Highland Woods Homes with Pickleball Amenities

Highland Woods Homes with Pickleball Amenities

Welcome to Highland Woods, a vibrant community nestled in the heart of Bonita Springs, Florida. This charming neighborhood is a hidden gem within Lee County, offering residents a perfect blend of relaxation and recreation. Known for its lush landscapes and friendly atmosphere, Highland Woods is an ideal place for families, retirees, and anyone seeking a warm, welcoming environment.

One of the standout features of Highland Woods is its commitment to an active lifestyle, particularly for pickleball enthusiasts. Homes in this community boast exclusive access to top-notch pickleball amenities, including well-maintained courts that cater to players of all skill levels. Whether you're a seasoned pro or just looking to learn the game, you'll find plenty of opportunities to engage with fellow residents and enjoy friendly matches in the sunshine.

Beyond pickleball, Highland Woods offers a wealth of amenities designed to enhance your living experience. Residents can take advantage of a beautiful clubhouse, refreshing swimming pools, and scenic walking trails that wind through the neighborhood. The community is also conveniently located near pristine beaches, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

In Highland Woods, you’re not just buying a home; you’re investing in a lifestyle filled with camaraderie, activity, and the joys of Florida living. Come discover the charm of Highland Woods, where your dream home awaits, and every day feels like a vacation!

Newest Highland Woods Homes with Pickleball Amenities

$299,000
2 Beds ⋅ 2 Baths ⋅ 226026036 MLS ⋅ ACTIVE Status ⋅ Heathermoor 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
$485,000
2 Beds ⋅ 2 Baths ⋅ 226027309 MLS ⋅ ACTIVE Status ⋅ St Andrews Verandas 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
$330,000
2 Beds ⋅ 2 Baths ⋅ 226025602 MLS ⋅ ACTIVE Status ⋅ Terrace I 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
$359,900
2 Beds ⋅ 2 Baths ⋅ 2026029004 MLS ⋅ ACTIVE Status ⋅ Terrace I BLDG.
Experience the relaxed lifestyle of Highland Woods Golf & Country Club from this beautifully maintained third-floor condominium in one of Bonita Springs' most desirable bundled golf communities. This move-in-ready, unfurnished 2-bedroom PLUS den, 2-bath residence offers the perfect opportunity to make it your own while enjoying the best of Southwest Florida living. Filled with natural light, the open-concept floor plan creates a warm and inviting atmosphere. The kitchen features granite countertops, stainless steel appliances, ample cabinetry, and a functional layout that's perfect for everyday living or entertaining guests. Neutral paint, tile flooring throughout the main living areas, and carpet in the den create a clean and comfortable feel, while plantation shutters throughout the home add timeless style, privacy, and elegant coastal charm. Step onto the screened lanai and enjoy peaceful views of the beautifully landscaped grounds with partial views of the golf course—the perfect place to relax with your morning coffee or unwind at the end of the day. An oversized private storage unit just outside the front door provides plenty of room for golf clubs, bicycles, beach gear, and seasonal items. As a resident of Highland Woods Golf & Country Club, you'll enjoy an exceptional array of amenities, including bundled golf on the 18-hole championship course, resort-style pools and spa, tennis, pickleball, bocce, a state-of-the-art fitness center, and an active social calendar. Meet friends for lunch at the Woods Café, enjoy drinks at the cabana bar, or dine at the beautifully renovated clubhouse. Ideally located in the heart of Bonita Springs, you're just minutes from Bonita Beach and Barefoot Beach, as well as premier shopping, dining, and entertainment at The Promenade, Coconut Point, and Mercato. Southwest Florida International Airport is also conveniently nearby. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this well-maintained condominium offers exceptional value, outstanding amenities, and the resort-style lifestyle that makes Highland Woods Golf & Country Club one of Southwest Florida's most sought-after communities.

