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GRANDE QUAY 02 - D6147970 - 16776 GRANDE QUAY DR, BOCA GRANDE, FL 33921 7 Days on yellowkey
$3,650,000 | Single Family Home | 3 beds | 2.5 baths | 3 gar
Experience exceptional waterfront living at 16776 Grande Quay Drive, Boca Grande, FL 33921, nestled within a quiet, gated waterfront community with 24-hour surveillance. Situated on the largest homesite in the community, this residence captures breathtaking 180-degree views of the Gasparilla Sound. With direct boating access to the Gulf, this elegant coastal residence blends luxury, comfort, and the ultimate island lifestyle. Designed with both everyday living and entertaining in mind, the home features soaring ceilings that fill the interior with natural light, an updated chef's kitchen showcasing quartz countertops and premium Bosch appliances. A cozy fireplace adds warmth and character to the spacious living area, while pre-wiring throughout the home provides a seamless foundation for a whole-home audio & video system. Recent improvements include a 2023 adobe tile roof, partial impact-rated windows, and hardiplank siding waiting for your choice of color (and association approval). A private elevator services all levels, and the home is outfitted with a fire suppression system and central vacuum. Outdoor living is equally impressive, featuring a spa pool, an outdoor kitchen, and spaces designed to capture the spectacular waterfront views. The oversized four car garage includes a mini-split air conditioning system, making it ideal for climate-controlled storage, hobbies, or a workshop. For boating enthusiasts, the property includes a deep water privately gated boat slip (Slip M) complete with a lift, providing effortless access to world-class fishing, cruising, and the pristine waters of Gasparilla Sound and the Gulf. This remarkable waterfront residence offers an exceptional combination of refined finishes, thoughtful updates, and unparalleled boating amenities in one of Boca Grande's most desirable waterfront communities.
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA
GOLDEN BEACH - D6147913 - 350 GASPARILLA ST, BOCA GRANDE, FL 33921 10 Days on yellowkey
$3,975,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Located just south of Boca Grande village in Golden Beach, this beautiful pool home offers the trifecta of coastal living; comfort, and privacy, all near the beach. Set on a large, landscaped lot with banana trees, coconut palms, and tropical plantings, the property provides a peaceful island setting. The main level features three bedrooms, three bathrooms, a spacious den, sunny kitchen, vaulted ceilings, warm wood floors, open decks and a large, screened porch. Taken to the studs and rebuilt in 2004 by McHugh Porter Builders, additional highlights include an elevator, impact-rated windows and doors, a whole-house water filtration system, new metal roof and generator. The first floor has an 800SF guest quarters, an ideal space for family and friends with a private entrance and walk out to the pool. Plenty of room for the toys with a two-car garage, carport, boat parking and air-conditioned tackle room/storage. This property is complete with a large, heated saltwater pool and spa surrounded by elegant stone decking and an open covered patio.
BG YACHT BASIN DAMFIWILL - D6147406 - 171 DAMFIWILL ST, BOCA GRANDE, FL 33921 51 Days on yellowkey
$3,700,000 | Single Family Home | 2 beds | 1.5 baths | 1 gar
“The Boat House” is a rare opportunity to own one of Boca Grande’s most compelling newly constructed deep-water boating properties, a refined waterfront retreat purpose-built for the avid sportfishing and boating lifestyle. Completed in 2024 by Yusk Construction and interiors masterfully curated by local designer, Sue Sligar, this custom residence delivers the increasingly rare combination of immediate Gulf access, new marine infrastructure, and elevated coastal luxury in an exceptionally efficient island footprint. Positioned along a protected deep-water canal with no fixed bridges to Charlotte Harbor or the Gulf, the property was designed for owners who prioritize quick access to open water, effortless dockage, and turnkey boating convenience. A newly constructed seawall and exceptional dock complex create a highly functional waterfront environment tailored to the serious fisherman and boating enthusiast alike. Features include a 24,000-pound Coastal Series boat lift, expansive ENDECK synthetic decking, aluminum-framed grated platform, illuminated fish-cleaning station, shore power, freshwater service, and direct deep-water access to the harbor and Gulf within minutes. Inside, the design aesthetic elevates the residence far beyond a traditional boating property. Refined coastal textures, nickel-gap shiplap walls and ceilings, designer wallpaper, curated lighting, brass stair railings, and bespoke cabinetry create interiors reminiscent of an elegant private yacht club...polished, timeless, and effortlessly luxurious. Andersen hurricane-impact windows and doors flood the home with natural light while delivering exceptional storm protection