About US Cape & Islands Realty Advisors

Tim Skelly, owner of Cape & Islands Realty Advisors has been buying, selling, and developing real estate on Cape Cod and Martha’s Vineyard since 1994! Cape and Islands Realty Advisors has built an experienced team of agents, attorneys, engineers, and builders to assist buyers and sellers in seamless transactions from offer to close.

Cape and Islands Realty Advisors specializes in Cape Cod and Martha’s Vineyard Luxury and Waterfront Homes, New Construction and Estate Sales .

Meet Cape & Islands Realty Experienced Team of Brokers


Timothy Skelly

Tim Skelly grew up in Falmouth in a waterfront home his father built in 1951. After graduating from The University of Massachusetts Amherst Eisenberg School of Management Tim spent nearly 15 years as a municipal bond trader starting on Wall Street.

Tim built his first house in Falmouth in 1994 and has invested in, developed and sold properties in Boston, Cape Cod and Florida.

Tim started Cape & Islands Realty Advisors over 10 years ago while specializing in Luxury and Waterfront properties on Cape Cod, Martha’s Vineyard and Southeastern Massachusetts. In addition, Tim has built multiple custom modular homes in the Falmouth area.

Tim currently lives in Falmouth with his wife and two children and is affiliated with local charities such as Big Brothers Big Sisters of Cape Cod, Samaritans and John Paul II Preparatory School.


Greg Holmes

Greg Holmes has been a resident of Cape Cod for most of his life. Born outside of Philadelphia moved to Sherborn Massachusetts where he graduated high school at Dover-Sherborn. After high school Greg graduated with a BS degree at the University of Maine and later completing his MBA going to night school. After a successful career in finance and management working for several international corporations, Greg has been selling real estate on Cape Cod in both residential and commercial markets getting his real estate license in 2003.

On Greg’s off time, he enjoys boating, fishing, golfing and the beautiful beaches of Cape Cod.


Dennis Reardon

Dennis Reardon  works with buyers and sellers on Cape Cod and the South Coast of Massachusetts. Dennis has been licensed for over four years  and has a passion for  working with people in this communities in which he serves .Dennis grew up in Falmouth  and went to Falmouth High School and on the  weekends Dennis can be found advising clients   or clamming in Waquoit Bay with his two children.

Ultimately Dennis is known to go over and above  to help his clients to  find their dream home or sell their current property  for the maximum price and within the clients projected time frame . Dennis has an extensive knowledge of home construction and rehab and is currently in the process of obtaining his construction supervisors license . In addition Dennis has acted as foreman in over 10 million dollars of new construction homes in Falmouth since 2019.