Private Islands vs. Urban Penthouses - A Buyer’s Guide to Two Worlds of Luxury

For those looking to purchase truly extraordinary real estate, two options stand out above the rest: the private island and the urban penthouse. They couldn’t be more different—and that’s exactly the point. Both promise exclusivity, luxury, and a lifestyle most can only dream of, but they offer it in very different ways. So, which one suits your vision of the good life?

Privacy or Proximity?

Living on a private island means you get to enjoy a level of solitude few other properties can match. There are no neighbors, no traffic, and no interruptions unless you’ve invited them. For those who value complete privacy and personal space, it’s hard to beat.

Meanwhile, a penthouse keeps you right in the center of the action. You're close to the best restaurants, shopping, and cultural events. The city is just an elevator ride away. It may not offer total seclusion, but top-tier penthouses often come with private entrances, concierge services, and dedicated staff—giving you the best of both worlds.

Who’s this for? If you prefer remote and quiet, the island lifestyle might be ideal. If you want luxury with access to everything, a penthouse is likely a better fit.

The View from the Top

There’s nothing like waking up to the sound of the ocean and a view that stretches over turquoise water for miles. A private island gives you just that—an untouched, natural landscape that feels entirely your own. No rooftops, no honking horns. Just open space.

In contrast, a penthouse offers a front-row seat to the skyline. High above the streets, you get to enjoy the pulse of the city from a peaceful perch. Floor-to-ceiling windows and wraparound terraces often give you panoramic views that can feel just as vast as the ocean.

Why it matters: Nature lovers tend to gravitate toward islands. Those who appreciate a dynamic, urban backdrop usually lean toward penthouses.

Lifestyle Differences

Life on a private island tends to be more laid-back. You’re setting your own pace. It’s perfect for those who want a retreat, or a space to truly disconnect. But keep in mind, you’ll want reliable access to transportation—think private boat docks, helipads, or nearby airports.

A penthouse, on the other hand, makes day-to-day living incredibly convenient. You’ve got luxury amenities right in the building‐gyms, pools, spas, and more. Entertaining is easy, and everything you need is just steps away.

Who’s this for? Choose an island if you want your home to feel like an escape. Choose a penthouse if you want an elevated version of everyday life.

Value and Investment

Private islands, especially in sought-after areas, are rare and often hold long-term investment appeal. They can also be passed down as family properties. But they can take time to sell if the market shifts.

Penthouses in cities like London, Toronto, or New York are generally easier to resell and tend to hold value well, particularly if located in iconic buildings or neighborhoods. Plus, they often attract interest from international buyers and renters.

Bottom line: Islands are about legacy and exclusivity. Penthouses are about prestige and practicality.

The Final Word

At the end of the day, it’s not about which one is “better”‐it’s about which one feels more like you. Whether you see yourself sipping coffee on a terrace high above the city, or watching the sun dip into the ocean from your own stretch of beach, the decision comes down to lifestyle.

The Hammond Team has deep experience with both ends of the luxury market—from private island retreats to landmark penthouse residences. If you're considering either path, we can help you navigate the journey.