Highland Woods Homes with Sidewalks Amenities

Highland Woods Homes with Sidewalks Amenities

Welcome to Highland Woods, a stunning community nestled in the heart of Bonita Springs, Florida, where the beauty of nature meets the comfort of modern living. Located in Lee County, this charming neighborhood offers a unique blend of tranquility and convenience, making it the ideal place to call home.

Highland Woods is designed with families and active lifestyles in mind, featuring beautifully landscaped streets lined with sidewalks that encourage leisurely strolls and vibrant community interactions. Imagine morning jogs, evening walks with loved ones, or simply enjoying the Florida sunshine while connecting with neighbors—all within the safety and serenity of your own community.

The homes in Highland Woods are thoughtfully crafted, offering a variety of floor plans to suit diverse lifestyles. Each residence is designed with modern amenities and stylish finishes, ensuring comfort and elegance. Many homes feature expansive outdoor spaces perfect for entertaining, gardening, or simply soaking up the sun.

Residents of Highland Woods enjoy a plethora of amenities, including a sparkling community pool, tennis courts, and lush green spaces that invite relaxation and recreation. The community is conveniently located near shopping, dining, and pristine beaches, making it easy to enjoy all that Bonita Springs has to offer.

Whether you are looking to retire in peace or raise a family in a friendly environment, Highland Woods is the perfect place to create lasting memories. Discover your dream home in this delightful community today, and experience the best of Florida living!

Newest Highland Woods Homes with Sidewalks Amenities

3 Beds ⋅ 2 Baths ⋅ 226029927 MLS ⋅ Highland Woods BLDG.

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

2 Beds ⋅ 2 Baths ⋅ 226030939 MLS ⋅ Highland Woods BLDG.

With vaulted ceilings, abundant natural light and an expansive screened lanai overlooking the 1st fairway, this home offers the perfect combination of comfort, views and the highly sought-after bundled golf lifestyle! LOOKING FOR RENTAL INCOME? This property offers an added advantage with renters already in place for October 2026 and February through April 2027, providing a new owner with built-in rental opportunities while still allowing the flexibility to enjoy the property personally during other times of the year. Inside, you'll find granite kitchen countertops, quartz bathroom surfaces and an open, airy floor plan ideal for both relaxing and entertaining. Step onto the spacious lanai to enjoy your morning coffee, evening cocktail or simply take in the peaceful golf course setting. A new A/C installed January 2026 adds even more value and peace of mind. At Highland Woods, you're not simply buying a home, you're embracing an active, social Southwest Florida lifestyle. Your bundled membership provides access to the 18-hole golf course along with an impressive array of amenities, including a resort-style pool, outdoor Woods Cafe bar and restaurant, tennis, pickleball, bocce, fitness facilities, clubhouse dining and an active calendar of golf, social and recreational events. Meet friends for a round of golf, spend the afternoon by the pool, enjoy dinner and drinks overlooking the 18th green, or take advantage of everything Highland Woods has to offer! The location is hard to beat! Highland Woods is just minutes from the white-sand beaches of the Gulf and close to The Promenade at Bonita Bay, Coconut Point, Mercato, restaurants, shopping. It's everything that makes Southwest Florida such a desirable destination!

