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Highland Woods Bonita Springs Florida Homes for Sale

Naples Florida Real Estate

Highland Woods Bonita Springs Real EstateHighland Woods Bonita Springs

Homes For Sale7$638K - $1.2M
Condos For Sale25$290K - $525K
Sold ( Past 6 Months )20$260K - $1.1M
Last updated at 6:29am 02/13/2026

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$1,150,000
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Highland Woods

26481 Summer Greens Dr, Bonita Springs, FL 34135

Homes - 2,124 ft² / 2,599 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool / Spa

Built 1996
Highland Woods Bonita Springs Homes for Sale: Nestled in the prestigious Highland Woods Golf and Country Club, this stunning home is a true masterpiece of style, comfort, and functionality. From the moment you pull up, the curb appeal will captivate you—custom lighting, a newly paved driveway and walkway framed by an elegant stone border, and low-maintenance lush landscaping with river rock accents set the tone for what’s inside. Step through the doors and into a completely renovated interior that exudes modern sophistication. The engineered wood flooring flows seamlessly throughout, complemented by custom cabinetry, gleaming granite countertops, and stainless steel appliances in the kitchen. The open den features new fixtures and a thoughtfully designed custom bar (complete with a wine fridge and ice maker), making it a dream for entertainers. Every detail has been meticulously curated, right down to the Hunter Douglas blinds and the remodeled master bath. The upgrades don’t stop there. New sliding doors and windows flood the home with natural light while offering full hurricane protection for peace of mind. Step out onto the expansive lanai, where you’ll find a heated pool and spa overlooking breathtaking golf course and lake views—the perfect backdrop for morning coffee or sunset gatherings. With a recently replaced roof, air conditioner, and water heater, this home is as move-in ready as it gets. Highland Woods isn’t just a community—it’s a lifestyle. At the heart of it all is the renowned Gordon Lewis-designed golf course, complemented by a newly completed pro shop, six pickleball courts, a resort-style pool with a chic cabana bar, and a state-of-the-art fitness center. The grand clubhouse offers dining options to suit every mood, from a casual grill room to elegant formal dining and picturesque al fresco spots where you can soak in Florida’s sunshine. For recreation, enjoy bocce, tennis, or simply relax in the lush, manicured surroundings. Beyond the gates, you’re just moments from The Promenade in Bonita, a vibrant hub for upscale shopping, dining, and entertainment. And when it’s time to hit the sand, the pristine shores of Bonita Beach and Barefoot Beach are just a short drive away, offering warm Gulf waters and those postcard-perfect sunsets this area is famous for. This home is the ultimate blend of luxury, leisure, and location.



$749,900
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Highland Woods

26065 Clarkston Dr, Bonita Springs, FL 34135

Homes - 1,735 ft² / 2,359 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 1998
Highland Woods Bonita Springs Homes for Sale: Welcome to Highland Woods Golf and Country Club. This impressive Cheshire villa is pristine. Totally renovated from top to bottom. Kitchen has quartz countertops, stainless steel appliances and beautiful built in cabinetry. Luxury vinyl flooring throughout the living area. Both baths have been updated as well. The split floor plan ensures ample space and privacy for family and guests. All windows and sliders are hurricane impact rated and are treated on the inside with plantation shutters. The roof is less than four years old and the air conditioning unit was replaced in November 2025. The spacious lanai with its picture window screening makes for great entertaining space. Highland Woods is an amenity rich community with a resort style pool, golf, tennis, pickleball, bocce, two restaurants and fitness center. If an active lifestyle is something you want this is the place for you.