and peace of mind. The chef’s kitchen was designed for elevated entertaining after a day on the water, featuring quartz countertops, custom soft-close cabinetry, and a premium appliance suite including a Liebherr refrigerator/freezer and Bosch induction range, dishwasher, and microwave drawer. Offering two bedrooms, one full bath, and two half baths, the residence was intentionally designed to function as the ideal luxury boating retreat, guest residence, or private quarters for a captain or crew supporting a larger island estate. Elevated approximately 13’3” above base flood elevation, the structure incorporates superior construction standards including a concrete block base, advanced steel cross-frame reinforcement system, standing seam metal roof, Hardie siding and soffits, open-cell spray foam insulation, tankless electric water heater, and a 2024 HVAC system. The pull-through garage operates as a fully equipped marine utility space complete with epoxy floors, EV charging readiness, rod storage systems, additional refrigeration, full size washer and dryer, plumbing for an ice-maker, and extensive storage for fishing gear, water toys, and boating equipment. Technology and security are seamlessly integrated with an Alert 360 security system, Lutron lighting controls, multiple WiFi access points, security cameras, and SONOS surround sound anchored by an 85-inch Samsung television in the living room. For the discerning Boca Grande owner seeking state-of-the-art dockage, immediate deep-water Gulf access, and a turnkey luxury residence designed around the boating lifestyle, “The Boat House” represents an exceptionally rare island offering.
Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT
GOLDEN BEACH - D6147419 - 362 BAILY ST, BOCA GRANDE, FL 33921 59 Days on yellowkey
$2,495,000 | Single Family Home | 3 beds | 2.0 baths | 2 car
This Single-Family 3-bedroom, 2-bathroom single-family home delivers exceptional value just steps from the Gulf’s pristine beaches and unforgettable sunsets just south of the village. Situated on a spacious and secluded 100’ x 153’ lot, the property is surrounded by native landscaping, offering true privacy and tranquility. Features include a Chicago brick paver driveway, propane fireplace, dumbwaiter, and a screened lanai, ideal for relaxation and entertaining. Updates include a new A/C system (July 2025), and a newer Roof (2022), Impact Windows in (2011), making this home ready for immediate enjoyment with room to personalize and expand. Tour the island by golf cart, take peaceful walks, and enjoy nearby access to the Johann Fust Library, shops, and dining. Whether you're seeking a quiet retreat or future potential, this is one of Boca Grande’s best single-family values, private, charming, and full of opportunity.
Listing is courtesy of: BOCA GRANDE REAL ESTATE, INC.
SEAWATCH BOCA GRANDE - D6147259 - 40 SEAWATCH LAKE DR, BOCA GRANDE, FL 33921 69 Days on yellowkey
$4,750,000 | Single Family Home | 5 beds | 6.5 baths | 2 gar
A rare and remarkable opportunity in the exclusive Seawatch community of Boca Grande, this fully reimagined lakefront residence offers the space and feel of a custom estate with the ease of coastal living. Originally two villas, this home was masterfully combined and rebuilt from the studs in 2017, creating a seamless five-bedroom, five-and-a-half-bath retreat designed for both luxury and livability. From the moment you enter, expansive living spaces unfold with walls of glass—four sets of triple-panel sliders frame tranquil lake views and invite natural light to pour in. Wood-look tile flooring, crown molding, and plantation shutters elevate the interiors, while thoughtful details throughout reflect the quality of the renovation. The gourmet kitchen is a true showpiece, featuring Patagonia granite countertops, equipped with a Wolf range, wall oven, and microwave, a Sub-Zero cabinet-front refrigerator, wine refrigeration, a warming drawer, and an additional prep sink—perfectly suited for entertaining on any scale. A massive island anchors the space, complemented by abundant cabinetry and exceptional storage throughout the home. The primary suite is a private sanctuary, featuring dual spa-inspired bathrooms, an oversized walk-in closet, and two sets of four-panel sliders that open to peaceful water views. Each additional bedroom offers comfort and privacy, making the home ideal for hosting family and guests. Modern systems—including hurricane-impact windows and doors, tankless propane water heaters, and a full gutter system—provide peace of mind, while the outdoor spaces are designed for effortless enjoyment with a propane-ready patio and seamless indoor-outdoor flow. Seawatch is a prestigious waterfront enclave of just 49 residences, thoughtfully positioned between the Gulf of Mexico and Lake Gasparilla. Residents enjoy exclusive amenities including access to the pristine Gulf shoreline, two community pools, and two tennis courts. This rare setting delivers a true barrier-island lifestyle—minutes from the charming village of Boca Grande for boutique shopping, fine dining, and world-class fishing and shelling.