9350 Highland Woods BLVD Unit 4308, Bonita Springs
$349,900
2 Beds ⋅ 2 Baths ⋅ 226022422 MLS ⋅ ACTIVE Status ⋅ Terrace Iv BLDG.
Life feels a little different when your backyard is a beautifully manicured golf course and every evening ends with a spectacular Southwest Florida sunset. Nestled within Highland Woods Golf & Country Club, this thoughtfully updated condo blends modern style, comfortable living, and the resort-inspired lifestyle that makes Bonita Springs such a sought-after destination. From the moment you step inside, you'll appreciate the thoughtful updates throughout. The stunning kitchen is the heart of the home, featuring white shaker cabinetry, quartz countertops, stainless steel appliances, and a built-in wine fridge, perfect for entertaining friends or enjoying a quiet evening at home. Contemporary dark tile flooring flows throughout the residence, while the updated bathrooms showcase designer-inspired vanities, stylish lighting, and timeless subway tile showers. The lanai is where this home truly shines. Overlooking the golf course, it's the perfect place to relax, watch the sunset paint the sky, and enjoy Florida's year-round outdoor living! Living in Highland Woods means enjoying one of Bonita Springs' most desirable bundled golf communities. In addition, the resort-style pool and spa, outdoor Woods Cafe cabana bar, state-of-the-art fitness center, pickleball, tennis, bocce, multiple dining venues, and a vibrant social calendar filled with activities and events await its new owners. Location is everything, and this home delivers! You're just minutes from Bonita Beach and Barefoot Beach, Coconut Point Mall, Mercato, fine dining, shopping, entertainment, and Southwest Florida International Airport. Everyday conveniences including grocery stores, banking, restaurants, and a seasonal farmers market are all just moments away. Whether you're searching for a seasonal retreat, an investment property, or your full-time Florida home, this condo offers the lifestyle, amenities, and location that make Southwest Florida one of the most sought-after destinations in the country.

9500 Highland Woods BLVD Unit 105, Bonita Springs
$350,000
2 Beds ⋅ 2 Baths ⋅ 226016870 MLS ⋅ ACTIVE Status ⋅ Terrace I BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. Imagine ending your day with a glass of wine in hand, watching the sun melt into the golf course right from your own living room. That’s everyday life in this top-floor, end-unit condo in Highland Woods Golf and Country Club, a bundled golf community. This 2-bedroom, 2-bath condo has been thoughtfully updated so you can move right in and start enjoying it, and is being offered turnkey. The kitchen feels fresh and inviting with shaker cabinets, granite countertops, and stainless steel appliances. Perfect whether you're hosting friends or just making a quiet dinner at home. The bathrooms have been upgraded, and the tile flooring and neutral paint throughout give the entire space a clean, modern feel. The newer AC and No-See-em screens offer additional piece of mind. Being a top-floor end unit means more light, more privacy, and some of the best views in the community. You’ll love the peaceful golf course backdrop and those stunning Southwest Florida sunsets that never get old! Plus, there’s an oversized private storage unit right outside your door, something you don’t always find. Life at Highland Woods is about more than just the condo, it’s about how you live. Spend your mornings on the 18-hole golf course, afternoons by the resort-style pool, or stay active with tennis, pickleball, bocce, and a full fitness center. When it’s time to unwind, grab a drink at the Woods Cafe cabana bar or enjoy dinner with friends, whether casual or a little more elevated. And the location makes everything easy. You’re just minutes from the Bonita and Barefoot Beaches, close to everyday conveniences at The Promenade, and a short drive to Coconut Point Mall, Mercato, and Southwest Florida International Airport. Whether you're looking for a seasonal escape or a full-time home, this is the kind of place where life feels a little lighter, a little easier, and a lot more enjoyable. Come see it for yourself, you’ll understand the moment you walk in!

9350 Highland Woods BLVD Unit 4401, Bonita Springs
$399,000
2 Beds ⋅ 2 Baths ⋅ 226018486 MLS ⋅ ACTIVE Status ⋅ St Andrews Verandas BLDG.
Enjoy Resort-Style Living with IMMEDIATE GOLF ACCESS! Welcome to Highland Woods Golf & Country Club, one of Bonita Springs most sought after bundled golf communities. The beautifully furnished top-floor Carlton Veranda offers 2 bedrooms and 2 bathrooms with a split bedroom design and a detached garage - perfect as a full-time residence or seasonal retreat. Step onto your private balcony and take in sweeping views of the golf course, lighted fountain and lake views. Offered turnkey, this home is move-in ready and includes electric hurricane shutters for peace of mind. Highland Woods residents enjoy exceptional amenities, including a beautiful club house, 18-hole Gordon Lewis-designed championship golf course, resort-style pool and spa, state-of-the-art fitness center, newly resurfaced tennis courts, pickleball, bocce, multiple dining venues from casual to formal, plus an outdoor cabana bar and restaurant and an active social events calendar. Ideally located across from the Promenade of Bonita Bay and just minutes to Coconut Point Mall, this community also puts you within 5 miles of Bonita and Barefoot Beaches and 20 miles from RSW Airport. Experience the perfect blend of luxury, leisure, and convenience!

