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1640 Jean Lafitte Drive, Boca Grande
$8,500,000
5 Beds ⋅ 5 Baths ⋅ Boca Grande Isles SubDv. ⋅ 33921 Zip Code
Bermuda-inspired coastal residence set within Boca Grande Isles, a private gated enclave overlooking sunrise views across Hole-in-the-Wall Bay. This spacious five-bedroom, four-and-a-half-bath home spans nearly 5,600 square feet of thoughtfully designed living space with classic architectural detail and relaxed island character. The exterior features clean stucco lines, white tile roof, and a gracious front porch. A circular paver drive leads to a maturely landscaped courtyard with palms and native coastal plantings. Inside, solid oak flooring, trowel-finished walls, and understated lighting create a calm backdrop for everyday living and entertaining. The living room includes a fireplace with custom carved woodwork and built-ins, and opens to a stone-floored sunroom framing views of the infinity pool and bay. The kitchen and keeping room form the center of the home, with granite counters, custom cabinetry, Sub-Zero refrigeration, Bosch dishwasher, double ovens, warming drawer, brick backsplash, and a wet bar with ice maker and wine refrigerator. The primary suite occupies the main level and offers dual walk-in closets, a sitting area, and a well-appointed bath with soaking tub and walk-in shower. Four additional bedrooms include two private guest suites, and an elevator provides convenient access to all levels. Outdoor living unfolds over terraced spaces surrounding the infinity pool, set along the bay and sheltered by mature landscaping. An oversized garage accommodates two vehicles plus a golf cart, with storage for kayaks, bikes, and beach gear. Located minutes from Boca Grande’s historic village and Gulf beaches, this property combines privacy, scale, and waterfront living in one of the island’s most desirable settings.

1640 Jean Lafitte Drive, Boca Grande

1660 16th Street E, Boca Grande
$4,900,000
4 Beds ⋅ 5 Baths ⋅ Boca Grande SubDv. ⋅ 33921 Zip Code
Virtual staging and several photos show virtual remodeling concepts. Positioned in a secluded and private corner of Boca Grande, this exceptional estate boasts prime deep-water dockage, with direct access to Charlotte Harbor and no bridges to the Gulf of Mexico. Expansive canal frontage and outstanding boat dockage with an 8,000 lb boat lift provides ample space for a large yacht and multiple smaller vessels. Immerse yourself in magnificent views of the bay, bayou, and Gulf from numerous rooms, porches, and balconies. With over 4,500 sq.ft. of living space, the home features 4 bedrooms, 4.5 baths, and a variety of sitting and study rooms. The grand living areas include soaring ceilings, formal dining, family, and breakfast rooms, and a master suite that is nothing short of enormous. Upstairs, you'll find an additional family room perfect for relaxation. The Victorian-style design is filled with intricate architectural details such as columns, corbels, large coral stone wood burning fire place, Venetian glass chandeliers, and stained-glass windows and doors. Restored cypress cabinetry and built-in loft beds in one of the guest bedrooms add unique custom touches to the interior. Just a short stroll or golf cart ride to the legendary Gasparilla Inn, the village of Boca Grande, renowned restaurants, and shops, or across the street to miles of pristine sandy beach. This paramount boating location is a dream for both anglers and pleasure cruisers, with world-class backwater and tarpon fishing right at your fingertips. Charming island destinations, including Don Pedro and Cabbage Key, are also just a short pleasure cruise away. The property includes the submerged land behind the home, which allows for tremendous flexibility if redesigning the dock.