$699,999
Decrease*
$25K
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Highland Woods Villas at Highland Woods

26025 Clarkston Dr, Bonita Springs, FL 34135

Homes - 1,888 ft² / 2,232 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 1998
Highland Woods Villas Highland Woods Bonita Springs Homes for Sale: Welcome to your dream home in the picturesque and vibrant community of Highland Woods. This beautifully remodeled Cheshire Villa is situated in a coveted bundled golf neighborhood, offering a luxurious and comfortable lifestyle. The heart of this home, the kitchen, has been meticulously remodeled and expanded, creating a perfect setting for entertaining guests. With modern amenities and increased space, it's the ideal spot to gather with family and friends. The living area has also seen significant enhancements with the addition of new vinyl flooring and the conversion of the covered lanai into an inviting interior space. The guest bathroom now features a new vanity and upgraded lighting, while the master bathroom has been transformed into a spa-like retreat with a large walk-in shower. Outdoors, enjoy the wavered lanai with a new cage and picture frame window—perfect for taking in stunning lake, golf course, and sunset views. A recently replaced roof and storm-protected openings provide peace of mind, ensuring your new home is not only beautiful but also secure. The community has recently seen significant upgrades, boasting a resort-style pool, a cabana bar and restaurant, pickleball courts, resurfaced tennis courts, a new pro shop, and an expansive putting green, enhancing its recreational appeal. Residents can participate in a lively social calendar with card and tennis leagues, weekly club events, and access to a cutting-edge fitness facility. Perfectly positioned across from The Promenade of Bonita, residents have convenient access to dining, shopping, a vibrant farmers market, and live music. Furthermore, key destinations such as the Gulf of Mexico beaches, Mercato's upscale shops and restaurants, Coconut Point mall, and RSW airport are just a short distance away. Highland Woods combines luxurious amenities, an excellent location, and an active lifestyle, making it a truly exceptional place to call home.



$674,900
Decrease*
$24.1K
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Highland Woods Villas at Highland Woods

26466 Clarkston Dr, Bonita Springs, FL 34135

Homes - 1,728 ft² / 2,197 ft² - 2 Car Garage

2+Den / 2 Baths

Built 1997
Highland Woods Villas Highland Woods Bonita Springs Homes for Sale: This stunning Cheshire Villa, nestled within the exclusive gated community of Highland Woods, perfectly marries luxury with comfort. From the moment you step inside, you'll be captivated by the thoughtful upgrades and elegant details throughout. The bathrooms have been beautifully updated with granite countertops, chic new vanities, and modern fixtures, while the master bathroom features a spacious walk-in shower. The bedrooms showcase luxurious laminate flooring, and the entire villa is accented with plantation shutters and crown molding, adding timeless sophistication. Step outside to your recently upgraded lanai, complete with a picture window for uninterrupted views, or enjoy the peace of mind that comes with a new roof and gutters (2020) and high-impact windows that make the entire home hurricane-protected (2023). Additional upgrades include epoxy flooring in the garage (2024), a new front lanai cage (2025), whole-home surround sound, and refreshed landscaping with river rock along the back lanai—every detail designed with convenience and style in mind. Highland Woods offers an unparalleled lifestyle for its residents, with access to an 18-hole championship golf course, three bocce courts, three tennis courts, six pickleball courts, and a large resort-style pool complete with a cabana bar and restaurant. The community also features a state-of-the-art fitness center and a beautifully appointed clubhouse with indoor and al fresco dining options. Beyond the gates, the villa’s prime southwest Florida location puts you moments away from the best the area has to offer. The Promenade of Bonita Springs is right across the street, while Coconut Point Mall, the Shops at Mercato, and the pristine Gulf beaches are all just a short drive away. Don’t miss your chance to live the ultimate Florida lifestyle in this exceptional villa, where elegance, convenience, and vibrant community living come together seamlessly.



$639,000
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Highland Woods Villas at Highland Woods

