Skysail Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Skysail and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

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
226026261 MLS

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
226025064 MLS

4519 Centaurus Circle, Naples $551,106 ▼

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
226025055 MLS

3980 Pegasus Way, Naples $520,000 ▼

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 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
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
6 Baths
226017144 MLS

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
226017243 MLS

4653 Centaurus Circle, Naples $469,000 ▼

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

3967 Pegasus Way, Naples $777,000 ▼

Your lucky number just came up—$777,000 ( LOWEST -PRICED POOL HOME in the entire Skysail Community plus -Fully Furnished ) Welcome to one of the most extensively upgraded...

3 Beds
2 Baths
226003064 MLS