Location: Boca Grande
Do Not Show Listings
16776 GRANDE QUAY DR, BOCA GRANDE, FL 33921
$3,650,0007 Days on yellowkey MLS ID: D6147970
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2493 Built: 2000Monthly Fee: $833 Tax: $32,188 (2025)Community: Grande Quay 02Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$32,188
Elementary School: The Island School
High School: Lemon Bay High
Tax Year: 2025
Middle School: L.A. Ainger Middle
Remarks: Experience exceptional waterfront living at 16776 Grande Quay Drive, Boca Grande, FL 33921, nestled within a quiet, gated waterfront community with 24-hour surveillance. Situated on the largest homesite in the community, this residence captures breathtaking 180-degree views of the Gasparilla Sound. With direct boating access to the Gulf, this elegant coastal residence blends luxury, comfort, and the ultimate island lifestyle. Designed with both everyday living and entertaining in mind, the home features soaring ceilings that fill the interior with natural light, an updated chef's kitchen showcasing quartz countertops and premium Bosch appliances. A cozy fireplace adds warmth and character to the spacious living area, while pre-wiring throughout the home provides a seamless foundation for a whole-home audio & video system. Recent improvements include a 2023 adobe tile roof, partial impact-rated windows, and hardiplank siding waiting for your choice of color (and association approval). A private elevator services all levels, and the home is outfitted with a fire suppression system and central vacuum. Outdoor living is equally impressive, featuring a spa pool, an outdoor kitchen, and spaces designed to capture the spectacular waterfront views. The oversized four car garage includes a mini-split air conditioning system, making it ideal for climate-controlled storage, hobbies, or a workshop. For boating enthusiasts, the property includes a deep water privately gated boat slip (Slip M) complete with a lift, providing effortless access to world-class fishing, cruising, and the pristine waters of Gasparilla Sound and the Gulf. This remarkable waterfront residence offers an exceptional combination of refined finishes, thoughtful updates, and unparalleled boating amenities in one of Boca Grande's most desirable waterfront communities.
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)
Listing Agent: Carol Stewart (941-276-1162)
16 GROUPER HOLE DR, BOCA GRANDE, FL 33921
$5,995,000149 Days on yellowkey MLS ID: TB8474700
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3317 Built: 1995 Tax: $61,815 (2025)Community: East Shore AcresSpa: YesSingle Family
Taxes:$61,815
Remarks: Private custom designed home with deepwater protected dockage on a lot and a half (150’) — situated directly across from the Boca Grande Club! This exquisite 3-bedroom, 3-bathroom BIG VIEW waterfront Estate Property is a 1996 National award winning architectural design, set within a lush tropical oasis with rich verdant greenery and mature native landscaping. Incredible and expansive views front Gasparilla Sound and the ICW, additionally with multiple decks facing East and West with over 4,000 sq. ft. under roof! The main level features an open-concept layout ideal for effortless entertaining, seamlessly connecting the kitchen, dining, and living areas, boasting soaring ceilings and abundant natural light throughout - all Andersen doors and windows. Enjoy a true indoor-outdoor lifestyle with panoramic coastal vistas and a fluid transition to the very cozy screened-in lanai over the pool – perfect for relaxing or hosting while taking in the serene surroundings. The gourmet kitchen is a chef’s haven featuring granite countertops & center-island with abundant prep space, a DCS professional 6 burner duel-fuel range / double oven, oversized paneled Sub Zero refrigerator and freezer designed to blend seamlessly with custom cabinetry, plus a breakfast nook/coffee bar and pantry… The dedicated Master level provides a serene private retreat showcasing exceptional 240° views with hers and his walk-in closets. Embrace the height of comfort and relaxation with a spacious ensuite bath with spa-like soaking tub and separate shower, and two private decks for taking in year-round breathtaking sunrises, moonrises, and sunsets. On the ground level, step outside to an expansive pool deck with plenty of space for outdoor entertainment with a very large waterfront pool and separate covered spa. Just steps away to your (cool-to-the-feet) shellstone tile deck out to your own private deep-water dockage complete with three boat lifts (13,000, 7,000, and 7,000 lbs) – a dream for avid boaters and fishermen alike. Two car plus golf cart garage with lots of storage, a wine cellar, and excellent Bonus space! This is the very best comfortable Island Living in this nearly 1 acre waterfront estate at the very best pricing! Come see why…?
