A Florida Broker’s 30-Year Perspective on Real Estate Timing and Market Cycles

Written by:

Steve Marcinuk

Date:

29 Oct 2025

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The real estate market operates in cycles, but timing those cycles requires experience and perspective. Few professionals have observed as many market shifts as Freddie Crespo, who has weathered California’s booms and busts, survived Florida’s foreclosure crisis, and now guides clients through today’s evolving conditions.

From Acting Aspirations to Real Estate

Crespo’s entry into real estate was unplanned. After pursuing acting in Los Angeles in the mid-1990s, he found himself selling surplus tents at a mall when a Century 21 agent invited him to a meeting. That invitation led him to Ron Prechtl, then the number two Century 21 agent worldwide, who recognized Crespo’s enthusiasm and brought him into the foreclosure business.

“I wasn’t necessarily looking to get into foreclosures. I kind of fell into that,” Crespo says. His early experience buying his first home with friends, combining their incomes to qualify, gave him insight into creative financing solutions that would prove valuable throughout his career.

The Move to Florida

In 2005, Crespo relocated from California to Florida, establishing Investor’s Real Estate LLC in the Lake Mary area. The timing initially appeared ideal. “Half of 2005 was great. 2006 was spectacular. And then 2007, things came to a screeching halt.”

His background in California foreclosures became an asset when Florida’s market collapsed. “You were either selling short sales and foreclosures, or you’re not in the business, because there were very, very few traditional sales back in that time,” he recalls of the 2008-2012 period.

The emotional impact of foreclosure work was significant. “It was totally bittersweet. When you’d go to homes to take pictures or do walk-throughs, you could see like a family was just decimated. You see the pink room and you see the blue room where kids were. It was this real bittersweet moment every time.”

Market Cycles and Timing

Crespo’s perspective on market timing is grounded in historical patterns. “The cycles are typically 17 to 18 years,” he notes, pointing to peaks in 1989, 2007, and projecting the next peak around 2027-2028. He emphasizes, though, that external factors can disrupt these patterns, as COVID-19 did by delaying builder activity and supply chain recovery.

Currently, the market stands at a critical point. “We had over 4 million homes on the market right before it crashed in 2007. Today, we have 1.1 million homes on the market,” Crespo observes, noting the significant difference even as the U.S. population has grown by 40 million.

The inventory shortage is rooted in delayed construction. “The builders started late. Around 2016 they really started building, and it takes them about 10 years to overbuild. But then we had COVID, and COVID stopped them in their tracks.”

Current Market Dynamics

Today’s buyers come from a particular demographic. “The majority of investors aren’t buying,” Crespo says. The market is primarily made up of first-time buyers and those with genuine housing needs who can afford current prices and rates.

“Your typical buyers are your first-time buyers, people like me in 1996 when I went to buy. I had no clue. I didn’t care what the market was doing. I just needed and wanted to buy a home, and I did it.”

Affordability is the main challenge: “It’s just very expensive to purchase, and you need a big down payment just to keep a normal payment with principal, interest, tax and insurance.”

Educating Sellers

Working with sellers requires ongoing education. “Sellers are always behind what’s actually happening, even like the news is always behind what’s actually happening,” Crespo explains. Many sellers expect to exceed their neighbor’s recent sale price, not realizing market conditions have shifted.

His pricing strategy is based on competitive positioning. “There’s no way you can underprice a home. If you want to get $10 for your home and we price it at $9, you’re going to get a flood of people coming through because it’s a good deal, and then you’re going to end up getting $11. But if I price it at $13 hoping to negotiate down to $10, you’re going to end up getting $9.”

Regional Variations in Florida

Within Central Florida, Crespo has seen notable strength in Winter Park’s luxury market. “The values have stayed really strong, even in the high-end luxury market. You still see luxury homes selling. Believe it or not, there’s a lot of really, really rich people out there, and they’re buying.”

The condo market, however, is facing different challenges, especially near coastal areas affected by new regulations after the Surfside collapse. “The HOAs have skyrocketed. You can see prices dropping in those, and that’s just the birthing pains of what’s to come in the future.”

Impact of New Construction

New construction is creating significant competition for existing home sales. Builders, after reducing agent commissions during the hot 2022 market, have returned to offering substantial incentives. “Now they’re back offering 3%, they’re offering all of these incentives for the buyer. If you have a listing anywhere near new construction with similar square footage, the resale is in a lot of trouble.”

This trend particularly impacts recently built homes. “Homes that were constructed two years ago within the same development where they’re still selling new construction—forget it. They’re basically upside down at this point because new buyers will just buy the new home with all the great incentives.”

Emerging Warning Signs

Crespo has noticed subtle shifts that may signal future distress. “We have seen an uptick in short sales and foreclosures in the MLS. Before there were maybe 110, and now there’s like 200.”

The concern is for recent buyers. “Anyone who bought in 2023, 2024, even 2025, if they lose their job and go to sell their home, they’re going to be upside down with closing fees because prices haven’t gone anywhere.”

Investment and Ownership Strategy

Despite uncertainties, Crespo advises focusing on strategic home ownership rather than trying to time the market. “I don’t think it’s wise to time the market. If you need a place to live and you can afford it, then go ahead and buy it.”

He encourages building wealth through owning more than one property. “I always say you should have at least two homes, even if you don’t want to be an investor. With two homes later in life, you’ve got double the appreciation.”

His suggested approach is straightforward. “Buy, live in this house for two years, buy the next house and move into that house. You have no capital gain on this, and then make this into a rental property. You already have the great loan on both properties, and it’s totally legal with no taxes.”

Outlook for the Market

Crespo’s projection for the market aligns with historical cycles. “I think 2027-2028 we’re going to start seeing some hurt.” He uses inventory levels as a benchmark for concern. “We need to get to about 30,000 homes, and that’s the crash number. Over 25,000 homes, that’s red alert. In 2007 when we peaked out, we had over 25,000 homes on the market in Orlando Regional. Right now we have 15,000.”

For real estate professionals and investors, Crespo’s three-decade perspective provides valuable context for navigating current market conditions. His experience through multiple cycles shows that while the market is cyclical, successful navigation depends on understanding both historical patterns and present fundamentals, combined with practical strategies that consider individual circumstances rather than attempting to time market peaks and valleys.