26841 Clarkston DR Unit 202, Bonita Springs
$425,000
2 Beds ⋅ 2 Baths ⋅ 226015149 MLS ⋅ ACTIVE Status ⋅ St Andrews Verandas BLDG.
Welcome to effortless Southwest Florida living at 26841 Clarkston Dr #105 in Bonita Springs. This beautifully maintained first-floor residence invites you in with a bright, open layout designed for comfort and ease. Natural light fills the main living area, creating a warm and welcoming space where relaxing and entertaining feel natural. The kitchen offers generous counter space and storage, making everyday living simple and enjoyable. The primary suite provides a peaceful retreat with a spacious layout and a well-appointed bath, while additional living space gives you flexibility for guests, a home office, or quiet downtime. Step outside to your private screened lanai and enjoy the calm surroundings—perfect for morning coffee or unwinding after a long day. Located in a well-kept community, you’ll enjoy convenient access to shopping, dining, and the beautiful Gulf beaches just a short drive away. This is the kind of property that fits your lifestyle, whether you’re here full-time or seasonally. If you’ve been waiting for the right opportunity in Bonita Springs, this is it. Schedule your private showing today and experience it for yourself.

26841 Clarkston DR Unit 105, Bonita Springs
$419,000
2 Beds ⋅ 2 Baths ⋅ 225076297 MLS ⋅ ACTIVE Status ⋅ St Andrews Verandas BLDG.
Welcome to your slice of paradise in the highly sought-after gated and bundled golf community of Highland Woods Golf & Country Club in Bonita Springs, FL. This beautifully updated first-floor condo offers a perfect blend of comfort, style, and resort-style living. Featuring tile flooring throughout, an updated kitchen with granite countertops, and renovated bathrooms, this veranda condo is move-in ready and designed for easy Florida living. Step out onto the screened lanai and take in the breathtaking views of the golf course, where lush fairways and serene landscapes create the perfect backdrop for your morning coffee or evening glass of wine. The detached one-car garage provides convenience and extra storage, while the condo’s prime location within the community ensures easy access to all the fantastic amenities Highland Woods has to offer. The recently renovated amenity center is truly exceptional — featuring a resort-style pool, tiki bar and grille, state-of-the-art fitness center, and clubhouse with panoramic views overlooking the finishing holes of the golf course. Enjoy casual or fine dining, unwind at the bar, or take advantage of the aqua driving range to perfect your swing. Additional amenities include tennis and pickleball courts, bocce courts, and a fully attended fitness center, ensuring there’s always something to do for everyone. Highland Woods offers an active, social lifestyle just minutes from world-class dining, shopping, and the white-sand beaches of Bonita Springs and Naples. Watch unforgettable sunsets along the Gulf, then return home to the comfort and charm of your private retreat. Whether you’re looking for a seasonal getaway or a year-round residence, this condo offers the perfect balance of luxury, leisure, and location.

26290 Sunderland DR Unit 6104, Bonita Springs
$399,999
2 Beds ⋅ 2 Baths ⋅ 225065160 MLS ⋅ ACTIVE Status ⋅ Terrace Iii BLDG.
Beautifully remodeled and tastefully turnkey furnished 2-bedroom, 2-bath second-floor condo with breathtaking western exposure, delivering spectacular Florida sunsets night after night. This exceptional residence also offers a strong proven rental history, making it an outstanding opportunity for both personal enjoyment and investment potential. Even better, the golf membership does not need to transfer with rentals, allowing owners to continue enjoying full golf and community privileges year-round while generating income. Step inside to discover a light, bright, coastal-inspired interior featuring luxury vinyl plank wood-look flooring throughout, an updated kitchen with granite countertops and stylish shaker cabinetry, and beautifully refreshed bathrooms with newer vanities, fixtures, and a remodeled walk-in shower in the primary suite. Additional upgrades include impact-resistant windows, newer air conditioning system, and a newer water heater, providing both comfort and peace of mind. This residence is located within one of Southwest Florida’s most desirable bundled golf communities, offering an incredible lifestyle centered around a championship 18-hole golf course and resort-style amenities. Residents enjoy a stunning new resort pool and spa, poolside cabana bar, beautifully renovated clubhouse and restaurant, active tennis and newly added pickleball courts, pro shop, fitness opportunities, and an incredibly social and welcoming atmosphere with exceptional dining and friendly staff. Perfectly positioned just minutes from Bonita Beach, world-class shopping, dining, entertainment, and every convenience imaginable, this condo truly captures the best of the Southwest Florida lifestyle. As an added bonus, the property already includes $18,000 in secured rental income for January, February, and March of 2027, offering immediate value and exceptional seasonal demand potential.

9450 Highland Woods BLVD Unit 6203, Bonita Springs
Start Your Search

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.