. I’ve spent over 25 years in the residential and commercial construction trades, working alongside my father as a General Contractor and Developer. During this time, I also obtained my Electrical Contractor’s License, which has given me a strong foundation in identifying the true quality and potential of a property—an invaluable skill when helping clients make smart real estate decisions.
For the past decade, I’ve served in public service, where I’ve had the privilege of building lasting relationships and trust within the community. That same commitment to people and service is what I bring into my career in real estate. I understand how important it is to find not just a house, but a home—something that fits your lifestyle, your goals, and your vision for the future.
When I’m not working, I enjoy spending time with my family and staying involved in community initiatives and volunteer efforts. My goal is simple: to help you find a quality home your family can grow in and feel proud of. Whether you’re buying your first home, upgrading, or investing, I’m here to guide you with honesty, expertise, and a hands-on understanding of both real estate and construction.
My Approach
Guidance Backed by Experience & Integrity
My vision is to help families find homes that are not only built well but also feel right—places where memories are made, goals are achieved, and life can truly be lived.
My mission is to serve each client with the same care and commitment I would offer my own family. From the initial consultation to closing day and beyond, I strive to make every experience smooth, stress-free, and rooted in your best interests.
Why Work With Me
Choosing the right REALTOR® is more than finding someone to unlock doors—it’s about partnering with someone who listens, understands your goals, and works relentlessly on your behalf. With a strong background in construction and a decade in public service, I bring a unique blend of knowledge, reliability, and people-first service to every real estate journey.
With over 25 years in the trades and an Electrical Contractor’s License, I bring a sharp eye for quality and potential, helping you make informed choices when buying or selling.
My roots in public service taught me the value of trust, communication, and building lasting relationships. I treat every client like family and every deal with care.
Your goals are my priority. Whether you’re buying your first home or upgrading to your forever one, I’m here to guide you with clarity, honesty, and commitment.
A Personalized Approach to Buying & Selling
Buying a Home?
Let’s find the perfect place to call home.
Whether you’re a first-time buyer or looking for your next property, I’ll guide you through the process with confidence and care. With my construction background and local market expertise, I can help you spot quality homes, avoid costly surprises, and negotiate with your best interests in mind. From pre-approval to handing over the keys, I’m with you every step of the way.
Selling Your Home?
Get the value you deserve with a smooth, stress-free sale.
Selling a home isn’t just about listing it—it’s about positioning it strategically to attract the right buyers and maximize your return. I’ll help you prepare your property, price it correctly, and market it effectively. With honest advice, skilled negotiation, and a hands-on approach, I make sure your home stands out and sells with success.