Remarks: 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.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Jeff Moore (941-855-0737)

Remarks: Under Construction. Completion Estimated Mid-January 2027. Experience the best of Boca Grande luxury living in this stunning new construction waterfront home, currently under construction and designed to capture breathtaking views of Charlotte Harbor. Thoughtfully elevated and built to the latest storm and hurricane codes, this residence combines timeless coastal style with modern, high-end construction—including impact-rated windows and doors throughout. The spacious floor plan offers 4 bedrooms plus a den, 4 full bathrooms, and 2 half baths, ideal for hosting family and guests while maintaining privacy and comfort. At the heart of the home, a custom-designed gourmet kitchen will feature top-of-the-line appliances, premium cabinetry, and designer finishes, perfectly suited for everything from casual island breakfasts to elevated entertaining. Open-concept living spaces flow seamlessly to expansive outdoor areas, where an elevated pool and spa combo, fire pit, and generous entertaining space create the perfect setting for evening gatherings overlooking the harbor. Boaters will appreciate the private dock with boat lift, providing direct access to world-class fishing and boating right from your backyard. Every detail is being carefully curated to reflect relaxed coastal elegance—where barefoot luxury meets refined craftsmanship. Whether you’re enjoying morning coffee with panoramic sunrise views or evenings by the fire as boats drift by, this home is designed for the ultimate island lifestyle. Secure your place in one of Boca Grande’s most desirable waterfront settings and watch your dream home come to life.

Listing is courtesy of: PARSLEY BALDWIN REAL ESTATE (941-964-2700)

Listing Agent: Olivia Jones (941-456-1281)

Remarks: Welcome to one of Boca Bay’s most extraordinary residences—an architecturally stunning home in the exclusive, gated enclave of Grande Bay. Designed by acclaimed Sarasota firm, Seibert Architects, to capture the expansive views of Charlotte Harbor and the natural environment, it is perfectly positioned on the neighborhood’s most private homesite - the only site without a neighboring home to the North, being directly bordered by Boca Bay preservation land. Spanning 4,982 square feet, this one-of-a-kind residence is a masterclass in light, space, and elegance. Towering ceiling volumes on the main level create a grand, airy ambiance, while floor-to-ceiling windows along the entire North side frame uninterrupted vistas of Charlotte Harbor and Boca Grande’s bayside coastline. Internal spaces are organized around the central volume flowing freely from area to area. Nearly every room enjoys a water view, and the top living level offers a rare, sweeping panorama that stretches from the radiant sunrises of Charlotte Harbor to breathtaking sunsets over the Gulf to the west. French doors along the waterfront façade blur the boundary between indoors and out, drawing in the beauty of the harbor at every turn. A private deep-water dock extends into the harbor, offering an exceptional vantage point to take in wide-open bay views and direct access to boating, fishing, and waterborne adventures right from your backyard. The reimagined chef’s kitchen is both functional and sophisticated, outfitted with Sub-Zero refrigeration, Wolf double ovens, a Viking induction cooktop, and a custom-designed coffee bar, all set against bespoke cabinetry and refined finishes. Every detail reflects craftsmanship and intention: level 5 smooth-finish walls, impact-rated windows and doors, a Control4 whole-home automation system with integrated LED scene lighting, a private elevator servicing all three levels, and hurricane-rated roll-down Magnatrack screens. A powerful whole home Kohler generator ensures uninterrupted comfort and security. As part of Boca Bay, residents enjoy access to resort-style amenities including four pools, the newly renovated Pass Club, a private beach club, a bayside fishing pier, a fitness center, Har-Tru tennis courts, pickleball courts, and a vibrant social calendar. Impeccably maintained and thoughtfully updated throughout, this exceptional Grande Bay estate is a rare offering—an exquisite blend of privacy, design, and waterfront splendor in one of Boca Grande’s most coveted communities.

