Our History

In one of Harold's initial entrepreneurial pursuits, he seized the opportunity to manage a fleet of Howard Johnson ice cream trucks at the age of 21, following two summers of hands-on experience working on one of the trucks. His managerial journey was temporarily interrupted when he was drafted into the Navy.

In 1959, Harold made a pivotal move by acquiring a two-family rental home in West Springfield, MA, marking his initial foray into the realm of real estate. This singular purchase served as the catalyst for the inception of the Aspen Square we recognize today with over 14,000 units on the market.

With a growing company needing more space and a centralized location, Aspen Square moved into 380 Union Street in West Springfield, MA. This converted brick mill building saw us through decades...and one memorable summer tornado! We ended up calling this location home for almost 50 years.

Established in 1991, the Harold Grinspoon Foundation began as a modest Jewish charity with a local focus on Western Mass. Swiftly evolving, it transformed into a global charitable organization, distributing thousands of books monthly to children worldwide, fostering a love for reading.

Over 100,000 square feet of commercial office space was purchased in Agawam, MA. First the home of the Harold Grinspoon Foundation, it also became the headquarters for Aspen Square Management in 2023. The grounds are also home to a sculpture park of our founder's artwork, and several walking trails.

Acquired in 2013, this stunning lakeside property in Naples, Florida marked our most significant venture yet, boasting over 500 units. It presented another opportunity for the Aspen team to glean valuable lessons and experience substantial growth in the thriving Florida real estate market.

Marking our inaugural acquisition in Arizona, Sedona Peaks became the cornerstone of our expanding portfolio in The Grand Canyon State. Offering an ideal retreat for snowbirds or a comfortable year-round residence, it exemplifies the beginning of our diverse property holdings in the region.

While already well-versed in the student housing market, Elevate 231 stands out as our most extensive student by-the-bed holding to date. Our team has enthusiastically embraced this challenge, delivering an exceptional customer experience even amidst the dynamic environment of a student turnover.

In 2023, after decades at our previous location at 380 Union, we transitioned to an exceptional custom-built office space at the Agawam Corporate Center. Designed by our own internal design team, the space is designed to enhance collaboration and teamwork through thoughtfully crafted spaces.