Skysail Real Estate

Welcome to Skysail, a prestigious subdivision nestled in the heart of Naples, Collier County, Florida. This exclusive community offers a luxurious lifestyle with stunning views and top-notch amenities.

Skysail is renowned for its upscale homes, beautifully landscaped streets, and a strong sense of community. Residents here enjoy the perfect blend of tranquility and convenience, with easy access to shopping, dining, and entertainment options in Naples.

The properties in Skysail boast modern architectural designs, spacious interiors, and high-end finishes. Whether you're looking for a cozy single-family home or an expansive estate, Skysail has something to suit every taste and lifestyle.

Living in Skysail means waking up to breathtaking sunrises, enjoying leisurely strolls along tree-lined streets, and taking in the serene beauty of the surrounding nature. Residents can also take advantage of the community's amenities, which may include a clubhouse, pool, tennis courts, and walking trails.

With its prime location in Naples, Skysail offers easy access to pristine beaches, championship golf courses, and cultural attractions. Whether you're a nature enthusiast, a foodie, or a shopping aficionado, Skysail puts you right in the center of it all.

Experience luxury living at its finest in Skysail, where every day feels like a vacation. Come home to elegance, comfort, and sophistication in this coveted Naples subdivision.

Newest Listings in Skysail

4003 Pegasus Way, Naples $649,000

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 appliance...

3 Beds
3 Baths
Skysail SubDv.

5034 Draco Circle, Naples $345,525

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...

3 Beds
3 Baths
Skysail SubDv.

4519 Centaurus Circle, Naples $581,106

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 THROU...

4 Beds
3 Baths
Skysail SubDv.

3980 Pegasus Way, Naples $525,000

Refined Lakeside Living in SkySail - Discover beautifully upgraded living in the sought-after SkySail community, where refined design meets the tranquility of lakeside li...

3 Beds
2 Baths
Skysail SubDv.

3993 Perseus Street, Naples $739,900

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to this RARELY AVAILABLE 3-bed plus den, New Construction, 2.5 bath BRIGHT MEADOW floor...

3 Beds
3 Baths
Skysail SubDv.

3995 Pegasus Way, Naples $895,900

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 Buil...

5 Beds
6 Baths
Skysail SubDv.

4647 SkySail Drive, Naples $958,732

The Sea Mist plan offers a spacious, open-concept main living area that brings together the great room, dining area, and island kitchen for effortless everyday living and...

3 Beds
3 Baths
Skysail SubDv.

4679 SkySail Drive, Naples $718,396 ▼

THE PRICE HAS BEEN REDUCED FOR MONTH OF JULY AND IS 50% OFF OF THE LOT PREMIUM, WHICH IS INCLUDED IN THE CURRENT LIST PRICE. New HARVEST 3 Single Family Home by Neal Co...

4 Beds
3 Baths
Skysail SubDv.

4653 Centaurus Circle, Naples $489,000 ▼

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...

3 Beds
2 Baths
Skysail SubDv.

5046 Draco Circle, Naples $369,970

Morgan Townhome - End Unit - Water View! Unit 3001 Come home to the Morgan - a new townhome design by award winning Neal Communities. This 2 story home includes ...

3 Beds
3 Baths
Skysail SubDv.

3967 Pegasus Way, Naples $790,000 ▼

LUXURY. LIFESTYLE. ZERO WAIT. Welcome to one of the most extensively upgraded and beautifully appointed homes in Skysail—a better-than-new lakefront masterpiece where eve...