Listing is courtesy of: BOCA GRANDE REAL ESTATE, INC. (941-964-0338)

Listing Agent: Randy Wojcik (941-204-0015)

Remarks: 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.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Maryjo Pigott (941-961-0630)

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 is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)

Listing Agent: Carol Stewart (941-276-1162)

Remarks: Truly a one-of-a-kind location rarely presented on exclusive Shore Lane will now be offered for purchase! Located just one estate off the Historic District and the closest in proximity to the downtown Village of Boca Grande, this prominent beachfront treasure will surely take your breath away. Built in 2016 with the owner’s vison for entertaining family and guests while creating a secluded tropical oasis unique to anything else on Gasparilla Island. This influenced Caribbean architectural gem encompasses a majestic courtyard offering the ultimate blend of solitude and spa like atmosphere. The 5-star resort style split plan lives exceptionally featuring a VIP beachside ensuite with three additional ensuite guest quarters connected by a charming covered breezeway lined with Bahama shutters and Brazilian Ipe wood hallways. Designed specifically to capture the azure seascape and green flash sunsets from nearly every room, this luxurious interior layout features an exquisite common living area with wood cladded vaulted ceilings, massive fixed-glass impact windows and doors, and a stunning dual faced coral stone handmade fireplace that commands your attention. The chef’s kitchen exudes elegance and is complimented by white oak wood cabinetry, a chic mosaic tiled mural backsplash, and a marble prep galley with cooking island & breakfast bar all being serviced by Wolf and Sub-Zero appliances. Enjoy the comfortable family and dining room concept with convenient access to the enclosed lanai operated with electric screens or relax on the open veranda with a cocktail secured by reinforced modern glass railings. The VIP master Gulfside wing features an integrated media room accompanied by a lovely terrace overlooking the courtyard pool in addition to a private covered sea watch lanai awarding the best views imaginable. Escape to the lush VIP bath enclave offering custom double wood and marble vanities, a beautiful free standing tub, and the showcase walk in marble laid shower with rain head controls. The guest wing quarters are just as impressive highlighted by a discrete office, and a unique bonus room that could serve as the 5th bedroom if needed. All the guest ensuites are complimented with white oak wood flooring, subway tiled showers, stone countertops, and each having its own personal Juliet balcony positioned prominently over the courtyard garden. Exterior storage is fantastic with over 4,000 square feet of space on lower level for all the beach toys and fishing equipment, and not to mention the additional 2 car detached twin bay garages for vehicles with convenient access to elevator. Whether spending the day basking in the sun next to the lap pool in your private courtyard or taking a swim in the warm cerulean waters of the Gulf of Mexico, this once in a lifetime setting will create a legacy retreat for family & guests that will be enjoyed for many generations to come.

Listing is courtesy of: BOCA GRANDE REAL ESTATE, INC. (941-964-0338)

Listing Agent: Heath Seckel (863-207-2586)

Remarks: Nestled on a rare 1.6-acre waterfront parcel with views of Gasparilla Sound is a coastal masterpiece that has just undergone a complete, top-to-bottom remodel by PCI, embracing a serene coastal theme with light, airy colors throughout. Conveniently located on Loomis Avenue, just moments from the charming shops, restaurants, and amenities of historic downtown Boca Grande, this exquisite estate offers tranquility with sweeping breathtaking unobstructed water views. Boasting an impressive 159 feet of prime waterfront, the property features 4 spacious bedrooms, a versatile flex den room, 4.5 luxurious baths, and multiple inviting living areas designed for seamless flow and relaxation. The chef’s dream kitchen is outfitted with premium Wolf brand appliances, perfect for culinary enthusiasts. Convenience abounds with laundry facilities on both the lower and top floors. Step outside to one of the largest pools on Boca Grande, ideal for lavish gatherings, complemented by a grand main-floor patio area and a private master suite balcony on the top floor—both perfect for entertaining guests in style. The estate includes a massive 5-6 car garage with convenient side-entry doors, ample parking via an elegant circle drive, hurricane-rated windows and doors for peace of mind, and a private elevator for effortless access between levels. An open floor plan enhances the home’s light-filled ambiance, while mature, lush landscaping envelops the grounds in tropical serenity. This is more than a home—it’s a slice of paradise, where luxury meets the laid-back charm of island living, all just a short stroll or bike ride from town.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Jeff Moore (941-855-0737)

