Refine Search
Map
Sort by
22 Seawatch Drive, Boca Grande
$4,295,000
3 Beds ⋅ 4 Baths ⋅ Seawatch Of Boca Grande SubDv. ⋅ 33921 Zip Code
Along a secluded stretch of Gasparilla Island shoreline, 22 Seawatch Drive brings an individual architectural character to beachfront living. Set within the gated Seawatch community and framed by mature tropical landscaping, this renovated, freestanding residence opens to Gulf views through expansive glass, with cathedral ceilings lending light and volume to the main living spaces. The reimagined kitchen introduces a fresh coastal sensibility, balancing clean lines and thoughtful function with the home’s distinctive architecture. Living and dining areas flow toward an enclosed patio with electric screens, creating a sheltered setting for meals, conversation and quiet afternoons beside the shore. Occupying the upper level, the primary suite offers a private Gulf-facing balcony, a walk-in closet and an updated bath. A newly added catwalk connects the suite to a loft-style office and lounge, giving the upper floor an open, connected feel. An additional bedroom offers flexibility for guests, fitness or creative pursuits. At the home’s highest point, the signature observation room provides a remarkable change in perspective, with panoramic views extending from the Gulf to the bay. It is a distinctive retreat within the house, a place to read, watch the weather move across the water or take in the island from above. A standing seam metal roof, impact windows and sliders, Trex decking and brick pavers complement the interiors, while smart-home systems provide remote control of lighting, temperature and water systems. Seawatch residents enjoy private beach access, two pools and tennis courts, with Boca Grande’s village, shops and restaurants within easy reach. A short golf cart ride or beach walk leads to the Boca Grande Club, recognized among the nation’s top 10 beach clubs by Platinum Clubs of America, with membership available separately. Here, the combination of a freestanding home, an intimate beachfront community and an unusually varied collection of spaces offers a setting as suited to gathering as it is to finding a quiet corner of one’s own.

22 Seawatch Drive, Boca Grande
5000 Gasparilla Road Unit VH25, Boca Grande
$1,995,000
3 Beds ⋅ 4 Baths ⋅ Boca Grande Club SubDv. ⋅ 33921 Zip Code
This 3-bedroom, 3 1/2-bath single-family residence is only steps from the pristine sands of the Gulf, offering the quintessential Boca Grande lifestyle. This redesigned floor plan features a renovated kitchen, updated baths, flooring and impact-resistant windows and sliders throughout. Uniquely offering 3 ensuite bathrooms PLUS an additional guest half bath along with a dedicated laundry room! The 1 car garage offers extra storage with built-in shelves and an outside shower. Sold furnished, this home is ready for immediate enjoyment. Whether you are watching the sunset over the Gulf from your balcony or walking the uncrowded private beach, this is island living at its finest. Purchasing this property provides immediate membership to the Boca Grande Club and all the amenities it is known for such as a fabulous gulf-front restaurant with new pool spa and tiki bar, private beach access with umbrella, lounge chair and towel service. The newly renovated fitness center is world class, and the 8 tennis courts offer a pro-shop with instruction with a very active tennis community.

