Skysail Homes with Fishing Pier Amenities

Welcome to Skysail, an enchanting subdivision nestled in the heart of Naples, Florida, where coastal charm meets modern living. Located in Collier County, Skysail is a hidden gem that offers the perfect blend of tranquility and convenience, making it an ideal destination for families, retirees, and everyone in between.

One of the standout features of Skysail is its stunning homes, designed with elegance and comfort in mind. Each property is thoughtfully crafted to provide a warm and inviting atmosphere, showcasing spacious layouts, contemporary finishes, and beautiful outdoor spaces. Here, you can enjoy the best of Florida living, with ample natural light flooding in and lush landscaping surrounding your home.

For those who appreciate the joys of waterfront living, Skysail boasts exclusive access to a community fishing pier. Imagine spending your evenings casting a line into the sparkling waters of Naples Bay, or simply relaxing as you watch the sunset paint the sky in hues of orange and pink. This amenity not only enhances your outdoor lifestyle but also fosters a sense of community among residents who share a love for fishing and the great outdoors.

Skysail is not just a place to live; it’s a lifestyle choice. With its proximity to pristine beaches, vibrant shopping districts, and top-rated dining options, you’ll find everything you need just a stone's throw away. Experience the allure of Naples living at Skysail, where every day feels like a vacation. Discover your dream home today and embrace the coastal lifestyle you've always desired!

Newest Skysail Homes with Fishing Pier Amenities

$345,525

3 Beds ⋅ 2.5 Baths ⋅ 226025064 MLS ⋅ Skysail BLDG.

Welcome home to the Winslow at Skysail, a stunning townhome designed for comfort, style and modern living and is READY NOW! This beautifully upgraded residence features 3 spacious bedrooms, 2.1 baths, and a 1 car garage - perfect for today’s lifestyle. Inside enjoy quartz countertops, soft closing cabinetry, a designer selected backsplash and under cabinet LED lighting that elevates the kitchen’s look and feel. GE stainless steel appliances, including a washer dryer, make every day living effortless. Step outside and experience the best of the SkySail community offering resort-style amenities including a clubhouse, tennis and pickleball courts, walking trails with fitness stations, two pools, a fitness room, outdoor gaming area, fishing pier and a cozy fire pit. Pet lovers will appreciate two dedicated dog parks and the convenience of a natural gas community adds even more value. This is more than a home. It’s a lifestyle. Come discovery SkySail today. The images are not an exact representation of this feature home and the feature home will not be sold furnished. This unit is built on homesite 2904

5034 Draco CIR, Naples

$895,900

5 Beds ⋅ 5.5 Baths ⋅ 226017144 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. PRICED TO SELL! This home would cost over ONE MILLION DOLLARS if purchased direct from the Builder. It is located on a SUPER PREMIUM lot size with stunning and expansive 180 degree lake views. With a fresh paint job throughout and only two years young, this looks and feels practically brand new! The community makes everyday life feel like an adventure—and every moment is designed for making memories. Nestled within Skysail by Neal Communities, one of Collier County’s newest and most exciting communities, this stunning lakeside residence offers the perfect blend of comfort, space, and connection. Surrounded by 246 acres of sparkling lakes, Skysail creates a peaceful, scenic setting where families can truly thrive. Step inside this beautifully upgraded two-story home featuring 5 spacious bedrooms and 4 full bathrooms, plus 2 half baths—thoughtfully designed with flexibility in mind. The main floor includes 3 bedrooms, including a luxurious primary suite, making everyday living easy and convenient. Upstairs, you’ll find 2 additional bedrooms and an expansive bonus room—perfect for a playroom, media space, friend gatherings, or guest retreat. The 2.5-car garage provides plenty of room for storage, bikes, or even your golf cart. Natural light fills the open-concept living space, where modern elegance meets comfortable living. From the plank tile flooring and tray ceilings to the custom lighting and refined finishes, every detail has been carefully selected. At the heart of the home, the chef’s kitchen is made for gathering—complete with quartz countertops, stainless steel appliances, gas cooking, a stylish tile backsplash, oversized pendant lighting, and a walk-in pantry. The primary suite offers a private escape, featuring dual vanities, a spacious walk-in shower, and a generous walk-in closet designed for both function and luxury. Step outside and experience your own backyard oasis. The screened lanai showcases a sparkling pool with a tranquil water feature, all overlooking a breathtaking lake view. Whether it’s morning coffee, afternoon swims, or sunset evenings with family, this space is designed to be enjoyed year-round. Life in Skysail extends far beyond your front door. The community is filled with amenities for every age and lifestyle—scenic walking and biking trails, a beautiful clubhouse and lakehouse, fitness center, tennis and pickleball courts, basketball, and a lap pool. Families will love the resort-style pool, playground, dog park, fishing pier, outdoor fire pit, and game room with a catering kitchen—perfect for celebrations and gatherings. This isn’t just a home—it’s a place where your family can grow, connect, and create lasting memories, and make new friends all set against the backdrop of one of Southwest Florida’s most beautiful lakefront communities. Don't delay!

3995 Pegasus WAY, Naples

$469,000

3 Beds ⋅ 2 Baths ⋅ 226009672 MLS

Built in 2023 and better than new, this 3-bedroom, 2-bath single-family home in gated Skysail offers upgraded finishes, impact windows and doors, natural gas, and move-in-ready convenience without the builder wait. Inside, the open great-room floor plan features high-end wood-look luxury vinyl flooring throughout the main living areas and an upgraded kitchen with quartz countertops, tile backsplash, under-cabinet lighting, stainless steel appliances, natural gas stove, pantry, and peninsula—perfect for entertaining. Additional owner upgrades include wood-look plantation shutters, remote-controlled rear blinds, whole-home air purifier integrated into the HVAC system, a water softener and filtration system, and upgraded lighting. The screened lanai overlooks a fenced backyard with western exposure—ideal for sunset evenings—and offers room for a future pool. Impact-resistant windows and doors provide peace of mind. Concrete block construction. 2-car garage. Smart home features. Skysail residents enjoy resort-style amenities including clubhouse, fitness center, community pool and lap pool, pickleball, tennis, basketball, fishing pier, kayak/canoe launch, bike/jog paths, and a dog park—all within a gated lake-centered community in one of Naples’ fastest-growing corridors.

4653 Centaurus CIR, Naples

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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.