Boca Grande Homes with Gated Community - Guard Community Features

Boca Grande Homes with Gated Community - Guard Community Features

Welcome to Boca Grande, Florida, a hidden gem nestled on the picturesque Gasparilla Island. Known for its pristine beaches, charming historic districts, and vibrant local culture, Boca Grande is a sanctuary for those seeking a tranquil coastal lifestyle. With its rich history as a former fishing village, the city has transformed into a sophisticated enclave that attracts discerning buyers from around the globe.

One of the most appealing aspects of Boca Grande is its exclusive gated communities, offering an unparalleled level of privacy and security. These guard-gated neighborhoods are designed to provide residents with peace of mind and a sense of community, making them ideal for families and retirees alike. Imagine waking up to stunning sunrises over the Gulf of Mexico, with easy access to world-class amenities just outside your doorstep.

Homes within these gated communities boast exquisite architectural designs, lush landscaping, and luxurious amenities. Many properties feature spacious floor plans, gourmet kitchens, and private pools, perfect for entertaining friends and family. Residents can enjoy exclusive access to pristine beaches, golf courses, and waterfront dining, all while being surrounded by the natural beauty that Boca Grande has to offer.

Whether you’re looking for a vacation retreat or a permanent residence, Boca Grande’s gated communities provide the perfect blend of luxury, security, and coastal charm. Embrace the opportunity to live in one of Florida’s most sought-after destinations, where every day feels like a vacation. Discover the enchanting lifestyle that awaits you in Boca Grande!

Newest Boca Grande Homes with Gated Community - Guard Community Features

1678 Jose Gaspar Drive, Boca Grande
$5,350,000
4 Beds ⋅ 4 Baths ⋅ Boca Grande Isles SubDv. ⋅ 33921 Zip Code
Welcome to 1678 Jose Gaspar Drive, a serene waterfront retreat tucked along the tranquil shores of “Hole in the Wall” Bay in the coveted Boca Grande Isles. This property boasts 96” of water frontage and offers an intimate, natural setting where mangroves, shorebirds, and calm waters create a true Old Florida backdrop.The protected bay is ideal for kayaking and paddle boarding, offering quiet waters to explore at your own pace while enjoying abundant native wildlife. It’s a nature lover’s paradise—private, picturesque, and beautifully unspoiled. The 3494 sq foot home 4 bedroom, 3.5 bath home is filled with natural light and designed to capture water views from the living areas. An open layout with cathedral ceilings and a cozy stone fireplace creates an effortless flow for entertaining or relaxing, while large hurricane glass doors invite the outdoors in. The screened lanai offers views of the water and the living space that Florida is known for. The gourmet kitchen serves as the heart of the home, boasting quartz countertops, eat in dining, generous workspaces, and a breakfast bar. This Island retreat offers plenty of gathering areas which are perfect for hosting family and friends. The primary suite on the main level provides a peaceful sanctuary with an elegant Master bath which includes, quartz countertops, dual sinks a walk in shower and soaking tub. Perfect for relaxing after a day filled with outdoor activities. The lower level contains an additional living room, three additional guest rooms, two baths and easy access to the beautiful pool, spa and patio. Perfect to entertain family and friends. Located in a gated community just minutes from the village of Boca Grande, with its charming shops, dining, and Gulf beaches, this property offers a rare opportunity to embrace quiet waterfront living in one of Florida’s most treasured island communities.