5000 Gasparilla Road Unit VH25, Boca Grande
420 Gulf Boulevard Unit 20, Boca Grande
$2,350,000
2 Beds ⋅ 3 Baths ⋅ Sundown Colony SubDv. ⋅ 33921 Zip Code
DIRECT GULF FRONT | PICTURE PERFECT GULF VIEWS | BEAUTIFULLY UPDATED | 2 BEDROOMS | 2.5 BATHROOMS | OUTDOOR LIVING SPACES | COMMUNITY POOL | DIRECT BEACH ACCESS A beautifully updated Gulf-front residence in Sundown Colony nestled along the pristine shoreline of Boca Grande on Gasparilla Island. With breathtaking views of the Gulf, inviting coastal interiors, and direct access to the island's renowned beaches, this exceptional property captures everything that makes Boca Grande such a sought-after destination. Designed to embrace its spectacular waterfront setting, this two-bedroom, two and a half bath townhome offers an inviting blend of casual coastal elegance and modern convenience. A soothing palette of soft blues, crisp whites, and natural wood tones creates a light, airy atmosphere that complements the surrounding landscape. Expansive impact-rated windows and sliding glass doors invite abundant natural light while showcasing the sparkling turquoise waters and endless Gulf horizon. The main living level features an open-concept design that seamlessly connects the kitchen, dining, and living areas, creating a welcoming space for everyday living and entertaining. The updated kitchen features white shaker-style cabinetry, stone countertops, stainless steel appliances, subway tile backsplash, and a convenient breakfast bar. The adjoining dining area provides generous seating, while the comfortable living room is perfectly positioned to capture stunning Gulf views. Step through the sliding glass doors to the screened Gulf-facing porch, where gentle sea breezes, spectacular sunsets, and the soothing sound of the surf provide the perfect backdrop for morning coffee, afternoon relaxation, or evening gatherings. The Gulf-front primary suite offers a peaceful retreat, complete with beautiful water views, direct access to its own outdoor balcony, and a well-appointed en-suite bathroom. The updated bath features a spacious double-sink vanity with stone countertops, contemporary fixtures, and a glass-enclosed tub/shower with attractive tile finishes. A dedicated workspace within the primary suite provides additional flexibility without sacrificing the beauty of the surrounding views. The guest bedroom offers a versatile layout with bunk beds and an additional bed, making excellent use of the available space. Soft coastal colors and natural light create a cheerful, comfortable atmosphere. The guest bathroom features a glass-enclosed walk-in shower, updated vanity, and stylish finishes. On the main living level, a separate powder room adds convenience. Outdoor living is truly at the heart of this property. In addition to the elevated Gulf-facing porches, the ground-level covered outdoor area offers a wonderful space for casual gatherings, enjoying the coastal surroundings and rinsing off in the outdoor shower after a dip in the gulf. Sundown's beautifully situated community pool, surrounded by tropical landscaping, provides another inviting place to unwind. The association updated to a metal roof in December 2023; AC was replaced in October 2024. Looking for an amazing investment property or a mix of use and income...this home fits both and comes turnkey furnished and with vacation rental income scheduled into 2027.

420 Gulf Boulevard Unit 20, Boca Grande
158 Carrick Bend Lane, Boca Grande
$4,695,000
3 Beds ⋅ 3 Baths ⋅ North Village Sub SubDv. ⋅ 33921 Zip Code
Tucked toward the quiet end of Carrick Bend Lane in the gated North Village of Boca Bay, this three-bedroom, three-bath home pairs serene lake views with a thoughtful renovation throughout. More than 3,200 square feet of living space spread across two levels give owners and guests room to spread out. The kitchen is the heart of the home and was rebuilt for people who love to cook and entertain: quartz counters beneath a shiplap ceiling, Thermador wall oven, microwave, and gas range, a Wi-Fi-enabled Monogram refrigerator, and a built-in ice maker. An eat-in dining area overlooks the water, and every bathroom has been tastefully updated. Peace of mind comes built in, with impact-rated windows and doors, a newer standing-seam metal roof, and plantation shutters throughout. A two-car garage adds room for cars, golf carts, and island gear. Life in Boca Bay comes with an enviable list of amenities: a private boat basin with slips, an organized tennis program led by a resident pro on Har-Tru courts, a croquet lawn, and four community pools including a lap pool. Evenings belong to the Pass Club, where elevated dining, an extensive wine list, and spectacular sunsets over the Gulf set the tone. And when it’s time for the Village, simply walk or bike to its shops, restaurants, and beaches. Live your Best Life in Boca Grande!

158 Carrick Bend Lane, Boca Grande
2021 20th Street W, Boca Grande
$7,300,000
8 Beds ⋅ 7 Baths ⋅ Acreage & Unrec SubDv. ⋅ 33921 Zip Code
Incredible Value! Set on more than half an acre along a quiet private street, 2021 20th Street W is the kind of property Boca Grande families hold onto for generations. Two separate residences give everyone room: a spacious five-bedroom main home and a charming three-bedroom guest cottage, totaling eight bedrooms, seven baths, and 5,792 square feet. The main home is bright and open, with soaring ceilings, oversized windows, and natural light throughout. A European-designed kitchen anchors the living spaces and opens to a beautiful private pool and patio, where long lunches, sunset cocktails, and family dinners happen naturally. The fully fenced yard, framed by mature tropical landscaping, offers true privacy and a safe, generous space for children and pets to play. Deeded beach access puts the Gulf moments away, and the Village is an easy bike ride down the path, with its shops, restaurants, and community center close by. Secluded yet central, this is island living exactly as it should be: private, relaxed, and made for making Boca Grande memories!