BETTON HILL ADD 12 - TB8502017 - 340 PALM AVE, BOCA GRANDE, FL 33921 73 Days on yellowkey
$3,295,000 | Single Family Home | 2 beds | 2.0 baths
Nestled in the heart of Boca Grande’s coveted “Historic District”, this enchanting two-bedroom, two-bathroom, plus bunkroom Palm Cottage built in 1906 has been thoughtfully reimagined with refined designer finishes and modern conveniences throughout. As you walk up to the property you are greeted by lush tropical landscaping, offering both privacy and vivacious natural beauty. Inside, the front sitting room and dining area is bathed in natural light, creating an inviting space equally suited for tranquil mornings or intimate gatherings with family and friends. At the center of the home, the living room and kitchen blend effortless comfort with understated sophistication. An open-concept design is enhanced by custom built-ins, a charming reading nook, and a generous central cooking island – ideal for entertaining. Overhead, a beautifully crafted tongue-and-groove stained wood ceiling adds warmth and architectural character. The primary suite serves as a serene retreat, complete with a spacious walk-in closet and a spa-inspired en-suite bath featuring a beautifully appointed shower. French doors open directly to the rear porch, inviting seamless indoor-outdoor living. The backyard presents a rare opportunity to curate your own private oasis, with ample space to envision a pool, pavilion, or thoughtfully designed entertaining terrace. This exceptional cottage captures the essence of Boca Grande living – timeless, relaxed, and effortlessly elegant. Both an addition and pool/spa have been professionally designed for the Property. The Cottage is Rental Ready and has excellent rental history! Schedule your private showing today and experience this Cozy Cottage firsthand.
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL
BOCA GRANDE ISLES - D6147162 - 1669 JOSE GASPAR DR, BOCA GRANDE, FL 33921 76 Days on yellowkey
$7,500,000 | Single Family Home | 5 beds | 6.5 baths | 2 gar
Under contract-accepting backup offers. Located in the Beautiful Boca Grande Isles, 1669 Jose Gaspar Drive is a striking example of Bermuda-style architecture, seamlessly blending timeless elegance with relaxed coastal living. Constructed of solid concrete with a durable concrete tile roof, the home features a classic stucco exterior and signature stepped rooflines—designed for both aesthetic appeal and resilience—capturing the essence of refined island design. Inside, light-filled interiors create an airy, sophisticated atmosphere. Expansive living spaces flow effortlessly, offering the perfect setting for both entertaining and everyday comfort. Thoughtful architectural details and curated finishes evoke understated luxury, while French doors and large windows and open layouts invite in natural light and gentle harbor breezes. Spanning approximately 4,500 square feet, the home features a gourmet kitchen complete with a sitting and casual dining area, along with a spacious great room anchored by a stunning shell stone fireplace—ideal for gatherings. The residence includes five bedrooms and six and a half baths, many with serene harbor views. An unfinished bonus room above the garage provides flexibility for a home office, studio, or additional bedroom. Outdoors, a beautifully elevated pool and patio create a private oasis, perfectly complementing the home’s stately presence within the Boca Grande Isles. Surrounded by lush tropical landscaping and some of the island’s finest fishing, the property offers a private retreat just moments from Boca Grande’s pristine beaches, charming village center, and scenic bike paths. This exceptional Bermuda-style residence embodies coastal sophistication and island luxury—an outstanding opportunity to experience the beauty and serenity of Boca Grande living.
