Highland Woods Homes for Sale

Welcome to Highland Woods, a hidden gem nestled in the heart of Bonita Springs, Florida. This charming neighborhood is renowned for its serene ambiance, lush landscapes, and a vibrant community spirit that makes it a perfect place to call home. Highland Woods offers residents a unique blend of tranquility and convenience, with easy access to nearby amenities, shopping centers, and beautiful beaches.

As you stroll through the tree-lined streets of Highland Woods, you’ll discover a variety of stunning homes that cater to diverse tastes and lifestyles. From elegant single-family residences to modern villas, the real estate market here boasts an impressive array of properties for sale. Each home is thoughtfully designed, featuring spacious layouts, modern finishes, and often, picturesque views of the surrounding nature.

Living in Highland Woods means embracing an active lifestyle. The community offers a plethora of recreational opportunities, including a championship golf course, tennis courts, and a state-of-the-art fitness center. Residents can enjoy leisurely afternoons at the clubhouse, participate in social events, or simply relax by the sparkling community pool.

Moreover, the neighborhood is conveniently located near some of Southwest Florida’s finest attractions. You’ll find world-class dining, shopping, and outdoor activities just a short drive away, making Highland Woods an ideal choice for those who appreciate both relaxation and adventure.

Whether you’re looking to buy your first home or seeking a seasonal retreat, Highland Woods has something for everyone. Explore the homes for sale today and discover the perfect place to create lasting memories in this enchanting Bonita Springs community.

Newest Highland Woods Homes for Sale

$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

$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

$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

$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

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.