1678 Jose Gaspar Drive, Boca Grande
5854 Gasparilla Road Unit MV20, Boca Grande
$1,240,000
2 Beds ⋅ 2 Baths ⋅ Marina Village SubDv. ⋅ 33921 Zip Code
Beautifully renovated and offered turnkey furnished, this coastal inspired two bedroom, two bath residence is ideally positioned on the coveted second floor within Marina Village at the Boca Grande Club. Encompassing 1,226 square feet, the condo is thoughtfully designed and drenched in soothing coastal hues and curated décor, creating a relaxed yet refined island retreat. The open living areas feature ceramic tile flooring with a warm wood appearance, perfectly complementing the home’s breezy beach aesthetic. The updated kitchen is equipped with new appliances less than two years old and a brand new washer and dryer, offering effortless everyday living. Both bathrooms have been tastefully remodeled. The primary bath showcases beautifully selected tile, a dual rain-head shower, and a frameless glass enclosure, while the guest bath features a stylish tiled shower with a rain-head and frameless glass. Beadboard detailing in the bathrooms and dining area adds timeless coastal charm, while the dining space is further enhanced by a custom built-in bench with integrated storage, a bespoke and highly functional design element. The home is further enhanced with impact-rated windows and sliding glass doors, plantation shutters, and custom-designed closet systems in both bedrooms, offering exceptional functionality without sacrificing style. The residence backs directly to the marina, where large impact sliders frame stunning water views and open to capture refreshing waterfront breezes. Enjoy spectacular marina views from the sunroom, an ideal spot for morning coffee or evening cocktails, where boats glide by and dolphins and manatees are frequent visitors. A separate, locked storage area provides ample space for bikes, beach gear, and more. Just steps from the sparkling community heated pool, Marina Village owners enjoy exclusive membership to the prestigious Boca Grande Club, a private, gated enclave offering resort-caliber amenities. Indulge in three resort-style swimming pools, a serene hot tub, Gulf-front dining and tiki bar, eight Har-Tru tennis courts, a state-of-the-art fitness center, and direct access to Boca Grande’s wide, pristine beaches. A rare opportunity to own a move-in-ready waterfront condo in one of Boca Grande’s most sought-after communities, where thoughtful craftsmanship meets the ultimate coastal lifestyle.

5854 Gasparilla Road Unit MV20, Boca Grande
5000 Gasparilla Road Unit VH25, Boca Grande
$1,995,000
3 Beds ⋅ 4 Baths ⋅ Boca Grande Club SubDv. ⋅ 33921 Zip Code
This 3-bedroom, 3 1/2-bath single-family residence is only steps from the pristine sands of the Gulf, offering the quintessential Boca Grande lifestyle. This redesigned floor plan features a renovated kitchen, updated baths, flooring and impact-resistant windows and sliders throughout. Uniquely offering 3 ensuite bathrooms PLUS an additional guest half bath along with a dedicated laundry room! The 1 car garage offers extra storage with built-in shelves and an outside shower. Sold furnished, this home is ready for immediate enjoyment. Whether you are watching the sunset over the Gulf from your balcony or walking the uncrowded private beach, this is island living at its finest. Purchasing this property provides immediate membership to the Boca Grande Club and all the amenities it is known for such as a fabulous gulf-front restaurant with new pool spa and tiki bar, private beach access with umbrella, lounge chair and towel service. The newly renovated fitness center is world class, and the 8 tennis courts offer a pro-shop with instruction with a very active tennis community.

5000 Gasparilla Road Unit VH25, Boca Grande
5000 Gasparilla Road Unit 27, Boca Grande
$1,895,000
3 Beds ⋅ 3 Baths ⋅ Boca Grande Club SubDv. ⋅ 33921 Zip Code
Tucked away on an exclusive private street shared by just three residences, Village Home 27 offers an exceptional blend of comfort and versatility. This light-filled Boca Grande Club residence features 1,540 square feet of living space, highlighted by beautiful wood flooring, vaulted ceilings, granite countertops, and custom built-ins. The thoughtfully designed floor plan includes a welcoming living room, a separate dining space, and a primary bedroom suite. A private guest wing offers an additional living area and multiple sleeping nooks. The top floor houses an additional bedroom and bath with a private deck and crow's nest. Outdoor living is equally inviting, with a ground-level paver patio in a garden setting, an outdoor shower, and a one-car garage. Enjoy the exceptional lifestyle of the amenity-rich, gated, beachfront Boca Grande Club. Residents can take advantage of multiple swimming pools, including the main pool with its inviting tiki bar overlooking the beach. The renowned clubhouse offers an exceptional fine-dining experience, while eight tennis courts and fitness center provide outstanding opportunities for and an active lifestyle.

