Highland Woods Homes with Cabana Amenities

Welcome to Highland Woods, an enchanting neighborhood nestled in the heart of Bonita Springs, Florida. This vibrant community offers a perfect blend of natural beauty, modern amenities, and a welcoming atmosphere, making it an ideal place for families, retirees, and everyone in between.

Highland Woods is renowned for its picturesque landscapes, featuring lush greenery and serene water features that create a tranquil environment. The neighborhood is conveniently located near some of the best shopping, dining, and entertainment options that Bonita Springs has to offer. Residents can enjoy easy access to beautiful beaches, golf courses, and parks, fostering an active lifestyle and a strong sense of community.

One of the standout features of Highland Woods is its stunning homes, many of which come equipped with luxurious cabana amenities. These inviting outdoor spaces are perfect for entertaining guests or simply relaxing in the sun. Imagine hosting summer barbecues by the pool, enjoying a refreshing drink under the shade of your cabana, or unwinding after a long day in your private oasis.

The homes in Highland Woods are designed with comfort and style in mind, offering spacious layouts, modern finishes, and the added bonus of outdoor living spaces. Whether you’re looking for a cozy retreat or a grand family home, you’ll find a variety of options that cater to your lifestyle.

Discover the charm of Highland Woods and experience the perfect blend of Florida living and community spirit. Your dream home awaits in this delightful neighborhood!

Newest Highland Woods Homes with Cabana Amenities

26751 Clarkston DR Unit 205, Bonita Springs

$374,900

2 Beds ⋅ 2 Baths ⋅ 226035915 MLS ⋅ St Andrews Verandas BLDG.

Welcome to the Carlton Veranda, a beautifully updated 2-bedroom, 2-bathroom residence that perfectly captures the relaxed, upscale lifestyle of Highland Woods. This isn't just a home; it’s your gateway to one of the most vibrant bundled golf communities in the area. Step inside to a bright, modern interior where the kitchen steals the show, featuring crisp white shaker cabinetry, elegant granite countertops, and sleek stainless steel appliances. The updates continue through both bathrooms, and the entire home offers total peace of mind with high-impact windows and doors throughout. A detached garage provides extra convenience and storage, while the screened veranda serves as the perfect spot to take in those lush, sweeping golf course views. The Highland Woods lifestyle has never been better, thanks to a massive recent transformation. You’ll have access to a brand-new resort-style pool, a cabana bar and restaurant for easy afternoons, and a top-tier fitness facility. Whether you’re hitting the resurfaced tennis courts, joining a pickleball match, or practicing on the expansive new putting green, there is always something to do. Location is everything here. You are perfectly positioned directly across from The Promenade at Bonita Springs, putting high-end dining, boutique shopping, and live music right at your doorstep. Plus, when you’re ready to explore further, the white sands of the Gulf of Mexico, the nightlife at Mercato, and the shops at Coconut Point are all just a quick drive away. This is Florida living, elevated.

26751 Clarkston DR Unit 205, Bonita Springs

$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

26841 Clarkston DR Unit 204, Bonita Springs

$375,000

2 Beds ⋅ 2 Baths ⋅ 226033772 MLS ⋅ St Andrews Verandas BLDG.

Step into an elevated lifestyle with this elegant second-floor Barrington Veranda, offered fully furnished and in pristine condition. The moment you enter, vaulted ceilings create an airy, expansive feel while large windows frame breathtaking views, offering a daily backdrop of natural beauty, while the layout provides ample storage and the convenience of a one-car detached garage. Living in Highland Woods means enjoying a resort-inspired lifestyle every single day. The community is packed with high-end amenities, including a championship 18-hole golf course, a modern fitness center, and a vibrant social scene. Whether you’re looking to play a match on the tennis or new pickleball courts, try your hand at bocce ball, or relax by the stunning resort-style pool and spa, there is always something to do. Dining options abound right within the gates, from casual bites at the cabana bar and grill room to sophisticated formal dining experiences. The location is truly hard to beat for convenience. You’ll find grocery stores, banks, fine dining, and a seasonal farmers market just moments away—many within walking distance. When you’re ready to explore further, the sparkling Gulf beaches are only three miles from your door. With quick access to the Shoppes at Mercato, Coconut Point Mall, and RSW airport, everything Southwest Florida has to offer is right at your fingertips. Don’t miss the chance to call this beautiful Veranda your own piece of paradise.

