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Browse All Highland Woods Villas Properties for Sale

$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

Courtesy of Compass Florida LLC. 804-614-5667

$649,000
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

Courtesy of Compass Florida LLC. 804-614-5667

$749,000
2 Beds 2 Baths 226029436 MLS Highland Woods Villas BLDG.
Imagine waking up in your completely renovated Florida home, enjoying coffee by your private saltwater pool, then heading out for a round of golf, pickleball with friends, or lunch at the Club, all just steps from your door. This stunning 2-bedroom + den pool home in highly sought-after Highland Woods Golf & Country Club. Designed for effortless Florida living and offered furnished, this home has been extensively renovated with a fresh, sophisticated coastal feel. The completely redesigned 2024 kitchen is the heart of the home, featuring high-end quartz countertops, beautiful cabinetry and upgraded appliances including an induction range with air-fryer oven, drawer microwave and upgraded dishwasher. Porcelain tile flows throughout the main living areas, bedrooms and baths, while the den features real wood flooring. Both bathrooms have been beautifully remodeled, and plantation shutters, updated lighting and fixtures add to the home's polished feel. Open the doors and step into your own private outdoor retreat. The resurfaced saltwater pool with solar heat, new pool deck and new no-see-um screened enclosure create the perfect setting for sunny afternoons, evening cocktails and entertaining friends. New pool equipment, landscaping and landscape lighting complete the space. Major improvements provide added peace of mind, including a 2021 roof, 2024 A/C and water heater and 2024 electric storm shutters. And then there’s the lifestyle. Highland Woods offers 18 holes of golf, pickleball, Har Tru tennis courts, bocce, fitness center, resort-style and lap pool, hot tub, outdoor bar and restaurant Woods Cafe! Located just minutes from Gulf beaches, dining, shopping, entertainment and RSW International Airport, this is more than a beautifully renovated home, it’s an opportunity to step right into the Southwest Florida lifestyle you've been waiting for.

26036 Clarkston DR, Bonita Springs

Courtesy of Coldwell Banker Realty.

$687,500
2 Beds 2 Baths 226011712 MLS
Step into the epitome of Florida living with this exquisite Cheshire Villa, nestled in the coveted gated, bundled golf community of Highland Woods. This home is a true retreat, featuring a spacious paver lanai with a sparkling pool surrounded by lush landscaping for ultimate privacy. Equipped with storm shutters on every door and window, you’ll enjoy peace of mind year-round. Inside, the open floor plan is perfect for entertaining, with updated bathrooms, fresh paint, elegant crown molding, and tasteful furnishings—all included in the sale. Every detail has been thoughtfully designed to create a warm, inviting, and move-in-ready space. Highland Woods offers an unparalleled lifestyle with endless amenities: an 18-hole championship golf course, three bocce courts, three tennis courts, six pickleball courts, and a resort-style pool complete with a cabana bar and restaurant. Stay active in the state-of-the-art fitness center or unwind at the beautifully appointed clubhouse featuring both indoor and al fresco dining. And the location? Unbeatable. Just outside the gates, you’re mere moments from the Promenade at Bonita Springs, Coconut Point Mall, the Shops at Mercato, and, of course, the stunning Gulf beaches. Don’t miss this opportunity to experience the perfect balance of elegance, convenience, and vibrant community living. This villa is your gateway to the ultimate southwest Florida lifestyle!

26476 Clarkston DR, Bonita Springs

Courtesy of Compass Florida LLC.

Selling Office: Keller Williams Elevate Luxury.

$605,000
2 Beds 2 Baths 225083876 MLS
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.

26406 Clarkston DR, Bonita Springs

Courtesy of Coldwell Banker Realty.

Selling Office: Coldwell Banker Realty.

$640,000
3 Beds 2 Baths 225082673 MLS
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.

26025 Clarkston DR, Bonita Springs

Courtesy of Compass Florida LLC.

Selling Office: Compass Florida LLC.

