Dylan Bear, 28, and Jesse Bear, 23, are pedigreed entrepreneurs: In 1996, their parents opened Wyndmoor Deli at 1000 Willow Grove Avenue.
Today, the Springfield Township High School graduates have accumulated three businesses between them: Bear Real Estate, founded in 2020, Bear Landscaping launched a year later, and Polar Express Cleaning came along in 2024.
Bear Group, the companies’ collective, launched in 2021.
Bear Group
The collective sponsors local organizations as much as possible “since they’re helping to keep us in business,” Dylan said.
“Every other month, we try to pick a municipality and bring them a free lunch. So far, we’ve done the Springfield Township police, Temple police, Roxborough Memorial Hospital, Springfield Township High School, Manayunk Fire Department,” Dylan said. “We’ve also sponsored various causes and foundations as well. We gave away 15 turkeys to families in need in Roxborough over Thanksgiving.”
In December 2024, Dylan hosted a Bear Real Estate Christmas Party toy drive in Manayunk and donated all the toys to the Children’s Hospital of Pennsylvania.
Other philanthropic endeavors have included:
- Roxborough Hospital Nurses’ Week donation with help from Alex’s pizza
- Springfield Township High School staff with help from Alex’s pizza
- Temple police donation with help from Alex’s pizza
Bear Real Estate
According to Dylan, Bear Group’s president, Bear Real Estate has grown steadily over the past five years.
“Last year was our biggest year. We sold 60 homes, and it’s been climbing every year,” he said. “I dropped out of college when I was 21 because I wanted to be in real estate. I was working with investors at the time, and I got my license right before the pandemic shut everything down.”
Dylan sold 155 N Keswick Avenue in Glenside (pictured above), which he says was the highest sale for a twin in 19038 at $600,000 | Far right: 126 East Street in Manayunk, recently sold for $870,000
For more on Bear Real Estate, you can visit their Facebook page.
Bear Landscaping
Jesse started Bear Landscaping right after high school. The company currently has two trucks, four trailers, and four staff members to handle an average of 400 annual jobs with 75 weekly clients.
“That number has climbed every year. We almost doubled in 2024 from 2023,” he said. “I always worked part-time landscaping throughout high school, and then I was left with no job and no idea what I wanted to do. I dropped out of college and it really took off. The support of the community has really helped me out.”
“I love seeing my clients happy and communicating with people everyday. I like knowing that we’re making the community look nicer,” Jesse said.
For more on Bear Landscaping, you can visit their website and Facebook page.
Polar Express Cleaning
Polar Express Cleaning started as a branch of Bear Real Estate, has 50+ five-star reviews on Google, and averages roughly 70 houses per month.
“I was getting listings cleaned for my clients, and it just became hard to find reliable people,” Dylan said. “We’ve also started cleaning local businesses in Oreland, Flourtown, Wyndmoor, Glenside, and Springfield. The majority of our business has been in Glenside.”
“We value our customers and our neighborhood. I think customer satisfaction has been huge for all three businesses. We try to put people’s needs first,” he said.
For more on Polar Express Cleaning, you can visit their website.
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Photos: Dylan Bear