Regatta Landing Real Estate

Welcome to Regatta Landing, an exquisite subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community is a hidden gem, offering residents a perfect blend of tranquility and vibrant coastal living.

Regatta Landing is renowned for its stunning waterfront properties, where residents can enjoy breathtaking views of the serene waterways and lush landscapes. The subdivision features a diverse selection of homes, from elegant single-family residences to upscale townhomes, each designed with modern comforts and stylish finishes. With meticulously manicured lawns and beautiful architecture, Regatta Landing is a feast for the eyes.

One of the standout features of this community is its prime location. Just moments away from the pristine beaches of Naples, residents can indulge in sun-soaked days by the Gulf of Mexico. The area is also rich in recreational opportunities, with nearby parks, golf courses, and nature reserves that invite outdoor enthusiasts to explore and enjoy Florida’s natural beauty.

In addition to its stunning surroundings, Regatta Landing is conveniently located near a variety of shopping, dining, and entertainment options. From upscale boutiques to gourmet restaurants, there’s always something to discover just around the corner. Families will appreciate the proximity to top-rated schools, ensuring a quality education for their children.

With its idyllic setting, welcoming community atmosphere, and unmatched amenities, Regatta Landing is the perfect place to call home. Experience the best of Naples living in this enchanting subdivision, where every day feels like a vacation. Come and explore the endless possibilities that await you in Regatta Landing!

Newest Listings in Regatta Landing

$1,195,000

3 Beds ⋅ 2 Baths ⋅ Regatta Landing SubDv.

SKIP THE WAITLIST! Windstar on Naples Bay Social Membership is available immediately with this property, offering buyers the opportunity to begin enjoying the Windstar lifestyle without the typical wait. Experience exceptional Southwest Florida living in this First-floor Coach Home in Regatta Landing, offering 2,348 square feet of spacious living with three Bedrooms, two Baths and an attached two-car Garage. Designed to live like a single-family home, this light-filled residence features a desirable split-bedroom floor plan, high ceilings, and an open-concept layout ideal for everyday living and entertaining. The spacious kitchen opens seamlessly to the main living and dining areas and features abundant cabinetry, a pantry, double ovens and a wine cooler. Significant upgrades include impact-resistant windows and doors for added peace of mind, along with an A/C system replaced in 2023. The expansive primary suite is a true private retreat, featuring generous proportions, two custom closets and a spacious primary bath with dual sinks, a soaking tub and oversized separate shower. Two additional bedrooms offer flexibility for guests, family or a home office. One of the home's standout features is the expansive oversized screened lanai, extending the living space outdoors and showcasing peaceful views across Windstar's beautifully maintained golf course. It's an exceptional setting for morning coffee, alfresco dining, entertaining or simply enjoying the Florida lifestyle. Residents of Regatta Landing enjoy a stunning private community pool and spa, along with a social grill area beautifully positioned along the waterway, creating an inviting setting to gather, entertain and enjoy Southwest Florida living. Windstar on Naples Bay offers one of Naples' most distinctive lifestyles, bringing golf, boating and beach living together within one gated community. Residents enjoy access to Windstar's private Keewaydin Island beach with boat transportation aboard the Keewaydin Queen. Optional Club membership opportunities provide access to additional amenities and experiences. Ideally located just minutes from downtown Naples, Fifth Avenue South, Third Street South, exceptional dining, shopping and Naples' renowned Gulf beaches, this residence presents an outstanding opportunity to enjoy the highly sought-after Windstar on Naples Bay lifestyle. Membership is optional, subject to Club approval, and requires a separate purchase.

2534 Windward Court Unit 15-101, Naples

$1,295,000

2 Beds ⋅ 3 Baths ⋅ Regatta Landing SubDv.

Welcome to 2439 Breakwater Way, Unit 9102 — a beautifully upgraded coach home in Regatta Landing, the newest enclave within the prestigious Windstar on Naples Bay community. This isn't just a home, it's a front-row seat to the boating, golf, and coastal lifestyle Naples is known for. Spanning over 2,600 square feet, this first-floor residence lives large with 2 bedrooms plus a den, 2.5 baths, and a 2-car attached garage. From the moment you walk in, quality is evident: beautiful French Oak hardwood floors run throughout, complemented by crown molding, plantation shutters, and frameless shower doors that elevate every room. The kitchen is a showpiece — stainless KitchenAid appliances, double wall ovens, quartz counters, and under-cabinet lighting come together for a space built for both everyday living and serious entertaining. Step out onto the spacious, fully enclosed lanai and take in tranquil canal and mangrove views — a private, peaceful backdrop that's hard to find this close to the water. Upgraded with glass doors, the lanai stays cool and comfortable year-round while offering the feel of an outdoor living space. Boat dock with lift options are available for purchase just steps behind the home, offering a short ride straight out to Naples Bay and the Gulf of Mexico. Beyond your door, Windstar delivers a resort-caliber lifestyle: a gated, boating and golf community with tennis courts, and a community pool, spa, and grill room just a short walk away. Built in 2017 and offered with quality upgrades throughout, this is a rare opportunity to own in one of Naples' most sought-after waterfront communities — where boating, golf, and bay views come standard.

2439 Breakwater Way Unit 9102, Naples

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