SEAWATCH BOCA GRANDE - D6146794 - 12 SEAWATCH DR, BOCA GRANDE, FL 33921 100 Days on yellowkey
$3,250,000 | Single Family Home | 3 beds | 3.0 baths | 2 car
Peaceful and private, this spacious Gulf-view single-family home offers nearly 4,000 total square feet and an excellent opportunity to make this property your own. Featuring three bedrooms, three full baths, a versatile loft, charming cupola, and a convenient three-stop elevator, the layout provides both flexibility and functionality. Set just back from the direct beachfront, the home still enjoys a pleasant Gulf view along with added privacy. The large glass-enclosed porch and open sundeck create inviting spaces to relax, entertain, and take in the coastal setting. Located in the gated Seawatch community at the north end of Boca Grande, this property is just a short walk to the beach, known for the island’s best shelling. Community amenities include two heated pools, tennis courts, walking paths, and boardwalk access to the beach—ideal for enjoying the laid-back island lifestyle and beautiful sunsets.
HARBOR DRIVE WATERWAYS - D6146498 - 252 WATERWAYS AVE, BOCA GRANDE, FL 33921 124 Days on yellowkey
$5,250,000 Reduced | Single Family Home | 4 beds | 4.0 baths
Experience the Boca Grande lifestyle in this highly desirable ground floor residence nestled in the heart of the Village on deep protected water. This one of a kind home is located in an "X flood zone" and it experienced no water intrusion during the storms. As you step into this lovely 4 bedroom and 4 bath classic Boca Grande style home, you will appreciate the sun filled great room which includes a beautiful coral stone fireplace and French doors that open to a stone patio, and heated pool. The unique residence is designed around the lush outdoor space which includes a fenced yard, and a dock for your large vessel. You will appreciate the convenience of single story living both indoors and out. In addition to the impressive great room, this Florida Style plan boasts a kitchen with stone counters and breakfast nook, a large primary suite and bathroom and a fantastic executive office, which can also serve as a den, and finally 3 ensuite guest rooms. This distinctive home has a new standing seam roof, tankless hot water, and beautiful mature landscaping. Outdoor activities are endless, as you take advantage of day trips to neighboring islands, world class fishing, paddleboarding and kayaking, or you can choose to bike the length of the island on the “bike path”, or golf cart to the beach for a walk on the beach or swim in the Gulf of Mexico. Boca Grande is famous for so much more than its Tarpon. Retreat to an idyllic lifestyle, where bicycles and golf carts are the preferred mode of transport, and old Florida charm abounds, where no street lights, traffic or high rises exist. There is no place quite like it!
BOCA GRANDE ISLES - D6146322 - 1627 GASPAR DR S, BOCA GRANDE, FL 33921 129 Days on yellowkey
$5,300,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
Located in the gated community of Boca Grande Isles, this well-maintained, 3 bedroom, 3 bathroom, waterfront home is a boater’s dream with direct access to Charlotte Harbor and no bridges to the Gulf of Mexico. The 2,715 sq. ft. residence features an open floor plan with vaulted open-beam ceilings, hardwood floors, custom built-ins, plantation shutters, and impact sliding glass doors framing serene canal views and leading to a screened lanai. The remodeled kitchen is appointed with quartz counters, Sub-Zero refrigerator, Wolf gas range, ample workspace, and a dumbwaiter. The living and dining areas flow effortlessly to a 48’ x 10’ screened outdoor space overlooking the water. The spacious primary suite offers canal views, patio access, a generous walk-in closet with washer/dryer, and a renovated bath with quartz counters, dual sinks, soaking tub, and separate rain shower. Outdoors, enjoy a composite dock with a 16,000-lb boat lift, 110’ seawall, two-car garage, golf cart garage, paved circular driveway, and plenty of backyard space with room to add a pool. An air-conditioned storage/workout room offers added versatility. This exceptional canal-front property delivers premier island living and easy Gulf cruising from your own dock.
