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From New York to Naples: A Perfect Second Home in Island Walk

1/23/2026

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Thinking About a Second Home or Relocating to Florida? Welcome to Island Walk, Naples


If you’re living in New York and dreaming about more sunshine, space, and a slower pace of life, this new listing in Island Walk, Naples might be exactly what you’ve been looking for. Located at 3766 Whidbey Way, this move-in-ready home offers the perfect blend of comfort, convenience, and resort-style living—ideal for New Yorkers seeking a winter retreat or a full-time Florida lifestyle.

This single-family home features approximately 2,000 square feet of living space with 3 bedrooms, a home office, and 3 full bathrooms, giving you plenty of room to spread out—something that’s hard to come by in New York. The home’s private, solar-heated pool with southern exposure makes everyday living feel like a vacation, while the spacious lanai offers room to create your own outdoor kitchen and entertaining space.

Inside, you’ll find an updated kitchen with granite countertops, plantation shutters, tile and laminate floors, and recent major upgrades including a new roof and A/C, making this an easy, low-stress transition for out-of-state buyers.

One of the biggest draws for New Yorkers is the lifestyle. Island Walk is a gated, amenity-rich community where you can walk to the Town Center for pools, fitness facilities, pickleball and tennis courts, scenic walking paths, and even on-site dining. You’re also just minutes from Naples’ white-sand beaches, world-class dining and shopping, and only 30 minutes from RSW Airport for easy trips back to NYC.

Whether you’re looking for a seasonal escape from winter, a long-term relocation, or a smart investment in Florida real estate, this home checks all the boxes.

For more information or to schedule a private virtual or in-person showing, call Colin O'Leary at 239-989-2385.

View the full listing on Zillow:
https://www.zillow.com/homedetails/3766-Whidbey-Way-Naples-FL-34119/55816681_zpid/?view=public
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