26841 Clarkston DR Unit 204, Bonita Springs

$950,000

3 Beds ⋅ 2 Baths ⋅ 226033524 MLS

Imagine a home where the boundaries between indoors and out simply melt away. From the moment you step inside this St. Charles floor plan, your eyes are drawn straight through the light-filled living area to the massive 55-foot lanai. It’s the true heart of the residence—a warm, airy, and expansive space designed for the way we love to live. Whether you’re sliding back the doors to let the breeze flow through or hosting a sunset gathering by the sparkling pool and spa, the transition is effortless. The lanai feels like a private sanctuary, offering a front-row seat to the lush, manicured grounds of the 11th hole. The quality of the home provides a sophisticated backdrop to this lifestyle, beginning with the curb appeal. The grounds are beautifully landscaped, featuring thoughtfully designed flowing beds, decorative rock, and low-maintenance greenery that makes a striking first impression. Inside, plantation shutters throughout allow you to control the natural light with ease, while genuine teak flooring adds a layer of organic warmth to the den and bedrooms. Soaring tray ceilings and crown molding give the open layout a sense of architectural grace. Because this home is offered turnkey and fully furnished, the transition to your new life is as seamless as the floor plan itself. You’ll also enjoy deep peace of mind with high-caliber upgrades, including PGT triple-impact windows, a 2020 roof, and recently updated mechanical systems. Life in Highland Woods Golf and Country Club is vibrant and active. Between rounds on the Gordon Lewis designed 18-hole championship course, you can find your rhythm at the fully staffed state-of-the-art fitness center, on the tennis and bocce courts, or at the brand-new pickleball facility. The resort-style pool and cabana bar are perfect for casual afternoons, while the clubhouse offers everything from a quick bite to eat or fine dining experience. The location puts the best of the Gulf Coast right at your doorstep. You’re just minutes from local favorites for dining, grocery runs, and the seasonal farmers market. When the coast calls, the white sands of the beach are only three miles away. With the upscale shopping of Mercato, Coconut Point Mall, and RSW International Airport all within easy reach, this is more than just a home—it’s an invitation to the very best of Florida living.

26307 Clarkston DR, Bonita Springs

26490 Sunderland DR Unit 1102, Bonita Springs

$405,000

2 Beds ⋅ 2 Baths ⋅ 226033334 MLS ⋅ St Andrews Verandas BLDG.

Imagine ending every single day with a front-row seat to those legendary Southwest Florida sunsets, drink in hand, right from your own private veranda. This Carlton Veranda in Highland Woods isn't just a home; it’s basically a permanent vacation pass. Inside, it’s all about easy, breezy living. We’re talking a smart split-bedroom layout that gives everyone their own space, sleek tile floors that stay cool underfoot, and a kitchen featuring granite counters and stylish raised-panel cabinets. Plus, with high-impact windows and an electric storm shutter, you can truly relax knowing everything is tucked away and secure. But let’s be real—you’re here for the lifestyle. Highland Woods is buzzing with energy. Whether you’re hitting the 18-hole course, getting a match in on the brand-new pickleball or tennis courts, or just lounging by the resort-style pool and spa, there’s always something to do. When hunger hits, grab a casual bite at the cabana bar or enjoy a nice al fresco dinner at the club. The location is the cherry on top. You’ve got grocery stores, local boutiques, and a seasonal farmers market just a stone’s throw away. When you’re craving some salt air, the Gulf beaches are only three miles from your door, and favorites like Mercato and Coconut Point are just a quick drive away. Ready to trade the grind for golf views and poolside hangs? Come see why life is just better here.

