Pilot Investments, LLC

Who We Are

Pilot Investments, a Massachusetts real estate investment company, was formed in 1998 to acquire and operate multi-family apartment, office, retail and industrial properties through private placement partnerships. Today, the company’s focus is most heavily weighted towards apartment properties. This is where Pilot sees the greatest demand coming from the tenant side, the strongest rent growth, and the most favorable financing options. Most importantly, it is the sector that is providing the largest margin of safety, while offering predictable returns for our investors.

Pilot's secondary area of focus in the current environment includes the acquisition of distressed "Class A" office properties. Pilot is interested in assets that can be purchased based on existing cash flows, and that allow for significant upside upon the completion of property enhancements, and the leasing of vacant space at a discount to similar competitive properties within the immediate marketplace.


Pilot's partners consist of institutional investors, including pension funds and college endowments, as well as individual investors and family offices.


Eden Milroy and Fred Kempton are the principals of Pilot Investments. They have been working together for the past 20 years and have acquired, redeveloped and managed over $200 million in real estate investments. They each have over 40 years of wide-ranging experience in the real estate investment industry. See Our Team for more background information about Eden and Fred.

Investment Team

Pilot Investments has always realized that its business success is in direct proportion to the skillfulness, creativity and integrity of the real estate professionals that it has chosen to do business with. The Principals have taken great care over the past 20 years to assemble a top notch team of professional architects and engineers, building contractors, environmental consultants, legal counsel, accountants, capital market specialists, property managers, leasing assistants and investment sales brokers. Individually and collectively, these highly regarded professionals contribute their respective areas of expertise to the success of each investment. Pilot is the asset manager and the hands on "day-to-day" operating partner for each of its properties.