Highland Woods Villas Homes with Cabana Amenities

Welcome to Highland Woods Villas, an exquisite subdivision nestled in the heart of Bonita Springs, Florida, within vibrant Lee County. This charming community offers a perfect blend of luxury, comfort, and a laid-back lifestyle that defines the essence of Southwest Florida living.

Highland Woods Villas is renowned for its beautifully designed homes that cater to a variety of lifestyles. Each residence is thoughtfully crafted with modern amenities and elegant finishes, providing a serene retreat for families, retirees, and everyone in between. One of the standout features of this community is the availability of homes with cabana amenities. Imagine stepping out of your door to your very own private cabana, where you can unwind in style, host gatherings with friends, or simply enjoy the warm Florida sun in a tranquil setting.

The community is also surrounded by lush landscaping and scenic views, making it an ideal place for nature lovers. Residents can take advantage of the nearby walking trails, golf courses, and recreational facilities that enhance the active lifestyle Highland Woods promotes. With its prime location, you are just minutes away from the stunning beaches of Bonita Springs, shopping at local boutiques, and dining at some of the finest restaurants in the area.

Whether you’re seeking a seasonal getaway or a permanent residence, Highland Woods Villas offers a unique opportunity to embrace the Florida lifestyle. Come discover the charm of this delightful community, where every day feels like a vacation!

Newest Highland Woods Villas Homes with Cabana Amenities

$639,000

3 Beds ⋅ 2 Baths ⋅ 226029927 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to your new favorite spot in Highland Woods! This remodeled Cheshire Villa is the perfect blend of modern style and total comfort. Right when you walk in, the open-concept layout hits you with that "I’m home" feeling, featuring gorgeous luxury vinyl floors and crisp crown molding that makes the whole space pop. One of the best parts about this specific home is the layout. While most Cheshire models have a den, this one has been smartly converted into a true third bedroom, giving you that extra dedicated space that’s so hard to find. Plus, with a brand-new A/C system, you’ll be staying cool and worry-free all year long. If you love being outside, just wait until you see the backyard. The lanai has been expanded to create a massive outdoor hangout spot, complete with your own private pool. It’s the ultimate place to relax while looking out over the lush, green preserve—it feels like your own private tropical retreat. The Highland Woods Lifestyle Living here means diving into the Highland Woods lifestyle. It’s a fun, active bundled golf community where there’s always something happening at the clubhouse, the fitness center, or on the tennis and pickleball courts. Everything is at your fingertips since you’re right in the heart of Bonita Springs, you’re just minutes away from the area's best dining and shopping at Coconut Point, and of course, those stunning Gulf beaches. It’s easy, breezy Florida living at its finest.

26394 Clarkston DR, Bonita Springs

$469,000

2 Beds ⋅ 2 Baths ⋅ 226032352 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Step into the highly sought-after lifestyle of Highland Woods Golf & Country Club with this Ashmoor Villa, a property that offers the perfect canvas for your personal vision. If you’ve been searching for a home with "great bones" in a premier gated community, this is the one. Major capital improvements are already crossed off the list, including a new roof installed in 2021 and a fresh AC system from 2019, allowing you to focus your energy on the fun part—interior updates and design. The layout is bright and open, providing a seamless flow that’s just waiting for a modern touch. Outside, the villa lifestyle means less time on maintenance and more time enjoying the incredible bundled golf amenities. Highland Woods is known for its championship golf course, but the perks don't stop at the greens. Residents enjoy a vibrant clubhouse, a state-of-the-art fitness center, tennis and bocce courts, and a resort-style pool. Location is everything, and this neighborhood sits right in the heart of Bonita Springs. You are positioned moments away from the high-end shopping and dining at Promenade at Bonita Bay and Coconut Point Mall. When you're craving the Gulf breeze, the white sandy beaches are just a quick drive away. Whether you are looking for a seasonal retreat or a creative renovation project, this villa represents a rare opportunity to build equity in one of the area’s most established bundled golf communities. Bring your toolkit and your imagination—the potential here is limitless.

26504 Clarkston DR, Bonita Springs

$599,000

2 Beds ⋅ 2 Baths ⋅ 226031518 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. This stunning Cheshire Villa in the gated enclave of Highland Woods is the kind of home that makes you exhale the moment you walk through the door. It’s a seamless blend of high-end upgrades and effortless comfort, designed for those who appreciate the finer details. Inside, the villa shines with timeless touches like crown molding and plantation shutters throughout. The bathrooms have been completely refreshed with granite countertops, stylish new vanities, and modern fixtures, including a spacious walk-in shower in the primary suite. The bedrooms feature sleek, high-end laminate flooring, while the rest of the home is wired for sound with a whole-house system—perfect for setting the mood whether you're hosting a dinner party or relaxing on a Sunday morning. Major updates provide total peace of mind, including a new roof and gutters (2020) and high-impact windows (2023) for full hurricane protection. The exterior is just as impressive, featuring a recently upgraded back lanai with a picture-window screen for clear, expansive views, refreshed landscaping with elegant river rock, and a brand-new front lanai cage (2025). Even the garage got a makeover with fresh epoxy flooring in 2024. Living in Highland Woods means embracing a vibrant, active lifestyle. The community is packed with amenities, from the 18-hole championship golf course and resort-style pool with a cabana bar to the tennis, pickleball, and bocce courts. You can hit the state-of-the-art fitness center or enjoy a meal at the clubhouse, which offers both indoor and al fresco dining. The location is truly unbeatable. You’re right across the street from the Promenade at Bonita Springs and just a quick drive from the high-end shopping and dining at Coconut Point and Mercato. Plus, the white sands of the Gulf beaches are only minutes away. This is more than just a villa; it’s your gateway to the very best of Southwest Florida living.

26466 Clarkston DR, Bonita Springs

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