Location: East Shore Acres, Boca Grande
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14 GROUPER HOLE DR, BOCA GRANDE, FL 33921
$10,825,000116 Days on yellowkey MLS ID: N6141937
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 6207 Built: 1997 Tax: $56,560 (2025)Community: East Shore AcresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$56,560
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: 2 DEEP-WATER DOCKS AND A COVERED 7,000 LB LIFT. 5 BEDROOMS AND 5.5 BATHROOMS. MYRTHA POOL. INDOOR GUN RANGE. NO FIXED BRIDGES TO GULF WATERS. ROOF 2017. Welcome to a true Sportsman’s Paradise at 14 Grouper Hole Drive on Gasparilla Island in Boca Grande, Florida. This exceptional waterfront estate offers an unparalleled lifestyle, where breathtaking views of the Gasparilla Sound greet you the moment you step through the grand double doors. Designed for both adventure and relaxation, this residence seamlessly blends refined elegance with world-class amenities. The main living area is on the second floor, accessible by a three-stop elevator. A bright foyer leads into the expansive living room, which is open to the third floor, creating an impressive sense of space with soaring ceilings. The dining area flows effortlessly into the kitchen, where a beautiful bay window breakfast nook offers the perfect setting to enjoy morning coffee with stunning water views. The kitchen features a WOLF gas stove, a Sub-Zero paneled refrigerator, a spacious pantry, and a breakfast bar. French doors from the living room open onto a large screened deck—ideal for entertaining or unwinding as boats pass by. The second floor hosts three guest bedrooms, each with nearly floor-to-ceiling windows and en-suite bathrooms. A half bath and a well-appointed laundry room are also on this level. A striking catwalk on the third floor, adorned with a sculptural iron railing, overlooks the living space below while offering sweeping views of the Sound. The luxurious primary suite is a serene retreat, with private access to an open-air deck to enjoy the waterfront breeze. The en-suite bath features dual vanities, a walk-in shower, and a separate soaking tub. A generous walk-in closet with custom shelving provides ample storage. An additional sitting area with a bay window offers yet another breathtaking vantage point. A well-appointed fifth bedroom, also with mesmerizing water views and an en-suite bath, is located opposite the primary suite. The estate’s crown jewel is the extraordinary sports pavilion, seamlessly connected to the main home. Designed for ultimate recreation, it features an indoor/outdoor sitting and dining area with a retractable mosquito screen and fire pit. Inside, a stylish living space and fully equipped kitchen boast Viking appliances, Kendall Cambria Quartz countertops, a built-in bar refrigerator, and an ice machine. At its heart is the Myrtha Ozone Pool—one of Florida’s most advanced residential pools. Competition-length, with stainless steel bolted technology for durability, it features a European lighting system, the only one of its kind in North America. Exceptionally pure, the water is free of chlorine and salt, making it pristine enough to drink. The pool is both heated and cooled for year-round enjoyment, with a standalone hot tub nearby. Remote controlled hurricane shutters add to piece of mind. The sports pavilion also includes a private, air-conditioned Pilates studio and areas for ping pong and pool. For shooting enthusiasts, the state-of-the-art gun range features two dedicated lanes—one for archery and one for firearms. Equipped with a high-tech camera system for precision accuracy, a retractable target retrievals, advanced bullet entrapment, and sound suppression, this range ensures top tier performance.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
5010 GROUPER HOLE CT, BOCA GRANDE, FL 33921
$4,500,00098 Days on yellowkey MLS ID: D6145351
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2648 Built: 1986 Tax: $5,933 (2024)Community: East Shore AcresSingle Family
Taxes:$5,933
Tax Year: 2024
Remarks: 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.
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)
Listing Agent: Richard Hugger (941-270-2816)
5020 GROUPER HOLE CT, BOCA GRANDE, FL 33921
$4,675,000 MLS ID: D6145898
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2951 Built: 2002Community: East Shore AcresSingle Family
Taxes:
Tax Year:
Remarks: 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.
Listing Agent: Kathleen Turner (941-234-7643)
4190 LOOMIS AVE, BOCA GRANDE, FL 33921
$2,755,000 MLS ID: D6142937
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 4608 Built: 1999Community: East Shore AcresSingle Family
Remarks: One or more photo(s) has been virtually staged. 200 Palms- a custom retreat bordering nature preserve positioned on 1.35 acres at the end of a quiet cul-de-sac and backing to a serene nature preserve, this custom-built home blends warm, natural elements with thoughtful design. Soaring Douglas Fir vaulted ceilings crown the expansive great room, where rich cherry cabinetry, Viking and Sub-Zero appliances, and an oversized kitchen island that seats eight create a comfortable space for gathering. The home’s two main levels feature 10-foot-wide, fully screened wraparound decks—ideal for enjoying the peaceful, private setting. Multiple sets of double French doors create seamless indoor-outdoor flow from nearly every room. With four spacious bedrooms, three full bathrooms, and an additional office or fifth bedroom with a half bath, the layout is both flexible and functional. The ground floor, with 4 car garage and workshop, is accessible—like all three levels—via a private elevator. Additional updates include a new metal roof (July 2021), fresh carpeting, and two recently replaced air conditioning units. This home offers a rare combination of craftsmanship, privacy, and modern comfort—perfect for relaxed island living.
Listing Agent: Carol Stewart (941-276-1162)
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