2021 20th Street W, Boca Grande
36 Seawatch Drive Drive, Boca Grande
$2,850,000
3 Beds ⋅ 3 Baths ⋅ Seawatch Of Boca Grande SubDv. ⋅ 33921 Zip Code
Experience the beauty of island living in this beautifully appointed 3-bedroom, 3-bath residence in Seawatch, an exclusive gated private beachfront community on Boca Grande. With 1,000 feet of pristine private Gulf-front shoreline, two community pools, three tennis courts, and lush tropical landscaping, Seawatch offers a truly exceptional coastal lifestyle just minutes from the charming village of Boca Grande. Designed to embrace the natural beauty of its surroundings, this inviting home features a light-filled, open floor plan, soaring cathedral ceilings, and beautiful water views from nearly every room. The spacious primary suite is a peaceful retreat, complete with a private balcony, two walk-in closets, and a spa-inspired bath featuring dual vanities, a soaking tub, a separate shower, and a private water closet. Two additional bedrooms comfortably accommodate family and guests, including one with its own ensuite bath. Thoughtful upgrades enhance both comfort and peace of mind, including high-impact windows, a durable standing-seam metal roof, ultraviolet air purification system, whole-home surge protection, upgraded electrical, and a complete water treatment system. A cozy loft provides the perfect setting for a home office, reading nook, or quiet escape, while the screened lanai invites you to unwind in the refreshing coastal breezes and enjoy the tranquil water views. Whether savoring a quiet morning coffee or taking in spectacular Gulf sunsets, this home offers a wonderful setting to embrace the relaxed rhythm of island life. The spacious lower-level garage and workshop provide ample room for vehicles, golf carts, beach essentials, and additional storage. Beyond the community, Boca Grande’s boutique shopping, fine dining, scenic biking and walking paths, and world-class beaches are just moments away. Discover the rare opportunity to own a beautiful coastal retreat in one of Boca Grande’s most desirable gated beachfront communities. At Seawatch, the best of beachside living awaits—where timeless coastal charm meets comfort, privacy, and the beauty of the Gulf.

36 Seawatch Drive Drive, Boca Grande
5000 Gasparilla Road Unit 19, Boca Grande
$2,100,000
3 Beds ⋅ 3 Baths ⋅ Village Boca Grande Club SubDv. ⋅ 33921 Zip Code
Boca Grande Club has earned Platinum Club of America recognition, ranking No. 8 in the nation’s beach club category. Within this distinguished beachfront community, Village Home 19 combines the privacy of a freestanding residence with beautifully renovated interiors and access to exceptional private club amenities. With no shared walls, its own garage and private outdoor space, the home enjoys an unusually open setting with glimpses of the Gulf from each level. Thoughtfully enclosed spaces expand the main living area and guest bedroom, adding versatility to the floor plan and providing room for reading, conversation or quiet retreat. Plantation shutters throughout lend architectural definition, complementing a restrained coastal palette. Mature landscaping frames the residence and its outdoor patio, creating a private setting for enjoying the coastal air. A 2022 standing seam metal roof, Trex stairs and decking, and predominantly impact-rated windows and sliding glass doors complement the interior renovation. Furnishings are available. An extensive renovation of the Club’s pool and tiki bar, alongside recently renovated restaurants, brings a fresh, sophisticated aesthetic to its beachfront gathering spaces. An expansive private beach, waterfront dining, multiple pools, eight Har-Tru tennis courts, an established tennis program and a fitness center offer a rich array of pursuits within this gated, professionally managed community.

5000 Gasparilla Road Unit 19, Boca Grande
162 Blackwall Court, Boca Grande
$3,995,000
3 Beds ⋅ 5 Baths ⋅ North Village SubDv. ⋅ 33921 Zip Code
This well maintained in-town North Village residence in the private Boca Bay community offers 3 bedrooms, 3 full en-suite baths, and 2 additional half baths, framed by lush tropical landscaping and vibrant cascading bougainvillea. Thoughtfully designed for both comfort and functionality, the home includes a two-car plus golf cart garage, ample storage, and a back of the garage attached workshop – perfect for the avid craftsman or hobbyist with additional storage! Enjoy desirable southern exposure, bathing the home in warm natural light throughout the day. The interior has been tastefully upgraded with modern finishes and appliances. The kitchen features stainless steel appliances, granite countertops with matching backsplash, and updated custom cabinetry, opening seamlessly to a spacious living area ideal for entertaining. A wet bar with mini beverage refrigerator is complimented by a cozy sitting room, creating an inviting gathering space for friends and family. The home also offers a separate dining room with abundant natural light, an enclosed front porch, and an enclosed rear lanai leading to a lounge deck with stairs descending to a sparkling pool with spa, and expansive pavered deck – ideal for relaxing or hosting under the Florida sun. Backing to a tranquil nature preserve, the property enjoys added privacy and peaceful surroundings. As part of the Boca Bay community, you'll enjoy access to its premier amenities with exclusive membership in the Boca Bay Pass Club offering exceptional resort-style amenities including fine dining, 8 Har-Tru courts, four swimming pools including a lap pool, community boat docks, as well as access to the Boca Bay Beach Club – offering a complete coastal lifestyle. Whether you're looking for a primary residence or a seasonal getaway, this home offers the perfect place for indulging in all that Boca Grande has to offer. Walk into the Village and onto the beach – close to everything. Please come and see this well placed and well priced Home!