5000 Gasparilla Road Unit 27, Boca Grande
158 Carrick Bend Lane, Boca Grande
$4,695,000
3 Beds ⋅ 3 Baths ⋅ North Village Sub SubDv. ⋅ 33921 Zip Code
Tucked toward the quiet end of Carrick Bend Lane in the gated North Village of Boca Bay, this three-bedroom, three-bath home pairs serene lake views with a thoughtful renovation throughout. More than 3,200 square feet of living space spread across two levels give owners and guests room to spread out. The kitchen is the heart of the home and was rebuilt for people who love to cook and entertain: quartz counters beneath a shiplap ceiling, Thermador wall oven, microwave, and gas range, a Wi-Fi-enabled Monogram refrigerator, and a built-in ice maker. An eat-in dining area overlooks the water, and every bathroom has been tastefully updated. Peace of mind comes built in, with impact-rated windows and doors, a newer standing-seam metal roof, and plantation shutters throughout. A two-car garage adds room for cars, golf carts, and island gear. Life in Boca Bay comes with an enviable list of amenities: a private boat basin with slips, an organized tennis program led by a resident pro on Har-Tru courts, a croquet lawn, and four community pools including a lap pool. Evenings belong to the Pass Club, where elevated dining, an extensive wine list, and spectacular sunsets over the Gulf set the tone. And when it’s time for the Village, simply walk or bike to its shops, restaurants, and beaches. Live your Best Life in Boca Grande!

158 Carrick Bend Lane, Boca Grande
5000 Gasparilla Road Unit 26, Boca Grande
$2,200,000
3 Beds ⋅ 3 Baths ⋅ Village Boca Grande Club SubDv. ⋅ 33921 Zip Code
Experience the Boca Grande Club lifestyle in this beautifully updated and expanded 3-bedroom, 3-bathroom Village Home with 1,640 square feet of inviting living area. The sunny living room features vaulted ceilings and is complemented by a separate dining room, spacious kitchen with granite countertops and top-of-the-line appliances, and a full laundry room for everyday convenience. The primary bedroom includes an elegant bathroom and large closet/office. The home has plenty of additional space with 2 storage areas and separate pantry. Extensive improvements enhance the home throughout, including HDF laminate floors, new window treatments, front entry door, and garage overhead and side doors. Outdoor living spaces have also been beautifully refreshed with new upper and lower decking, railings, and stairs, creating inviting spaces to relax and enjoy the Florida lifestyle. Designed with durability and peace of mind in mind, the residence features impact-resistant windows and doors, Hardie Plank siding, and a metal roof installed in 2023. Enjoy the exceptional amenities of Boca Grande Club, including tennis courts, Tiki Bar, a community swimming pool, a clubhouse, and workout facility. This residence offers a wonderful opportunity to experience the relaxed, resort-style living that makes Boca Grande Club so desirable.

5000 Gasparilla Road Unit 26, Boca Grande
5850 Gasparilla Road Unit M4, Boca Grande
$495,000
1 Beds ⋅ 1 Baths ⋅ Boca Grande Club SubDv. ⋅ 33921 Zip Code
Sometimes, you don’t need more space. You just need the right space. And when that space is within the prestigious Boca Grande Club, recently recognized as a Platinum Club of America and ranked No. 8 among the nation’s Top 20 Beach Clubs, the lifestyle is anything but ordinary. Set on the top floor of Marina Village, this 1-bedroom, 1-bath residence captures beautiful views of Gasparilla Sound and Uncle Henry’s Marina, offering the best of carefree island living. The open-concept interior extends to a private waterfront balcony, perfect for watching boats come and go. Thoughtful improvements include hurricane-impact windows and doors throughout, a durable metal roof, newer siding and soffits, and a 2023 HVAC system and water heater. Residents enjoy access to miles of pristine Gulf-front beaches, waterfront dining, premier tennis facilities, a state-of-the-art fitness center, and an active social calendar. Adding to the excitement, the Club is just weeks away from unveiling its spectacularly reimagined Gulf-front pool, featuring a stylish new tiki bar, contemporary design, beautiful new poolside furnishings, and an elevated resort-style atmosphere. The Marina Village pool is also just steps away. An exceptional opportunity to enjoy the beauty of Boca Grande, the distinction of a nationally recognized private beach club, and the simplicity of a low-maintenance island retreat.