26053 Clarkston Dr, Bonita Springs, FL 34135

Homes - 1,752 ft² / 2,232 ft² - 2 Car Garage

2+Den / 2 Baths

Built 1998
Highland Woods Villas Highland Woods Bonita Springs Homes for Sale: This exquisite Cheshire Villa, located in the prestigious gated community of Highland Woods, offers a perfect blend of luxury and comfort. The villa boasts an updated kitchen featuring quartz countertops and refaced cabinetry, complemented by luxury vinyl flooring. Elegant touches such as plantation shutters and crown molding throughout enhance its charm. Enjoy outdoor relaxation with a recently upgraded lanai cage complete with a picture window, and rest easy knowing a new roof was been installed in 2022. Nestled within the fantastic bundled golf community of Highland Woods, residents enjoy access to eighteen holes of championship golf, three bocce courts, three tennis courts, six pickle ball courts a new large resort style community pool with a cabana bar and restaurant, a state-of-the-art fitness center, and a stunning clubhouse with dining and grill rooms along with al fresco outdoor dining. The villa's prime location in southwest Florida provides convenient access to everything the area has to offer. Just across the street lies the Promenade of Bonita Springs, with Coconut Point Mall and the Shops at Mercato only a short drive away. Plus, the pristine shores of the Gulf of Mexico are a mere four miles from your doorstep. Experience the ultimate Florida lifestyle in this gorgeous villa, where comfort, convenience, and community come together seamlessly.



$639,000
Decrease*
$26K
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Highland Woods Villas at Highland Woods

26394 Clarkston Dr, Bonita Springs, FL 34135

Homes - 1,743 ft² / 2,197 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 1998
Highland Woods Villas Highland Woods Bonita Springs Homes for Sale: $10,000. BUYER CONCESSION OFFERED FROM SELLER!!! Welcome to Highland Woods Golf & Country Club — where pristine living meets resort-style amenities. This beautifully maintained 3-bedroom, large kitchen and family room home is ideally situated in one of Naples’ most desirable bundled golf communities, featuring an 18-hole prestige championship course and a vibrant country club lifestyle. Step inside to find stylish vinyl flooring, a spacious family room, and a large eat-in kitchen perfect for gatherings. Enjoy peace of mind with key updates including a brand-new water heater (2017), AC system replaced in October 2025, large utility sink in laundry area and a new roof maintained by the HOA. The highlight of the home is the expansive screened lanai with a private pool—offering up to 6 feet of depth—creating the perfect retreat for relaxation or entertaining. Experience the best of Naples living in this pristine Highland Woods residence, where comfort, community, and convenience come together



$638,000
Decrease*
$12K
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Highland Woods Villas at Highland Woods

26406 Clarkston Dr, Bonita Springs, FL 34135

Homes - 1,707 ft² / 2,173 ft² - 2 Car Garage

2+Den / 2 Baths / Spa

Built 1996
Highland Woods Villas Highland Woods Bonita Springs Homes for Sale: Discover the ultimate bundled golf and resort-style lifestyle in the highly sought-after gated community of Highland Woods Golf & Country Club! This vibrant community offers everything you need to enjoy the full Southwest Florida experience including championship golf, top-tier amenities, an active social atmosphere, and an unbeatable location close to beaches, shopping, and dining! From your Cheshire Villa, you’ll appreciate a beautiful view of the green on Hole 13, along with the privacy of the surrounding preserve. The spacious lanai is ideal for relaxation or entertaining and includes a built-in hot tub, perfect for unwinding after a round of golf. Inside, the villa features a kitchen with granite countertops and stainless steel appliances, plus a remodeled guest bathroom. You’ll have peace of mind with storm shutters on all windows, a Storm Smart electric shutter for the covered lanai, new roof in 2023 and a new water heater in 2020. Offered turnkey so pack your suitcase and start enjoying Your Piece of Paradise! Residents of Highland Woods enjoy 18 holes of championship golf, three Har-Tru tennis courts, six pickleball courts, three bocce courts, a large resort-style pool with cabana bar and restaurant, and a state-of-the-art fitness center, all included through bundled membership! Located just steps from the Promenade at Bonita Bay, minutes to Coconut Point Mall and Mercato, and about four miles from the sandy beaches and world-class sunsets of the Gulf of America, Highland Woods provides one of the most convenient and desirable locations in Bonita Springs.