1660 16th Street E, Boca Grande

5010 Grouper Hole Court, Boca Grande
$3,975,000
4 Beds ⋅ 3 Baths ⋅ East Shore Acres SubDv. ⋅ 33921 Zip Code
Tucked away on a quiet cul-de-sac and set well back on a private shelled driveway, this elevated two-story residence offers a rare blend of acreage, privacy, and timeless Florida craftsmanship. The home’s welcoming entry is framed by two stately columns, creating an elegant sense of arrival. Situated on 1.7 acres private estate the property enjoys tranquil water views through the mangroves with partial views of Gasparilla Sound, offering a serene Old Florida setting. The location also provides close proximity to the Boca Grande Club, combining privacy with convenient access to island amenities. Built in 1986 by respected builder Dick Yusk, this four-bedroom, two-and-a-half-bath single-family home features a thoughtfully designed floor plan, including two primary bedrooms, ideal for multigenerational living or hosting guests. The great room is a standout, showcasing vaulted ceilings, tongue-and-groove oak hardwood flooring, beadboard detailing, and chair rail accents that create warmth and architectural character. Bedrooms are comfortably carpeted, while the bathrooms are finished with tile. The open kitchen is dramatic and light-filled, highlighted by a vaulted ceiling with atrium windows, tile flooring, and a breakfast bar that opens to the dining area—perfect for everyday living and entertaining. A versatile den provides additional flexibility and may be used as a home office, library, or sitting room. The outdoor setting embraces the property’s natural surroundings with mature landscaping, an irrigation system, and a peaceful, private atmosphere that complements the creekside location. An outdoor shower adds coastal practicality, while the expansive grounds offer ample opportunity to enjoy the outdoors or further customize the property to suit your lifestyle. The home is constructed with a HardiPlank Cement Siding, topped with a metal roof, and equipped with 175mph rated PGT hurricane windows for durability and peace of mind. Additional features include zoned 2.5-ton central air conditioning, an indoor laundry room, French door entry, and an inviting front porch. Completing the property is an oversized 24’ x 28’ detached two-car garage with workshop, ideal for storage, hobbies, or recreational equipment. The home is serviced by a private pre-treatment effluent pump. Public water and sewer is onsite. Furnishings are negotiable, offering a potential turnkey opportunity. This is a rare offering for those seeking privacy, acreage, and waterfront tranquility—where classic Florida architecture, natural beauty, and thoughtful design come together in a peaceful and sought-after setting.

5010 Grouper Hole Court, Boca Grande

5000 Gasparilla Road Unit VH20, Boca Grande
$2,485,000
3 Beds ⋅ 3 Baths ⋅ Village Boca Grande Club SubDv. ⋅ 33921 Zip Code
STAGED/FURNISHED – Please review the updated pictures. Fully renovated Village Home in the gated Boca Grande Club offering 3BR/3BA + 4th Kids Room and 1,600+ SF with approx. 400 SF of added living space. Coastal contemporary design with open-concept layout, vaulted ceilings, abundant natural light, enclosed sunrooms, and new fireplace. Gourmet kitchen features premium LG appliances, quartz countertops, and designer fixtures. Primary suite includes a re-imagined layout with a large walk-in closet, and spa-like bath with dual vanities and walk-in shower. Loft area has been transformed to include a full bathroom and private bedroom. The home features designer tile, new hardwood floors, doors, trim, and hardware throughout. Modern conveniences include full-size in-home washer/dryer, and outdoor elevator lift. Major upgrades: Newer roof, impact windows, Hardy siding, Trex decking, open-air lift, and 2017 AC. West-facing deck with sunset views and Bay/Gulf glimpses, plus garage and garden area. Steps to secluded beach. Boca Grande Club amenities include Gulf-front dining, 3 pools, tiki bar, fitness center, yoga/water aerobics, 8 tennis courts, and gated security. Village Home will come fully furnished and move-in ready.

