(Sept. 27, 2019) Bob Jester has spent the majority of his life in Worcester County. The 72-year-old has been working in the real estate business for 50 years, which has made him an essential part of Ocean City’s growth as a resort town.


Bob Jester of Ocean City has been selling real estate for 50 years.

Jester currently works with Keller Williams Realty on 75th Street. He also worked for 14 years at Coldwell Banker, which bought out the company he had worked for previously, Moore, Warfield and Glick, where he spent 25 years.

He also worked at the Sea Watch high rise when it was first developed as well as a company called Fulton Real Estate.

Jester attended Stephen Decatur High School in Berlin and found his interest in real estate when he was a teenager, while babysitting the owner of Caine Real Estate’s children.

“Mr. Caine was responsible for most of the major land development,” Jester said. “He developed 63rd Street where the city has all the maintenance area, he developed 94th Street going back all the way to the bay, and he developed all the way up to Montego Bay. He was the single largest developer in Ocean City … and he would let me babysit his kids.

“I used to babysit for him and I liked being around all these guys,” he continued. “I liked being around the agents … because they had fast cars and good-looking duds.”

Jester spent most of his life living in Ocean City except the time he went to the University of Maryland, College Park and a brief stay in Annapolis while his father worked at the Naval Academy.

Jester remained interested in the real estate industry when he joined the United States Coast Guard. He was able to be stationed in Ocean City through connections of his father and uncle, both of whom had also been in the Coast Guard.

“[During the Vietnam War] I knew I was gonna get drafted because there weren’t a lot of young people in this county,” Jester said. “So, before I was gonna get drafted, I had connections and got the Coast Guard because I saw this coming.”

Jester was stationed in the Coast Guard in February of 1968 and was moved to Ocean City in 1970. During this time, he was able to work both in the Coast Guard and begin his career in real estate.

“I was a gopher … I just did things for [Bounds Real Estate] around the office,” he said. “The owner asked me, ‘So why don’t you get your real estate license?’ So, I went ahead and studied for it and I passed immediately.”

During his time in the Coast Guard, he had a six-day week where he worked for three and was off for three. Jester spent his time working three days for the Coast Guard and another three as a real estate agent every week, until his term ended in 1972.

One of his most interesting experiences came in 1974, which had been a bad year for real estate with an economic downturn. During this time, several high rises like the Carousel and other condominiums were being built, one of which was the Sea Watch on 115th Street.

“The Sea Watch was going to go into receivership, which means the developers were going to lose it and the bank was going to take it back and to lower the prices and just get rid of it like a foreclosure,” Jester said. “One of the banks that lent the money on it, I knew one of the senior vice presidents. I said I’d like to interview to run the job … I was the first guy to be hired. So long story short, there were 400 units in the building and we sold 360 of them in 13 months and five days.”

Within this story, however, there was another.

“I sold a Chinese doctor a unit … he liked the building and he was a very nice man,” he said. “He called me like the next week or whatever he said, I want to come down and we want to buy a unit. He comes down and he brings another man with him. It’s one of his friends, which is another Chinese doctor.

“He in turn, goes home and tells his friends, and in the next eight to 12 weeks, I sold 18 units, all to doctors through this one gentleman,” he continued. “That went on for seven or eight years. The office called me the ‘Head Chinaman.’”

Having so many years of experience, Jester offered advice for anyone interested in buying a home in Ocean City or near the resort.

“You want to have another source of income or you have income and you work on holidays or weekends and then get into where you’re comfortable enough to go full time,” he said. “You have to have enough money to put down whether it’s 10 percent or 20 percent or whatever you to get a 20-, 25- or 30-year loan.

“A lot of these places are second homes,” he continued. “Ocean City is a great place to live. It’s a great place to raise your family.”

He also offered advice for anyone who wanted to get into real estate.

“If you want to get into this business, you have got to have a real outgoing personality because you have to talk to people,” Jester said. “You are helping them make one of the single biggest decisions in their life financially because you’re helping them buy a home.

“You have to know the territory,” he continued. “People should have a real good understanding of the area like Ocean City, the Boardwalk, know about the bay, know about the fishing, know about South Point Association because you don’t want to have a lot of questions where you don’t know the answers.”

For more information about Jester or real estate, call Keller Williams on 75th Street at 410-726-8829.

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