26490 Sunderland DR Unit 1102, Bonita Springs

26841 Clarkston DR Unit 101, Bonita Springs

$479,000

2 Beds ⋅ 2 Baths ⋅ 226033228 MLS ⋅ St Andrews Verandas BLDG.

Experience the seamless blend of luxury and leisure in this first-floor Abbey Model Veranda, perfectly positioned within the sought-after Highland Woods bundled golf community. From the moment you step inside, the attention to detail is evident, featuring elegant crown molding, a mix of warm wood and sleek tile flooring, and the peace of mind provided by electric and manual storm shutters. The heart of this home is the screened lanai with its "picture frame" screening, offering an unobstructed, panoramic view of the lush fairways. It’s the perfect spot for a morning coffee or an evening glass of wine while soaking in the scenery. A detached one-car garage adds convenience and extra storage for your coastal lifestyle. Living in Highland Woods means embracing a resort-inspired pace. The community has recently elevated its offerings with a brand-new resort-style pool and spa, a cabana bar and restaurant for casual afternoons, and freshly resurfaced tennis and pickleball courts. Golf enthusiasts will appreciate the championship eighteen-hole course, while the fitness center and bocce courts keep the social calendar full. Whether you prefer the casual atmosphere of the grill room or the elegance of formal dining, the culinary options are right at your fingertips. The location is truly unbeatable. You are mere minutes from everyday essentials, including upscale shopping, diverse dining, and seasonal farmers markets. When the Gulf calls, the area’s pristine beaches are only three miles away. With easy access to the Shoppes at Mercato, Coconut Point Mall, and RSW airport, everything Southwest Florida has to offer is within reach. Come see why this Veranda is the perfect place to claim your slice of paradise.

26841 Clarkston DR Unit 101, 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

26190 Clarkston DR Unit 203, Bonita Springs

$435,000

2 Beds ⋅ 2 Baths ⋅ 226032374 MLS ⋅ St Andrews Verandas BLDG.

Discover this elegant second-floor Barrington Veranda, fully furnished and ready for you to move right in. The interior is in pristine condition, featuring a fresh coat of paint throughout and brand-new tile floors in the den that add a sleek, modern touch. You’ll love the airy feel of the vaulted ceilings and the convenience of ample storage space, plus a one-car detached garage. Highland Woods offers an incredible lifestyle with amenities that truly set it apart. Between the 18-hole golf course, modern fitness center, and illuminated bocce and tennis courts, there is always something to do. The community recently leveled up with a resort-style pool and spa, a cabana bar and restaurant, and new pickleball courts. When it comes to dining, you can choose between the casual grill room, formal dining, or a meal outdoors to soak up the atmosphere. Situated in a prime location, this home puts grocery stores, shopping, and a variety of local restaurants right at your fingertips. Plus, the beautiful sands of Bonita Beach and Barefoot Beach are just a quick drive away. It’s the perfect spot to experience the very best of the Florida lifestyle.

26190 Clarkston DR Unit 203, Bonita Springs

$1,099,000

3 Beds ⋅ 2 Baths ⋅ 226032344 MLS

Welcome to a true masterpiece of style and modern sophistication, tucked away in the highly sought-after Highland Woods Golf and Country Club. From the moment you arrive, the custom lighting and newly paved driveway with elegant stone borders signal that every detail here has been meticulously curated. Step inside to find a completely transformed interior where engineered wood flooring flows seamlessly underfoot. The kitchen is a chef’s delight, boasting custom cabinetry, gleaming granite countertops, and premium stainless steel appliances. For those who love to host, the open den features a thoughtfully designed custom bar, complete with a wine fridge and beverage cooler. The primary suite serves as a private retreat, featuring a beautifully remodeled bathroom and elegant Hunter Douglas blinds. Beyond the aesthetics, this home offers total peace of mind with new hurricane-protected windows and sliding doors, along with a recently replaced roof, AC, and water heater. The living space extends effortlessly to an expansive lanai, where a heated pool and spa overlook breathtaking views of the golf course and lake—the ultimate backdrop for morning coffee or evening relaxation. Life in Highland Woods is all about the experience. The community centers around a renowned Gordon Lewis-designed golf course and features a brand-new pro shop, six pickleball courts, a state-of-the-art fitness center, and a resort-style pool with a chic cabana bar. The grand clubhouse offers everything from casual grill room bites to elegant formal dining. When you’re ready to explore, you are just moments from the upscale shopping and dining at The Promenade at Bonita Springs. Plus, the pristine sands of Bonita Beach and Barefoot Beach are just a quick drive away. This is more than just a home; it’s a gateway to the very best of the Florida lifestyle.

