Skysail market snapshot
Homes, condos and townhomes. Source: Naples MLS listing data, updated October 27, 2026. Information deemed reliable but not guaranteed.
About Skysail
SkySail is a gated master-planned community in Northeast Naples, located in the growing 34120 area near Oil Well Road and Immokalee Road. Developed by Neal Communities, SkySail encompasses approximately 640 acres, including more than 240 acres of lakes, creating a water-oriented residential setting with expansive lake views throughout the community. The neighborhood includes both townhomes and single-family residences, providing a range of ownership options within the same master-planned environment. Sidewalks, trails, landscaped streets and extensive recreational facilities are incorporated throughout the community.
A defining feature of SkySail is its substantial lakeside amenity complex, which includes the Lakehouse and Wellness Building along with resort and lap pools, a spa, fitness facilities, tennis, pickleball, trails, playground and dog park. Residents can also enjoy fishing, kayaking and canoeing, outdoor gathering areas and other recreational spaces centered around the community’s lakes. SkySail offers this broad lifestyle package without a mandatory golf or country club membership, while its Northeast Naples location provides convenient access to Big Corkscrew Island Regional Park, Paradise Coast Sports Complex, shopping, dining, schools and everyday services.
Why People Like the SkySail Community
- Extensive Lake Setting: More than 240 acres of lakes are incorporated throughout the community, providing water views and opportunities for outdoor recreation.
- Multiple Housing Choices: SkySail includes townhomes and single-family residences with a variety of sizes, settings and garage configurations.
- Two Amenity Buildings: The Lakehouse provides social and gathering spaces, while the Wellness Building is centered around fitness and recreation.
- Strong Racquet Amenities: Eight pickleball courts and two tennis courts provide substantial opportunities for recreational play.
- Multiple Pools: Residents have access to a resort-style lagoon pool, lap pool and spa.
- Outdoor Recreation: Trails, fitness stations, fishing, kayaking, canoeing, playground areas, dog parks and outdoor gathering spaces extend recreation throughout the community.
- No Mandatory Golf Membership: SkySail provides an extensive amenity package without requiring residents to maintain a golf or country club membership.
What You Need to Know About Living in SkySail
- SkySail Is Gated: The community has controlled access and is governed through a homeowners association.
- There Is a Mandatory HOA: Buyers should review current association fees, included services, reserves and governing documents for the specific property they are considering.
- There Is Also a CDD: Buyers should evaluate the applicable Community Development District assessment as part of the property’s overall carrying costs.
- Housing Types Differ: Townhomes and the various single-family home collections can have different maintenance responsibilities, association costs, lot characteristics and ownership considerations.
- The Community Is Relatively New: Individual homes can differ in age, builder options, hurricane protection, pools, outdoor living features and owner improvements.
- Private Pools Are Property-Specific: Residents have access to community pools, while some individual single-family homes also feature private pools and spas.
- Current Rules and Costs Should Be Verified: Association fees, CDD assessments, leasing, pets, maintenance responsibilities and other requirements should be confirmed for the specific property.
Current listings
Skysail Homes for Sale
See the newest homes for sale in Skysail, updated throughout the day from the Naples MLS. Want a private showing or an honest read on value? Call Renee Hahn at (239) 287-2576.
The source of this real property information is the copyrighted and proprietary database compilation of the M.L.S. of Naples, Inc. Accuracy of this information is not warranted or guaranteed. Information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Skysail Amenities
SkySail offers one of the more extensive recreational packages among newer communities in this part of Collier County. The lakeside amenity complex includes both a Lakehouse and Wellness Building overlooking one of the community’s large lakes. The Lakehouse provides a gathering hall, catering kitchen and screened veranda along with indoor and outdoor spaces for relaxing and socializing. The Wellness Building includes a weight room, fitness studio, group fitness room and multipurpose spaces, providing residents with dedicated facilities for both individual and organized fitness activities.
Outdoor recreation is equally substantial. Residents have access to a lagoon-style resort pool, lap pool, spa, eight pickleball courts, two tennis courts, playground, dog park and walking and biking trails with outdoor fitness stations. The lake-oriented environment also provides a fishing pier and opportunities for kayaking and canoeing, while event lawns, outdoor gaming and gathering areas create additional places to enjoy the community. With more than 240 acres of lakes spread throughout SkySail, water is an important part of both the recreational experience and the views available from many residences.
SkySail’s Northeast Naples location places the community near Big Corkscrew Island Regional Park and Paradise Coast Sports Complex, expanding the recreational opportunities available nearby. Shopping, restaurants, schools and everyday services continue to grow throughout the surrounding 34120 area, while Immokalee Road provides connections toward I-75 and destinations throughout Naples. For buyers seeking a newer gated community with townhomes and single-family residences, extensive lakes, resort-style amenities, strong pickleball and tennis facilities and no mandatory golf membership, SkySail offers a comprehensive master-planned lifestyle.
What Is Near Skysail?
Downtown Naples (5th Avenue South): 19.8 miles
Closest beach: Clam Pass Park, 18.6 miles
RSW Airport: 22 miles
Notable shopping & dining nearby: Seed to Table, 14.2 miles
(Distances are approximate straight-line distances.)
Skysail Floor Plans
Floor plans are provided as a complimentary resource to help you understand the layouts available in Skysail. Plans and specifications can change, so confirm details for any specific home.
View Skysail floor plans (PDF)
Where Is Skysail?
Skysail FAQ
Where is SkySail located?
SkySail is in Northeast Naples in the 34120 area, near Oil Well Road and Immokalee Road. Big Corkscrew Island Regional Park and Paradise Coast Sports Complex are nearby, and Immokalee Road connects to I-75.
What types of homes are in SkySail?
SkySail, developed by Neal Communities, offers townhomes and single-family residences in a range of sizes, settings and garage configurations. Some single-family homes include private pools and spas.
Is SkySail gated, and is there an HOA or CDD?
SkySail is gated with a mandatory HOA, and there is also a CDD assessment to factor into carrying costs. There is no mandatory golf or country club membership, and fees and rules should be confirmed for the specific property.
What amenities does SkySail offer?
The lakeside complex includes the Lakehouse, with a gathering hall, catering kitchen and screened veranda, plus a Wellness Building with a weight room and fitness studios. Outdoors there is a lagoon-style pool, lap pool, spa, eight pickleball courts, two tennis courts, a playground, dog park, trails with fitness stations and a fishing pier.
How big a role does water play at SkySail?
A big one. More than 240 of SkySail's roughly 640 acres are lakes, so many homes enjoy water views, and residents can fish, kayak and canoe right in the community.
Last updated October 2026 by Renee Hahn, Your Naples Expert. Community details, fees and amenities can change, so confirm specifics for any home you are considering.
