From Morristown to Naples: Why So Many NJ Homeowners Choose Florida’s Gulf Coast for Their Second Home
Each winter, as the temperature dips and the snow begins to blanket New Jersey’s neighborhoods, many Morristown residents quietly start their migration south. But this is no ordinary snowbird story—this is a tale of strategic second-home ownership, generational wealth, and the growing connection between Morristown, NJ and Naples, Florida.
While exact numbers are hard to pin down, the trends are impossible to ignore. Naples, FL, has become a go-to destination for affluent Morristown homeowners looking for sunshine, lifestyle, and investment-grade real estate. Here’s what the data reveals—and why this migration is building a bridge between two seemingly distant communities.
The Data: What We Know About Second Homes in Florida
Although there is no official government tally that pinpoints how many Morristown homeowners own a second home in Naples specifically, real estate research and national reports offer compelling insights into this growing trend:
New Jersey Is a Top Buyer State for Luxury Second Homes
In 2024, national housing data revealed that New Jersey homeowners are among the leading purchasers of high-end vacation homes. This is primarily attributed to the substantial growth in home equity across the state. Homeowners have leveraged their increased home values—especially in affluent towns like Morristown—to invest in second properties, often in warmer climates.
Florida: America’s Second-Home Capital
Florida continues to lead the nation when it comes to second-home ownership. A 2024 housing market analysis identified over 1 million second homes in Florida, accounting for more than 15% of all vacation properties in the U.S. That figure alone highlights Florida’s enduring appeal—especially to East Coast buyers.
Naples Is a Premier Second-Home Market
Drilling deeper into the Florida market, Naples stands out as a hotspot, particularly for luxury second homes. In 2023, over 53% of all mortgages approved in the Naples-Marco Island metro area were designated for second-home use. That’s an incredibly high percentage, showing how the region has become a magnet for wealthy out-of-state buyers—especially from places like New Jersey and New York.
New Jersey Buyers Flock to Florida
According to a 2024 second-home ownership study, Florida dominated the top five markets for New Jersey-based buyers. The state’s tax benefits, coastal lifestyle, and warm weather are key drivers. And among Florida cities, Naples routinely appears at the top of the list for NJ residents seeking a luxury retreat or a future retirement property.
Why Morristown Homeowners Are Eyeing Naples
Several factors make Naples the ideal match for Morristown residents thinking about a second home:
Weather & Lifestyle
It’s no secret—New Jersey winters are long, gray, and cold, while Naples offers sunny skies and 75-degree afternoons, even in January. For homeowners looking to escape snow shoveling and icy commutes, Naples provides the ultimate seasonal upgrade.
Wealth Demographics
Morristown has long been home to financially successful families and retirees. These individuals often possess the income and equity required to maintain dual properties. Naples appeals to this same demographic—offering gated communities, high-end golf courses, beach clubs, waterfront dining and estates, and the highly sought-after “Millionaires Row” custom to affluent lifestyles.
Coastal Living & Outdoor Luxury
From beach days and sunset cruises to championship golf and dining al fresco, Naples offers a year-round outdoor lifestyle that contrasts sharply with the northeast’s seasonal limitations. For many, the chance to enjoy their golden years or family vacations in a warm, luxurious setting is too good to pass up.
Easy Access
Morristown homeowners also benefit from direct flights between Newark and Southwest Florida International Airport (RSW). That makes a weekend getaway or seasonal relocation convenient and stress-free—especially for those who want to split time without giving up their Morristown roots.
The Morristown-to-Naples Pipeline: Not Just a Trend, But a Lifestyle Shift
This growing migration reflects more than just seasonal preferences—it’s a strategic lifestyle decision that blends real estate investment with family legacy.
Many Morristown families now own second homes in Naples, not only for personal enjoyment but to create generational wealth, host family gatherings, or prepare for eventual retirement in a low-tax, high-luxury state
As financial advisors often note, buying a second home is one of the most stable, long-term wealth strategies—especially in prime Florida markets. And with Naples real estate appreciating steadily, the returns can be both emotional and financial.
Meet The Whitcomb Group: Naples Real Estate Experts with Deep Roots
At the heart of this trend are Naples’ top-performing realtors—The Whitcomb Group, whose deep local roots, personalized service, and unmatched knowledge of the luxury market have made them the go-to team for Northeast transplants.
With a client-first philosophy and an insider’s understanding of Naples’ best communities, The Whitcomb Group helps Morristown homeowners find their perfect Florida home—whether it’s a seasonal escape, a rental-income property, or a future forever home.
Their Naples-native background gives them a true edge. They know the neighborhoods, understand the trends, and—most importantly—treat each client like family.
Featured Listings from The Whitcomb Group (Fall/Winter 2025)
If you’re considering making the leap from New Jersey to Naples, here’s a snapshot of some of the 2025 beautiful properties currently available through The Whitcomb Group.
- 541 Whispering Pine Ct. – A contemporary masterpiece in the heart of the prestigious Park Shore. With soaring high ceilings, an open feel and a modern pool with all the amenities, luxury is endless. This stunning home is ideal for entertaining guests or a relaxing evening.
- 188 West Street – A sophisticated, expansive, corner lot and beautifully landscaped home is in Pine Ridge. The architecture is superior, with abundant windows enhancing its openness. Complimenting the large, spacious house, resort-style pool, cabana, and fire features is the 5-bay climate-controlled garage.
- 337 West Street – Brand new construction estate home with an infinity pool overlooking the lake. This is where elegance meets contemporary design in this 6-bedroom, 8-bath gem. A true culinary delight, this home is equipped with top-of-the-line Wolf and Sub-Zero appliances.
- 137 Tupelo Rd. – Genuine coastal elegance and beautiful tropical landscaping, this home is a new construction “Sand Dollar Winning” furnished custom home just minutes from the beach.
- 16484 Talis Park Dr. – Located in one of Naples’ most exclusive communities, this waterfront estate is designed for those who crave both luxury and lifestyle—complete with access to golf, dining, and spa amenities.
- Condo Listings Galore – From beachfront penthouses to investment-grade golf villas, The Whitgromb Group also has access to a wide variety of condo listings in every price range—perfect for those seeking a seasonal escape without the upkeep of a large property.
Ready to Explore Naples Real Estate?
Whether you’re dreaming of sun-soaked weekends, planning for retirement, or simply investing in your future, Naples offers a world of possibilities—and Morristown homeowners are leading the way.
To learn more or browse the latest listings, visit The Whitcomb Group and start your journey from Morristown to Naples with the help of trusted local experts.
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