Windward Bay Homes with Pickleball Amenities

Welcome to Windward Bay, a hidden gem nestled in the heart of Naples, Florida, within the beautiful Collier County. This vibrant subdivision offers a unique blend of serene living and active lifestyle, making it the perfect destination for those seeking both relaxation and recreation.

Windward Bay is renowned for its stunning waterfront properties, lush landscapes, and a welcoming community atmosphere. Residents enjoy a variety of amenities that cater to an active lifestyle, including access to pickleball courts, which have become a popular feature for both seasoned players and beginners. Imagine spending your mornings perfecting your serve or enjoying friendly matches with neighbors, all while soaking in the warm Florida sunshine.

The homes in Windward Bay are thoughtfully designed, featuring spacious layouts and modern finishes that reflect the coastal charm of Naples. Many properties boast breathtaking views of the surrounding waterways, providing a tranquil backdrop for your daily life. Whether you’re interested in a cozy retreat or a spacious family home, Windward Bay has something to suit every taste and lifestyle.

In addition to its recreational amenities, Windward Bay is conveniently located near Naples' finest shopping, dining, and entertainment options. Explore the vibrant local culture, indulge in exquisite cuisine, or take a short drive to the beautiful beaches that Naples is famous for.

Experience the best of Florida living at Windward Bay, where community, comfort, and an active lifestyle come together seamlessly. Your dream home awaits!

Newest Windward Bay Homes with Pickleball Amenities

$349,000

2 Beds ⋅ 2 Baths ⋅ 226033041 MLS ⋅ Windward Bay BLDG.

Set in one of North Naples’ most convenient locations, this beautiful home in Tarpon Bay offers a new roof, new exteriors, turnkey easy living, a private preserve view and an entire community that has just undergone a complete coastal refresh. Inside, you will find new kitchen appliances, new light coastal flooring, a new air-conditioning system, a new water heater, a new washer and dryer, and the rare convenience of natural gas. Large windows fill the home with natural light while overlooking the quiet preserve, creating a bright, relaxed coastal atmosphere. Elevator service provides easy community access. The entire Tarpon Bay community has recently been refreshed with brand-new roofs as well, beautifully updated building exteriors and a renewed coastal aesthetic throughout. Directly across the private, quiet street is the Castaways Club, the centerpiece of Tarpon Bay’s resort-style lifestyle, with an infinity-edge pool overlooking a massive lake, a spa, a full fitness center, pickleball and clay tennis courts, grilling areas, professional on-site management, a boat dock and a kayak launch. Beautiful lakes, fountains, mature palms, paver roundabouts and an impressive illuminated entrance create a peaceful, polished setting. Just minutes from Interstate 75 and approximately 15 minutes from Mercato, Naples beaches, shopping and dining, with Southwest Florida International Airport just under 30 minutes away. This is an exceptional opportunity to enjoy a fully updated residence in a beautifully located North Naples community with low-maintenance living.

1886 Tarpon Bay DR S Unit 204, Naples

$364,000

3 Beds ⋅ 2 Baths ⋅ 226011834 MLS ⋅ Windward Bay BLDG.

Rarely available three-bedroom, two-bath first-floor end residence in the active, gated community of Tarpon Bay. This residence features tile flooring, a desirable split bedroom floor plan and an open, functional layout designed for comfortable living. A quiet screened lanai provides privacy and a relaxing outdoor setting surrounded by natural landscape. This pet-friendly community offers a full amenity package including Har-Tru lighted tennis courts, pickleball, basketball, bocce, a children's play area, lakefront gazebo, fishing, canoe and kayak storage, and scenic sidewalks for recreation or jogging. The community also features a clubhouse with fitness center, business center, resort-style infinity pool and spa, clubroom with catering kitchen, covered outdoor grilling area, card room and billiards room. Ideally located in North Naples, Tarpon Bay is close to shopping, dining, approximately 20 minutes to Vanderbilt Beach and RSW Airport.

1882 Tarpon Bay DR S Unit 101, Naples

Start Your Search

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Regional Multiple Listing Service of Minnesota. Real estate listings held by brokerage firms other this firm are marked with the Broker Reciprocity logo. Information Deemed Reliable But Not Guaranteed. Property locations as displayed on any map are best approximations only and exact locations should be independently verified.

Listing data © 2026 Regional Multiple Listing Service of Minnesota. All rights reserved. By searching, you agree to the EULA.