162 Blackwall Court, Boca Grande
350 Gilchrist Avenue, Boca Grande
$4,975,000
3 Beds ⋅ 3 Baths ⋅ Boca Grande SubDv. ⋅ 33921 Zip Code
LOCATION LOCATION LOCATION-Walk to everything from this truly exquisite 3 bedroom, 2 ½ bathroom Gilchrist Cottage in the heart of the “Historic District”. Loaded with mid-century charm, updated professionally with modern coastal contemporary influence throughout, all nestled onto a deep 50’ by 150’ lot. The property is being beautifully remodeled nearly new and will be delivered Designer furnished for immediate use! This delightful home offers a very private swimming pool area tucked behind privacy fencing covered with fragrant Jasmine, among just planted new lush and additional landscaping. A standing seam metal roof protects the Cottage along with back-alley access to a large, covered carport. The main living area provides a Great Room concept with Philippine Shellstone flooring throughout and a comfortably spacious 10’ by 28’ old fashioned front porch facing the Gulf of Mexico! Estate Wall, extensive pavers, and luminous night lighting offers a very special ambiance at this superb location. A rare opportunity to own in this very limited heart of the Village

350 Gilchrist Avenue, Boca Grande
290 Gulf Boulevard Unit 18, Boca Grande
$3,595,000
3 Beds ⋅ 3 Baths ⋅ Lighthouse Residence 18 SubDv. ⋅ 33921 Zip Code
Virtually Staged. Newly Constructed Beach Front 3-Bedroom, 3-Bath Gulf-View Townhome Experience luxury coastal living in this brand-new, custom-built townhome! Beginning with engineer-approved original pilings, the home was rebuilt in 2025 with 6-inch exterior framing, ½” sheathing, cement plank siding, foam insulation, Marvin Signature Coastline windows and doors, and a standing seam metal roof—ensuring superior strength, energy efficiency, and durability. Step inside to an open-concept living, dining, and kitchen area, all showcasing stunning Gulf views. Enjoy your morning coffee and spectacular sunsets from your private waterfront open lanai. The interior features tile and wide plank engineered hardwood floors and rift-sawn oak custom cabinetry. The chef’s kitchen boasts quartz countertops, matte white GE Café appliances with brushed bronze accents, and a dedicated bar area with beverage refrigerator—perfect for entertaining. The main-level bedroom includes custom built-ins and access to a full guest bath. Upstairs, the Gulf-front primary suite offers custom cabinetry, and a luxurious ensuite bath with dual sinks accented with bronze fixtures. A spacious third bedroom, also with custom built-ins, and features its own private ensuite bathroom. Other features include solid core doors and a whole house carbon and sediment dual water filtration system and tankless water heater. Over 1,000 additional square feet of covered parking for your car, golf cart and bikes. Every detail has been thoughtfully designed to create a refined coastal retreat just minutes from town, offering quick access to island shops, dining, and community events!

