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Real estate talk with local retired agent William Roger Cummings

Real estate talk with local retired agent William Roger Cummings

  • Retired, local real estate agent William Roger Cummings gives us a clue as to how the housing market will fare over the next twelve months.
Real estate talks with local retired agent William Roger Cummings

Some say it’s like the speculative boom of the 1920s and the consequent crash of the stock market in the United States in 1929. Others liken it to a guessing game. Nobody can really figure out when the housing landscape will flatten as there are so many moving pieces that change daily. But for real estate professional William Roger Cummings, who bought his first real estate property at the age of 21, and who is now a retired real estate agent in the Palm Beaches with over 40 years of experience, the housing market is pure adrenaline. South Florida is hot, he says. And he’s obviously not talking about the weather.

Since the pandemic, he’s seen home prices skyrocketing in South Florida. Partly due to a mismatch between supply and demand, he says. While some experts predicted that the pandemic would cause a housing crash like the Great Depression, to the delight or dismay of many, according to data from, properties in the South Florida counties of Palm Beach, Broward, and Miami-Dade are overvalued by more than 11%. In the same three counties, single-family home sales increased by 28.7% in March 2021, with the median sales price also increasing by 20.4% to $457,500.

This colossal phenomenon is not ending anytime soon, on the contrary. While sellers are eager to sell their homes before interest rates increase, buyers fear they will never be able to buy a home, as residents and business relocations from out of state from high-tax urban areas like New York and California are driving the demand for real estate in South Florida. They’re coming in droves, Cummings observes, offering cash and sometimes even double the asking home price, leaving many locals on the sidelines, not even able to afford the high rents, let alone the purchase of today’s homes.

I sat down with Cummings at a coffee shop in Downtown West Palm Beach, a place he calls home. He’s clearly well known and loved in our community, and not a day passes by that you won’t catch him doing something to help someone, or entertaining himself, in his iconic attire: suit, dress shoes, and matching hat.

Real estate talks with local retired agent William Roger Cummings

As someone who’s been hoping to buy a small house in South Florida, I wanted to hear from an expert. I wanted to know: Is the housing market ascending or is it on the decline? I also wanted to know: why rental growth and the demand for rental property are so strong in South Florida. And how South Florida, a region that spans more than 6,000 square miles and three counties—Palm Beach, Broward, and Miami-Dade, which is home to more than 6.7 million residents, is still growing! But more than anything, I wanted to know why our city officials are not just putting up a sign on our Florida borders saying: “Sorry, we’re closed. We Have Reached Full Capacity.” Just saying.

William, reportedly, the job market, low taxes, and quality of life have made our region very attractive to people and businesses migrating from high-tax urban areas. So, how do you think this housing market is affecting locals, most especially those who are trying to buy properties but are faced with interference from out-of-state buyers who are primarily providing cash offers and even in some cases, offering double the asking price?

This has some new components, but the basics haven’t changed for years. That is a lack of state income tax, climate, growth, increased opportunity, etc. The new elements are the dramatic swing in politics that has locked down and driven many entrepreneurs, small businessmen, and good families out of their home states, especially New York and California. The lesson emphasized during the pandemic is many businesses can employ people remotely with little loss in productivity.

As reported by, as the 12th-largest economy in the U.S., the economic output of South Florida is about the same as Hong Kong, Israel, Colombia, and Chile. In fact, the 120 miles between Miami-Dade, Broward, and Palm Beach counties in South Florida are often thought of as Florida’s Gold Coast because of the thriving amount of international trade and domestic commerce. Single-family home sales in South Florida’s housing market are soaring, with total home sales in Miami-Dade County surging 142% compared to one year ago. So, do you think investors are icing out homebuyers who can’t compete in South Florida’s red-hot housing market? What can locals do about that?

It has always been a wonderful idea to invest in multi-unit residential properties for long-term positive passive income. The internet has spread the word through webinars and seminars. In addition to individuals seeking these investments, third-party websites and institutions have taken a strong position for acquisition, either to flip for profit or hold for cash flow.

Inflation has been predicted due to the decisions of the administration and other economic factors, which also makes the ownership of income-producing assets like real estate a good investment. Investors may not be the biggest competition for home buyers. Families relocating from other states are often selling their homes for higher prices in their home state than the asking price of Florida homes. Because they have the capital, it allows them to be more competitive in making offers on homes for sale here.

Local buyers will have the mindset that the homes are overpriced or that there is an artificial bubble that will burst if they wait for a future timeframe. The numbers of the population that are moving here seem to indicate the demand will remain strong. Buyers who are very conservative in their offers are oftentimes passed by due to a higher competitive offer. 