$655,000
2 Beds 2 Baths 225036448 MLS
Welcome to your dream home in the highly sought-after-gated golf community of Highland Woods in sunny Southwest Florida! This fully remodeled 2 bedroom/2 bathroom villa with den/office offers amazing views of the 13th green & sunsets every evening from the comfort of your expanded living space. Designed for entertaining & effortless indoor-outdoor living, this home is the perfect blend of function & style. Soaring 10ft ceilings and spacious open floor plan provides seamless flow between living, dining, kitchen & back lanai. Hurricane-impact patio doors span full width of living area, flooding the home with natural light. Every inch of this home has been remodeled. The kitchen island boasts book-end dolomite counters creating a river of color across the island, floor-to-ceiling custom solid wood cabinetry & under cabinet lighting, pull-out pantry, built-in pull-out mixer stand, in drawer charging capabilities & wine-rack cabinet pre-plumbed for an 18” ice maker. Stainless steel appliances include a 48” Z-line dual fuel commercial range & hood with 7-burner propane cooking surface & dual electric ovens, counter-depth refrigerator, built-in drop door microwave, beverage center & wine cellar refrigerator. The primary suite has a bay window (hurricane impact windows) with a beautiful view. Spa-like bathroom with custom cabinetry, dual Artisan hammered polished metal sinks, large walk-in shower with dual rain & handle shower heads, built-in bench and niche, and a gorgeous dolomite counter. Office/den with custom built-ins and Queen size Murphy bed. The guest bedroom has canned lighting & a low-profile ceiling fan to accommodate bunk beds. The guest bathroom boasts an extra deep Kohler soaking tub with high end fixtures, subway tile surround with blue waterfall accents, vanity with dolomite top. The convenience of a pocket door provides guests privacy by separating the guest suite from the rest of the home. The backyard is on a zero-lot line offering room to expand the lanai & add a pool. All interior doors replaced with solid wood Shaker style doors as well as 7” baseboards, crown molding & trim installed. Complete flooring upgrade with elegant large format travertine tile throughout the entire home. Highland Woods bundled community has an abundance of amenities including an 18-hole championship golf course, resort-style pool in addition to 6 neighborhood pools, outdoor cabana bar & restaurant, Har-Tru tennis courts, pickleball courts, bocce, fitness center, dining room, grille room, patio dining, and a calendar of social events. A prime location! Walk or bike to grocery stores, restaurants, & a seasonal farmers market. Just minutes from the beach (appx. 3.5 miles), RSW International Airport, Coconut Point Mall, Mercato, downtown Bonita Springs, Fort Myers, & Naples. Don’t miss this rare opportunity to own a fully remodeled, move-in ready home in one of Southwest Florida’s best-kept secrets. (Owners are licensed Florida Real Estate Professionals)

26452 Clarkston DR, Bonita Springs

Courtesy of Royal Shell Real Estate, Inc..

Selling Office: .

$675,000
2 Beds 2.5 Baths 225023947 MLS
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.

26398 Clarkston DR, Bonita Springs

Courtesy of Premiere Plus Realty Company.

Selling Office: Dellatore Real Estate Company.

$620,000
2 Beds 2 Baths 225011307 MLS
Experience elevated Florida living in this exceptionally remodeled villa, where modern luxury meets effortless convenience, perfectly situated in the prestigious Highland Woods community. From the moment you step inside, you’ll be captivated by the thoughtfully redesigned interiors, featuring a beautifully refinished kitchen complete with a wine cooler, as well as updated bathrooms that exude spa-like elegance. An expansive floor plan invites you to entertain in style or simply unwind in comfort, as wide windows and high ceilings fill the space with natural light. The den provides a versatile area—ideal for a home office, cozy reading nook, or media room. Step into your personal oasis as you head out to the west-facing backyard, where you can delight in breathtaking sunsets over the serene lake and meticulously maintained golf course. Best of all, you have your very own pool—an uncommon luxury in the Villas—offering the perfect spot for refreshing dips or poolside gatherings. This home is being sold, Turn-key Furnished. Set in the heart of Bonita Springs, you’re only minutes away from gorgeous beaches, shopping destinations, and a variety of dining options. Whether you’re looking for a relaxed afternoon along the Gulf Coast or an evening out on the town, the best of Southwest Florida awaits right outside your doorstep. Highland Woods is more than just a neighborhood—it’s an experience, where residents enjoy a beautifully maintained golf course, dining options ranging from casual bites to fine cuisine, a busy calendar of social events, and an active lifestyle featuring pickleball, tennis, bocce, and a brand-new zero-entry pool complete with tiki bar and food service. With every detail polished and ready, all you need to do is arrive.

