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$4,675,000
3 Beds ⋅ 4 Baths ⋅ East Shore Acres SubDv.
Located on Gasparilla Island beyond a private driveway, this one-of-a-kind retreat spans generous acreage and captures panoramic bay and coastal water views. Positioned on 1.88 acres and framed by native landscaping, the serene setting feels worlds away, yet remains just minutes from the charm of Boca Grande village. Spanning 2,951 square feet of refined living space with a total footprint of 6,287 square feet, the residence features three bedrooms plus a study or bonus room that can easily serve as a fourth bedroom, along with three-and-a-half baths. An interior elevator services all floors, ensuring effortless access throughout. The interiors reflect a sophisticated coastal aesthetic, highlighted by light-colored hardwood floors and thoughtfully designed living spaces. The study features a wet bar, opens to an exterior porch, and offers a perfect spot for stargazing, while the upstairs primary suite enjoys its own private porch—both providing sweeping Bay views and front-row seats to abundant wildlife, including osprey, pelicans, and egrets. An expansive porch running the length of the home invites morning coffee with sunrises over the water and evenings bathed in soft sunset hues. Electric hurricane shutters provide peace of mind, while the three-car, climate-controlled garage plus dedicated golf cart space adds everyday convenience. Leisurely bike rides or golf cart trips along the paved path lead directly into the village of Boca Grande, known for exceptional dining, unique shopping, world-class fishing, and outstanding boating. Properties of this size, setting, and water-view presence are exceptionally rare on the island, making this a truly special opportunity.

5020 Grouper Hole Court, Boca Grande
$3,975,000
4 Beds ⋅ 3 Baths ⋅ East Shore Acres SubDv.
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