The former food industry executive says he was called "crazy" when he started his quest to transform what used to be a hangout for drug users between two busy avenues.
Today, there stands the Tiquatira Park with thousands of trees of 160 species stretched over 3.2 kilometers (two miles) long and 100 meters (328 feet) wide.
Da Silva, 73, told AFP he did it because he "wanted to leave a legacy to the city that hosted (me). I started and never stopped."
Da Silva hails from the town of Promissao, about 500 kilometers from Sao Paulo, the biggest city in Latin America, where he moved decades ago.
Without any formal authorization, Da Silva started in 2003, with no funding but his own savings, to collect and buy cuttings to plant in his adopted city.
Five years later, Sao Paulo formally named his project the city's first linear park.
According to the municipality, 45 types of birds have been identified in the park.
"Look how he has transformed that degraded area. It's splendid!" said Angela Maria Fiorindo Pereira, a 69-year-old retired teacher who frequently walks in the park.
Experts say green spaces like these are crucial to lower the temperature in concrete urban centers and to improve air quality.
Sao Paulo, a city of 12 million people, is highly polluted and has seen air quality degrade even further in recent weeks due to the forest fires ravaging Brazil.
- Tree hugger -
Da Silva said he got his idea while out walking with his wife Leda in 2003 in what was then a derelict area of the metropolis.
He estimates he has spent about $7,000 per year on the project, at the current exchange rate, but did not share his total outlay.
Retired since 2022, he spends his days checking on his trees, seeing whether they need pruning or composting.
He is proud of his work, and likes to stroll among the trees, stopping occasionally to hug a trunk or point out a family of trees from great-grandfather to great-grandson.
Da Silva often travels with two photo albums depicting the transformation of the land and is greeted affectionately wherever he goes.
He says it takes him about 10 minutes to plant a cutting, and he likes talking to them "in a low voice" so people don't think he is crazy "once again."
Da Silva gets sporadic help from volunteers, but his vigor for his work remains untainted by age.
His ultimate goal is to plant 50,000 trees, said the man whose business card reads: "Helio da Silva, Tree Planter."
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