NORTH VILLAGE SUB - D6146184 - 160 SHEEPSHANK CT, BOCA GRANDE, FL 33921 136 Days on yellowkey
$3,875,000 | Single Family Home | 3 beds | 3.5 baths | 2 gar
Perfectly situated in Boca Bay’s coveted North Village, this fully reimagined residence at 160 Sheepshank Ct offers 3 bedrooms, 4 baths, and 2,663 square feet of beautifully curated living space. Remodeled from top to bottom, the villa features an expanded gourmet kitchen with custom cabinetry, quartz countertops, a Wolf gas range, Sub-Zero refrigeration complemented by two separate built-in Sub-Zero refrigerator drawers, a wine cooler, and a Miele dishwasher. Bathrooms have been updated with modern selections, and generous walk-in closets are found throughout the home. High-end interior finishes include custom hand-painted wall finishes by a nationally recognized artist, solid wood flooring, Level 5 smooth drywall, impact-rated windows and doors, motorized window shades, and zoned Sonos audio. Extensive structural and mechanical upgrades include a standing-seam metal roof, composite decking, spray-foam insulation, a second-floor laundry chute, tankless hot water, an alarm system, a 22kW whole-house generator supported by a 500-gallon buried propane tank, and two Level 2 electric car chargers in separate locations. The two-car garage is outfitted with epoxy flooring and a dedicated mini-split HVAC system, and custom cabinets. Covered golf cart parking is located beside the home. On the waterside, a 512 sq. ft. porch—including a 190 sq. ft. screened lanai—captures ideal southern exposure and long, tranquil water views, perfect for morning coffee or effortless entertaining. Off the upstairs primary suite, a second private porch provides an additional outdoor retreat. Enjoy Boca Bay’s exceptional amenities, including North Village tennis and pickleball, community docks, and neighborhood pools. The Boca Bay Beach Club and Pass Club—offering dining, a fitness center, and a Har-Tru tennis complex—are just minutes away, along with Gulf beaches and the shops, restaurants, and historic charm of Boca Grande Village. Move-in ready and masterfully finished, this North Village home is a standout opportunity within Boca Bay.
ACREAGE & UNREC - D6146286 - 2021 20TH ST W, BOCA GRANDE, FL 33921 136 Days on yellowkey
$7,500,000 Reduced | Single Family Home | 8 beds | 7.0 baths | 2 gar
Welcome to 2021 20th Street, Boca Grande, FL! A Family Compound close to the Village on a Private Street with deeded Beach access! Nestled on over half an acre on a Private street in the heart of Boca Grande, 2021 20th Street offers the perfect setting for family gatherings where memories are made. This one of a kind property boasts a large 5 bedroom main home and a charming 3 bedroom guest cottage. The tropical setting provides an ideal backdrop for family gatherings, vacations, and creating cherished moments for generations to come. The spacious main home features an open and airy floor plan with high ceilings, a European designed kitchen,large windows, and lots natural light, offering a seamless flow between indoor and outdoor living. Whether you’re hosting family dinners, relaxing by the pool, or gathering for sunset cocktails on the patio, the home's inviting atmosphere fosters connection and togetherness. Surrounded by tropical landscaping, the property ensures privacy while offering plenty of room for outdoor activities and relaxation. For guests or extended family, the delightful 3-bedroom guest cottage provides a perfect retreat with its own kitchen, living area, and comfortable, coastal-inspired design. This separate dwelling allows for privacy and comfort, while keeping everyone close together on the same property. The cottage is also perfect for use as a rental for those owners desiring income to offset the expenses of Island home ownership. One of the standout features of this compound is its deeded beach access, granting direct entry to Boca Grande's beaches. Imagine waking up to the sound of waves, walking down to the beach with loved ones, or enjoying a sunset stroll along the shore—this property gives you the luxury of beach living just steps from your door. The expansive lot provides ample space for family activities, outdoor games, or simply enjoying the tropical surroundings. Whether you're hosting a holiday gathering, a summer barbecue, or a quiet evening with family, this home is designed for lasting memories. With its prime location in Boca Grande, this property offers the perfect balance of seclusion and convenience, just a short distance from the island's charming shops, restaurants, community center, and bike path.
