Skysail Homes with Pickleball Amenities

Welcome to Skysail, Naples’ hidden gem nestled in the heart of Collier County, Florida. This vibrant subdivision is a sanctuary for those seeking a blend of luxury, community, and an active lifestyle. With its meticulously designed homes and stunning landscapes, Skysail offers an unparalleled living experience that captures the essence of Florida’s coastal charm.

One of the standout features of Skysail is its commitment to providing residents with exceptional amenities, particularly for pickleball enthusiasts. As the sport continues to grow in popularity, Skysail has embraced this trend by incorporating dedicated pickleball courts within the community. Imagine stepping out of your beautifully appointed home and finding yourself just moments away from engaging matches with neighbors or honing your skills in a friendly game. The courts are designed to cater to players of all skill levels, ensuring that everyone can enjoy the thrill of competition and camaraderie.

Beyond pickleball, Skysail boasts a wealth of amenities that foster a sense of community and well-being. Residents can enjoy scenic walking trails, lush green spaces, and inviting gathering areas perfect for socializing or unwinding after a long day. The subdivision’s strategic location in Naples means that you’re just a short drive away from pristine beaches, exquisite dining options, and vibrant shopping districts.

Whether you’re a retiree looking to embrace an active lifestyle or a family seeking a welcoming community, Skysail offers the perfect blend of relaxation and recreation. Discover your dream home in Skysail, where every day feels like a vacation, and the spirit of community thrives!

Newest Skysail Homes with Pickleball Amenities

$639,900

3 Beds ⋅ 2.5 Baths ⋅ 226034738 MLS

Experience refined lakeside living in SkySail, one of Naples’ most exciting gated communities. Brand new, and positioned on a premium homesite with an expansive water views, this beautifully upgraded White Star residence by Neal Communities offers a thoughtfully enhanced floor plan designed to feel open, spacious and effortlessly connected. The single-story layout features 3 bedrooms, 2.5 baths, a private den and 2-car garage, with an open-concept great room, kitchen and café creating an inviting centerpiece for everyday living and entertaining. Architectural enhancements include an expanded entry and foyer, upgraded den configuration, butler's pantry, enhanced primary suite, additional interior utility/storage space, and recessed ceiling details in both the great room and primary bedroom, bringing added dimension and a more custom feel throughout the home. The oversized great room flows naturally into the upgraded kitchen and café before extending to the covered private lanai, where the wide, unobstructed lake backdrop becomes part of the living experience. The private primary suite is positioned at the rear of the home to take advantage of the peaceful waterfront views and features a generous bedroom, spacious bath and walk-in closet. Two additional bedrooms and a full guest bath are thoughtfully separated from the primary suite, while the dedicated den provides the flexibility for a sophisticated home office, media room or additional retreat. Enjoy custom plantation shutters/window treatments, lighting, and fans throughout, for a hassle free move in ready experience. This home is truly meticulous! Beyond the residence, SkySail delivers a true resort-inspired lifestyle, with a Lakehouse and Wellness Center, resort-style lagoon pool, lap pool, fitness facilities, pickleball and tennis courts, walking trails, parks, dog park, fishing pier, and kayak/canoe access throughout a community distinguished by its extensive lakes and natural surroundings. A premium water-view homesite, upgraded White Star floor plan and one of SkySail’s most desirable settings come together to create an exceptional opportunity for Naples living.

4101 Pegasus WAY, Naples

$1,180,661

3 Beds ⋅ 3 Baths ⋅ 226035114 MLS

The Captiva by Neal Communities is designed for entertaining! A spacious great room is open to the dining area and kitchen. The kitchen also offers a walk-in pantry to keep staples handy. Nice day or evening outside? Hang out on the covered lanai! When it is time for fun and games, head to the club room to play foosball, pool or video games. For guests, the guest suite with private bath will be appreciated The other secondary bedroom is also convenient to a bath. The primary suite includes two walk in closets and bath with two sink vanities and water closet. The home also offers an office and a 3 car garage. SkySail is a beautiful community offering a clubhouse, tennis and pickleball courts, walking stations and work out stations, 2 pools, a fitness room, outdoor gaming area, a fishing pier and fire pit. There are two dog parks. SkySail is a natural gas community. This home i being built on Homesite 320 and will be Ready Soon!

