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$649,000
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
$435,000
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
$1,099,000
3 Beds ⋅ 2 Baths ⋅ 226032344 MLS ⋅ Highland Woods BLDG.
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
$389,000
2 Beds ⋅ 2 Baths ⋅ 226031933 MLS ⋅ Highland Woods BLDG.
Step into a lifestyle of effortless luxury with this stunning first-floor Barrington Veranda, perfectly positioned within the vibrant Highland Woods community. This isn't just a place to live; it’s a turnkey sanctuary where every detail has been handled. From the moment you walk in, the upgrades shine—think sleek stainless steel appliances, refreshed cabinetry, and a seamless flow of tile through the main living areas. The bedrooms and den are finished with high-end laminate, creating a space that feels both modern and warm. Living here means enjoying total peace of mind, thanks to high-impact windows at the rear and electric storm shutters protecting both lanais. Whether you’re sipping your morning coffee or winding down in the evening breeze, these outdoor spaces are designed for year-round enjoyment. And since it’s being offered fully furnished, the transition to your new Florida life is as simple as unpacking a suitcase. Highland Woods is famous for its energetic, social atmosphere. The amenities are world-class, featuring an 18-hole championship golf course, a state-of-the-art fitness center, and seven sparkling pools—including a resort-style oasis with a cabana bar. Between the tennis, pickleball, and bocce courts, there is always a way to stay active. When it's time to relax, the clubhouse offers everything from casual bites in the grill room to elegant Al Fresco dining. The location is truly unbeatable. You are moments away from the upscale shopping and dining at the Promenade at Bonita Bay, and just a short drive from the white sands of Bonita Beach and Barefoot Beach. With Coconut Point Mall and RSW Airport nearby, everything you need is right at your fingertips. Come see why this Veranda is the gem of Highland Woods.

26931 Clarkston Dr Unit 104, Bonita Springs
$369,000
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
$299,000
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
$485,000
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
$330,000
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
$359,900
2 Beds ⋅ 2 Baths ⋅ 2026029004 MLS ⋅ Highland Woods 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 ⋅ Highland Woods 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 ⋅ Highland Woods 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 ⋅ Highland Woods 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 ⋅ Highland Woods 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
$398,900
2 Beds ⋅ 2 Baths ⋅ 225076297 MLS ⋅ Highland Woods 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 ⋅ Highland Woods 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