Winding Cypress is a master-planned gated community located in southeast Naples, Florida, offering residents a harmonious blend of modern living and natural tranquility. Developed by DiVosta Homes, it encompasses approximately 766 homes set within a expansive landscape that prioritizes preservation and outdoor enjoyment. The community stands out for its thoughtful integration of residential spaces with extensive natural features, creating an inviting atmosphere for those seeking both comfort and connection to the environment.
History of the community traces back to its development as a DiVosta project focused on quality construction and lifestyle amenities in the growing Naples area. Positioned to capitalize on the region's appeal, it has grown into a vibrant neighborhood emphasizing harmony with its surroundings.
The location in Naples, FL 34114 provides excellent accessibility. Situated off Collier Boulevard near Interstate 75, it offers convenient access to major routes while maintaining a sense of seclusion. Proximity to Tamiami Trail enhances connectivity to broader Southwest Florida.
Lifestyle within Winding Cypress revolves around relaxation, recreation, and community engagement. Residents appreciate the peaceful setting surrounded by preserves and lakes, fostering a calm yet active daily routine. Social opportunities abound through various clubs and gatherings centered around fitness, games, and nature.
Real estate in Winding Cypress features a mix of single-family homes and villas in styles like Coastal Contemporary and Mediterranean Revival. Properties often include custom options, professional landscaping, and views of water or preserves, ranging from villas to larger custom estates. The market reflects demand for this upscale yet approachable living option.
Nearby attractions include shopping at Tamiami Crossing and Freedom Square, with restaurants and retail just minutes away. Beaches, Marco Island, and downtown Naples attractions are within a short drive, providing cultural and recreational options.
Parks and recreation opportunities are abundant on-site with trails, boardwalks, and outdoor spaces, complemented by the adjacent Picayune Strand Forest for additional exploration and wildlife viewing.
Shopping and dining options nearby feature everyday conveniences like Publix along with upscale choices in Naples. The on-site Shady Palm Café adds a convenient dining experience for residents.
Transportation is straightforward with easy highway access for commuting or travel. The gated design enhances security while sidewalks and paths support pedestrian-friendly movement within the community.
Demographics reflect a diverse resident base drawn to the area's appeal, though specific current data is limited in public sources.
Safety and livability are high priorities, with the gated entrance, professional management, and low crime indicators contributing to a secure environment. The community's design promotes walkability and outdoor enjoyment in a well-maintained setting.
Local highlights include the extensive natural preserves, active social scene, and resort-like amenities that set it apart. Events and clubs enhance the sense of belonging.
People choose to live in Winding Cypress for its balance of luxury amenities, natural beauty, convenient location, and strong community focus, making it an ideal choice for those desiring a serene yet engaging Florida lifestyle.
Community Amenities
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Name: ** ** Clubhouse
- Type of Amenity: Clubhouse
- Availability within the community or nearby: Within the community
- Description: Elegant space for events, gatherings, and relaxation with access to pool area.
- Key features: Lounge areas, event spaces, connection to resort-style pool
- Capacity or size: Details not publicly available
- Hours of operation: Details not publicly available
- Access restrictions: Residents and guests
- Ratings and reviews: Details not publicly available
- Email: Details not publicly available
- Phone number: (239) 732-7171 (HOA management)
- Office Phone number: (239) 732-7171
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Name: ** ** Resort-Style Pool & Spa
- Type of Amenity: Swimming pool
- Availability within the community or nearby: Within the community
- Description: Luxurious pool with spa, waterfall, and lounge chairs surrounded by landscaping.
- Key features: Heated options, lap swimming area, electronically monitored
- Capacity or size: Maximum load 131 persons
- Hours of operation: Sunrise to sunset
- Access restrictions: Residents and accompanied guests; key fob access
- Ratings and reviews: Details not publicly available
- Email: Details not publicly available
- Phone number: (239) 732-7171 (HOA management)
- Office Phone number: (239) 732-7171
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Name: ** ** Shady Palm Café
- Type of Amenity: Resort-style amenity
- Availability within the community or nearby: Within the community
- Description: Poolside bar and restaurant for casual dining and drinks.
- Key features: Outdoor seating, resident-focused menu
- Capacity or size: Details not publicly available
- Hours of operation: Varies seasonally (e.g., summer hours listed on site)
- Access restrictions: Residents and guests
- Ratings and reviews: Details not publicly available
- Email: spmanager@swpropmgt.com
- Phone number: (239) 261-3440
- Office Phone number: (239) 732-7171
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Name: ** ** Fitness Center
- Type of Amenity: Fitness center
- Availability within the community or nearby: Within the community
- Description: State-of-the-art facility with cardio, strength equipment, and views.
- Key features: Movement room for classes, natural light
- Capacity or size: Details not publicly available
- Hours of operation: 5:00 a.m. to midnight daily
- Access restrictions: Residents and accompanied guests; key fob
- Ratings and reviews: Details not publicly available
- Email: Details not publicly available
- Phone number: (239) 732-7171 (HOA management)
- Office Phone number: (239) 732-7171
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Name: ** ** Tennis Courts
- Type of Amenity: Tennis court
- Availability within the community or nearby: Within the community
- Description: Five clay tennis courts for play and events.
- Key features: Lighting for evening use
- Capacity or size: 5 courts
- Hours of operation: 7:00 a.m. to 11:00 p.m.
- Access restrictions: Residents and guests
- Ratings and reviews: Details not publicly available
- Email: Details not publicly available
- Phone number: (239) 732-7171 (HOA management)
- Office Phone number: (239) 732-7171
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Name: ** ** Pickleball Courts
- Type of Amenity: Resort-style amenity
- Availability within the community or nearby: Within the community
- Description: Four well-maintained pickleball courts.
- Key features: Part of sports complex
- Capacity or size: 4 courts
- Hours of operation: 7:00 a.m. to 11:00 p.m.
- Access restrictions: Residents and guests
- Ratings and reviews: Details not publicly available
- Email: Details not publicly available
- Phone number: (239) 732-7171 (HOA management)
- Office Phone number: (239) 732-7171
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Name: ** ** Dog Parks
- Type of Amenity: Park
- Availability within the community or nearby: Within the community
- Description: Two designated areas for small and large dogs.
- Key features: Secure, off-leash play
- Capacity or size: Details not publicly available
- Hours of operation: Dawn to dusk
- Access restrictions: Residents and pets
- Ratings and reviews: Details not publicly available
- Email: Details not publicly available
- Phone number: (239) 732-7171 (HOA management)
- Office Phone number: (239) 732-7171
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Name: ** ** Boardwalk and Trails
- Type of Amenity: Park
- Availability within the community or nearby: Within the community
- Description: Wooden boardwalk through preserves leading to overlook.
- Key features: Birdwatching, nature immersion
- Capacity or size: Details not publicly available
- Hours of operation: Closes at sunset
- Access restrictions: Residents; no entry to preserve areas
- Ratings and reviews: Details not publicly available
- Email: Details not publicly available
- Phone number: (239) 732-7171 (HOA management)
- Office Phone number: (239) 732-7171
Notes
Management company: Seacrest Southwest Property Management. Sources: Official HOA website windingcypress.org (community-amenities and contact pages); real estate listings on Redfin, Homes.com, and Naples sites for context on availability. Contact and hours primarily from HOA site and management references.