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)
Listing Agent: Robert Melvin (941-380-8891)
350 GASPARILLA ST, BOCA GRANDE, FL 33921
$3,975,00010 Days on yellowkey MLS ID: D6147913
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2993 Built: 1977 Tax: $11,270 (2025)Community: Golden BeachSpa: YesSingle Family
Taxes:$11,270
Remarks: Located just south of Boca Grande village in Golden Beach, this beautiful pool home offers the trifecta of coastal living; comfort, and privacy, all near the beach. Set on a large, landscaped lot with banana trees, coconut palms, and tropical plantings, the property provides a peaceful island setting. The main level features three bedrooms, three bathrooms, a spacious den, sunny kitchen, vaulted ceilings, warm wood floors, open decks and a large, screened porch. Taken to the studs and rebuilt in 2004 by McHugh Porter Builders, additional highlights include an elevator, impact-rated windows and doors, a whole-house water filtration system, new metal roof and generator. The first floor has an 800SF guest quarters, an ideal space for family and friends with a private entrance and walk out to the pool. Plenty of room for the toys with a two-car garage, carport, boat parking and air-conditioned tackle room/storage. This property is complete with a large, heated saltwater pool and spa surrounded by elegant stone decking and an open covered patio.
40 SEAWATCH LAKE DR, BOCA GRANDE, FL 33921
$4,750,00069 Days on yellowkey MLS ID: D6147259
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5064 Built: 1988Monthly Fee: $1,733 Tax: $45,656 (2025)Community: Seawatch Boca GrandeSingle Family
Taxes:$45,656
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)
204 WATERWAYS AVE, BOCA GRANDE, FL 33921
$6,450,000146 Days on yellowkey MLS ID: D6146117
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3027 Built: 1982 Tax: $62,277 (2025)Community: Harbor Drive WaterwaysSingle Family
Taxes:$62,277
High School: Mariner High School
Middle School: Mariner Middle School
Remarks: 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.
Listing is courtesy of: BOCA GRANDE REAL ESTATE, INC. (941-964-0338)
Listing Agent: Heather Wolfe (813-240-6963)
367 NIGHT HERON DR, BOCA GRANDE, FL 33921
$4,150,000539 Days on yellowkey MLS ID: D6140022
REDUCED by $450,000 (9.8%) on 07/03/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3568 Built: 1991Monthly Fee: $100 Tax: $16,565 (2025)Community: North BaySpa: NoSingle Family
Taxes:$16,565
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.
17 SEAWATCH DR, BOCA GRANDE, FL 33921
$3,900,000239 Days on yellowkey MLS ID: D6144740
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2644 Built: 1989Monthly Fee: $708 Tax: $46,627 (2025)Community: Seawatch Boca GrandeSpa: NoSingle Family
Taxes:$46,627
Remarks: The crown jewel of Boca Grande’s North Shore, this direct beachfront paradise offers rare privacy and timeless coastal elegance. Featuring 3 bedrooms and 3.5 baths—all ensuite—this retreat includes expansive living areas, a two-plus-car garage, and a beautifully appointed kitchen with stainless steel appliances, perfect for entertaining or quiet mornings by the Gulf. With no public beach access nearby, the shoreline feels like your own, with world-class shelling and endless views. Sunsets paint the Gulf in gold, casting a warm glow over a home designed for peace and connection. Whether enjoying the Gulf breeze or gathering under the stars, this is more than a residence—it’s a private sanctuary of luxury, solitude, and unspoiled natural beauty.