5850 Gasparilla Road Unit M4, Boca Grande
5000 Gasparilla Road Unit 19, Boca Grande
$2,100,000
3 Beds ⋅ 3 Baths ⋅ Village Boca Grande Club SubDv. ⋅ 33921 Zip Code
Boca Grande Club has earned Platinum Club of America recognition, ranking No. 8 in the nation’s beach club category. Within this distinguished beachfront community, Village Home 19 combines the privacy of a freestanding residence with beautifully renovated interiors and access to exceptional private club amenities. With no shared walls, its own garage and private outdoor space, the home enjoys an unusually open setting with glimpses of the Gulf from each level. Thoughtfully enclosed spaces expand the main living area and guest bedroom, adding versatility to the floor plan and providing room for reading, conversation or quiet retreat. Plantation shutters throughout lend architectural definition, complementing a restrained coastal palette. Mature landscaping frames the residence and its outdoor patio, creating a private setting for enjoying the coastal air. A 2022 standing seam metal roof, Trex stairs and decking, and predominantly impact-rated windows and sliding glass doors complement the interior renovation. Furnishings are available. An extensive renovation of the Club’s pool and tiki bar, alongside recently renovated restaurants, brings a fresh, sophisticated aesthetic to its beachfront gathering spaces. An expansive private beach, waterfront dining, multiple pools, eight Har-Tru tennis courts, an established tennis program and a fitness center offer a rich array of pursuits within this gated, professionally managed community.

5000 Gasparilla Road Unit 19, Boca Grande
367 Night Heron Drive, Boca Grande
$4,125,000
3 Beds ⋅ 3 Baths ⋅ North Bay SubDv. ⋅ 33921 Zip Code
Virtually Staged. Set along the shores of Charlotte Harbor in North Bay, this home offers a distinctive blend of architectural character, handcrafted details, and captivating waterfront views. The dramatic two-story living room features a hand-painted coffered ceiling, custom staircase, terra cotta tile flooring, and a hand-carved pecky cypress fireplace mantel. The adjoining dining room opens to harbor views, while the updated kitchen and family room showcase cherry flooring, designer cabinetry, granite countertops, and a spacious island. A waterfront sunroom spans the rear of the home, connecting the living spaces to the garden and mangrove coastline. Two main-level guest bedrooms provide comfortable accommodations, while the upper-level primary suite features vaulted ceilings, expansive harbor-facing windows, a Roman-style bath, walk-in closet, and private waterfront deck. A circular staircase leads to a widow's walk with panoramic views of Gasparilla Island and beyond. Additional highlights include a finished elevator, impact glass windows and doors, a 2023 metal roof, freshly painted interiors, and a two-car garage. Combining timeless craftsmanship, exceptional views, and the Boca Bay lifestyle, this remarkable residence offers a truly special opportunity for waterfront living in Boca Grande.

367 Night Heron Drive, Boca Grande
700 S Harbor Drive, Boca Grande
$2,125,000
3 Beds ⋅ 3 Baths ⋅ Beach View At Boca Bay SubDv. ⋅ 33921 Zip Code
3 Bedroom, 3 bathroom, 2 car garage home with new impact windows and a 3-stop elevator! This “Kentia” townhome is located in the highly sought-after Boca Bay community of Boca Grande. Inside, expansive windows and a wall of sliders invite in natural light while framing stunning water views from nearly every vantage point. The spacious main living area transitions seamlessly to the large sitting area, with its desirable western exposure, you can enjoy breathtaking sunsets over the Gulf. The primary suite serves as a tranquil retreat, offering a generous ensuite bathroom, serene waterfront ambiance, and a private porch. Boca Bay offers an upscale resort style experience, including the exclusive Boca Bay Pass Club, a members-only facility offering elevated dining. Additional amenities include tennis and pickleball courts, three swimming pools, a private fishing pier, multiple clubhouses, and a fitness center. There are also private deepwater docks available by reservation! Ideally located on the iconic island of Boca Grande, this property places you just moments from world-class boating and fishing, pristine beaches, boutique shopping, and renowned island dining, all while preserving the tranquility and exclusivity the area is known for. Schedule your private showing today and discover the beauty and distinction of Boca Bay.