Remarks: Welcome to your island paradise on Boca Grande Isles. With 100 feet of waterfront and direct access to the Intracoastal Waterway, this stunning modern take on West Indies architecture residence has been completely renovated and offers an island sanctuary. Key features to this four bedroom, five and one-half bath residence spans 4,900+ square feet of meticulously updated living with unparalleled sophistication. The spectacular great-room is a masterpiece, boasting a wood beam ceiling, porcelain tile and wood flooring, crown molding with intricate detailing, built-in bar area with wine cooler, a decorative fire-place, and an expansive wall of glass overlooking Gasparilla sound offering an abundance of natural light. This cozy serene space connects by a wall of expansive sliding glass doors to an open-air porch with breathtaking water views. This home is crafted with the finest materials and finishes, seamlessly blending modern elegance with durability. The open-concept kitchen and breakfast area create a versatile floor plan perfect for daily living. The gourmet kitchen features quartz countertops, soft-close cabinets and drawers, Bosch appliances, 6-burner gas range located on the center island, and a Sub-Zero cabinet-faced refrigerator. The expansive primary suite, on the main living level, serves as a luxurious escape, featuring a sprawling walk-in closet and a spa-like bathroom with high-end finishes, dual vanities, a soaking tub, and an oversized shower. The upper level offers three additional bedrooms, each offering its own unique charm and character. Outside, embraces the epitome of island living. Beautiful mature landscaping, a two-car garage, a captivating pool, and a cozy fire pit create an idyllic haven for relaxation under starlit skies. With deep sailboat water access, and a 16k lb boat lift, nest in this beautiful island waterside home.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Jeff Moore (941-855-0737)

Remarks: Brand New Construction Now Complete***Quite possibly the most unique waterfront location ever offered for sale in Southwest Florida! Sunrises and Sunsets will be enjoyed here in the winter months together with 180 degrees of Gulf to Bay cerulean waterscape, pristine beaches, nostalgic lighthouse view, and the Historic Boca Grande Pass – AKA ‘The Tarpon Capital of the World’! This exquisite BCB Homes custom built estate offers 8,100 square feet of living space and nearly 3,000 square feet of additional outdoor & garage accommodations. The generous floor plan headlines two magnificent Master / VIP mega suites which is a must see even for the most selective Buyer along with three additional luxurious bedroom ensuites, and a bonus room with full bath that could serve as the sixth guest quarters. In addition, the home showcases a waterfront club room for entertaining, an elegant dining room with decorative ceiling details, and the captivating Sea Watch lounge on second level overlooking the heart of Boca Grande Pass. The well appointed kitchen and family room combination will certainly be a popular gathering place offering panoramic water views and convenient access to the outdoor lanai, pool / spa, and waterfront garden. There is also a spacious den conveniently located off the main entry with a picturesque window overlooking the front garden. The interior finishes were thoughtfully selected by owner to ensure the highest of quality. Ruffino custom Maple cabinetry will be presented in nearly every room together with walnut engineered flooring, meticulously hand crafted cypress and poplar wood finished 12 foot + ceilings, Pompeii quartz & quartzite countertops, and hand laid Walker Zanger tile & stone flooring. Other interior selections will include Sub Zero & Wolf appliances, Lutron lighting control / audio surround, and a custom elevator cabin servicing all floors. The outdoor space is exceptional offering 184 feet of water fronting beachscape and direct access to the inclusive East Beach and Pier. Enjoy entertaining and cooking out in your well equipped outdoor kitchen poolside with convenient remote control shutters and bug screens for added protection against all elements. Exterior construction is just as impressive with storm security being the focal point. The all concrete block structure is fortified with Anderson 400 hurricane rated windows and doors together with a hand etched concrete stucco finish for superior strength and durability. Other exterior construction upgrades include remote hurricane rated shutters, Englert standing seam metal roof, and Clopay hurricane rated garage doors. Multiple outdoor terraces will enhance the exterior profile combined with custom decorative shutters, and the prominent Cupola representing the Architects vision of elegance. All current selections and finishes will be available upon serious inquiries. Hill Tide Estates is majestically positioned along the shores of Boca Grande Pass, Charlotte Harbor, and the Gulf of Mexico. The Gated Community features a private tiered beach, and a unique private fishing / observation pier exclusive for the 19 homeowners.***The photos containing furniture have been virtually staged for visual demonstration.

