Windward Isle market snapshot
Homes, condos and townhomes. Source: Naples MLS listing data, updated October 27, 2026. Information deemed reliable but not guaranteed.
About 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.
Current listings
Windward Isle Homes for Sale
See the newest homes for sale in Windward Isle, 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.
Windward Isle Amenities
Windward Isle takes a distinctly different approach to amenities than many gated communities in Naples. There is no centralized clubhouse or recreational complex, allowing the neighborhood to remain primarily residential. Instead, homes were designed to provide much of the lifestyle experience privately, with swimming pools, covered lanais and generous outdoor living areas common throughout the community. The central lake, tropical landscaping, gated entrance and landscaped streetscapes enhance the neighborhood environment without requiring residents to support a large collection of shared recreational facilities.
For some buyers, this simplicity is an important advantage. Those who already belong to a private golf, beach or social club, or who simply prefer to enjoy recreation independently, may not want to pay for an extensive amenity package within their residential community. Windward Isle allows buyers to own a newer luxury single-family home within a gated setting while choosing their own recreational and social experiences throughout Naples.
The community’s North Naples location effectively becomes one of its most important lifestyle amenities. Vanderbilt Beach, Clam Pass Park and other Gulf destinations are accessible to the west, while Mercato, Waterside Shops, Artis-Naples and numerous restaurants, shops and services are within convenient reach. Airport-Pulling Road also provides straightforward access north and south through Naples, while nearby Vanderbilt Beach Road and Pine Ridge Road connect residents with I-75 and other parts of Collier County. For buyers seeking an intimate gated North Naples enclave with just 28 luxury single-family homes, newer-established construction, private pools and outdoor living, and convenient access to Naples’ beaches, shopping and dining without mandatory club membership, Windward Isle offers a distinctly private residential alternative.
What Is Near Windward Isle?
Downtown Naples (5th Avenue South): 6.3 miles
Closest beach: Clam Pass Park, 3.1 miles
RSW Airport: 21.2 miles
Notable shopping & dining nearby: Waterside Shops, 2.5 miles
Closest park: North Collier Regional Park, 2.5 miles
(Distances are approximate straight-line distances.)
Windward Isle Floor Plans
Floor plans are provided as a complimentary resource to help you understand the layouts available in Windward Isle. Plans and specifications can change, so confirm details for any specific home.
View Windward Isle floor plans (PDF)
Where Is Windward Isle?
Windward Isle FAQ
Where is Windward Isle located?
Windward Isle is in North Naples off Airport-Pulling Road, just south of Orange Blossom Drive. Vanderbilt Beach, Clam Pass Park, Mercato, Waterside Shops and Artis-Naples are all within convenient reach.
What types of homes are in Windward Isle?
Windward Isle is made up of just 28 single-family luxury homes by Seagate Development Group, with no condos, villas or townhomes. Homes feature mostly coastal and West Indies-inspired architecture, private pools and generous indoor and outdoor living spaces, and development began in the mid-2010s.
Is Windward Isle gated, and is there an HOA?
Yes, Windward Isle is gated and governed by a homeowners association. There is no mandatory golf or country club membership.
What amenities does Windward Isle offer?
Windward Isle intentionally skips shared amenities, so there is no clubhouse, community pool, fitness center, golf course or racquet complex. The lifestyle centers on each home's private pool and outdoor living space, along with a central lake, tropical landscaping and a privacy wall.
How often do homes come up for sale in Windward Isle?
Not very often. With only 28 residences, resale inventory is naturally limited, so buyers interested in this quiet cul-de-sac enclave may need some patience. Only select homes sit on the central lake, so views should be evaluated home by home.
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.
