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SkySail Homes for Sale in Naples, FL
SkySail is a Neal Communities lake community on Oil Well Road in northeast Naples (34120), on about 642 acres that include roughly 246 acres of lakes, so most homesites have a water view. Neal opened SkySail in 2022 with plans for about 1,500 single-family and multi-family homes, built around a Lakehouse and Wellness amenity center. It is one of the more affordable ways to buy new construction with a Naples address.
Market snapshot (MLS, November 6, 2026): about 22 SkySail homes were listed, from roughly $345,000 for townhomes to about $1,180,000, averaging around $590,000 and $280 per square foot. Neal also sells new and quick move-in homes directly; its single-family homes have been advertised from the low $400,000s.
SkySail at a Glance
- Builder: Neal Communities
- Homes: townhomes and single-family homes, about 1,500 to 3,700 square feet, with two- and three-car garages
- Amenities: Lakehouse and Wellness buildings, resort pool, fitness center, tennis, pickleball, trails and dog parks
- Location: Oil Well Road east of Everglades Boulevard, near Paradise Coast Sports Complex, Big Corkscrew Island Regional Park and Ave Maria
- Not age restricted: open to all ages; Collier County public schools
Who SkySail Fits
SkySail fits buyers who want a new home, lake views and resort-style amenities at a lower price per square foot than west Naples, and who are comfortable with a longer drive to the beaches and downtown. Compare it with Ave Maria, Golden Gate Estates new construction, Valencia Sky (55+) and the full list of new communities in Naples.
Buying New at SkySail
Quick move-in homes with designer finishes often carry the best incentives, while to-be-built homes let you choose the homesite and options. Ask for the HOA and any Community Development District (CDD) amounts in writing and confirm the flood zone of the exact homesite. Register me as your agent at your first model visit so I can negotiate for you at no cost to you.
SkySail FAQ
Who builds SkySail?
Neal Communities, a Southwest Florida homebuilder.
Where is SkySail?
On Oil Well Road in northeast Naples, Florida 34120.
Is SkySail a 55+ community?
No. It is open to buyers of all ages.
Want the current SkySail quick move-in list? Call or text Glen Bigness at 239-272-4663.
SkySail Homes for Sale - Updated Daily from the MLS
Welcome home to the PARKER at Skysail, a stunning townhome designed for comfort, style and modern living. This beautifully upgraded residence features 3 spacious bedrooms...
- 3 Beds
- 2.5 Baths
- 226038914 MLS
- Skysail Bldg.
Courtesy of Neal Communities Realty, Inc..
Welcome to this pristine,TURNKEY Tuscan-style home located in SKYSAIL, one of Naples' most desirable resort-style communities. Featuring 4 bedrooms, 3 full bathrooms, and...
- 4 Beds
- 3 Baths
- 226038661 MLS
Courtesy of Realty One Group MVP.
Better than new and available now! This fully furnished 3-bedroom, 3-bath plus den Harvest 3 home offers expansive lake views and a private cul-de-sac location in SkySa...
- 3 Beds
- 3 Baths
- 226033679 MLS
Courtesy of John R Wood Properties.
EXPANSIVE LAKEFRONT VIEWS & PREMIUM LOT!!! Experience refined lakeside living in SkySail, one of Naples’ most exciting gated communities. Brand new, and positioned on a p...
- 3 Beds
- 2.5 Baths
- 226034738 MLS
Courtesy of Compass Florida, LLC.
The Captiva by Neal Communities is designed for entertaining! A spacious great room is open to the dining area and kitchen. The kitchen also offers a walk-in pantry to ...
- 3 Beds
- 3 Baths
- 226035114 MLS
Courtesy of Neal Communities Realty, Inc..
READY NOW! New Home by Neal Communities in SkySail. This beautiful BRIGHT MEADOW floor plan has 2309 SF, 3 bedrooms, den, 2.1 baths and a 3- car garage. The kitchen of...
- 3 Beds
- 2 Baths
- 226035107 MLS
Courtesy of Neal Communities Realty, Inc..
READY NOW! New Home by Neal Communities in the popular SkySail community! This beautiful White Star floor plan has 2064 SF, 3 bedrooms, den, 2.1 baths, a 2- car garage...
- 3 Beds
- 2.5 Baths
- 226035099 MLS
Courtesy of Neal Communities Realty, Inc..
Welcome to this beautiful "Dream" model lakefront home in the highly desirable Skysail community. Featuring over $130,000 in thoughtfully selected upgrades, this beautifu...
- 3 Beds
- 2 Baths
- 226034986 MLS
Courtesy of Realty One Group MVP.
Discover the spacious Eventide 4 plan at SkySail, thoughtfully designed for both relaxation and entertaining. Located on Homesite 383, this feature home showcases an eleg...
- 2 Beds
- 2 Baths
- 226034975 MLS
Courtesy of Neal Communities Realty, Inc..
Ready Now! This brand-new Triumph single-family home by Neal Communities is available now in the highly desirable SkySail community. Situated homesite 277, this beautiful...
- 4 Beds
- 3 Baths
- 226034972 MLS
Courtesy of Neal Communities Realty, Inc..
New Dream 2 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 ...
- 3 Beds
- 2 Baths
- 226034968 MLS
Courtesy of Neal Communities Realty, Inc..
Welcome home to the SAWYER at Skysail, a stunning townhome designed for comfort, style and modern living. This beautifully upgraded residence features 3 spacious bedrooms...
- 3 Beds
- 2.5 Baths
- 226034964 MLS
- Skysail Bldg.
Courtesy of Neal Communities Realty, Inc..
Welcome home to the Avery at Skysail, a stunning townhome designed for comfort, style and modern living and is READY NOW! This beautifully upgraded residence features 3 s...
- 3 Beds
- 2.5 Baths
- 226034958 MLS
- Skysail Bldg.
Courtesy of Neal Communities Realty, Inc..
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to an exceptional Starlight home in the highly sought-after SKYSAIL community of Naples...
- 3 Beds
- 2.5 Baths
- 226034764 MLS
Courtesy of Realty One Group MVP.
Welcome to Skysail, one of Naples' newest resort-style communities by Neal Communities. This beautiful Sandcastle villa features an open floor plan with spacious living a...
- 3 Beds
- 2 Baths
- 226033834 MLS
Courtesy of Realty One Group MVP.
Introducing the brand new Imagination 2 style floor plan by Neal Communities now in SkySail. This stunning home offers impact resistant windows and doors, 3 bedrooms plus...
- 3 Beds
- 2 Baths
- 226031212 MLS
Courtesy of Neal Communities Realty, Inc..
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
Courtesy of Coldwell Banker Realty.
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.
Courtesy of Neal Communities Realty, Inc..
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
Courtesy of John R Wood Properties.
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
Courtesy of ND Realty.
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
Courtesy of Neal Communities Realty, Inc..
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
Courtesy of Realty One Group MVP.
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