Listing is courtesy of: BOCA GRANDE REAL ESTATE, INC. (941-964-0338)

Listing Agent: Heath Seckel (863-207-2586)

Remarks: Under contract-accepting backup offers. Located in the heart of the Village within the historic charm of Boca Grande, this exceptional 6-bedroom, 6-bath coastal retreat artfully blends timeless architecture with modern craftsmanship. Designed by Stofft Cooney Architects and built in 2020 by the island’s premier builder, Safety Harbor Construction, the residence offers over 3,800 square feet under air, including two beautifully appointed sunrooms, and was thoughtfully conceived for refined entertaining and seamless indoor–outdoor living. A custom mahogany front door opens to a classic “Gasparilla Inn” inspired sun porch with green high-gloss painted wood floors, introducing interiors rich with antique wormy chestnut reclaimed flooring, tongue-and-groove ceilings with decorative beams, and a striking Isokern Magnum wood-burning fireplace. The open-concept kitchen is a chef’s showpiece, appointed with leathered Taj Mahal quartzite countertops, dual dishwashers, WOLF and Monogram appliances, and a fully equipped butler’s pantry with ice maker, beverage drawers, wine refrigerator, and generous storage. A beautifully integrated dry bar in the living area features a copper countertop, additional beverage drawers, and an ice maker. British-inspired Origin bi-fold aluminum doors fully recess to transform the living space into an open-air sanctuary, complemented by a remote-controlled screen at the touch of a button. The outdoor kitchen is anchored by a custom built-in Kalamazoo Gourmet Fire Grill, designed to cook with wood, charcoal, or gas, with additional space for preferred appliances. The main-level primary suite captures serene outdoor views and features a private, spa-like bath with dual vanities, walk-in closet, and a full-size laundry room. Two additional guest suites complete the main level, including one reimagined as a den inspired by BZ’s Lounge at the iconic Gasparilla Inn. Upstairs, a cozy TV room provides an inviting setting for movie nights and game time. Three additional guest suites include one transformed into a bright craft room with charming views of Palm Avenue, along with a convenient second-floor laundry closet. Set on 81 feet of deepwater canal frontage with direct, no-bridge access to the Harbor and Gulf, the property is a boater’s dream. The private dock features over 600 square feet of Azek decking, a 20,000-pound boat lift (2020), and a 10,000-pound lift added in 2023. The main living level is elevated over 11 feet and constructed on a solid concrete base for peace of mind. A residential elevator services all floors from the extended one-car garage with golf cart side entry and additional storage. Andersen impact windows, Boral exterior siding, a corrugated metal roof, solid wood soffits, and a whole-home Reme Halo air purifier complete this impeccably built residence, offering the rare union of Village character, architectural integrity, and exceptional boating and beach access.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Jamie Curry (941-716-1018)