9300 Highland Woods Blvd Unit 3305, Bonita Springs

2 Beds ⋅ 2 Baths ⋅ 226033772 MLS ⋅ Highland Woods 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

2 Beds ⋅ 2 Baths ⋅ 226033334 MLS ⋅ Highland Woods 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

2 Beds ⋅ 2 Baths ⋅ 226033228 MLS ⋅ Highland Woods 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

2 Beds ⋅ 2 Baths ⋅ 226032352 MLS ⋅ Highland Woods BLDG.

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

2 Beds ⋅ 2 Baths ⋅ 226031518 MLS ⋅ Highland Woods BLDG.

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

2 Beds ⋅ 2 Baths ⋅ 226032374 MLS ⋅ Highland Woods 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

2 Beds ⋅ 2 Baths ⋅ 226014141 MLS ⋅ Highland Woods 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

2 Beds ⋅ 2 Baths ⋅ 226026036 MLS ⋅ Highland Woods BLDG.

Some homes simply make you exhale the moment you walk through the door and this top-floor condo is one of them. Freshly painted from top to bottom with Dove White on the walls, this neutral palette is perfect for the new owner. With soaring vaulted ceilings, beautiful natural light, and panoramic views from the double-sided screened lanai, this home offers the perfect setting to enjoy everything that makes Southwest Florida so special. With quartz countertops in the kitchen, granite countertops in both bathrooms, a beautifully remodeled guest bath, custom woodwork, plantation shutters, crown molding, and tasteful finishes that create a warm, welcoming feel. Whether you're hosting family and friends or enjoying a quiet evening at home, every space has been designed for comfort and easy Florida living. The expansive lanai quickly becomes your favorite room in the house. It's the perfect place to sip your morning coffee as the community comes to life on the first fairway or unwind in the evening while taking in spectacular sunsets from your top-floor vantage point! Located in the highly sought-after bundled golf community of Highland Woods Golf & Country Club, you'll enjoy unlimited opportunities to stay active and social. With bundled golf, a state-of-the-art fitness center, pickleball, tennis, bocce, multiple dining venues, and a vibrant calendar of social events. The recently renovated clubhouse, resort-style pool and spa, and popular Woods Cafe cabana bar create the perfect place to relax after a round of golf or spend the afternoon with friends. Outside the gates, everything you need is just minutes away. Walk to grocery stores, restaurants, coffee shops, banking, shopping, and the seasonal farmers market. Bonita Beach and Barefoot Beach are only three miles away, while Coconut Point, Mercato, and Southwest Florida International Airport are all within an easy drive. Whether you're searching for a seasonal getaway, an investment opportunity, or your forever Florida home, this move-in-ready condo offers the views, upgrades, amenities, and location that make Highland Woods one of Bonita Springs' most desirable bundled golf communities. Come experience the lifestyle for yoursel, you may never want to leave!

9300 Highland Woods Blvd Unit 3307, Bonita Springs

2 Beds ⋅ 2 Baths ⋅ 226027309 MLS ⋅ Highland Woods BLDG.

Step into the quintessential Florida lifestyle with this beautifully appointed two bedroom two bathroom plus den Abbey Model Veranda. Perched on the second floor, this home is perfectly positioned to capture sweeping golf course vistas and those iconic golden sunrises that make mornings here so special. Inside, the space feels light and elevated, featuring airy vaulted ceilings accented by elegant crown molding. The kitchen is a chef’s delight with sleek granite countertops and updated appliances, while plantation shutters and enclosed lanais add a sophisticated, polished touch to the entire layout. Living in Highland Woods is about more than a beautiful interior; it’s about joining a vibrant, active community. This bundled golf destination is currently leveling up its amenities, with a resort-style pool, spa, cabana bar, and brand-new pickleball courts all nearing completion. Whether you’re hitting the links, enjoying a match on the lit bocce or tennis courts, or heading to the fitness center, the options for staying active are endless. When it’s time to unwind, choose between a casual bite in the grill room, an elegant meal in the formal dining room, or sunset drinks al-fresco. The location offers incredible convenience for everyday living. You’re just moments away from high-end shopping, local boutiques, and an array of dining options. The seasonal farmers market is a local favorite, and the pristine Gulf beaches are only three miles away. Complete with a detached one-car garage and storm shutters for added peace of mind, this Veranda offers the perfect blend of luxury and easy living. Don't miss the chance to secure your own slice of paradise in one of the area's most sought-after communities.

26160 Clarkston Dr Unit 201, Bonita Springs

2 Beds ⋅ 2 Baths ⋅ 226025602 MLS ⋅ Highland Woods BLDG.

Welcome to the Southwest Florida lifestyle you’ve been dreaming about! Perfectly positioned on the fourth floor in the highly sought-after Highland Woods Golf & Country Club community, this beautiful condo offers some of the most spectacular views you’ll find — overlooking five different golf holes, sparkling lakes, and unforgettable sunsets that turn every evening into something special. Imagine starting your mornings with a cup of coffee as the sun fills your home with natural light and golfers make their way along the perfectly manicured fairways. From sunrise to sunset, this bright and inviting space captures everything people love about Florida living. Inside, you’ll find a thoughtfully designed home that blends comfort and convenience. The kitchen features granite countertops, stainless steel appliances, and a charming eat-in area surrounded by peaceful golf course views. The open living space is ideal for relaxing or entertaining, and the dining area offers a custom built-in Murphy bed — a smart addition that creates extra sleeping space for visiting family and friends while maintaining the elegance and functionality of the room. Beyond your front door, Highland Woods offers the resort-style lifestyle buyers are searching for. Enjoy an 18-hole championship golf course, state-of-the-art fitness center, tennis, pickleball, bocce, multiple dining venues, and a vibrant social calendar filled with activities and events. Spend your afternoons relaxing by the newly added resort-style pool and spa, meeting friends at the cabana bar, or enjoying dinner at the clubhouse. One of the best parts of Highland Woods is the unbeatable Bonita Springs location. You’re just minutes from everyday conveniences including grocery stores, restaurants, shopping, and a seasonal farmers market — plus only 3 miles from the beautiful Gulf beaches. With Coconut Point, Mercato, Naples, and RSW International Airport all nearby, everything you love about Southwest Florida is within easy reach. This is more than a condo, it’s your opportunity to enjoy golf, sunsets, friendships, and the carefree Florida lifestyle you’ve been waiting for. Your Piece of Paradise is ready!

9350 Highland Woods Blvd Unit 4405, Bonita Springs

Start Your Search