5000 Gasparilla Road Unit VH20, Boca Grande

17 Seawatch Drive, Boca Grande
$3,900,000
3 Beds ⋅ 4 Baths ⋅ Seawatch Of Boca Grande SubDv. ⋅ 33921 Zip Code
The crown jewel of Boca Grande’s North Shore, this direct beachfront paradise offers rare privacy and timeless coastal elegance. Featuring 3 bedrooms and 3.5 baths—all ensuite—this retreat includes expansive living areas, a two-plus-car garage, and a beautifully appointed kitchen with stainless steel appliances, perfect for entertaining or quiet mornings by the Gulf. With no public beach access nearby, the shoreline feels like your own, with world-class shelling and endless views. Sunsets paint the Gulf in gold, casting a warm glow over a home designed for peace and connection. Whether enjoying the Gulf breeze or gathering under the stars, this is more than a residence—it’s a private sanctuary of luxury, solitude, and unspoiled natural beauty.

17 Seawatch Drive, Boca Grande

870 Grande Pass Way, Boca Grande
$3,995,000
Hill Tide Estates SubDv. ⋅ 33921 Zip Code
The Ultimate Gulf-Front Homesite – Iconic Views & Unparalleled Luxury Discover a rare opportunity to own Lot #6, “The Lighthouse Lot,” in Hill Tide Estates—Boca Grande’s most renowned waterfront community. Perfectly positioned for breathtaking panoramic views of the Gulf of Mexico and Boca Grande Pass, this exclusive homesite offers a front-row seat to some of Florida’s most spectacular sunsets. Build your dream custom estate with the builder of your choice on this prized island location, featuring coveted southern and western exposures that bathe your future home in sunlight all day. Included are masterfully designed plans for a luxury residence, ensuring a seamless transition to your vision of coastal elegance. Hill Tide Estates is an intimate gated community of just 19 homes, offering residents a private tiered beach and an exclusive fishing and observation pier in Boca Grande Pass—home to world-class tarpon fishing. A short golf cart ride takes you to the historic village of Boca Grande, the renowned Gasparilla Inn, and some of the finest dining, shopping, and leisure activities on the Gulf Coast. This is more than just a homesite—it’s an invitation to a lifestyle of luxury, tranquility, and adventure. Secure your place in paradise today.

870 Grande Pass Way, Boca Grande

1639 Jean Lafitte Drive, Boca Grande
$3,495,000
Boca Grande Isles SubDv. ⋅ 33921 Zip Code
Located within the exclusive, gated community of Boca Grande Isles, this expansive western-facing waterfront homesite presents an unparalleled opportunity to create your coastal dream retreat. The property boasts 96 feet of direct water frontage on approximately 0.30 acres and offers seamless access to the Intracoastal Waterway and the Gulf without obstructing bridges. Conceptual house plans designed by the renowned architectural firm, Stofft Cooney, are available for both a one-story and two-story design, along with a current survey and a comprehensive site study to inspire your vision. Essential utilities, including electricity, sewer, and water, are in place, and the property has undergone extensive site preparation to ensure a smooth building process. A concrete seawall and a picturesque wooden dock provide immediate water access, while recent landscaping enhances privacy and natural beauty. Just moments from Boca Grande’s historic village, pristine beaches, and renowned boating community, this exceptional homesite is the perfect setting for an elegant island retreat. The listing agent is the owner.

1639 Jean Lafitte Drive, Boca Grande

370 E Railroad Avenue Unit 1, Boca Grande
$890,000
2 Beds ⋅ 1 Baths ⋅ 370 East Railroad SubDv. ⋅ 33921 Zip Code
MOTIVATED SELLER! Discover the perfect blend of Old Florida charm and modern comfort in this beautifully remodeled condominium, ideally located in the heart of Boca Grande. Just steps away from boutique shops, acclaimed restaurants, and the laid- back island lifestyle, this inviting retreat offers both convenience and timeless appeal. This charming condo has been thoughtfully renovated and tastefully redecorated, creating a light airy space with a warm cottage feel. Offered turnkey, it's ready to enjoy from day one, whether as your private getaway or a desirable rental investment. Minutes from one of the Gulf Coast's most beloved beaches, known for its powdery white sand, abundant seashells and dog friendly atmosphere. Spend your days shelling, enjoying the shoreline, or simply soaking in the tranquil beauty of Boca Grande. Hot water tank is 2024, and AC is 2025. 2021 manufactured; rebuilt 2024 golf cart included! Whether you're seeking a serene escape or a charming income producing property, this coastal gem delivers the best of island living.