4310 Cepheus WAY, Naples

$832,185

3 Beds ⋅ 2 Baths ⋅ 226035107 MLS

READY NOW! New Home by Neal Communities in SkySail. This beautiful BRIGHT MEADOW floor plan has 2309 SF, 3 bedrooms, den, 2.1 baths and a 3- car garage. The kitchen offers a spacious island, designer Chef’s Kitchen, Wall oven, 42” Cabinetry with Quartz counters, and upgraded tile floors. IMPACT WINDOWS/DOORS, 8-ft doors, pocket sliders, coffer ceilings, and a beautiful lanai. Many benefits to living in this wonderful community is enjoying NATURAL GAS, LOW HOA FEES AND FULL OF AMENITIES! SkySail is a beautiful community offering a clubhouse, tennis and pickleball courts, walking stations and work out stations, 2 pools, a fitness room, outdoor gaming area, a fishing pier, fire pit and dog parks. SkySail is a natural gas community. The images are not an exact representation of this feature home and the feature home will not be sold furnished. This home is built on Homesite 388.

4691 SkySail DR, Naples

$554,621

3 Beds ⋅ 2.5 Baths ⋅ 226035099 MLS

READY NOW! New Home by Neal Communities in the popular SkySail community! This beautiful White Star floor plan has 2064 SF, 3 bedrooms, den, 2.1 baths, a 2- car garage, upgraded kitchen package with 42” cabinetry, quartz counters, pantry and stainless appliances, impact windows/doors and 8-ft doors. SkySail is a beautiful community offering a clubhouse, tennis and pickleball courts, walking stations and work out stations, 2 pools, a fitness room, outdoor gaming area, a fishing pier and fire pit. There are two dog parks. SkySail is a natural gas community. The images are not an exact representation of this home and the feature home will not be sold furnished nor is a pool included with this home. This home is built on Homesite 283.

4236 Pegasus WAY, Naples

$554,900

3 Beds ⋅ 2 Baths ⋅ 226034986 MLS

Welcome to this exceptional lakefront home, beautifully situated in the sought after Skysail community of Naples. Featuring over $130,000 in thoughtfully selected upgrades, this beautifully maintained residence blends elegant finishes, modern conveniences, and effortless Florida living. This beautifully maintained Smart Home features an inviting screened front porch and a light-filled, open concept floor plan with crown molding throughout. The spacious great room with tray ceiling and fan flows seamlessly into the dining area and beautifully appointed kitchen featuring white cabinetry, quartz countertops, a generous center island, natural gas range, and abundant storage. A private study/den with French doors provides the perfect space for working from home or relaxing. The primary suite offers a peaceful retreat with two custom walk-in closets and ensuite bath featuring dual vanities and a tiled walk-in shower. Additional bedrooms provide comfortable accommodations with walk-in closets, full bath with tub/shower enclosure for family and guests. The laundry room includes a gas dryer, electric washer, utility sink, and additional storage. Step out to the covered lanai and enjoy serene lake views and spectacular Southwest Florida sunsets. The two-car garage features epoxy flooring, mini-split air conditioning, and an electric vehicle charger. Skysail offers resort- style amenities including a Lakehouse, resort-style pool, lap pool, fitness center, pickleball and tennis courts, walking and biking paths, dog park, scenic lakes and more- all with low HOA fees and no flood insurance required. Conveniently located near shopping, dining, schools, white sandy beaches, and all Naples has to offer, Skysail provides the perfect blend of resort-style living and everyday convenience. Your dream home awaits!

4564 Centaurus CIR, Naples

$566,802

2 Beds ⋅ 2 Baths ⋅ 226034975 MLS

Discover the spacious Eventide 4 plan at SkySail, thoughtfully designed for both relaxation and entertaining. Located on Homesite 383, this feature home showcases an elegant elevation and offers an open-concept layout centered around an expansive great room with a recessed ceiling, dining area, and a beautifully equipped kitchen featuring an island, quartz countertops, 42” upper cabinetry, GE stainless appliances, dovetail drawers and doors and a stylish backsplash. The large primary suite offers a walk-in closet, recessed ceiling, and a luxurious bath with a walk-in shower and private water closet. A well-placed guest bedroom sits near the second full bath, while a private den with French doors provides additional flexibility. Additional features include 8’ doors throughout, a screened lanai, impact-resistant glass, wood-look tile flooring, and a pocket sliding glass door that blends indoor and outdoor living. SkySail is a natural gas community offering low HOA fees and exceptional amenities—making it the perfect place to call home. Schedule your private showing today and experience the comfort and convenience for yourself. Images are not an exact representation of this feature home. This home is being built on Homesite 383.

