windward isle

Windward Isle is an intimate gated community of just 28 single-family luxury homes located off Airport-Pulling Road in North Naples, just south of Orange Blossom Drive. Developed by Seagate Development Group, the community was designed as a low-density residential enclave centered around a quiet cul-de-sac rather than an extensive collection of shared amenities. Homes feature predominantly coastal and West Indies-inspired architecture, with generous indoor and outdoor living spaces, private swimming pools and upscale finishes that reflect the community's luxury positioning. A central lake provides water views for select residences, while tropical landscaping, a privacy wall and landscaped streetscapes contribute to the secluded residential setting.

What distinguishes Windward Isle is the combination of its small scale, newer luxury homes and central North Naples location. With only 28 residences, the community offers a very different experience from larger master-planned developments, while its location provides convenient access to many of North Naples' most popular destinations. Vanderbilt Beach, Mercato, Waterside Shops, Artis-Naples, Clam Pass Park, shopping, dining, healthcare and private golf opportunities are all within convenient reach. For buyers who prefer a private luxury residence and neighborhood setting over a community built around shared recreational facilities, Windward Isle offers a compelling alternative.

Why People Like the Windward Isle Community

• Only 28 Homes: Windward Isle is one of the smaller gated luxury residential enclaves in North Naples, creating an intimate neighborhood environment.

• Single-Family Luxury Homes: The community consists exclusively of detached residences rather than condominiums, villas or townhomes.

• Newer-Established Construction: Windward Isle was developed beginning in the mid-2010s, making its homes considerably newer than those in many established central North Naples neighborhoods.

• Private Pools and Outdoor Living: Homes were designed with substantial private outdoor living areas, and swimming pools are an important part of the individual residential experience.

• Lakefront Opportunities: Select residences are positioned around the community's central lake, providing water views and additional separation between properties.

• Distinctive Architecture: Coastal and West Indies-inspired architectural influences give the neighborhood a cohesive luxury aesthetic.

• No Mandatory Golf or Country Club Membership: Windward Isle is a residential community without the additional membership obligations associated with a private club.

• Central North Naples Location: Airport-Pulling Road provides convenient access to Vanderbilt Beach Road, Pine Ridge Road, U.S. 41 and many of Naples' shopping, dining, beach and cultural destinations.

What You Need to Know About Living in Windward Isle

• Windward Isle Is Gated: The community has controlled access and is governed through a homeowners association.

• There Are Only 28 Residences: Because Windward Isle is so small, resale inventory can be limited and opportunities to purchase within the community may be relatively infrequent.

• There Are No Shared Recreational Amenities: Windward Isle does not have a community clubhouse, swimming pool, fitness center, golf course or racquet-sports complex. The lifestyle is centered around each private residence and the surrounding North Naples location.

• Homes Are Individually Distinct: Although the community was developed with a cohesive architectural character, residences include customized designs, finishes and owner improvements, making property-specific comparison important.

• Lake Views Are Limited to Select Properties: Only a portion of the homes are positioned around the central lake, so buyers should evaluate the individual homesite and view.

• Private Amenities Are Property-Specific: Pools, spas, outdoor kitchens, fireplaces, expanded lanais and other recreational features belong to the individual residence rather than the community.

• There Is No Golf Course or Private Club: Buyers who want golf, tennis, fitness or country club amenities will need to pursue those opportunities independently outside Windward Isle.

• Current Costs and Rules Should Be Verified: HOA assessments, architectural requirements, leasing policies, pet restrictions and other community provisions can change and should be confirmed through current documents.