Real estate talks with local retired agent William Roger Cummings

South Florida has the 3rd fastest-growing rental market in the U.S., with average rents up 27% year-over-year (August 2020 vs August 2021). According to a report from WPTV, the reopening of local economies has “turbocharged” the rental market, with rent price increases making up for the lost time. One local real estate expert is seeing rental increases of sometimes $1,000 a month. With more people relocating from the Northeast to South Florida, it’s likely that the demand for rental property will continue increasing? 

I believe that people will continue relocating to South Florida, which will sustain high levels of rental demand. There are amazing building projects underway right now in all of South Florida, as well as in Orlando and other parts of Florida. The Related Group is building six towers on North Flagler, which will offer 1,045 new rentals. There is a permit in the Brickell section of Miami for a brand-new 843-foot tall rental apartment building, and on and on. This, plus the huge influx of newly built homes and condominiums for sale.

I know this market is hard to predict, but can you give us a clue as to how the housing market will fare over the next twelve months in West Palm Beach, particularly? Meaning, will the prices continue to soar?

They may increase at a slower rate, but continue to rise. There is less of a seasonal effect from the approaching summer.

How long have you been in the business?

I bought my first four-unit property when I was 21 years old. I think at that time, 21 was more or less considered an adult. My father helped me by introducing me to a real estate broker whom we trusted. I found a spot and I bought it in my hometown of Portland, Maine. I lived in one apartment and rented the other three.

So, your father really taught you the basics of business well.

Yes, I think he had a wise and practical approach to life. He was also an investor in real estate. He believed that it was a smart way for the future to have some income that was in addition to your job.

Supposedly, real estate is the most valuable investment that a person can make, better than stocks. Thoughts? 

Well, my impression is that very few people don’t have any real estate. It typically appreciates every year, and if you have rental properties, you collect rent, which gives you cash flow to help you pay your expenses. It’s very simple, while the stock market is very complex. I, personally, like a simple-directions type of market. The stock market goes up one day and down the next. The stock market can be influenced by large purchases. I believe that fund managers can make those purchases when that demand shows up on the big board, which is when everybody gets excited. The sad thing is when you see a small guy investing in a stock whose price suddenly goes back down, even at a lower pressure starter, and that’s when you lose money. That’s when the small guy gets scared, and rightly so.

Nothing is obviously 100% certain, not even real estate. But I think it is the best investment that you can make. I have a goddaughter who’s 20 and that’s what I told her. You always have to live somewhere and if you start out living as an adult, the responsibilities of real estate can impact your future. It did for me.

Where did you study?

I studied law at the University of Miami and graduated in 1974. At first, real estate wasn’t a career for me just something I learned and then fell in love with.

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Real estate talks with local retired agent William Roger Cummings

When did you move to Palm Beach County?

I relocated from Miami here at that time and I wasn’t in a position to make investments in real estate at that juncture. So, I was working on that and fell in love with Palm Beach County. I got married, then divorced, with no children. But did get the incredible opportunity to serve as an advisor for the Dean of the Rinker School of Business at Palm Beach Atlantic University in Downtown West Palm Beach, where I’ve been blessed to have worked with some wonderful young students.

As their mentor, what are some of the key nuggets that you’ve shared with them?

My first lesson is that paying interest is a mistake. Collecting rent is good. Well, of course, that’s a no-brainer. But, if you put those two thoughts together, then you get lesson number two: if you pay your credit cards every month without incurring interest that gives you savings, which you can then invest in real estate. Another tip is: It’s a sound idea to stay within your means after you graduate from college and find a good job. What I mean by that is, if you have a place to live, clothes on your back, good transportation, a healthy lifestyle with good friends, etc., don’t focus on buying fancy clothes and fancy cars. Stick with your old ride, and any extra income you get, put it aside for an emergency or possible investments.

But again, the trick is to be able to afford a place, and the way this market is presently . . .

Well, yes, that is one of the challenges that I, and other real estate professionals, face trying to match the people with the properties as best as possible.

So, in the meantime, you are cruising around downtown, enjoying the town.

Yes, I like to be downtown amongst the people. I like to be out on the sidewalk, seeing and talking to people that know me. I know them, which makes me feel so much a part of things. I love South Florida and its multicultural aspect. I have Caribbean friends, I have friends who come from European countries, and it’s all here. West Palm Beach is a beautiful city. How can you blame anyone for wanting to be here?

A great conversation with Cummings, I must say. But I still want to know: why is it that our city officials are not just putting up a sign on our Florida borders saying: “Sorry, we’re closed. We Have Reached Full Capacity.” As idealistic as that may sound, don’t think that will ever happen.

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