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Lemon Bay High - D6147192 - 312 BAILY ST, BOCA GRANDE, FL 33921 1 Day on yellowkey
$3,250,000 | Single Family Home | 3 beds | 3.0 baths | 3 gar
Welcome to 312 Baily St — a charming 3-bedroom, 3-bath home in the Golden Beach neighborhood on the south end of Boca Grande, just one block from the Gulf of Mexico. Built in 2003, this custom 2,572 sq ft home offers an open floor plan with a third-level bonus room featuring expansive island views. Inside, vaulted ceilings, hardwood floors, oversized windows, and a skylight bring in natural light throughout, with a tucked-away reading nook for relaxed afternoons. The kitchen offers a gas cooktop, ample counter space, and a breakfast bar for casual meals and gathering. The primary suite includes a private deck, office space, and a spacious bath with soaking tub, walk-in shower, and double sinks. A large screened porch overlooks the oversized, beautifully landscaped lot, offering a private, quiet setting. A three-car garage provides ample space for vehicles, golf carts, storage, and beach gear, so parking is never a concern. This property boasts concrete block construction at the ground level, along with an elevated structure, Hardiplank siding, and a metal roof for lasting durability. Close to the beach, the village of Boca Grande, the lighthouse, and the Gasparilla Inn & Club, the property’s location makes it easy to enjoy everything the island has to offer. Nearby amenities include pickleball and tennis courts, a local farmers market, and a dog park. Comfortable coastal living in one of Boca Grande’s most desirable neighborhoods. Don’t miss your chance to call Boca Grande home.
Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT
Lemon Bay High - D6146964 - 6030 BOCA GRANDE CSWY #B21, BOCA GRANDE, FL 33921 1 Day on yellowkey
$1,375,000 | Condo | 3 beds | 3.0 baths
One or more photo(s) has been virtually staged. Some island properties are easy to understand from photos. Others reveal their value the moment you step inside. Boca Grande North Unit B21 is one of those residences—renovated, flexible, beautifully positioned, and offering far more usable space than buyers may expect in a Boca Grande condominium. Here, you do not have to choose between sunrise over the Bay and sunset over the Gulf. This beautifully renovated three-bedroom, three-bath residence with den/office captures both perspectives, creating a coastal living experience that feels connected to the water throughout the day. Inside, volume ceilings, impact windows and sliders, luxury vinyl flooring, updated finishes, and a thoughtful two-level layout give the home a sense of openness, comfort, and versatility that sets it apart. The main living level offers an open-concept kitchen, comfortable living and dining areas, two bedrooms, two full bathrooms, and a private front lanai that extends the living experience outdoors. It is easy to picture slow mornings, island weekends, extended stays, and effortless hosting in a space designed to live comfortably. The bonus second level is the feature buyers will remember. Upstairs, an additional bedroom, full bathroom, and den/office create valuable separation for guests, family, remote work, hobbies, or quiet retreat space. This added flexibility makes Unit B21 feel less like a standard condo and more like a true island residence with room to adapt. Boca Grande North is a gated waterfront community offering a heated pool and spa, tennis/pickleball, kayak launch, fishing, boat docks when available, and private beach access across the road. Minutes from the village of Boca Grande, Gulf beaches, boating, restaurants, and shops, this location delivers the ease of island living with the amenities buyers want most. For buyers who have been searching for a Boca Grande residence that offers more than the expected, Unit B21 deserves to be seen in person. The photos introduce the views, the renovation, and the coastal setting—but the walk-through is where the value becomes clear. The extra bedroom, full bath, den/office, volume ceilings, and Bay-to-Gulf perspective come together in a way that feels larger, smarter, and more livable than a typical island condominium. This is the one buyers will understand the moment they step inside.
Listing is courtesy of: COLDWELL BANKER SUNSTAR REALTY
Lemon Bay High - TB8502017 - 340 PALM AVE, BOCA GRANDE, FL 33921 3 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
Lemon Bay High - D6147162 - 1669 JOSE GASPAR DR, BOCA GRANDE, FL 33921 6 Days on yellowkey
$7,500,000 | Single Family Home | 5 beds | 6.5 baths | 2 gar
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.