SEABREEZE - D6146199 - 281 SEABREEZE CT, BOCA GRANDE, FL 33921 142 Days on yellowkey
$2,400,000 | Single Family Home | 3 beds | 2.0 baths | 1 gar
REDUCED PRICE - Welcome to your private tropical retreat offering relaxed coastal living just minutes from convenient beach access. This residence captures the charm and style of Boca Grande without the premium price. Surrounded by lush palms and mature landscaping, the home features expansive outdoor living areas designed for year-round enjoyment. An oversized upper deck provides a serene setting for entertaining or unwinding, while the beautifully paved lower-level pool and spa area creates an additional private gathering space. Multiple outdoor options make this home ideal for hosting and embracing the Florida lifestyle. Inside, natural light fills the thoughtfully designed interior. Warm wood floors upstairs add character and comfort. The bathrooms have been tastefully updated with spa-inspired finishes, including frameless glass showers, stone accents, and a freestanding soaking tub. A spacious laundry area with cabinetry adds everyday convenience. This home appeals to buyers seeking the charm and style of Boca Grande without the premium price — offering comfort, flexibility, and exceptional outdoor living in a highly desirable location near the beach.
Listing is courtesy of: PARSLEY BALDWIN REAL ESTATE
HARBOR DRIVE WATERWAYS - D6146117 - 204 WATERWAYS AVE, BOCA GRANDE, FL 33921 146 Days on yellowkey
$6,450,000 | Single Family Home | 4 beds | 3.5 baths | 1 car
Elegantly remodeled and ideally located, this waterfront retreat in Boca Grande offers 127 feet of private canal frontage with dockage and boat lift—perfect for boaters seeking easy Gulf access. Situated on a quiet cul-de-sac, the home is just a short walk or golf cart ride from the village’s shops, restaurants, and beaches. Inside, you'll find elevated finishes, open living spaces, and private guest accommodations, offering both comfort and flexibility. This rare in-town offering combines effortless island living with premium dockage—an exceptional opportunity in one of Boca Grande’s most sought-after neighborhoods. 4 bedrooms/ 3.5 bath.
BOCA GRANDE - D6146072 - 260 GILCHRIST AVE, BOCA GRANDE, FL 33921 146 Days on yellowkey
$4,950,000 Reduced | Single Family Home | 7 beds | 4.0 baths
Offered for the first time since 1962, 260 Gilchrist Avenue presents a rare opportunity to acquire a true Boca Grande legacy estate, defined by provenance, architectural presence, and the enduring romance of Old Florida. Built in 1925 and thoughtfully stewarded for generations, this storied residence reflects a time when homes were crafted with intention, scale, and permanence. Sited on an exceptional 100' x 150' in-town parcel, the property is ideally positioned in downtown Boca Grande, just moments from the Village, beaches, dining, and boutiques, yet remarkably private, with a sense of prominence befitting its lineage. The home spans over 3,900 square feet under air, offering seven bedrooms and four bathrooms, with gracious proportions designed for multigenerational living and extended coastal stays. Vaulted ceilings lend volume and elegance, while two original fireplaces anchor the interiors with warmth and authenticity. Original wood floors remain intact, and the home’s cypress walls speak to the craftsmanship and character of an earlier era. A newly completed kitchen introduces a refined modern counterpoint, thoughtfully executed to meet today’s standards for daily living and entertaining while remaining respectful of the home’s historic architectural character. Recent improvements include new HVAC, electrical, and plumbing systems, delivering modern reliability while preserving the home’s timeless soul. A driveway permit is already in place, and the estate is accompanied by a current certified survey. A dedicated local historic specialist has also been engaged to outline the full architectural potential of this exceptional property. Rarely does a Gilchrist Avenue residence of this scale, significance, and authenticity come to market. 260 Gilchrist Avenue is a once-in-a-generation offering rich in history, exceptional in presence, and ideally positioned for thoughtful restoration or inspired reimagination. A true Boca Grande heritage estate, ready for its next distinguished chapter.