4671 SkySail DR, Naples

$669,404

4 Beds ⋅ 3 Baths ⋅ 226034972 MLS

Ready Now! This brand-new Triumph single-family home by Neal Communities is available now in the highly desirable SkySail community. Situated homesite 277, this beautifully upgraded 4-bedroom, 3 bath, 2-car garage home offers luxury, style, and functionality throughout. The open-concept design boasts a gourmet kitchen package with quartz countertops, GE stainless steel appliances, 42” upper cabinets with dovetail drawers and soft-close doors, designer-selected backsplash, roll-out shelves, and a spacious center island—perfect for entertaining. Elegant details like upgraded tile flooring throughout, coffered ceiling, 8-foot doors, and a pocket sliding glass door leading to the screened-in lanai elevate the living experience. Built with impact-resistant windows this home combines beauty and peace of mind. SkySail is a natural gas community with low HOA fees and a wealth of amenities, making it the perfect place to call home. Schedule your private showing today and experience the comfort and convenience this home has to offer! The images are not an exact representation of this feature home and the feature home will not be sold furnished, nor is an outdoor kitchen included. This home is built on Homesite 277.

4239 Pegasus WAY, Naples

$496,500

3 Beds ⋅ 2 Baths ⋅ 226034968 MLS

New Dream 2 Single Family Home by Neal Communities in SKYSAIL is READY NOW!. This single family home is a 3 bedroom, Den, 2 bath and offers a 2 car garage home. UPGRADES THROUGHOUT! Gourmet kitchen package, quartz counters, upgraded cabinets, coffered ceiling, pocket sliding glass doors stainless steel appliances, upgraded tile floors throughout, IMPACT WINDOWS/DOORS, 8-ft doors, with a beautiful screened in lanai. Make your appointment to come see it today! Many benefits to living in this wonderful community is enjoying NATURAL GAS, LOW HOA FEES AND FULL OF AMENITIES! This home is built on lot 426. *Photos are of Dream Model * The images are not an exact representation of this feature home and the feature home will not be sold furnished.

4475 Centaurus CIR, Naples

$355,517

3 Beds ⋅ 2.5 Baths ⋅ 226034964 MLS ⋅ Skysail BLDG.

Welcome home to the SAWYER at Skysail, a stunning townhome designed for comfort, style and modern living. 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 2906.

5042 Draco CIR Unit 2906, Naples

$346,780

3 Beds ⋅ 2.5 Baths ⋅ 226034958 MLS ⋅ Skysail BLDG.

Welcome home to the Avery 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 0105.

5129 Draco CIR Unit 0105, Naples

$719,900

3 Beds ⋅ 2.5 Baths ⋅ 226034764 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to an exceptional Starlight home in the highly sought-after SKYSAIL community of Naples! Offering 2,235 sf of beautifully designed living space, this impressive single-story home features 3 bedroom, 2.5 baths, a private office/den, and a 2-car garage. Designed for effortless Florida living and entertaining, the open-concept floor plan flows beautifully from the spacious great room and dining area into the well-appointed kitchen with a generous walk-in pantry. The private primary suite featuring two walk-in closets and a spacious bath with a large walk-in shower, while two additional bedrooms offer plenty of space for family and guests. The showstopper is outdoors! Step into your own private tropical retreat featuring a gorgeous ins ground pool and outdoor kitchen- the perfect backdrop for sunny Naples afternoons, weekend gatherings, and year-round outdoor living. Located in SkySail, one of Naples' most exciting communities, this home delivers the lifestyle - beautiful indoor spaces, incredible outdoor living, and outstanding community amenities. This is more than a home- it's the Naples lifestyle you've been waiting for!

4056 PEGASUS WAY, Naples

$454,900

3 Beds ⋅ 2 Baths ⋅ 226033834 MLS

Welcome to Skysail, one of Naples' newest resort-style communities by Neal Communities. This beautiful Sandcastle villa features an open floor plan with spacious living areas, three bedrooms, two bathrooms, and a versatile den ideal for a home office, hobby room, or additional guest space. The modern kitchen offers quartz countertops, stainless steel appliances, and a large center island perfect for entertaining. The split-bedroom layout provides privacy for both owners and guests, while the screened lanai offers peaceful outdoor living overlooking the landscaped surroundings. Residents of Skysail enjoy outstanding amenities, including a resort-style pool, lap pool, fitness center, tennis and pickleball courts, lakehouse/clubhouse, walking and biking trails, a new amenities director will soon join the community. Conveniently located near shopping, dining beaches, and everything Naples has to offer. Enjoy the Florida lifestyle in this growing amenity-rich community with natural gas and low HOA Fees!

4636 Skysail DR, Naples

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