14 Grouper Hole Dr

Boca Grande, FL 33921

$10,825,000
Price
5
Beds
6,207 Sq. Ft.
$1,744 / Sq. Ft.
6,207
Sq. Ft.
$1,744
per Sq. Ft.
Open: 2/28 01:00PM - 04:00PM
Open: 2/28 01:00PM - 04:00PM

Description

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. 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...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. 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. The sports pavilion also includes a private, air-conditioned Pilates studio and areas for ping pong and billiards. 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.
  1. Listed by Michelle Hupp • Brokerage DRE #1049894 • KELLER WILLIAMS ISLAND LIFE REAL ESTATE
    P: (941)-773-5464 C: (941)-773-5464 michellehupp@thehuppgroup.com
  2. Listed by Lisa Naum • Brokerage DRE #1049894 • KELLER WILLIAMS ISLAND LIFE REAL ESTATE
    P: (207)-458-1011 C: (207)-458-1011 lisanaum@thehuppgroup.com

Property Details for 14 Grouper Hole Drive

Architectural Style
Elevated, Florida
Subdivision Name
EAST SHORE ACRES
Garage Spaces
4
View
Water
Waterfront
Yes
Water View
Bay/Harbor - Full
Furnished
Unfurnished

Open Houses

Saturday, Feb 28th

1:00 PM - 4:00 PM

Public

LISTING UPDATED: 02/17/2026 04:22 PM

Property Details for 14 Grouper Hole Drive

StatusActive
MLS #N6141937
Days on Market65
Taxes$57,022 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1997
Lot Size0.98 AC / 42,662 SF
CountyCharlotte County

Location

Listing Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE, Michelle Hupp; KELLER WILLIAMS ISLAND LIFE REAL ESTATE, Lisa Naum
Add your commute

Building Information for 14 Grouper Hole Drive

Stories3Year Built1997Building Size-Lot Size0.98 AC / 42,662 SF

Payment Calculator

$57,511 per month

30 year fixed, 6.15% Interest

Principal and Interest

$52,759

Property Taxes

$4,752

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 14 Grouper Hole Drive

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 18294.0
  • Building Area Units: Square Feet
  • Direction Faces: West
  • Directions: Take the Boca Grande Causeway. Turn left on Grouper Hold Drive. House will be on your right.
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • SW Subdiv Community Name: Not Applicable
  • Unit Number: No
  • Street Number: 14
  • Street Name: GROUPER HOLE
  • Street Suffix: DRIVE
  • State: FL
  • City: BOCA GRANDE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Circular Driveway, Tandem
Taxes and HOA Information
  • Association: No
  • CDD: No
  • Tax Legal Description: ESA 000 0000 0014 EAST SHORE ACRES LT 14 0.70 AC. & A TRACT OF SUBMERGED LAND COM AT NE COR LT 14 TH E ALG N LINE OF LT 14 141 FT TH S 100 FT TH W TO SE COR LT 14 TH N 100 FT TO POB AKA P-14A 929/421 968-1293 1114/1801&02 1357/878&79 3264/1569 3264/1 571 ESA 000 0000
  • Tax Lot: 14
  • Tax Year: 2024
Property
Lot Information
  • Additional Parcels Description: 422035400005
  • Additional Parcels: Yes
  • Lot Features: FloodZone, In County, Landscaped, Oversized Lot
  • Parcel Number: 422035303001
  • Total Acreage: 1/2 to less than 1
  • Water Access: Bay/Harbor, Intracoastal Waterway
  • Water Access: Yes
  • Water Body Name: GASPARILLA SOUND; GULF
  • Water Extras: Bridges - No Fixed Bridges, Minimum Wake Zone, No Wake Zone, Sailboat Water
  • Water Extras: Yes
  • Water: Bridges - No Fixed Bridges, Minimum Wake Zone, No Wake Zone, Sailboat Water
  • Living Area: 6207
Property and Assessments
  • Year Built Numeric: 1997
  • Building Elevator: Yes
  • Flood Zone Code: AE
  • Home Warranty: No
  • Homestead: Yes
  • New Construction: No
  • Dock YN: Yes
  • Dock Description: Dock - Composite, Dock w/Electric, Dock w/Water Supply, Lift, Other
  • Dock Lift Capacity: 7000
  • Dock Dimensions: N/A
Utilities
  • Sewer: Public Sewer
  • Utilities: Electricity Connected, Public, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Concrete, Wood Frame
  • Exterior Features: Balcony, Hurricane Shutters, Other, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
  • Foundation Details: Stem Wall
  • Levels: Three Or More
  • Other Structures: Outdoor Kitchen
  • Pool Features: Chlorine Free, Heated, Indoor, Lap, Lighting, Other, Outside Bath Access, Screen Enclosure
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Metal
  • Vegetation: Mature Landscaping
  • Waterfront Features: Bay/Harbor, Intracoastal Waterway
  • Waterfront Feet Total: 300
  • Number Of Stories: 3
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 5
  • Additional Rooms: Breakfast Room Separate, Great Room, Inside Utility, Storage Rooms
  • Appliances: Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace: No
  • Flooring: Luxury Vinyl, Tile, Travertine
  • Heating: Central, Electric
  • Interior Features: Eating Space In Kitchen, Elevator, High Ceilings, Open Floorplan, Other, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Owner
  • Living Area Units: Square Feet
  • Room Count: 10.0
  • Water View: Yes
  • Window Features: Storm Window(s)
  • Bathrooms Half: 1
Rental
Rental Information
  • Pets Allowed: Yes

