Developer Paul Castaldo Sr. reflects on more than 50 years building success stories in Oswego
By Tom and Jerry Caraccioli
In 1950 the global life expectancy was 46-48 years.
While life expectancy in 2025 has evolved well past those mid-20th century marks, celebrating anything 50 years or more is a notable achievement. Whether it be life, marriage, business an historic event, technological advances or art and literature, it is cause for a golden celebration.
For more than 50 years, Paul Castaldo Sr. and his family have been building, renovating and growing businesses in Oswego.
“My primary business was the construction company, PAC Masonry, which I started in 1972 as a masonry contractor and expanded to PAC Associates General Contractor where my son Paul Jr. took over after my retirement,” Castaldo, Sr. said. “My father owned Castaldo Construction, both my grandfathers were masons, my brother and uncles were carpenters, and we were just a family of people building things. In those days I started just pointing up a chimney or doing a block foundation for new homes.”
At the time, business was seasonal, so Castaldo decided to buy and develop real estate. “Later in the ‘70s, I bought out my parents’ property and in the early ‘80s I built some properties and bought some,” he said. “After that, I purchased the Netherland Milk Processing property, which was about 4 ½ acres.”
The original building that stood in the area known today as Hillside Commons, was built in 1928 to store produce. In the late 1940s, the building became Netherland Milk Processing.
Through good and bad economies, booming and busting housing markets, Castaldo developed the area into Hillside Commons, which is where he moved his construction business to. Through the years, Hillside Commons has developed toward service-oriented businesses with some retail and has been operating well between service-oriented businesses and office space. The south part of the former Netherlands land was developed and is now Hillside Park Real Estate townhomes.
“Over the years, I was simple in my thinking,” Castaldo said. “I just wanted to survive, live well and take care of my family. Living well pushed me to expand and I found it comfortable to expand. I never took on, at one time, more than I could handle. I never put myself in a position where I could collapse. I was pretty conservative with growth.”
Hillside Park Real Estate is a family-owned and operated business that maintains a level of reliability, adaptability, resilience and longevity that makes more than five decades in business a notable accomplishment. The well-maintained apartments, clean exteriors and living spaces, as well as accommodating amenities on-site, have been a distinguished characteristic of the properties since inception.
Whether in spring, summer, fall or winter, Hillside Park Real Estate features modern two- and three-bedroom townhomes that cater to singles, families with young kids, professionals and others just starting out within conveniently located and walkable neighborhoods.
“We take great pride in providing properties that are safe, clean, well-maintained, and regularly updated,” Hillside Park Real Estate property manager and co-owner Stephanie Castaldo said. “We care about who we rent and lease to, their proximity to amenities and all Oswego has to offer. In return, our tenants care about where and how they live.”
And when it comes to reflecting on more than 50 years of business in the city of Oswego, Castaldo Sr. is confident that his contributions of more than five decades are in good hands with his daughter, Stephanie, and son, Paul, Jr.
“I liked building and developing,” he said. “Anything you develop is 24/7 but there was a reward at the end. When you grow a business there are always concerns about taking care of your family, so you look for opportunities that are available. At the time there were real estate opportunities and it really hasn’t changed.”
As Oswego’s population continues to grow, new industry enters the region and the city develops, that growth is reflected in business expansion.
“As far as Oswego, in the last 10 years or so, it’s all been progressive,” the successful patriarch businessman said. “When you start to think about business growth, what happened downtown is fabulous. The programs that were available to help the city leaders achieve that were fantastic. It feeds down and creates entrepreneurship. There’s a lot to look forward to in the community.”
Hillside Commons has remained stable and proactive, maintaining tenant relationships and reinvesting in property improvements to stay competitive.
Between 2024 and 2025 renewed interest in Hillside Commons has flourished. Historically, with a tenant renewal rate exceeding 85%, the real estate portion of the company, Hillside Park Real Estate, has maintained its strong rate of renewal and long-term occupancy with many tenants remaining for 20 years or more.
“At the end of the day, everyone looks for convenience, amenities and a clean, safe place to live and raise their families or retire to,” Stephanie Castaldo said. “And our locations near the Oswego State University campus keep our residents close to everything, whether it’s work or play.”
Tom and Jerry Caraccioli are freelance writers originally from Oswego, who have co-authored three books. They also host a monthly television and multi-platform segment on WSYR-Channel 9 (ABC) on its “Bridge Street” show called “Backroads to Bridge Street with Tom & Jerry.”
