Our History

What began as a modest ice cream truck venture has blossomed into a national powerhouse in property management, overseeing 14,000 units across 75 properties. Our growth is a testament to our unwavering commitment to excellence and our passion for transforming challenges into opportunities.

From humble beginnings to a remarkable present


A Chilly Start on the HJ's Ice Cream Truck

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.
Harold Grinspoon and friends standing in front of a Howard Johnson ice cream truck.

First Steps into Real Estate in Agawam, MA

In 1959, Harold made a pivotal move by acquiring a two-family rental home in Agawam, 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.
Harold Grinspoon standing outside his first real estate purchase, a two family home in Agawam.

A Great New Office Space in West Springfield, MA

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.
A street view shot of 380 Union, West Springfield, a large brick mill building.

Giving Back - Harold Grinspoon Foundation

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.
Harold Grinspoon Foundation logo

Agawam Corporate Center - Mixing Things Up

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.
An exterior shot of the Agawam Corporate Center, with a brick building and a driftwood sculpture by Harold Grinspoon.

River Reach - An Opportunity for Growth

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.
Sun-drenched loungers, encircling the pristine pool on a spacious deck, beckon residents to unwind in the embrace of crystal-clear waters and lush greenery.

Sedona Peaks - Heading Out West

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.
An aerial view of the property, with mountains in the backdrop.

Elevate 231 - Our Biggest Student Venture

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.
The exterior of the apartment buildings that house townhome floor plans, with private entrance and patio.

A New Home at Agawam Corporate Center

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.
An exterior shot of the Agawam Corporate Center, with a brick building and a driftwood sculpture by Harold Grinspoon.

Our Growing Portfolio

A fire pit surrounded by Adirondack chairs on a lushly landscaped pool deck
MAISON Burbank

Purchased on 06/21/2023

Vibrant pool with sun loungers, inviting for a dip.
The Avenue

Purchased on 12/28/2022

A front entrance with sign for ONYX

Purchased on 11/03/2022

A landscaped front entrance and sign.

Purchased on 11/03/2022

An aerial snapshot of Charleston Cay, revealing the picturesque blend of greenery, glistening waters, and its close proximity to Peace River.
Charleston Cay

Purchased on 05/27/2022