Skysail Real Estate

Welcome to Skysail, a premier subdivision nestled in the heart of Naples, Collier County, Florida. This exclusive community offers a luxurious coastal lifestyle with a touch of Southern charm.

Skysail is renowned for its upscale homes, pristine landscaping, and top-notch amenities. Residents can enjoy stunning views of the Gulf of Mexico, lush greenery, and beautiful sunsets right from their doorstep.

Living in Skysail means having access to world-class dining, shopping, and entertainment options just a stone's throw away. Whether you prefer relaxing on the beach, playing a round of golf, or exploring the vibrant arts scene, there is something for everyone in this vibrant community.

With easy access to major highways and airports, Skysail is perfect for those who value convenience and connectivity. Whether you're looking for a permanent residence or a vacation home, Skysail offers the perfect blend of luxury and comfort.

Come experience the best of Naples living at Skysail – where every day feels like a vacation in paradise.

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...