Lemon Bay High - D6147048 - 420 GULF BLVD #9, BOCA GRANDE, FL 33921 13 Days on yellowkey
$2,100,000 | Townhouse | 2 beds | 2.5 baths | 1 car
Direct Gulf-front opportunity on the coveted south end of Boca Grande. This beachfront townhome offers panoramic views of The Gulf and direct access to miles of pristine sandy shoreline. Recently updated and positioned as one of the best values on the Boca Grande beachfront, Sundown Colony #9 now features a remodeled kitchen with quartz countertops and stainless steel appliances, along with an updated primary bathroom. Private stairs provide direct access to the beachfront, enhancing the seamless indoor-outdoor coastal lifestyle. Located just moments from the historic village, you’ll enjoy the charm of local shops, dining, and island amenities right at your fingertips. Whether you’re seeking a peaceful getaway or a Gulf-front investment, this is your chance to secure a true piece of paradise. Incredible sunsets, relaxed island living, and exceptional value await. Don’t miss it.
Listing is courtesy of: BOCA GRANDE REAL ESTATE, INC.
Lemon Bay High - D6146999 - 739 S HARBOR DR #2, BOCA GRANDE, FL 33921 13 Days on yellowkey
$2,450,000 | Condo | 3 beds | 2.5 baths | 1 gar
Under contract-accepting backup offers. Live the pinnacle of Boca Grande waterfront living in this exceptional three-bedroom, two and a half bath Harborside condominium. Perched on the top floor with an enviable end-unit location, this residence delivers sweeping, unobstructed views of Charlotte Harbor that captivate from sunrise to moonrise. Step inside to discover an elegant open-concept floor plan bathed in natural light, where soaring ceilings, crown molding, plantation shutters throughout the home, and marble tile flooring create a refined sense of space and sophistication. The gourmet kitchen features stainless steel appliances and granite countertops, while the expansive glassed lanai serves as the heart of the home—an idyllic setting for morning coffee, sunset cocktails, or simply marveling at the ever-changing panorama of azure waters, abundant wildlife, and graceful boating activity. Additional peace of mind comes from electronic hurricane roll-down shutters, ensuring effortless protection during storm season. Designed for effortless coastal living, this lock-and-leave retreat offers the perfect blend of privacy and convenience with its private garage, dedicated storage, and elevator access. The community of Boca Bay surrounds you with a resort-style lifestyle: four sparkling swimming pools, a private bayside beach, a fishing pier, seven clay tennis courts, a state-of-the-art fitness center, and exclusive access to the world-class Boca Bay Pass Club for casual gulf-side dining.
Lemon Bay High - D6146747 - 5000 GASPARILLA RD #BC306, BOCA GRANDE, FL 33921 22 Days on yellowkey
$1,150,000 | Condo | 1 beds | 2.0 baths
Experience effortless coastal living in this beautifully appointed one bedroom, two bath condo, perfectly positioned on the desirable 3rd floor with sweeping Gulf of Mexico views. Offered fully furnished, including a built in queen Murphy bed for guest, and ready for immediate enjoyment or rental income potential. Located within the exclusive Boca Grande Club, residents enjoy an array of resort style amenities, including three sparkling pools, a gulf front private restaurant, a lively tiki bar, a state-of-the-art fitness center, and eight Har-Tru tennis courts. A premier tennis program with professional instruction, along with on site rental management and housekeeping services, ensures both convenience and exceptional lifestyle appeal. Just a short golf cart ride away, you’ll find the charming Village of Boca Grande, offering boutique shopping, dining, and Old Florida charm. Whether you’re seeking a serene getaway or a smart investment opportunity, this exceptional beachfront condominium delivers the best of both worlds. Membership fees apply for ownership. Please inquire for cost.
Lemon Bay High - D6146862 - 1671 JOSE GASPAR DR, BOCA GRANDE, FL 33921 28 Days on yellowkey
$3,995,000 Reduced | Single Family Home | 4 beds | 4.0 baths
Experience waterfront living in this recently updated Boca Grande residence, ideally positioned along the serene shores of Gasparilla Sound. This four-bedroom, four-bath pool home blends timeless coastal charm with thoughtful modern upgrades, starting with its inviting curb appeal and welcoming entry. Inside, elegant shiplap detailing enhances the interior walls, adding warmth and character throughout. The home features an updated kitchen and breakfast room with stunning water views. The second-floor primary suite serves as a private retreat, complete with a updated bath and its own waterfront deck. Three additional bedrooms, two en suite, offer private entrances off the pool, creating a perfect setup for guests or extended family. Storm-resistant doors and windows flood the home with natural light while providing peace of mind and added protection. Step outside to embrace the ultimate waterfront lifestyle. The expansive pool area overlooks the water, complemented by a private boardwalk and dock—ideal for kayaks, paddleboards, fishing, or simply enjoying breathtaking sunsets. This exceptional property is a perfect opportunity to own an island home in Boca Grande —where comfort, and coastal beauty come together seamlessly.
