Like you, we love Portland. We're dedicated to improving the community and the lives of those living here through thoughtful development that creates unique spaces for people to live, work, and play.


Casey Prentice

Managing Partner

Casey Prentice believes in making the experience and quality of his work meaningful. From reviving the economy of an island community off the coast of Maine via strategic investments that generate trickle-down benefits, to preserving historical community structures through thoughtful adaptive reuse, Casey looks for transformational opportunities that have maximum impact on community constituents.

Casey’s career is an unusually happy byproduct of the Great Recession. A graduate of Middlebury College in Vermont, where he received a BA in Political Science in fall 2009, he entered the work force during a dive in real estate development. Rather than fret, he bartended, lived with his parents, and in his spare time created the Prentice Organization with a short-term goal of attracting contracting work.

Things moved quicker than initially expected: Within a year Casey had sourced and closed his first business acquisition using creative financing options to acquire the historic Chebeague Island Inn on the largest island in Casco Bay. Through historic renovations, business repositioning and outreach to the local community, he began building his business reputation. Over the years that followed, he grew what has become a family company into a diverse entity employing nearly 100 people in the operation of multiple businesses and real estate holdings. His success didn’t go unnoticed: In 2014 he was honored with a Maine Family Business Award from the Institute for Family-Owned Business.

Casey’s vision and leadership continue to fuel the Prentice Organization’s growth while his attention to detail leads to positive financial results. Recognizing that real estate development and hospitality are “experience driven” industries, he keeps focus on enhancing the experience of the end user. The strategy has proven a three-pronged success, garnering awards and accolades for Prentice Organization’s operating companies while improving the quality of life of his employees and his professional reputation in the community. Meantime, the company ethos has led to a proven financial model that has enabled Prentice Organization to grow at a rapid rate while leveraging both principal and external capital with financial returns well above the market.

Active and engaged in his community and profession, Casey serves on the board of University of Southern Maine Foundation, is a member of the Portland Museum of Art Contemporaries, was one of the six members of the steering committee charged with forming the Portland Conservancy and now serves as a founding board member. He is also an active member of Portland Society for Architecture, a speaking contributor for Build Maine, and a LEED® Accredited Professional by the US Green Building Council.

A proud resident of Portland, Maine where he enjoys “everything the city has to offer,” Casey summers in Casco Bay and winters in the Appalachian Mountains. An avid traveler, he also roams far afield finding professional inspiration in experiencing new scenes and natural beauty that create a meaningful “sense of place”. 

Kevin Costello

Managing Partner

Kevin left the financial markets in 2012 with the desire to find a legacy development project that would make a difference in the experience of others, creating a place the community will celebrate for generations to come.  Kevin has held a full-time role with CPB2 Management since 2013, where he’s been primarily responsible for deal structuring, financing, and modeling of the Portland Foreside development. Kevin was instrumental to the creation and coordination of public presentations utilized throughout the four-year entitlement process. Additionally, Kevin is a personal investor in the Portland Foreside redevelopment and is proud to be a part of a project that will transform the waterfront of one of the great port cities of the eastern seaboard of the Unites States.


Kevin brings 12 years of financial markets experience to the team having held positions at Goldman Sachs, JPMorgan and Royal Bank of Canada specializing in institutional sales of mortgage backed securities. Throughout his career, Kevin’s client list included a number of global priority clients such as BlackRock, Wellington, Fidelity, Paulson & Co, NY Life and MetLife. Kevin’s travel between NYC and Boston throughout the last 12 years has led to the development of a substantial network of high net worth contacts. His experiences in the financial markets offer a thorough knowledge of the banking industry, deal structuring, financial securitization, and real estate markets.


Kevin is on the Board of Trustees of the Boston Architectural College, and serves alongside a number of Boston’s most influential architects, real estate developers, and designers.  Kevin has traveled extensively and is inspired to incorporate that experience into the development of a world class waterfront development and marina in Portland. A graduate of Boston College, BA degree in Economics from the School of Arts and Sciences, Kevin recently moved from Boston to Marblehead Massachusetts.