370 E Railroad Avenue Unit 1, Boca Grande

6040 Boca Grande Causeway Unit 5, Boca Grande
$189,000
Boca Grande North SubDv. ⋅ 33921 Zip Code
NEW LOWER PRICE - BOCA GRANDE NORTH SLIP |10,000 LB. LIFT | NEWER MOTOR | ELECTRIC | FISH CLEANING STATION | DIRECT GULF ACCESS | NO FIXED BRIDGES | RENTABLE | Enjoy direct Gulf access with no fixed bridges and deep water, ideal for serious boaters. Boat slip can accommodate a vessel approximately 26 -27 feet in length with a beam of approximately 10.5 feet (buyer to verify). Cruise the back bays or head straight to the Gulf — some of Southwest Florida's best fishing waters are just minutes away. Features include a 10,000 lb. lift with newer motor, electric, water, and a fish cleaning station, all set on recently rebuilt composite docks for low maintenance. OWNERSHIP IS NOT CONTINGENT ON RESIDENCE IN THIS COMMUNITY, offering flexibility for both local and off-island buyers. Slips may be rented, providing an opportunity for seasonal income or offsetting ownership costs. A standout value for buyers seeking a well-equipped slip with direct Gulf access, no fixed bridges, and the ability to own without residence in the community. Easy to show.

6040 Boca Grande Causeway Unit 5, Boca Grande

869 Hill Tide Lane, Boca Grande
$2,800,000
Hill Tide Estates SubDv. ⋅ 33921 Zip Code
NOW OFFERED! Rare opportunity to own one of the last remaining custom-buildable lots in coveted Hill Tide Estates on Gasparilla Island. This deep, oversized premier homesite offers exceptional flexibility for designing a custom residence and features favorable AE flood-zone elevation and state-of-the-art infrastructure. Enjoy convenient access to private East Beach and an exclusive fishing pier on Boca Grande Pass. Hill Tide Estates is a luxury gated community with brick-paved streets and custom residences overlooking the Gulf of Mexico, Boca Grande Pass, and Charlotte Harbor. The community is the only subdivision on Gasparilla Island that fronts Boca Grande Pass, renowned as the “Tarpon Capital of the World.” Included with the sale are two exceptional deepwater boat slips, Slip 10 and Slip 39, at Uncle Henry’s Marina, at no additional cost. The approximately 35' and 60' slips offer convenient access to the Gulf of Mexico and are located in a well-managed marina with dock staff, restrooms, fuel station, and boat ramp. Slips transfer as a sublease hold estate. No storm damage to the lot from past hurricanes. A rare opportunity to secure a premier homesite with exceptional boating amenities in one of Boca Grande’s most exclusive communities.

869 Hill Tide Lane, Boca Grande

5850 Gasparilla Road Unit M1&3, Boca Grande
$1,700,000
2 Beds ⋅ 2 Baths ⋅ Marina Village SubDv. ⋅ 33921 Zip Code
No damage from Hurricane Milton ! This first floor all one level beautifully furnished property was originally 2 units that were combined to afford an open floor plan and an extra bonus room that serves as a 3rd bedroom if so desired! Full view harbor waterfront where dolphins and manatees are often present! Enjoy majestic sunrises with expansive views in this special property. Boca Grande Club is an amenity rich community with several pools, private beach access, 8 tennis courts, state of the art fitness center and the best private restaurant on the island! Enjoy an end of day cocktail at the poolside Tiki bar, overlooking the beach and a glorious sunset. One time Club Initiation fee of $50,000.00 and one time Capital Improvement Fee of $15,000.00 upon membership.

5850 Gasparilla Road Unit M1&3, Boca Grande

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