EAST SHORE ACRES - TB8474700 - 16 GROUPER HOLE DR, BOCA GRANDE, FL 33921 149 Days on yellowkey
$5,995,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Private custom designed home with deepwater protected dockage on a lot and a half (150’) — situated directly across from the Boca Grande Club! This exquisite 3-bedroom, 3-bathroom BIG VIEW waterfront Estate Property is a 1996 National award winning architectural design, set within a lush tropical oasis with rich verdant greenery and mature native landscaping. Incredible and expansive views front Gasparilla Sound and the ICW, additionally with multiple decks facing East and West with over 4,000 sq. ft. under roof! The main level features an open-concept layout ideal for effortless entertaining, seamlessly connecting the kitchen, dining, and living areas, boasting soaring ceilings and abundant natural light throughout - all Andersen doors and windows. Enjoy a true indoor-outdoor lifestyle with panoramic coastal vistas and a fluid transition to the very cozy screened-in lanai over the pool – perfect for relaxing or hosting while taking in the serene surroundings. The gourmet kitchen is a chef’s haven featuring granite countertops & center-island with abundant prep space, a DCS professional 6 burner duel-fuel range / double oven, oversized paneled Sub Zero refrigerator and freezer designed to blend seamlessly with custom cabinetry, plus a breakfast nook/coffee bar and pantry… The dedicated Master level provides a serene private retreat showcasing exceptional 240° views with hers and his walk-in closets. Embrace the height of comfort and relaxation with a spacious ensuite bath with spa-like soaking tub and separate shower, and two private decks for taking in year-round breathtaking sunrises, moonrises, and sunsets. On the ground level, step outside to an expansive pool deck with plenty of space for outdoor entertainment with a very large waterfront pool and separate covered spa. Just steps away to your (cool-to-the-feet) shellstone tile deck out to your own private deep-water dockage complete with three boat lifts (13,000, 7,000, and 7,000 lbs) – a dream for avid boaters and fishermen alike. Two car plus golf cart garage with lots of storage, a wine cellar, and excellent Bonus space! This is the very best comfortable Island Living in this nearly 1 acre waterfront estate at the very best pricing! Come see why…?
EAST SHORE ACRES - D6145898 - 5020 GROUPER HOLE CT, BOCA GRANDE, FL 33921 155 Days on yellowkey
$4,675,000 | Single Family Home | 3 beds | 3.5 baths | 4 gar
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.
BOCA GRANDE - D6145442 - 1660 16TH ST E, BOCA GRANDE, FL 33921 183 Days on yellowkey
$6,500,000 | Single Family Home | 4 beds | 4.5 baths
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.
BOCA GRANDE - D6145439 - 760 E RAILROAD AVE, BOCA GRANDE, FL 33921 184 Days on yellowkey
$5,450,000 | Single Family Home | 3 beds | 4.5 baths | 2 gar
Nestled in the heart of Boca Grande's charming historic district, just steps from downtown amenities, this impeccable custom-built home offers the epitome of luxury island living. Constructed in 2012, architecture by T.A. Krebs with unparalleled craftsmanship and attention to detail, this move-in-ready home exudes timeless elegance and modern sophistication. Upon entering, you are immediately captivated by the soaring 24-foot cupola and exquisite 6-inch tongue-and-groove board ceilings, setting a grand tone for the open and inviting interior. The home features three spacious bedrooms and four and a half well-appointed bathrooms, providing ample space for family and guests. Cozy up by one of two stunning brick fireplaces—one gracing the living room and the other in the serene primary bedroom. Throughout, luxurious travertine and wood flooring flows seamlessly, complemented by granite countertops in the gourmet kitchen. Equipped with top-of-the-line Wolf and sub-zero appliances, a convenient garden sink, gas stove, gas oven, and generous pantry, this kitchen is a chef's dream. French doors seamlessly connect the interior to the outdoor oasis: a brick-paved patio overlooking a heated pool and spa and a dedicated pool bathroom for ultimate convenience. Additional highlights include a large upper-level bonus room ideal for extra sleeping or living area or relaxation, durable Hardy board siding, all impact-resistant glass windows and doors for peace of mind, a 2+ car garage, and lush, mature landscaping that envelops the property in privacy and natural beauty. Truly a rare gem in the heart of Boca Grande, this exceptional home blends historic charm with contemporary luxury—ready for you to call it your own.
