SKYSAIL

SkySail is a gated Neal Communities neighborhood off Oil Well Road in northeast Naples (ZIP 34120). Neal opened it in June 2022 on a plan of 642 acres for about 1,500 homes, with 246 of those acres set aside as lakes (Neal Communities, May 2022). As of the 2025 tax roll there were 189 finished homes and 116 vacant lots, so a large share of the community is still being built (Momentum Realty, Sep 2026). Streets are named for constellations, including Centaurus Circle, Draco Circle, Pegasus Way and Aquila Place.
Homes and Prices
Single-family plans run from about 1,500 to 3,500 sq ft, up to five bedrooms, with two- or three-car garages. Attached townhomes, such as the Winslow at SkySail series, start near 1,500 sq ft. In October 2026 a new 1,778 sq ft Imagination 2 model with a den and lake view was listed at $495,736, and a 2026 townhome was asking $345,525 (MLS, 2026). Resale values have cooled: 32 closings in the year to September 2026 had a $508,000 median, 7.7 percent lower than the prior year, or about $245 per sq ft (Momentum Realty, Sep 2026).
Amenities and Lifestyle
The 4,237 sq ft Lake House has a gathering hall, a catering kitchen and a screened veranda. A separate 6,350 sq ft wellness building has a weight room, group fitness studio, and kids and teen lounges. Outside are a lagoon-style pool and lap pool, eight pickleball courts, two tennis courts, a kayak launch, a fishing pier and a lakeside trail with workout stations (Neal Communities, May 2022).
HOA and Fees
A new single-family listing showed $658 per quarter ($2,632 a year). A resale townhome that closed at $420,000 in August 2026 carried $926 per quarter, covering insurance, grounds, pest control, irrigation, roads and reserves (MLS, 2026). No CDD was on record for the listings we checked, but some lots are in flood zone AH, so get a flood quote. SkySail’s association portal is not public, so request the declaration and budget from Neal or the seller.
Location
Oil Well Road links SkySail west to Collier Boulevard and Immokalee Road, and east to Ave Maria. Listed schools are Estates Elementary, Corkscrew Middle and Palmetto Ridge High.
Other Oil Well Road and Immokalee Road options are on our Naples listings, and a SkySail resale can go on the market through the Naples flat fee listing. Call Sal DiBenedetto, Licensed Real Estate Broker, The DiBe Group, brokered by eXp Realty, at 239-256-5005 to compare new and resale homes.
Close by, buyers also look at Bent Creek Preserve, Orange Blossom Ranch and Greyhawk at Golf Club of the Everglades.