Southwest Florida’s Real Estate Shift: From Seasonal Retreat to Year-Round Community

Written by:

Steve Marcinuk

Date:

15 Apr 2026

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Southwest Florida’s real estate market has changed dramatically over the past two decades, moving from a seasonal retirement haven to a full-time residential destination that attracts a broad mix of buyers from across the country. This change is driven by shifting attitudes about lifestyle, remote work, and long-term value in housing.

Jesse McGreevy, co-founder of Domain Realty and leader of The Domain Group, has observed these changes since he started his career in 2004. His experience, from working solo during the boom years to building a brokerage of 300 agents, highlights both the opportunities and complexities that now define the region. He now works alongside his partner Marc Comisar at McGreevyandComisar.com, where they operate independently while also serving as sales managers for the broader Domain Realty Group.

What Makes Southwest Florida Stand Out

Southwest Florida’s appeal rests on a combination of access, amenities, and thoughtful infrastructure. The region spans Naples and Fort Myers, is anchored by Southwest Florida International Airport (RSW), and includes rapidly growing areas such as Bonita Springs and Estero. “Between those two main entities, you have Bonita Springs and Estero, which I call honey hole areas,” McGreevy says.

Development has kept pace with demand. Estero, once farmland, has seen explosive growth over the past 20 years. Major projects continue to reshape the area, including Kingston on Corkscrew Road, which is expected to add between 20,000 and 40,000 homes and commercial spaces. Other notable developments include Ave Maria, a community built around a university and church, and Babcock Ranch, which McGreevy describes as “the only solar town in the United States—the whole place runs off solar energy.”

Market Dynamics

After a period of sharp price increases during the COVID-19 pandemic, Southwest Florida’s housing market is now stabilizing. McGreevy describes the current period as a correction. Demand surged during the pandemic, creating a strong seller’s market, but prices have since moderated.

Inventory levels illustrate this shift. In February 2025, Lee County had 14.5 months of single-family home inventory; by February 2026, that figure had dropped to 7.5 months. “I’d say we’re in a balanced market now,” McGreevy explains. This balance creates new opportunities for agents who are proactive and knowledgeable about local conditions.

The region’s complexity requires agents to understand the nuances of different communities. Some neighborhoods, even when located side by side, see very different demand based on amenities and lifestyle factors. “I can have a listing in a community right next door to another one, and I can have 20 showings on one and sell it in a week, and the other one’s priced well but just trickling,” McGreevy says.

Insurance Costs and Market Stability

Rising insurance costs have been a major concern for Florida homeowners, especially after Hurricane Ian. Insurance premiums spiked, creating uncertainty for buyers and sellers. However, recent policy changes have started to reverse this trend. Legislative reforms in Tallahassee, including limits on lawsuits against insurers, have encouraged more carriers to return to the market.

“We doubled that next year, but then in 2022 we had a 23% decrease, and the following year we had a 25% decrease. You normally don’t hear of those costs coming down, but they have definitely come back down,” McGreevy reports. While insurance remains a challenge, the situation has improved from its post-storm peak.

Changing Demographics and Buyer Motivations

Southwest Florida’s buyer base has diversified significantly since the pandemic. The area, once dominated by retirees and seasonal residents, is now attracting year-round residents, including young professionals and families. “Our year-round population has grown substantially. It’s much more of a melting pot now,” McGreevy notes.

The sources of out-of-state buyers have also shifted. While Chicago, Michigan, and Ohio were traditional feeder markets, the past five years have seen a surge in buyers from New York and New Jersey. More recently, Minnesota has become a notable source, with McGreevy’s office fielding a growing number of calls from the 612 area code.

Political factors are influencing buying and selling decisions more than in the past. Some Canadians, for example, have sold properties in response to political changes. “I’ve seen a lot more political motivation than almost anything else, even more than weather,” McGreevy observes.

Investment Strategies

For investors, Southwest Florida offers three main rental categories. Super short-term rentals, such as Airbnb and VRBO, are only allowed in certain communities, often limited to grandfathered properties or specific neighborhoods like Naples Park. Annual rentals are most feasible for cash buyers, as current interest rates make financing less attractive.

Seasonal rentals remain a strong option for those seeking both lifestyle and income. Owners of golf course condos or similar properties can use their home for a few weeks each year and rent it out for the rest of the season, often covering most or all of their annual expenses. “They’ll pay six or seven thousand dollars a month to come down and rent your place for 30 days, and some homes get 10 to 15 to 20 thousand dollars a month,” McGreevy says.

Opportunities in Older Homes

Looking ahead, McGreevy sees remodeling as the next major opportunity. Much of the best-located land has already been developed, so buyers who want to live close to amenities will often need to purchase and update older homes. “I think the next big industry is the remodeling industry, because everything in Florida seems to age a little bit quicker,” he says.

This trend favors buyers willing to invest in improvements. “You can do a lot of personal equity building just by going in and doing some projects on a house and making it appealing for the next person.”

Buyer Behavior and Market Outlook

Today’s buyers are more deliberate than during the pandemic boom. Many current clients first considered buying in Southwest Florida before the COVID run-up, missed the initial surge, and are now re-entering the market. McGreevy’s team tracks a database of 200,000 leads, many from the 2017–2020 period, and finds that these buyers are now closing deals.

McGreevy expects the market to remain stable over the next 12 to 24 months, with no dramatic swings in either direction. “I think we’re in a healthy enough, balanced position to be pretty much what I would call standard market over the next 12 to 24 months.” He points out that factors such as interest rates and fuel prices will have a greater impact on the region than local changes will.

The Road Ahead

Southwest Florida’s evolution from a seasonal retreat to a year-round destination reflects a broader change in how Americans choose where to live. The region’s mix of infrastructure, amenities, and accessible location has put it on the map for a wider range of buyers. While the days of rapid price appreciation may be over, the area’s foundation appears solid.

For buyers and investors, success now depends on understanding local nuances, long-term trends, and the rising importance of community features and property condition. The region’s future growth looks steady rather than explosive, with opportunities favoring those who adapt to changing market realities and prioritize value over short-term speculation.

About the Expert: Jesse McGreevy is the co-founder of Domain Realty and leader of The Domain Group in Southwest Florida, where he oversees a brokerage of approximately 300 agents serving the Naples and Fort Myers region. With more than two decades of experience across multiple market cycles, he specializes in residential real estate and team leadership in a rapidly evolving year-round housing market.

This article is based on information provided by the expert source cited above. It is intended for general informational purposes only and does not constitute legal, financial, or real estate advice. Readers should conduct their own research and consult qualified professionals before making any real estate or financial decisions.