26007 Clarkston DR, Bonita Springs

Courtesy of William Raveis Real Estate.

Selling Office: Premiere Plus Realty Company.

$530,000
2 Beds 2 Baths 225009911 MLS
Welcome to the stunning Cheshire Villa, located in the exclusive gated community of Highland Woods in Bonita Springs, FL. This delightful home features 2 spacious bedrooms, 2 bathrooms, a den, and a private pool. As you step inside, you'll find an open living and dining area filled with natural light, perfect for both entertaining and relaxation. The villa is elegantly appointed with plantation shutters, crown moldings, and a custom kitchen backsplash. The master suite is a private retreat, complete with a walk-in shower and a large walk-in closet. The den, with its built-in desk, is ideal for a home office or study. Upgrades include a new roof in 2021, full storm protection with shutters, and an air-conditioned garage. Last, but certainly not least, are the spectacular unobstructed golf course views. Highland Woods offers a wealth of amenities, including an 18-hole golf course, bocce and tennis courts, multiple community pools, and a top-tier fitness center. The community's appeal is further enhanced by a newly completed resort-style pool and spa, cabana bar, restaurant, and 6 pickleball courts. Ideally located, this home is just a short distance from the Promenade of Bonita Springs, providing access to dining, shopping, and entertainment. With the beautiful beaches of the Gulf of Mexico only 4 miles away, this villa offers the perfect blend of luxury, comfort, and location. Don't miss out on this exceptional opportunity

26550 Clarkston DR, Bonita Springs

Courtesy of Compass Florida LLC.

Selling Office: Compass Florida LLC.

$645,000
2 Beds 2 Baths 224038535 MLS
Discover the charm of this exceptional Cheshire Villa nestled in the gated bundled golf neighborhood of Highland Woods. Boasting captivating water front views and panoramic golf course vistas from across the lake, this unit offers a blend of modern updates and timeless elegance. Inside, you'll find features such as granite countertops, engineered wood floors, updated bathrooms, crown moldings, and a host of recent upgrades including a new A/C, water heater, roof, gutters, washer & dryer, and pristine guest bedroom carpet. The seamless extension of the interior space effortlessly brings the outdoors in, offering additional comfort and a perfect setting for potential pool installation. Highland Woods is undergoing an impressive transformation with the addition of a resort-style pool, cabana bar and restaurant, pickleball courts, tennis court resurfacing, a new pro shop, and a sprawling putting green – all designed to elevate the community's recreational appeal. Beyond the gates, residents enjoy a vibrant social scene with card leagues, tennis leagues, and weekly club events, as well as access to a state-of-the-art fitness facility. Convenience is key, as the property is conveniently located across from The Promenade of Bonita, which offers an array of dining and shopping options, a lively farmers market, and live music at the center bar. The beautiful Gulf of Mexico beaches, upscale shops and restaurants at Mercato, and the Coconut Point mall are all within easy reach. Additionally, the RSW airport is just a short twenty-minute drive away. It's rare to find a neighborhood that combines such a rich array of amenities, prime location, convenience, and lifestyle. Come and experience the unique allure of Highland Woods for yourself.

26443 Clarkston DR, Bonita Springs

Courtesy of Compass Florida LLC.

Selling Office: Premiere Plus Realty Company.

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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.

Highland Woods Villas Real Estate & Homes