290 Gulf Boulevard Unit 18, Boca Grande
16271 N Island Court, Boca Grande
$8,999,000
3 Beds ⋅ 5 Baths ⋅ Gulf Shores North 04 SubDv. ⋅ 33921 Zip Code
Private Gulf-Front Estate on Boca Grande Positioned on 1.26 acres with 127 feet of direct Gulf frontage, this exceptional estate offers substantial Gulf-front acreage, an expansive beach, natural dunes, and remarkable privacy. A private boardwalk leads directly from the property to the Gulf, while the absence of nearby public beach access contributes to the quiet, secluded character of this stretch of shoreline. The elevated custom residence encompasses 3,465 square feet of living space with three bedrooms, four full baths, and one half bath. High ceilings and generous proportions create a light and open interior, while the kitchen, living, and dining areas are oriented toward the Gulf to take full advantage of the home's western exposure and water views. Spacious open and screened porches, breezeways, and Gulf-front gathering areas create a natural connection between indoors and out, offering multiple settings for entertaining, relaxing, and enjoying Boca Grande's renowned sunsets. Beneath the home is substantial additional space for storage as well as an expansive screened recreation and game area. A three-car garage provides ample room for vehicles, golf carts, and the necessities of island living. Ready for its next owner's personal vision, the residence provides an opportunity to personalize a well-built custom home while preserving what cannot be recreated: more than an acre of Gulf-front land, 127 feet of beachfront, natural dunes, exceptional privacy, and direct access to one of Boca Grande's most beautiful stretches of shoreline. Located on the North end of Gasparilla Island, the property experienced no flooding during the recent hurricanes and storms that affected the area. Private showings available by appointment.

16271 N Island Court, Boca Grande
367 Night Heron Drive, Boca Grande
$4,125,000
3 Beds ⋅ 3 Baths ⋅ North Bay SubDv. ⋅ 33921 Zip Code
Virtually Staged. Set along the shores of Charlotte Harbor in North Bay, this home offers a distinctive blend of architectural character, handcrafted details, and captivating waterfront views. The dramatic two-story living room features a hand-painted coffered ceiling, custom staircase, terra cotta tile flooring, and a hand-carved pecky cypress fireplace mantel. The adjoining dining room opens to harbor views, while the updated kitchen and family room showcase cherry flooring, designer cabinetry, granite countertops, and a spacious island. A waterfront sunroom spans the rear of the home, connecting the living spaces to the garden and mangrove coastline. Two main-level guest bedrooms provide comfortable accommodations, while the upper-level primary suite features vaulted ceilings, expansive harbor-facing windows, a Roman-style bath, walk-in closet, and private waterfront deck. A circular staircase leads to a widow's walk with panoramic views of Gasparilla Island and beyond. Additional highlights include a finished elevator, impact glass windows and doors, a 2023 metal roof, freshly painted interiors, and a two-car garage. Combining timeless craftsmanship, exceptional views, and the Boca Bay lifestyle, this remarkable residence offers a truly special opportunity for waterfront living in Boca Grande.

367 Night Heron Drive, Boca Grande
585 Buttonwood Bay Drive, Boca Grande
$5,600,000
3 Beds ⋅ 4 Baths ⋅ South Bay Sub SubDv. ⋅ 33921 Zip Code
Experience refined coastal living in this beautifully remodeled 3-bedroom, 3.5-bath waterfront residence with bonus space in the highly sought-after Boca Bay Buttonwood community. Perfectly positioned on large open water with private dockage, this exceptional home blends timeless design with comprehensive 2025 upgrades for true peace of mind. The exterior has been completely transformed with a new metal roof (2025), all-new Hardie siding and trim, hurricane-rated windows and sliding glass doors, and a hurricane-rated side garage door. Exterior lighting has been fully replaced, and the third-floor balcony was rebuilt following Hurricane Ian. The private dock has been significantly enhanced in 2025 with an additional 159 square feet, raised walk path (permitted), and electrical modifications to accommodate boat lifts—creating a premier waterfront setup. Inside, the home showcases new hardwood flooring throughout staircases, third-floor loft, and bedrooms, along with freshly painted walls and trim. Plantation shutters and four new motorized shades elevate both style and comfort. The main living area features a custom-built entertainment center designed to accommodate a 70-inch TV. The 2025 chef’s kitchen is a showpiece, offering new stainless-steel Thermador appliances including a 36” gas cooktop, refrigerator, and dishwasher, along with a 24” drawer microwave, wine cooler, Cortez countertops, tile backsplash, new faucets, and updated disposal. Both garages feature new epoxy floors and LED lighting, with a new mop sink in the north garage. Additional highlights include a Grundfos booster pump, certified backflow preventer, new Electrolux washer and dryer, and fully renovated bathrooms with Cortez countertops, new tile, updated fixtures, and dual vanities in the third-floor primary suite. An extraordinary opportunity to own a move-in-ready waterfront home in Boca Bay.

585 Buttonwood Bay Drive, Boca Grande
5010 Grouper Hole Court, Boca Grande
$3,975,000
4 Beds ⋅ 3 Baths ⋅ East Shore Acres SubDv. ⋅ 33921 Zip Code
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.

5010 Grouper Hole Court, Boca Grande

How much is your home worth?

Get instant property value now!