Winding Cypress sits on more than 1,100 acres and has over 80 acres of lakes and a large area set aside for nature preserves, so people say it feels very quiet and peaceful, and the tall cypress trees and winding roads make walking or driving around the neighborhood feel like you're living in a private park, and you can always spot birds out by the boardwalk and overlook. The community's gated entrance leads into different neighborhoods, each with separate views of the lakes, preserves, or winding trails, and you'll see homes with tile roofs, covered lanais, landscaped yards, and designs that range from the smaller attached villas like the Cressida, which has two or three bedrooms, two full bathrooms, a gathering room with kitchen and dining areas, and a two-car garage, all on one level so it's easy to get around, to the Estate Series homes, which can have two to five bedrooms and reach up to 3,656 square feet if you need more space. Home models include names like Serenity, Abbeyville, Summerwood, Martin Ray, Pinnacle, Tangerly Oak, and Infinity, and they have between two and five bedrooms, two to four-plus bathrooms, and sizes from about 1,500 to over 3,600 square feet, and most homes have views of natural water or preserve land.
People living here use natural gas, which is a detail that means appliances and heating are a little more efficient, and the developers, DiVosta Homes, made space for 774 homes, though they do have a plan to grow by another 550 homes in their next phase, and homes now sell from the mid-$200,000s up to the $600,000 range, depending on size and location. Winding Cypress runs as a senior community for people 55 and older, and it's got places for independent living, assisted living, memory care, nursing homes, and what's called a continuing care retirement community, which means people can stay in the same area even if their needs change later on, and every home has safety features like an Emergency Alert System and offers 24-hour supervision and care.
The main clubhouse at Winding Cypress covers about 13,000 square feet, and you'll find things like a library, WiFi café and lounge, a fitness center with a movement studio, a multipurpose activity room, and a state-of-the-art fitness center for group or solo workouts, plus an arts room, spa, beach area, cabanas, and a heated resort-style lagoon pool with a spa for soaking away aches, plus outdoor spaces for yoga, walking, and just sitting with neighbors. Folks here have access to a barefoot bar and grill, a fire pit for evening conversations, bocce ball and pickleball courts, tennis courts, a dog park, and a community garden for growing vegetables or fruit, and there are always scheduled activities with an on-site Activities Director who plans community events, movie nights, music programs, and resident-led clubs. The walking trails, boardwalk with an overlook, and bird-watching spots make it easy for people who like to stay close to nature or just want to enjoy a quiet afternoon outside.
Dining is flexible, with restaurant-style menus, all-day dining, allergy-friendly meals, meal preparation services, and chefs who make sure people have options, and room amenities include private bathrooms, Wi-Fi, cable TV, kitchenettes, air conditioning, phone lines, and furnished units if you need them, while community services cover housekeeping, laundry or dry cleaning, move-in help, concierge services, and family support. Healthcare services offer help with daily needs like bathing, dressing, medication management, and people who need more support-such as non-ambulatory care or memory help-can get that within the community.
Winding Cypress sits north of U.S. 41 and east of Collier Blvd, also including the neighborhood VeronaWalk, and living here means having access to shared green space, water views, and a full social and care program if you want it, with a simple process for moving in and getting set up, along with a secure community that still feels connected to the natural beauty of the area.
