Why Buyers are Opting for Long Island as Their 2025 Second Home

Think that second homes were reserved for the Hamptons set or ski-chalet aspirers upstate? Well, hello 2025—where Long Island has become quietly (read: not-so-quietly) the go-to choice for second-home buyers seeking something greater than a mortgage and a view. From North Shore quaintness to North Fork wineries and South Shore marinas, buyers are not merely purchasing square footage—dollar for dollar, they are also investing in lifestyle, rental potential, and potentially an improved bagel.

Lifestyle First, Commute Optional

Today's second-home shopper isn't escaping the city—they're reworking their life. Telework remains real, and that old vacation cottage is now serving as a Tuesday-to-Friday Zoom retreat. Buyers are seeking calm, porches, and Wi-Fi that can sustain a board meeting and a night of binge-watching on Netflix simultaneously.

Affordability (Yes, Relatively Speaking)

Look—nothing is *inexpensive* on Long Island. Relative to the Hamptons, Hudson Valley, or Connecticut coastline, however, places like Bellport, Rocky Point, and East Moriches begin to seem downright affordable. Many homes in those areas are still selling for less than \$700K, and for that, you’re receiving character, community, and quite possibly a hydrangea hedge you never requested.

Potential for Short-Term Rentals

It's not all about having a spot to share your sunset selfies. It's about allowing that spot to fund itself. STR-friendly municipalities are booming—particularly along the North Fork and South Shore. AirDNA shows year-round revenue growth with top-tier properties generating in excess of \$80K in a year. And yes, that includes quaint cottages complete with clawfoot tubs and mid-century homes complete with "vintage" kitchens.

Micro-neighborhoods are growing in popularity

You know what's better than buying in a brand-name beach town? Buying in the quaint pocket beside that hasn't yet exploded—yours yet, that is. Buyers are tapping into local hidden treasures like Sayville, Jamesport, and Sea Cliff. They have walkability, hyperlocal eateries, and the type of residents who'll shovel your driveway just in order to guilt you into signing up for the Civic Association.

Sustainable and Low-Maintenance Living

Second-home owners in 2025 don't want their weekend getaway homes sporting outdated 80s wallpaper and hidden asbestos. They want turnkey or darn near. They want solar panels, smart thermostats, and locally planted landscaping. They don't want total gut rehabs. They want the sense of being able to unpack their weekend bag, pour the wine, and have the property just take care of itself.

Emergence of "Flex-Homes" and Blended Lifestyles

The divide between primary residence and vacation home is less clear-cut than ever. More and more buyers are spending weeks—if not months—living out of their "second" home, repurposing it as a creative retreat, satellite office, or full-on headquarters. The vacation home designation is being supplanted by "flex base," and Long Island municipalities are adapting with it—fiber internet, cafes with outlets, and school systems worth Googling.

Appeals Across Generations

Second homes are not a boomer flex nor a millennial pipe dream. Gen Xers are utilizing them for legacy planning and portfolio diversification. Boomers are downsizing their large primary residence and retaining their "escape" as their new residence. And Gen Z? They’re pooling household money together and co-owning a beach house that they use as a content creation studio. Say hello to multi-generational ROI.

Tax Benefits and Diversification of Wealth

Second homes, with proper handling, have significant financial benefits. They are complemented by interest on mortgages, depreciation on the property (in case of rentals), and long-term appreciation. They are not mere lifestyle purchases. They are vehicles of wealth with the added advantage of being within proximity of a winery, a beach, or, fortunate you, both.

Your Next Property Should Do More Than Look Pretty—Let’s Make It Work for You

Whether you're craving a North Fork retreat, a South Shore marina escape, or a Wi-Fi-worthy flex home with wine and ROI, Long Island is calling—and it’s not just for weekends anymore.

Call Dean Miller, Long Island’s only AI-certified real estate strategist, for insider access to the towns, homes, and numbers that make sense—today, tomorrow, and ten years from now.

📞 Visit www.deanmillerrealestate.com or shoot a message to get started.
Because a second home shouldn’t just look good on Instagram—it should work in your portfolio, too.