$1,095,000
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Highland Woods

26421 Summer Greens Dr, Bonita Springs, FL 34135

Homes - 2,174 ft² / 2,658 ft² - 2 Car Garage

3 Bed / 3 Baths / Pool / Spa

Built 1996
Highland Woods Bonita Springs Homes Under Contract: This stunning, remodeled Pinehurst model home in the coveted Highland Woods Golf and Country Club is truly one of a kind. Featuring three spacious bedrooms and three full bathrooms, this residence has been thoughtfully designed with an open-concept layout that’s perfect for entertaining and free of wasted space. Every detail exudes quality and charm, from the high-impact windows and doors to the custom woodwork, crown moldings, plantation shutters, and custom closet systems. The outdoor space is a showstopper—a sprawling area with a covered lanai, paver patio, and a picture-window lanai cage that perfectly frames the breathtaking golf course views. Plus, with a new A/C, water heater, and pool heater all replaced in the past three years, this home is as functional as it is beautiful. Highland Woods isn’t just a community—it’s a lifestyle. At the heart of it all is the renowned Gordon Lewis-designed golf course, complemented by a newly completed pro shop, six pickleball courts, a resort-style pool with a chic cabana bar, and a state-of-the-art fitness center. The grand clubhouse offers dining options to suit every mood, from a casual grill room to elegant formal dining and picturesque al fresco spots where you can soak in Florida’s sunshine. For recreation, enjoy bocce, tennis, or simply relax in the lush, manicured surroundings. Beyond the gates, you’re just moments from The Promenade in Bonita, a vibrant hub for upscale shopping, dining, and entertainment. And when it’s time to hit the sand, the pristine shores of Bonita Beach and Barefoot Beach are just a short drive away, offering warm Gulf waters and those postcard-perfect sunsets this area is famous for. This home is the ultimate blend of luxury, leisure, and location. Your dream lifestyle awaits!



$1,050,000
Sold Price:
$925,000
Sold Date:
11/06/2025
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Highland Woods

26470 Summer Greens Dr, Bonita Springs, FL 34135

Homes - 2,553 ft² / 3,131 ft² - 3 Car Garage

4 Bed / 3 Baths / Pool

Built 1999
Highland Woods Bonita Springs Homes: Welcome to this magnificent single-family home located in the exclusive, gated, bundled golf community of Highland Woods. Rarely on the market, this property offers a 3-car garage and picturesque lake views. It comprises 4 generously sized bedrooms and 3 full bathrooms. The home’s interior features soaring vaulted ceilings, and is equipped with impact windows and storm shutters for added security. Enjoy sweeping sunset views from the comfort of your home. Recent updates include a newly installed roof in 2024 and a modernized kitchen, enhancing its many standout features. Highland Woods is celebrated for its outstanding amenities, including an 18-hole championship golf course, three bocce courts, four tennis courts, a large community pool complete with a cabana bar and restaurant, a cutting-edge fitness center, and a stunning clubhouse featuring dining and grill rooms. Situated in the vibrant heart of sunny Southwest Florida, this home is conveniently located near the Promenade of Bonita Springs, Coconut Point Mall, the Shops at Mercato, and the stunning Gulf of Mexico, just four miles away. This property promises a relaxed, luxurious lifestyle in a prime setting. Don’t miss the opportunity to make this exceptional home yours—schedule a viewing today and experience the unparalleled offerings of Highland Woods.



$675,000
Sold Price:
$675,000
Sold Date:
08/22/2025
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Highland Woods Villas at Highland Woods