Remarks: This unique bayfront home offers stunning sunrises and moonscapes over Charlotte Harbor. The spacious open main floor begins with an entry leading into the two-story living room with hand painted coffered ceiling. This space is accented by the hand painted staircase, custom tera cotta tile floors and a fireplace surrounded by a hand carved pecky cypress mantle. The adjoining dining room continues into the heart of the home providing quiet dining and harbor views. Step down into the kitchen and open family room. The kitchen is completely updated with stainless appliances, granite countertops and a spacious island with a second sink. Both rooms feature cherry flooring, custom woodwork and designer cabinetry with storage features. Adjacent to the kitchen and family room, a waterfront sunroom spans the width of the home, leading to a custom, window filled stairwell to the first-floor storerooms, doubled garage spaces and a garden patio. The property finishes with a garden view leading to the mangrove coastline. There are two large main level guest rooms, one en-suite and a second with an adjacent full bath. The upstairs primary suite welcomes you with built-in shelving and desk, vaulted ceiling and expansive windows facing Charlotte Harbor. The open Roman bath, large walk-in closet and laundry room complete the space. Open the large French doors in the primary bedroom to enter a private deck with amazing harbor views. To complete the deck, a circular staircase leads to a widow's walk with a panoramic view of Gasparilla Island and beyond. Additional highlights include a finished elevator to the first floor, impact glass on all windows and doors, a new metal roof installed in 2023 and all interior walls freshly painted. This North Bay gem, in the amenity rich Boca Bay community, is a true sanctuary combining location, style and natural beauty.

Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)

Listing Agent: Carol Stewart (941-276-1162)

Remarks: 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.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Jamie Curry (941-716-1018)

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)

Remarks: Custom-built by McHugh Porter Builders and designed by historic preservation architect Henry Browne, this 4BR/4.5BA waterfront home offers timeless architecture within the historic district of Boca Grande. Located on a no-bridge boating canal, this property features yellow pine floors, cathedral ceilings with beams, a first-floor primary suite and guest suite, open kitchen, and spacious waterfront porch. Two additional bedrooms and a family room loft with full bath were added in 2011. Xeriscape landscaping, Hardiplank siding, 2022 Metal roof, and a private dock with a 10,000-lb lift complete this exceptional coastal property.

Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)

Listing Agent: Carol Stewart (941-276-1162)

Remarks: 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.

Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)

Listing Agent: Carol Stewart (941-276-1162)

Remarks: 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!

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Maryjo Pigott (941-961-0630)

Remarks: 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.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Maryjo Pigott (941-961-0630)

Remarks: Extraordinary legacy estate in the heart of Boca Grande’s Historic District is a true West Indies–inspired sanctuary where timeless architecture, artisan craftsmanship, and tropical elegance converge. Expansive estate lot, 6,417-sq ft residence offers complete privacy and an undeniable sense of discovery—with enchanting architectural moments revealed around every corner. Natural stone, rich woods, and refined detailing of understated luxury. Custom mahogany and cypress accents, intricate ceiling designs, sculpted wood columns, and expansive French doors define the home’s open, flowing footprint. Impact-rated windows and doors flood each room with natural light, while it is notable that none of the living areas experienced water intrusion during past hurricanes. Dominican coral stone extends across both exterior and interior surfaces, architectural continuity reinforces the home’s island character. Designed for effortless gatherings of any size, offers an exceptional array of indoor and outdoor entertaining spaces. Expansive living and dining areas flow seamlessly to beautifully appointed patios, covered lounges, and inviting courtyard retreats. Multiple conversation areas and a well-equipped kitchen make hosting intimate dinners and large celebrations easy. Outdoors, resort-style amenities create a private backdrop for poolside afternoons, evening cocktails, and unforgettable events—an entertainer’s dream. Over 4,000 sq ft of space that opens to a breathtaking courtyard oasis, where cascading waterfalls, lush landscaping and ambient lighting transform the grounds into a private retreat. Stunning heated pool & spa, glass-tile sunshelf complemented by an outdoor kitchen, mosquito-misting system, and whole-property landscape lighting for effortless living year-round. The chef’s kitchen boasts river granite countertops, island, custom cabinetry, premium appliances, and multiple bar areas. Modern technology integrates discreetly with the whole-home Sonos sound system and automated Lutron lighting control. Curated living and entertaining spaces include a gracious dining room, expansive living areas, a dedicated home office, and an upper-level media/entertainment room. The private owner’s wing is an intimate sanctuary with a vast bedroom offering tranquil views across the pool and gardens. The spa-inspired bath offers a luxurious retreat with an oversized walk-in shower, oversized jacuzzi tub, exotic stonework, dual vanities, and elegant lighting. Dual walk-in closets provide generous storage and customization. This 5-bedroom, 6-bath estate offers four additional guest suites, each beautifully appointed with its own ensuite bath, spacious closets, and custom finishes. For boating enthusiasts, the property’s location is second to none—moments from premier local marinas, effortless access to Gasparilla Sound and the Gulf. Enjoy a day of island hopping, world-class fishing, or a sunset cruise, and every adventure begins with ease. Privately enclosed and secured by dual power-operated gates and a paver driveway with decorative turf inlays and a fully gated perimeter for exceptional security and privacy. For pet lovers, dedicated spaces, conveniences, and secure landscaped outdoor areas provide room to roam. Perfectly equipped for pets to enjoy the luxury lifestyle right alongside their owners. The estate is just a golf cart ride from Boca Grande’s world-renowned beaches, shopping, dining, and historic village center—yet feels worlds away.