Property History for 14 Grouper Hole Drive

DateEvent & SourcePriceAppreciation
Dec 19, 2025

Listed (Active)

MFRMLS #N6141937

$10,825,000—
Aug 8, 2025

Expired

FORTMLS #225022842

$10,825,000—
Aug 8, 2025

Expired

MFRMLS #N6137497

$10,825,000—
Mar 19, 2025

Listed (Active)

FORTMLS #225022842

$10,825,000—
Feb 28, 2025

Listed (Active)

MFRMLS #N6137497

$10,825,000—
Jun 15, 2024

Expired

MFRMLS #D6133828

$12,250,000—
Dec 22, 2023

Listed (Active)

MFRMLS #D6133828

$12,250,000—
Jul 15, 2022

Expired

MFRMLS #D6119329

$13,450,000—
Jun 8, 2021

Listed (Active)

MFRMLS #D6119329

$13,450,000—
Mar 2, 2008

Sold

MFRMLS #D513479

—
Mar 2, 2008

Pending

MFRMLS #D513479

—
Feb 29, 2008

Sold (Public Record)

Public Record #233618909

$3,900,000—
Feb 29, 2008

Sold

MFRMLS #D513479

$4,000,000—
Aug 21, 2006

Expired

MFRMLS #C635141

$4,295,000—
Mar 31, 2006

Listed (Active)

MFRMLS #C635141

$4,295,000—
Mar 31, 2006

Listed (Active)

MFRMLS #D513479

$4,295,000—
DateEvent & SourcePrice
12/19/2025

Listed (Active)

MFRMLS #N6141937

$10,825,000
08/08/2025

Expired

FORTMLS #225022842

$10,825,000
08/08/2025

Expired

MFRMLS #N6137497

$10,825,000
03/19/2025

Listed (Active)

FORTMLS #225022842

$10,825,000
02/28/2025

Listed (Active)

MFRMLS #N6137497

$10,825,000
06/15/2024

Expired

MFRMLS #D6133828

$12,250,000
12/22/2023

Listed (Active)

MFRMLS #D6133828

$12,250,000
07/15/2022

Expired

MFRMLS #D6119329

$13,450,000
06/08/2021

Listed (Active)

MFRMLS #D6119329

$13,450,000
03/02/2008

Sold

MFRMLS #D513479

—
03/02/2008

Pending

MFRMLS #D513479

—
02/29/2008

Sold (Public Record)

Public Record #233618909

$3,900,000
02/29/2008

Sold

MFRMLS #D513479

$4,000,000
08/21/2006

Expired

MFRMLS #C635141

$4,295,000
03/31/2006

Listed (Active)

MFRMLS #C635141

$4,295,000
03/31/2006

Listed (Active)

MFRMLS #D513479

$4,295,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 14 Grouper Hole Drive

Taxable ValueLand-Additions-Total-
Tax Record2025$57,686 ($4,807 / month)
Home Facts
Beds4Total Finished SqFt4,494 SqFtAbove Grade Finished SqFt4,494 SqFtStories1Lot Size36,023 SqFtStyleSingle Family ResidenceYear Built1997ZoningRSF3.5CountyCHARLOTTEAPN42-20-35-303-001

Schools near 14 Grouper Hole Drive

This home is within Charlotte.
Rating
School
Type
Grades
Distance
Myakka River Elementary School
Public - PK to 5
The Academy
Public - 6 to 12
Charlotte Technical Center
Public - 9 to 12
Charlotte Virtual Instruction Program
Public - K to 12
Rating
School
Distance
Myakka River Elementary School
PublicPK to 5

The Academy
Public6 to 12

Charlotte Technical Center
Public9 to 12

Charlotte Virtual Instruction Program
PublicK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 14 Grouper Hole Drive, Boca Grande, FL 33921

14 Grouper Hole Drive is a single family home for sale in Boca Grande, FL 33921. This property was listed for sale on December 19, 2025 by KELLER WILLIAMS ISLAND LIFE REAL ESTATE, it's currently listed at $10,825,000. It has been on the market for a total of 65 days and was last sold on March 3, 2008. This listing's school district is Charlotte. Nearby schools include Myakka River Elementary School, The Academy and Charlotte Technical Center. 14 Grouper Hole Drive is a 5-bed, 6-bath, 6,207 sqft single family home built in 1997.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE, Michelle Hupp; KELLER WILLIAMS ISLAND LIFE REAL ESTATE, Lisa Naum

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.