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA
Lemon Bay High - D6146719 - 43 SEAWATCH LAKE DR, BOCA GRANDE, FL 33921 29 Days on yellowkey
$2,500,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Nestled in the exclusive gated community of Seawatch, this thoughtfully updated single-family Seawatch presents a rare lakefront sanctuary offering unparalleled privacy, serene water views, and refined coastal living. It boasts approximately 3,092 square feet of bright, open living space with three bedrooms and three bathrooms. Vaulted bead board ceilings and an abundance of natural light create an airy, inviting atmosphere throughout the open floor plan—ideal for both relaxed everyday living and sophisticated entertaining. The upper-level primary suite is a true retreat, featuring a private terrace with sweeping views over Lake Gasparilla, an upgraded bathroom and office. Multiple expansive outdoor living areas, including a screened lanai and open porches, invite al fresco dining, sunset gatherings, or simply unwinding amid the tranquil surroundings. At the heart of the home is the tastefully renovated eat-in kitchen, showcasing premium appliances including a paneled Sub-Zero refrigerator, double ovens, induction cooktop, and warming drawer, along with abundant storage and elegant finishes. Recent renovations by renowned local firm McHugh Porter Builders have elevated the property with refreshed kitchen and baths, new engineered hardwood flooring, and impeccable interior finishes throughout. Additional highlights include a convenient elevator, hurricane-impact windows and sliders for peace of mind, a 2011 roof, an air-conditioned storage room just off the garage, and ample parking. 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 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.
Lemon Bay High - D6146794 - 12 SEAWATCH DR, BOCA GRANDE, FL 33921 30 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.
Lemon Bay High - D6146748 - 6010 BOCA GRANDE CSWY #C32, BOCA GRANDE, FL 33921 35 Days on yellowkey
$1,129,000 | Condo | 2 beds | 2.0 baths
Perched on the top floor of Boca Grande North, Residence 32 captures sweeping views of the Intracoastal Waterway and delivers the relaxed elegance that defines island living. This beautifully updated two-bedroom, two-bathroom condominium blends contemporary design with coastal charm, highlighted by striking ceiling beams, engineered hardwood floors, and thoughtfully upgraded finishes throughout. Natural light pours through impact-rated windows and sliding glass doors, enhancing the open living spaces and framing tranquil water views. The well-appointed layout offers both comfort and functionality, ideal for everyday living or as a refined island retreat. Offered unfurnished, the residence presents a blank canvas to create your own coastal vision. Boca Grande North is a gated waterfront community known for its exceptional amenities and boating lifestyle. Residents enjoy a heated community pool overlooking the water, tennis and pickleball courts, a fully equipped clubhouse with card room and fitness center, and beautifully maintained grounds. Community propane grills provide the perfect setting for outdoor entertaining, while dedicated golf cart parking and charging stations add convenience for exploring the island. Whether you are seeking a personal getaway or a strong investment opportunity, this residence offers excellent rental potential in one of Boca Grande’s most desirable communities. With close proximity to the Village, pristine Gulf beaches, world-class tarpon fishing, and renowned island dining, Boca Grande North 32 is a rare opportunity to experience the very best of Southwest Florida coastal living.
Lemon Bay High - D6146472 - 5000 GASPARILLA RD #VH20, BOCA GRANDE, FL 33921 56 Days on yellowkey
$2,450,000 | Condo | 3 beds | 3.0 baths | 1 gar
Fully renovated Village Home in the gated Boca Grande Club, offering 3 bedrooms, 3 baths plus a fourth kids’ room and over 1,600 square feet of living space, including approximately 400 square feet of thoughtfully added living area. Designed with a coastal-contemporary aesthetic, the home features an open-concept layout with vaulted ceilings, abundant natural light, enclosed sunrooms, and a striking new fireplace that anchors the main living space. The gourmet kitchen showcases premium LG appliances, quartz countertops, and designer fixtures, seamlessly blending style and functionality. The reimagined primary suite offers a spacious walk-in closet and a spa-inspired bath with dual vanities and a large walk-in shower. The loft level has been expertly transformed to include a private bedroom and full bath, creating an ideal retreat for guests or family. Throughout the home you’ll find designer tile, new hardwood flooring, updated doors, trim, and hardware, along with modern conveniences including a full-size in-home washer and dryer and outdoor elevator lift. Significant upgrades include impact windows, Hardie siding, Trex decking, a newer roof, open-air lift, and a 2017 HVAC system, ensuring both durability and peace of mind. Enjoy west-facing outdoor living with beautiful sunset views and glimpses of the Bay and Gulf, along with a garage and private garden area. Located just steps from the secluded beach, this home offers the perfect blend of privacy and coastal lifestyle. Residents of the Boca Grande Club enjoy an exceptional amenity package including Gulf-front dining, three pools, tiki bar, fitness center, yoga and water aerobics, eight tennis courts, and gated security.
