Skysail Homes with Streetlight Amenities

Welcome to Skysail, an enchanting subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community is a hidden gem that perfectly blends modern living with the serene beauty of nature, making it an ideal place for families, retirees, and anyone seeking a vibrant lifestyle.

Skysail boasts a variety of beautifully designed homes that cater to a range of tastes and preferences. From contemporary single-family residences to elegant townhomes, each property is thoughtfully crafted to ensure comfort and style. With streetlight amenities illuminating the charming streets, evening strolls become a delightful experience, enhancing the sense of community and safety that Skysail proudly offers.

One of the standout features of Skysail is its proximity to Naples' pristine beaches and lush parks, providing residents with ample opportunities for outdoor activities and relaxation. Enjoy a day soaking up the sun on the sandy shores or explore the nearby nature trails, all just a short drive away. The community is also conveniently located near top-rated schools, shopping districts, and gourmet dining options, ensuring that everything you need is within easy reach.

In Skysail, you’ll find more than just a home; you’ll discover a lifestyle enriched by friendly neighbors, beautiful surroundings, and a welcoming atmosphere. Whether you’re sipping coffee on your porch or enjoying a sunset walk under the glow of the streetlights, Skysail invites you to experience the best of Naples living. Come and explore this vibrant community, where your dream home awaits!

Newest Skysail Homes with Streetlight 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

$554,900

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

$650,000

3 Beds ⋅ 3 Baths ⋅ 226031475 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to 3998 Perseus Street, an exceptional lakefront home in SkySail offering luxury finishes, extensive upgrades, and move-in-ready convenience. This beautifully upgraded Neal Communities Harvest 3 model features 3 bedrooms plus a den, 3 full bathrooms, and a spacious 3-car garage on a premium lakefront homesite with peaceful water views and beautiful Florida sunsets. Better than building new, the original owners invested more than $72,000 in builder upgrades plus thousands more in improvements after closing, bringing the total investment in upgrades and improvements to over $80,000. Inside, you'll find beautiful Buckingham Oak luxury vinyl plank flooring throughout most of the home, whole-house impact windows, upgraded lighting, premium finishes, and an open-concept layout designed for entertaining and everyday living. The chef-inspired kitchen is the centerpiece of the home and features premium quartz countertops, an oversized island, upgraded Aristokraft cabinetry with crown molding and soft-close features, designer hardware, under-cabinet lighting, a dramatic tile backsplash, stainless steel appliances, and a pull-out trash and recycling cabinet. All three bathrooms feature upgraded finishes including quartz countertops, premium cabinetry, designer tile, upgraded shower glass, plumbing fixtures, and luxury hardware. Additional upgrades include an outdoor kitchen rough-in, recessed lighting, additional electrical outlets, upgraded interior doors, trim and hardware, a garage utility sink, garage service door, designer lighting, ceiling fans throughout the home and covered lanai, custom Venetian blinds, blackout curtains, decorative curtain rods, Maytag washer, and Maytag gas dryer. Step outside to the screened and covered lanai overlooking the lake and enjoy a peaceful waterfront setting with an expansive backyard offering plenty of room for a future custom swimming pool. SkySail offers natural gas and an incredible resort-style lifestyle with a clubhouse, fitness center, resort-style pool, tennis and pickleball courts, fishing pier, walking and biking opportunities, and an active social calendar. The surrounding Randall Boulevard and Orangetree corridor continues to grow, bringing shopping, dining, healthcare, schools, and everyday conveniences closer to home, with easy access to Immokalee Road, Oil Well Road, I-75, Downtown Naples, Gulf beaches, and Southwest Florida International Airport. Why wait months to build and then spend thousands more after closing? With premium lake views, impact protection, a 3-car garage, over $80,000 in upgrades and improvements, and the finishing touches already completed, this SkySail home is ready to enjoy from day one.

3998 Perseus ST, Naples

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