Tom Riley

Tom Riley’s connection to Cape Cod began in childhood, spending summers at his grandparents’ home and developing an early fascination with both the area and real estate. After graduating from Boston College, Tom made Chatham his year-round home and turned that lifelong interest into a career helping buyers and sellers navigate the Cape Cod market.

Today, Tom is a real estate agent with Pine Acres Realty, working alongside Chatham’s #1 real estate team for the past 22 years and backed by the resources and reach of Compass. He combines local knowledge with a modern, highly hands-on approach to selling real estate, bringing experience in photography, videography, design, social media, digital marketing, and technology to every listing.

For Tom, listing a home means far more than simply putting it on the market. He becomes personally invested in the entire process, helping prepare the property, coordinating vendors, organizing photography and marketing, accommodating showings, communicating with buyers and agents, managing deadlines, and staying closely involved through closing. Whether that means helping declutter before photos, meeting a contractor at the property, answering a late-night question, or solving an unexpected problem days before closing, Tom believes exceptional service comes from being present and willing to do whatever is needed.

Marketing is another area where Tom brings a unique advantage. An accomplished Cape Cod photographer, his work has twice appeared on the cover of Cape Cod Life Magazine and has been featured in the Chatham Chamber of Commerce Guidebook, The Cape Cod Chronicle, Cape & Islands Magazine, and other publications. In 2026, he released Chatham, a coffee table book celebrating the town through his photography. His Instagram audience of more than 17,000 followers also provides an additional platform for showcasing listings to people who already know, love, and aspire to own property on Cape Cod.

Tom’s approach is built around preparation, presentation, communication, and attention to detail. Every home has a story, and his goal is to position that story in a way that creates excitement, reaches the right buyers, and puts his sellers in the strongest possible position.

Above all, Tom understands that selling a home is a major financial and personal decision. His commitment is simple: be available, be proactive, protect his clients’ interests, and work relentlessly from the first conversation through the closing table.