Lemon Bay High - D6146411 - 320 GASPARILLA ST, BOCA GRANDE, FL 33921 58 Days on yellowkey
$2,775,000 | Single Family Home | 3 beds | 2.0 baths
Discover 320 Gasparilla Street located just south of the village in Golden Beach. This 3-bedroom, 2-bathroom pool home offers comfortable living with a desirable one-level layout, situated on a large, south facing lot. The main living areas feature a living and dining room combination, complemented by a glassed-in Florida room that fills the home with natural light. The kitchen is clean and functional, and the bedrooms are generously sized. The fully fenced backyard includes a freshwater pool and a tiki-style bungalow, creating a private outdoor haven. Conveniently located near a beach access, the property offers the laid-back coastal lifestyle Boca Grande is known for. Whether as a primary residence, seasonal getaway, or investment property, this presents a wonderful opportunity to own on Gasparilla Island.
Lemon Bay High - D6146257 - 150 1ST ST E, BOCA GRANDE, FL 33921 69 Days on yellowkey
$6,995,000 | Single Family Home | 6 beds | 6.0 baths | 1 gar
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.
Lemon Bay High - D6146199 - 281 SEABREEZE CT, BOCA GRANDE, FL 33921 72 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
Mariner High School - D6146117 - 204 WATERWAYS AVE, BOCA GRANDE, FL 33921 76 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.
Lemon Bay High - D6146072 - 260 GILCHRIST AVE, BOCA GRANDE, FL 33921 76 Days on yellowkey
$5,750,000 | 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.
Lemon Bay High - D6145898 - 5020 GROUPER HOLE CT, BOCA GRANDE, FL 33921 85 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.
Lemon Bay High - D6145442 - 1660 16TH ST E, BOCA GRANDE, FL 33921 113 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.
Lemon Bay High - D6145319 - 45 SEAWATCH LAKE DR, BOCA GRANDE, FL 33921 125 Days on yellowkey
$2,100,000 | Villa | 3 beds | 3.5 baths
Newly renovated with luxury wide plank hardwood floors throughout, impact windows and doors throughout, composite decking and fresh interior paint. The paver driveway into the gated community of Seawatch that introduces a charming lakefront spacious 3 bedroom, 3 and one-half bath Villa graced by Lake Gasparilla. The solarium entry with a circular staircase comes complete with an open floor living/dining area, wood cathedral ceilings, and a screened lanai with excellent lake views. The kitchen showcases wood cabinets, wainscot backsplash and plenty of counter space. Other features include plantation shutters throughout, turret style guest bedroom with beadboard vaulted ceiling, one car garage, and ample storage. The spacious master suite offers a vaulted ceiling, and open balcony with easterly lake views. Seawatch is a waterfront gated community of 49 residence featuring 4 beach accesses, 2 tennis courts and 2 pools and located between Lake Gasparilla and the Gulf of Mexico.
Lemon Bay High - D6145289 - 160 1ST ST E, BOCA GRANDE, FL 33921 129 Days on yellowkey
$4,500,000 | Single Family Home | 4 beds | 4.5 baths
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.
Lemon Bay High - D6145227 - 5000 GASPARILLA RD #BC105, BOCA GRANDE, FL 33921 130 Days on yellowkey
$799,000 | Condo | 1 beds | 1.0 baths
With breathtaking gulf views and direct beach access, this condo is the perfect retreat for those seeking tranquility and beachfront relaxation. Natural light, tasteful beach decor and a screened lanai create an island oasis. This easy to maintain condo not only offers your own slice of paradise, but also grants access to a host of exclusive amenities. Enjoy a world class tennis facility, state of the art fitness center, three swimming pools, Tiki bar and a fantastic gulf front restaurant. All within the Boca Grande Club, a private, gated community located on the Gulf of Mexico. Initiation fees and yearly Club dues apply. Please inquire for cost.
Lemon Bay High - D6144651 - 4070 LOOMIS AVE, BOCA GRANDE, FL 33921 164 Days on yellowkey
$12,500,000 | Single Family Home | 4 beds | 4.5 baths | 5 gar
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.