26481 Summer Greens DR, Bonita Springs

26931 Clarkston DR Unit 104, Bonita Springs

$389,000

2 Beds ⋅ 2 Baths ⋅ 226031933 MLS ⋅ St Andrews Verandas BLDG.

Step into a lifestyle of effortless luxury with this stunning first-floor Barrington Veranda, perfectly positioned within the vibrant Highland Woods community. This isn't just a place to live; it’s a turnkey sanctuary where every detail has been handled. From the moment you walk in, the upgrades shine—think sleek stainless steel appliances, refreshed cabinetry, and a seamless flow of tile through the main living areas. The bedrooms and den are finished with high-end laminate, creating a space that feels both modern and warm. Living here means enjoying total peace of mind, thanks to high-impact windows at the rear and electric storm shutters protecting both lanais. Whether you’re sipping your morning coffee or winding down in the evening breeze, these outdoor spaces are designed for year-round enjoyment. And since it’s being offered fully furnished, the transition to your new Florida life is as simple as unpacking a suitcase. Highland Woods is famous for its energetic, social atmosphere. The amenities are world-class, featuring an 18-hole championship golf course, a state-of-the-art fitness center, and seven sparkling pools—including a resort-style oasis with a cabana bar. Between the tennis, pickleball, and bocce courts, there is always a way to stay active. When it's time to relax, the clubhouse offers everything from casual bites in the grill room to elegant Al Fresco dining. The location is truly unbeatable. You are moments away from the upscale shopping and dining at the Promenade at Bonita Bay, and just a short drive from the white sands of Bonita Beach and Barefoot Beach. With Coconut Point Mall and RSW Airport nearby, everything you need is right at your fingertips. Come see why this Veranda is the gem of Highland Woods.

26931 Clarkston DR Unit 104, Bonita Springs

26991 Clarkston DR Unit 8202, Bonita Springs

$369,000

2 Beds ⋅ 2 Baths ⋅ 226014141 MLS ⋅ St Andrews Verandas BLDG.

Welcome to your new sanctuary—a meticulously updated two-bedroom, two-bathroom Carlton Veranda tucked away in the prestigious gated community of Highland Woods. This isn’t just a home; it’s a gateway to the quintessential Florida lifestyle, where every day feels like a stay at a five-star resort. From the moment you step inside, the attention to detail is clear. The desirable split floor plan offers a sense of privacy and flow, anchored by elegant laminate wood flooring and the timeless charm of plantation shutters. The kitchen is a chef’s delight, boasting brand-new stainless steel appliances that shine against the natural light. Peace of mind comes standard here, with a brand-new A/C system installed in 2024 to keep you cool while you soak in the view. And what a view it is—enjoy your morning coffee or evening cocktail while overlooking the lush fairways and shimmering lake waters. Life in Highland Woods is all about the "bundled golf" experience. Whether you’re an avid golfer ready to tackle the 18-hole championship course or looking to stay active at the state-of-the-art fitness center, there is something for everyone. The community has recently elevated its game with a stunning new resort-style pool and spa, a vibrant cabana bar, and brand-new pickleball courts to complement the tennis and bocce facilities. Location is everything, and this address delivers. You are mere minutes from a variety of local dining, high-end shopping, and daily conveniences. When the Gulf of Mexico calls, the white sands of the local beaches are just three miles from your front door. With the Shoppes at Mercato, Coconut Point Mall, and RSW Airport all within easy reach, you are perfectly positioned to enjoy the very best of Southwest Florida. Come see why this Carlton Veranda is the perfect place to call home. Your piece of paradise is waiting.

26991 Clarkston DR Unit 8202, Bonita Springs

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