Skysail Real Estate

Welcome to Skysail, an enchanting subdivision nestled in the heart of Naples, Florida, within the vibrant Collier County. This idyllic community offers a perfect blend of luxury, comfort, and the quintessential Florida lifestyle, making it an ideal choice for families, retirees, and everyone in between.

Skysail is renowned for its meticulously designed homes, featuring modern architecture and stunning landscapes that reflect the beauty of the Sunshine State. Residents enjoy spacious floor plans, high-end finishes, and serene outdoor spaces that invite relaxation and entertainment. With a variety of options available, from cozy single-family homes to elegant estates, there’s something to suit every taste and lifestyle.

One of the standout features of Skysail is its prime location. Just a short drive away, you’ll find Naples’ world-famous beaches, where sun-soaked days and breathtaking sunsets await. The area is also home to an array of upscale shopping, gourmet dining, and cultural attractions, including art galleries and theaters, ensuring that residents have access to the best that Naples has to offer.

For those who appreciate an active lifestyle, Skysail boasts proximity to numerous parks, golf courses, and recreational facilities, making it easy to embrace the outdoors. The community fosters a welcoming atmosphere, with friendly neighbors and a strong sense of camaraderie, perfect for creating lasting friendships.

Experience the charm and allure of Skysail, where your dream home awaits in one of Florida’s most sought-after locales. Come explore this captivating community and discover why so many choose to call Skysail home!

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

4491 Centaurus CIR, Naples $506,023

New Dream 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 TH...

3 Beds
2 Baths
226025053 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

4580 Skysail DR, Naples $424,900 ▼

WELCOME TO SKYSAIL, ONE OF NAPLES' NEWEST RESORT-STYLE COMMUNITIES BY NEAL COMMUNITIES. THIS NEW SANDCASTLE MODEL/VILLA OFFERS AN OPEN-CONCEPT FLOOR PLAN WITH SPACIOUS LI...

3 Beds
2 Baths
226022829 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

4235 Pegasus WAY, Naples $739,349 ▲

The Lighthouse home design by Neal Communities offers an open layout for the common living areas. The beautifully-equipped kitchen comes with an island, corner walk in pa...

4 Beds
3 Baths
226012128 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...