700 S Harbor Drive, Boca Grande
585 Buttonwood Bay Drive, Boca Grande
$5,600,000
3 Beds ⋅ 4 Baths ⋅ South Bay Sub SubDv. ⋅ 33921 Zip Code
Experience refined coastal living in this beautifully remodeled 3-bedroom, 3.5-bath waterfront residence with bonus space in the highly sought-after Boca Bay Buttonwood community. Perfectly positioned on large open water with private dockage, this exceptional home blends timeless design with comprehensive 2025 upgrades for true peace of mind. The exterior has been completely transformed with a new metal roof (2025), all-new Hardie siding and trim, hurricane-rated windows and sliding glass doors, and a hurricane-rated side garage door. Exterior lighting has been fully replaced, and the third-floor balcony was rebuilt following Hurricane Ian. The private dock has been significantly enhanced in 2025 with an additional 159 square feet, raised walk path (permitted), and electrical modifications to accommodate boat lifts—creating a premier waterfront setup. Inside, the home showcases new hardwood flooring throughout staircases, third-floor loft, and bedrooms, along with freshly painted walls and trim. Plantation shutters and four new motorized shades elevate both style and comfort. The main living area features a custom-built entertainment center designed to accommodate a 70-inch TV. The 2025 chef’s kitchen is a showpiece, offering new stainless-steel Thermador appliances including a 36” gas cooktop, refrigerator, and dishwasher, along with a 24” drawer microwave, wine cooler, Cortez countertops, tile backsplash, new faucets, and updated disposal. Both garages feature new epoxy floors and LED lighting, with a new mop sink in the north garage. Additional highlights include a Grundfos booster pump, certified backflow preventer, new Electrolux washer and dryer, and fully renovated bathrooms with Cortez countertops, new tile, updated fixtures, and dual vanities in the third-floor primary suite. An extraordinary opportunity to own a move-in-ready waterfront home in Boca Bay.

585 Buttonwood Bay Drive, Boca Grande
5000 Gasparilla Road Unit BC205, Boca Grande
$955,000
1 Beds ⋅ 1 Baths ⋅ Beach Chalet Boca Grande SubDv. ⋅ 33921 Zip Code
Virtually Staged. Platinum! #8 of the top 10 beach clubs in America! Experience effortless island living at Beach Chalet Unit 205. This charming, turnkey-furnished one-bedroom coastal retreat is nestled within the highly sought-after gated Boca Grande Club. Offering endless, breathtaking views of the Gulf from every room in this second-floor unit! Plus, just moments from the beach, this inviting residence captures the essence of relaxed luxury and the laid-back elegance that defines life on Gasparilla Island. The kitchen features stainless steel appliances and modern finishes, while the bright, open living spaces flow seamlessly into the Florida room—every room is an ideal setting to enjoy morning coffee, a quiet afternoon with a book, or the gentle Gulf breezes. Beyond the residence itself, owners enjoy access to the exceptional resort-style amenities that make the Boca Grande Club so desirable. Get ready for the ultimate pool & lounge oasis! A massive pool complex transformation is in the final stages and looks stunning!(completion deadline of Oct. 31, 2026 - see attached renderings and new photos coming soon). The new complex expands by 20% to a spacious 2,027 square feet, transitioning to a sleek, 62-foot T-shaped layout. These enhancements feature a brand-new main pool, a relaxing spa, a dedicated kiddie pool, expanded seating for 100+ sunbathers, and a newly expanded Tiki Bar (growing by 25–40%) for effortless poolside entertaining. Spend your days lounging on the club’s uncrowded private beach, relaxing by the Gulf-front swimming pools, grab a drink at the tiki bar, dine at the beachfront restaurant, or take advantage of the premier tennis facilities(eight Har-Tru) and state-of-the-art fitness center. All of this includes a top-tier tennis program with professional instruction, as well as on-site rental management and housekeeping services. With beautifully maintained grounds and a vibrant yet tranquil coastal atmosphere, this is a place where every day feels like a vacation. Whether you're seeking a serene personal getaway, seasonal escape, or investment opportunity, this charming island residence offers the perfect blend of comfort, convenience, and the unmatched lifestyle of Boca Grande. This unit is rental-ready and can continue to offer investment income if desired. Peace of mind is built right in: this property will soon have a brand-new roof engineered to meet current, coastal specifications for maximum hurricane resistance. Notably, the previous roof survived Hurricanes Helene and Milton with zero leaks; this proactive upgrade was fully funded by association reserves with no special assessment passed on to the buyer. With the major milestone-required structural reinforcements completed, the entire building is in top-tier condition, ensuring you can buy with confidence. Schedule your private tour and discover the luxury Florida lifestyle. Initiation fees and yearly Club dues apply. Please inquire for cost.

5000 Gasparilla Road Unit BC205, Boca Grande
Start Your Search

How much is your home worth?

Get instant property value now!