26398 Clarkston Dr, Bonita Springs, FL 34135

Homes - 2,263 ft² / 2,740 ft² - 2 Car Garage

2+Den / 2 Baths / 1 Half / Pool

Built 1997
Highland Woods Villas Highland Woods Bonita Springs Homes: Rarely available! Being 1 of only 8 two-stories built in the community puts this unit configuration in high demand! This oversized Villa - nearly 2,500 sq. ft - has a great floor plan, including the 2+ Den and 2.5 baths. This turn-key home has been beautifully updated and tastefully appointed with light coastal furniture, including a treadmill for the exercise area. Each window is finished with white plantation shutters and electric Hurricane shutters easily covering every opening with a quick touch of a button. The vaulted ceilings and the open floor plan give this home, a light and uplifting vibe. Relax and enjoy the exquisitely landscaped backyard from your own private pool; the perfect place to enjoy a tranquil and peaceful afternoon. The lanai is furnished with teakwood lounges to relax and fully embrace your own piece of paradise. Nestled within this stunning championship 18-hole golf course facility, you’ll find the brand new resort-style pool and spa, cabana, bar and restaurant, and recently remodeled clubhouse with dining and grill rooms offering al fresco outdoor dining. The updated Pickleball and tennis courts, as well as a state of the art pro shop and expansive putting green are designed to entice you to join your neighbors in this active community. The social calendar includes weekly Club events, card league, tennis leagues and a state of the art fitness facility. This bundled golf community is centrally-located near the promenade of Bonita Springs where you can explore fine dining and boutique shopping, a fresh farmers market, and live music at the central bar. Only a few miles from Bonita Beach and a short drive to Naples beaches where you can explore the natural splendor of Southwest Florida. This Resort lifestyle is the finest around, conveniently located just a quick 20-minute drive to RSW International airport, which makes traveling a breeze.



$579,000
Sold Price:
$555,000
Sold Date:
12/04/2025
View Details

Highland Woods Villas at Highland Woods

26458 Clarkston Dr, Bonita Springs, FL 34135

Homes - 1,720 ft² / 2,189 ft² - 2 Car Garage

2 Bed / 2 Baths

Built 1997
Highland Woods Villas Highland Woods Bonita Springs Homes: This is your opportunity to purchase a beautiful villa in Highland Woods. This is a two-bedroom, two-bath home with an office/den, all stainless appliances kitchen, ample closet space, dual main bath sinks, with beautiful flooring throughout and 10-foot ceilings. Enjoy golf course and sunset views from your lanai. This is a sought-after bundled golf community that has just undergone a $13 million renovation, resort pool and cafe, with an additional six pools throughout the community, five new pickleball courts, three tennis courts, three bocce courts, and driving range with putting and chipping green. It also has the ever-popular grille room with outdoor patio dining. Highland Woods is ideally 18 miles from Southwest Florida International Airport, two miles from the gulf for swimming, boating, fishing and more. Near some of the finest restaurants and shopping in Southwest Florida. A beautiful home, in a wonderful community in a great location can be yours. This home has a generator and electronic storm shutters.



$479,000
Sold Price:
$457,000
Sold Date:
08/20/2025
View Details

Highland Woods Villas at Highland Woods

26002 Clarkston Dr, Bonita Springs, FL 34135

Homes - 1,532 ft² / 2,019 ft² - 2 Car Garage

2+Den / 2 Baths / Pool / Spa

Built 1999
Highland Woods Villas Highland Woods Bonita Springs Homes: Discover this quaint Ashmoor Villa, nestled within the prestigious gated community of Highland Woods. This charming property features two bedrooms, two bathrooms, and a versatile den, making it ideal for entertaining. The villa boasts elegant quartz countertops, an electric storm shutter for added security, and crown molding throughout. Step outside to enjoy the expansive pool and hot tub, complete with an extended lanai that offers additional outdoor living space and a breathtaking lake view overlooking the 3rd hole. With its eastern exposure, you'll relish the stunning Florida sunrises each morning. Highland Woods is renowned for its exceptional amenities, including an 18-hole golf course, bocce and tennis courts, multiple community pools, and a state-of-the-art fitness facility. The newly completed resort-style pool and spa, along with a cabana bar, restaurant, and pickleball courts, further enhance the community's allure. Conveniently located, this villa is just moments from the Promenade of Bonita Springs, providing a variety of dining, shopping, and entertainment options. Plus, the pristine beaches of the Gulf of Mexico are only 4 miles away, offering the perfect blend of luxury, comfort, and prime location. Don't miss this incredible opportunity to own a piece of paradise!




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*Just Listed: new properties that came on the market within the last 30 days.
*Decrease/Increase: listing values that are being recorded within the last 30 days.
*Foreclosures/Short Sale: Please note, all properties are subject to bank approval. Buyers must be pre-approved or show proof of funds before submitting an offer.

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