14 Grouper Hole Dr: A $10.8 Million Waterfront Sportsman’s Estate Redefining Luxury Living in Boca Grande

Date of Publishing: December 20, 2025

Priced at $10.8 million, 14 Grouper Hole Dr stands among the most distinctive offerings currently available within Boca Grande real estate, combining direct Gulf access, advanced recreational amenities, and a level of privacy rarely found on Florida’s barrier islands. Located on Gasparilla Island, this five-bedroom, five-and-a-half-bath waterfront estate spans 6,207 square feet across a nearly one-acre lot, positioning it as a true legacy property rather than a conventional luxury listing.

Aerial view of 14 Grouper Hole Dr on Gasparilla Sound Boca Grande Florida

From the moment one arrives at 14 Grouper Hole Dr, the Boca Grande real estate communicates a clear identity: a residence designed for those who live by the water, not merely beside it. With no fixed bridges to the Gulf of Mexico, two deep-water docks, and a covered 10,000-pound boat lift, the home offers immediate and unrestricted access to some of Florida’s most prized boating and fishing grounds. According to the listing agents, this maritime advantage is central to the property’s long-term appeal. “This is a home that was conceived around access and performance,” an agent told Luxury Houses Magazine. “The owner prioritized functionality on the water just as much as comfort on land.”

Elevated Architecture Framed by Gasparilla Sound

Built in 1997 in an elevated Florida architectural style, 14 Grouper Hole Dr unfolds across three levels, with the primary living spaces positioned on the second floor to capture panoramic views of Gasparilla Sound. Accessed via a three-stop elevator or a grand staircase, the main level opens into a light-filled foyer that immediately draws the eye toward the waterfront beyond.

The living room rises dramatically to the third floor, creating a vertical volume that enhances both natural light and airflow. French doors extend the interior outward to a screened waterfront deck, where shifting coastal light and passing boats become part of the daily rhythm of life. Adjacent to the living area, the dining space transitions seamlessly into the kitchen, anchored by a bay-window breakfast nook that offers a quiet vantage point over the water.

The kitchen itself reflects a careful balance between professional-grade performance and understated elegance. Outfitted with a Wolf gas range, a paneled Sub-Zero refrigerator, a spacious pantry, and a generous breakfast bar, the space supports both intimate daily use and large-scale entertaining. One of the agents noted to Luxury Houses that the kitchen was intentionally designed to avoid excess. “Everything here serves a purpose,” the agent explained. “It’s refined, but it’s meant to be used.”

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Guest Accommodations and a Secluded Primary Suite

Three guest bedrooms occupy the second level, each featuring en-suite bathrooms and expansive windows that frame water views and invite natural light. These rooms are complemented by a discreet powder room and a well-appointed laundry space, reinforcing the home’s emphasis on practicality without compromising elegance.

Above, a sculptural iron-railed catwalk overlooks the living room below while offering sweeping sightlines across Gasparilla Sound. The primary suite functions as a private retreat within the home, with direct access to an open-air deck where coastal breezes and waterfront sunsets define the experience. The en-suite bathroom includes dual vanities, a walk-in shower, and a separate soaking tub, while a custom walk-in closet provides ample storage.

An additional sitting area with a bay window adds a contemplative layer to the suite, creating a space suited for reading or quiet reflection. Opposite the primary suite, a fifth bedroom with its own en-suite bath offers flexibility for extended family or guests, maintaining privacy while preserving views of the water.

SEE MORE: A $26 Million Tropical Modern Waterfront Estate Redefining Private Island Living in Miami Beach

A Sports Pavilion Designed Without Compromise

What truly distinguishes 14 Grouper Hole Dr from other home in Boca Grande for sale is its purpose-built sports pavilion, seamlessly connected to the main residence. Designed as a multifunctional recreational environment, the pavilion blends indoor and outdoor living through retractable mosquito screens, a fire pit, and expansive seating and dining areas that open toward the water.

At the heart of the pavilion is a competition-length Myrtha Ozone Pool, one of the most technologically advanced residential pools in Florida. Constructed using stainless steel bolted technology and illuminated by a European lighting system unique in North America, the pool is both heated and cooled for year-round use. The ozone-treated water eliminates the need for chlorine or salt, resulting in exceptional purity rarely found in private residences.

“The pool alone places this property in a category of its own,” one agent told Luxury Houses Magazine. “The Boca Grande home for sale reflects a level of investment and technical understanding that goes far beyond typical luxury amenities.”

Inside the pavilion, a fully equipped kitchen with Viking appliances, Kendall Cambria Quartz countertops, a built-in bar refrigerator, and an ice machine supports entertaining at scale. Additional features include an air-conditioned Pilates studio, dedicated areas for billiards and table tennis, and a state-of-the-art indoor gun range. Designed with sound suppression, advanced bullet entrapment, retractable targets, and a precision camera system, the range accommodates both firearms and archery, underscoring the estate’s identity as a true sportsman’s compound.

SEE MORE: A Breathtaking $85 Million Ultra Luxury Dual Waterfront Estate Redefining Manalapan Living

Waterfront Infrastructure and Gulf Access

Beyond its architectural and recreational offerings, 14 Grouper Hole Dr delivers exceptional maritime infrastructure. Two deep-water docks and a covered boat lift allow for seamless transitions from home to open water, while the absence of fixed bridges ensures unrestricted navigation to the Gulf of Mexico. For serious boaters, this feature alone places the estate among the most desirable Boca Grande home for sale.

Boca Grande Lifestyle and Community

Situated within the East Shore Acres subdivision, the property benefits from Boca Grande’s longstanding reputation as one of Florida’s most discreet and exclusive coastal communities. Known for its historic charm, boutique shopping, and refined dining scene, Boca Grande attracts residents who value privacy and authenticity over spectacle.

From yacht clubs and golf courses to nature preserves and beaches, the island offers a balanced lifestyle that combines leisure with natural beauty. Despite its tranquil character, Boca Grande remains connected to mainland amenities and regional airports, making it both secluded and accessible.

Transaction History and Market Positioning

Public records indicate that the land associated with 14 Grouper Hole Dr traded for $495,000 in 1994, prior to the home’s construction in 1997. The property later sold for $4 million in 2008 before changing hands again in 2012 for $550,000 during a period of broader market correction.

In recent years, the Boca Grande real estate has been listed at various price points, including $13.45 million in 2021 and $12.25 million in 2023 and 2024. The current asking price of $10,825,000 reflects both market recalibration and the seller’s positioning strategy within the upper tier of Boca Grande real estate, where direct Gulf access and specialized amenities continue to command long-term interest.

A Singular Offering on Gasparilla Island

For buyers seeking more than a traditional waterfront residence, 14 Grouper Hole Dr represents a rare convergence of location, infrastructure, and purpose-driven design. With its elevated architecture, advanced recreational facilities, and immediate access to Gulf waters, the estate stands apart even within Boca Grande’s most prestigious addresses.

As one agent summarized to Luxury Houses Magazine, “This property isn’t just about luxury, it’s about capability. It’s built for someone who genuinely lives the coastal lifestyle“. To know more about this property, view on Zillow listing.

For inquiries or to schedule a private showing, please contact:

Michelle Hupp
941-773-5464
KELLER WILLIAMS ISLAND LIFE REAL ESTATE

Lisa Naum
207-458-1011
KELLER WILLIAMS ISLAND LIFE REAL ESTATE

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*

A $10.825 Million Waterfront Sportsman’s Compound Sets a New Benchmark in Boca Grande