Listing is courtesy of: PARSLEY BALDWIN REAL ESTATE (941-964-2700)

Listing Agent: Michelle Finley (941-204-4000)

Remarks: One or more photo(s) has been virtually staged. Modern Coastal Luxury - NEW HOME - Just Completed! Discover one of Boca Grande’s newest and most exclusive homes on the prestigious North Shore of Gasparilla Island. This brand-new 5-bedroom, 5-bathroom estate (each bedroom featuring en-suite bathrooms) offers over 4,000+ sq. ft. designed for effortless coastal entertaining on one level. Set at the end of a private living cul-de-sac and positioned on one of the highest elevated lots on the island, the property is surrounded by masonry privacy walls and features professionally designed lush tropical landscaping. Once inside, you’ll find soaring ceilings, custom millwork, 7.5” white oak flooring, and impact-rated sliders that blend indoor and outdoor living. A unique zero-post sliding glass door system leads to an expansive covered lanai (600+ sq. ft.) featuring a retractable Phantom Screen, custom outdoor kitchen with Coyote appliances, while overlooking the elegantly designed pool and spa. The home is an entertainer's dream featuring a chef’s inspired kitchen complete with designer cabinetry, Thermador appliances, extra-large workstation sink, dual dishwashers, quartz countertops, and a 12' center island perfect for hosting. Additional highlights include a wet bar and prep area coupled with a wine chiller tower, beverage center, spacious walk-in pantry, and discreet mudroom/laundry area. The primary suite is thoughtfully designed offering a majestic view of the pool and backyard with separate walk-in closets. The primary bathroom is a serene retreat offering heated floors, an oversized shower and soaking tub, along with custom Robern medicine cabinets and designer lighting. The additional en-suite bathrooms offer their own privacy and Bedroom 2 can also serve as a den or office if desired. Guest suite bathrooms provide private comfort with curbless walk-in showers and custom designer finishes throughout. Designed by nationally recognized T.A. Krebs Architects, and crafted by preferred island builder L.J. Silva Construction, this 2025 masterpiece combines masonry block construction with energy-efficient spray foam insulation, premium concrete tile roofing, "cool touch" Shellock pool and lanai pavers, and a 24 kW Generac generator. With an attached 3-car garage, the home has ample storage for your Moke or golf cart and other outdoor island toys. Smart home technology includes an app-controlled pool/spa & fireplace lighting, irrigation, sound pre-wiring throughout and a 75" Samsung Frame Pro TV in the family room. Deeded beach access is just steps away and ownership boat dockage with lift capability (up to 65') is just across the road, for easy and quick access if desired. This estate offers both tranquility and accessibility to the island’s best amenities. Along with Coral Creek Jet Center/Airport and a Tom Fazio Signature Golf Course just across the Bridge. A few photographs are virtually staged. Experience the pinnacle of Boca Grande living - modern coastal luxury at its finest.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Jeff Moore (941-855-0737)

Remarks: 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.

Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)

Listing Agent: Zeke Sieglaff, Jr (610-357-5073)