Skysail Homes with Streetlight Amenities

Welcome to Skysail, a hidden gem nestled in the heart of Naples, Florida, where coastal charm meets modern living. This vibrant neighborhood is a haven for those seeking a serene lifestyle without sacrificing convenience. Skysail is known for its beautifully designed homes, each exuding a unique character while maintaining a cohesive community aesthetic. With the promise of a welcoming atmosphere, residents enjoy well-maintained streets adorned with streetlight amenities, ensuring safety and comfort during evening strolls.

The allure of Skysail extends beyond its picturesque homes. The neighborhood is surrounded by lush landscapes and vibrant greenery, providing a tranquil retreat from the hustle and bustle of city life. Families and individuals alike will appreciate the nearby parks and recreational areas, perfect for outdoor activities and community gatherings.

Living in Skysail means you’re just a stone’s throw away from Naples’ pristine beaches, upscale shopping, and gourmet dining options. The area boasts an array of cultural attractions, including art galleries, theaters, and the renowned Naples Botanical Garden, making it an ideal locale for those who appreciate both nature and the arts.

With its friendly community spirit and convenient amenities, Skysail offers the perfect blend of relaxation and engagement. Whether you’re enjoying a sunset walk under the glow of the streetlights or hosting a barbecue in your backyard, Skysail is more than just a neighborhood; it’s a place to call home. Discover the charm of Skysail today and embrace the Naples lifestyle you’ve always dreamed of!

Newest Skysail Homes with Streetlight Amenities

$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

$495,736

3 Beds ⋅ 2 Baths ⋅ 226031212 MLS

Introducing the brand new Imagination 2 style floor plan by Neal Communities now in SkySail. This stunning home offers impact resistant windows and doors, 3 bedrooms plus a den, 2 full bathrooms and a 2 car garage. There are a range of premium features including a smart home package, 8 foot doors, upgraded tile flooring, stainless steel appliances and quartz countertops. 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, fishing pier and fire pit. There are two dog parks. SkySail is a natural gas community. This home is being built on Homesite 428. 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.

4467 Centaurus CIR, Naples

$649,000

3 Beds ⋅ 2.5 Baths ⋅ 226026261 MLS

This Beautiful NEARLY NEW FURNISHED 3 bedroom 3 bath home offers tile throughout, a gorgeous chef's kitchen with 42" cabinetry, quartz counters, stainless steel appliances including double oven & GAS cooktop. Beautiful views of the lake from the great room and lanai.You will love the breath taking sunrises and sunsets from your own private oasis! Naples newest gated community Skysail afford you the active Florida lifestyle you've been dreaming of! Resort amenities for all ages with 2 pools..spa..fitness center... lake front Clubhouse... fire pit.. pickleball..tennis.. fishing pier.. walking and biking trails.

4003 Pegasus WAY, Naples

$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

$560,106

4 Beds ⋅ 2.5 Baths ⋅ 226025055 MLS

New HERITAGE Single Family Home by Neal Communities in SKYSAIL is Ready Now! This single-family home is a 4-bedroom plus loft, 2.1 bath, 2 car garage home. UPGRADES THROUGHOUT! Gourmet kitchen package, quartz counters, upgraded 42"cabinets, stainless steel appliances, IMPACT WINDOWS/DOORS, 8-ft doors and a beautiful lanai. SkySail is beautiful community offering a clubhouse, tennis and pickleball courts, walking stations and work out stations, 2 pools, a fitness room, outdoor gaming area, fishing pier and fire pit. There are two dog parks. Skysail is a natural gas community! This home is built on lot 415. *Photos are of Heritage Model * Not of actual home. Images are not an exact representation of this feature home and the feature home will no be sold furnished.

4519 Centaurus CIR, 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.