EAST SHORE ACRES - D6145351 - 5010 GROUPER HOLE CT, BOCA GRANDE, FL 33921 184 Days on yellowkey
$3,975,000 Reduced | Single Family Home | 4 beds | 2.5 baths | 4 gar
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.
HARBOR DRIVE WATERWAYS - D6145389 - 161 1ST ST E, BOCA GRANDE, FL 33921 185 Days on yellowkey
$4,995,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Discover this beautifully renovated cottage nestled in the Historic Village of Boca Grande, where old-world charm meets modern convenience. This 4-bedroom, 3-bathroom home spans 2,548 square feet and showcases thoughtful upgrades throughout, including a durable metal roof, Hardie plank siding, improved kitchens and bathrooms, and stunning wide plank wood flooring. The heart of the home features an open living area with custom wood ceilings, a cozy gas fireplace, a charming cupola that fills the space with natural light and flows to a large 335 sqft screened porch looking over the canal for true indoor-outdoor living. The primary bedroom and additional bedrooms provide comfortable accommodations, while an in-law suite with kitchenette on the lower level offers flexible living options. You will enjoy the lower-level outdoor living space from the shade of a covered porch or sunbathe around the custom in-ground heated pool and hot tub that create the perfect setting for relaxation. Your waterfront lifestyle includes an impressive 80-foot dock with a covered 20,000-pound boat lift on the Harbor Drive Waterways canal just steps from your back door. Practical amenities abound with dual garages equipped with electric vehicle charging stations, a golf cart charging station, and a convenient laundry room. The circular driveway features classic Chicago brick pavers, while mature landscaping and fencing complete the picturesque setting. Location is everything here – in minutes you can hop on your boat and be cruising Charlotte Harbor; or enjoy a short golf cart ride to the pristine Gulf beaches, charming shops and restaurants of Historic Boca Grande. The renowned Gasparilla Inn, exceptional golf courses, local marinas, and even Coral Creek private airport are all nearby, making this the perfect blend of peaceful retreat and convenient access to island attractions.
BOCA GRANDE ISLES - D6145104 - 1600 JEAN LAFITTE DR, BOCA GRANDE, FL 33921 205 Days on yellowkey
$8,500,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
Under contract-accepting backup offers. Welcome to waterfront living at its finest in the exclusive gated community of Boca Grande Isles on Gasparilla Island. This stunning five-bedroom, five and one half-bathroom home sits on an impressive tip lot with 170 feet of deepwater frontage, offering expansive dockage with direct access to Charlotte Harbor and the Gulf with no bridges to navigate. The southern exposure has breathtaking sunrise and sunset views from every room of Charlotte Harbor and the Gasparilla Inn Golf Course. Built with concrete construction for superior storm protection and impact glass windows and sliding doors throughout, this elevated 4,799 square foot home features an elevator and places the primary bedroom conveniently on the main living floor. The spacious primary suite includes a large bedroom with expansive water views, an office or workout room, and a spacious bathroom with dual vanities, dual closets, and dual water closets. The gourmet kitchen will make any chef smile with high-end appliances including a Subzero refrigerator, double ovens, induction cooktop, and ice maker. Granite countertops, an island, and breakfast bar complete this culinary paradise. Hardwood flooring flows throughout the home, while walls of glass in the living room and sunroom showcase those incredible water views. The large family room is the perfect spot to gather or entertain with multiple seating areas and a gas fireplace. Your family and guests will appreciate the four ensuite guest rooms that share a cozy television room to ensure everyone has privacy and room to spread out. The spectacular outdoor living space at this home is where you will want to spend your time. There is a large, heated pool surrounded by multiple expansive patios and porches, palm trees and grassy areas, and a 50’ deep water dock with lift. Spend your days sunning by the pool or exploring the blue coastal waters. An oversized two-car garage plus additional golf cart storage keeps your vehicles protected. Located in secure Boca Grande Isles with guard-gated access, you're just a short golf cart ride from the beautiful beaches of the Gulf or the charming shops and restaurants in Historic Boca Grande. The nearby Gasparilla Inn, Coral Creek private airport, multiple exceptional private and public golf courses, and local marinas all add to the island's appeal. This is coastal living done right.