Skysail Real Estate

Welcome to Skysail, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This vibrant neighborhood is a perfect blend of natural beauty and modern convenience, making it an ideal place for families, retirees, and everyone in between.

Skysail is known for its stunning waterfront properties and lush landscapes, offering residents breathtaking views and a serene atmosphere. The community is designed with an active lifestyle in mind, featuring numerous walking trails, parks, and recreational facilities. Whether you enjoy a leisurely stroll along the shoreline or a spirited game of tennis, Skysail has something for everyone.

One of the standout features of Skysail is its proximity to Naples' world-class amenities. Just a short drive away, you’ll find upscale shopping at the renowned Waterside Shops, exquisite dining options, and the pristine beaches that Naples is famous for. The vibrant downtown area, with its charming boutiques and art galleries, is also within easy reach, providing a perfect backdrop for weekend outings.

Families will appreciate the excellent educational opportunities, with highly-rated schools serving the area. For nature enthusiasts, the nearby parks and nature preserves offer a chance to explore Florida's unique ecosystems, making it easy to enjoy the great outdoors.

In Skysail, you’re not just buying a home; you’re investing in a lifestyle. With its friendly community spirit, beautiful surroundings, and convenient location, Skysail truly embodies the best of Naples living. Come discover your dream home in this enchanting neighborhood, where every day feels like a vacation!

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
2.5 Baths
226026261 MLS

5034 Draco CIR, Naples — Skysail $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
2.5 Baths
226025064 MLS
Skysail Bldg.

4519 Centaurus CIR, 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
2.5 Baths
226025055 MLS

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
226024186 MLS

3993 Perseus ST, 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
2.5 Baths
226023130 MLS

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
5.5 Baths
226017144 MLS

4647 SkySail DR, 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
2.5 Baths
226017243 MLS

4679 SkySail DR, 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
226017242 MLS

4653 Centaurus CIR, 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
226009672 MLS

5046 Draco CIR, Naples — Skysail $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
2.5 Baths
226004819 MLS
Skysail Bldg.

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...