Listing Agent: Ralph Dilena, Jr. (941-380-0878)
894 HILL TIDE LN, BOCA GRANDE, FL 33921
$16,850,000877 Days on yellowkey MLS ID: D6134942
Bed: 6 Bath: 7.5 Gar: 3 Liv Area Sq Ft: 8100 Built: 2025Monthly Fee: $1,583 Tax: $41,468 (2023)Community: Hill Tide EstatesSpa: YesSingle Family
Taxes:$41,468
Elementary School: Vineland Elementary
Tax Year: 2023
Remarks: Virtually Staged. 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 Agent: Heath Seckel (863-207-2586)
1600 JEAN LAFITTE DR, BOCA GRANDE, FL 33921
$8,500,000205 Days on yellowkey MLS ID: D6145104
0 Days Off yellowkey (back on 5/15/2026)
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4799 Built: 2011Monthly Fee: $138 Tax: $34,635 (2025)Community: Boca Grande IslesSingle Family
Taxes:$34,635
Remarks: Under contract-accepting backup offers. Welcome to waterfront living at its finest in the exclusive gated community of Boca Grande Isles on Gasparilla Island. This stunning five-bedroom, five and one half-bathroom home sits on an impressive tip lot with 170 feet of deepwater frontage, offering expansive dockage with direct access to Charlotte Harbor and the Gulf with no bridges to navigate. The southern exposure has breathtaking sunrise and sunset views from every room of Charlotte Harbor and the Gasparilla Inn Golf Course. Built with concrete construction for superior storm protection and impact glass windows and sliding doors throughout, this elevated 4,799 square foot home features an elevator and places the primary bedroom conveniently on the main living floor. The spacious primary suite includes a large bedroom with expansive water views, an office or workout room, and a spacious bathroom with dual vanities, dual closets, and dual water closets. The gourmet kitchen will make any chef smile with high-end appliances including a Subzero refrigerator, double ovens, induction cooktop, and ice maker. Granite countertops, an island, and breakfast bar complete this culinary paradise. Hardwood flooring flows throughout the home, while walls of glass in the living room and sunroom showcase those incredible water views. The large family room is the perfect spot to gather or entertain with multiple seating areas and a gas fireplace. Your family and guests will appreciate the four ensuite guest rooms that share a cozy television room to ensure everyone has privacy and room to spread out. The spectacular outdoor living space at this home is where you will want to spend your time. There is a large, heated pool surrounded by multiple expansive patios and porches, palm trees and grassy areas, and a 50’ deep water dock with lift. Spend your days sunning by the pool or exploring the blue coastal waters. An oversized two-car garage plus additional golf cart storage keeps your vehicles protected. Located in secure Boca Grande Isles with guard-gated access, you're just a short golf cart ride from the beautiful beaches of the Gulf or the charming shops and restaurants in Historic Boca Grande. The nearby Gasparilla Inn, Coral Creek private airport, multiple exceptional private and public golf courses, and local marinas all add to the island's appeal. This is coastal living done right.
Listing Agent: Zeke Sieglaff, Jr (610-357-5073)
2021 20TH ST W, BOCA GRANDE, FL 33921
$7,500,000136 Days on yellowkey MLS ID: D6146286
REDUCED by $450,000 (5.7%) on 06/27/2026
Bed: 8 Bath: 7.0 Gar: 2 Liv Area Sq Ft: 5792 Built: 1998 Tax: $21,027 (2026)Community: Acreage & UnrecSingle Family
Taxes:$21,027
Elementary School: None
High School: None
Tax Year: 2026
Middle School: None
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 Agent: Maryjo Pigott (941-961-0630)
5020 GROUPER HOLE CT, BOCA GRANDE, FL 33921
$4,675,000155 Days on yellowkey MLS ID: D6145898
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 2951 Built: 2002 Tax: $61,803 (2025)Community: East Shore AcresSpa: NoSingle Family
Taxes:$61,803
Remarks: 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.
Listing Agent: Kathleen Turner (941-234-7643)
36 SEAWATCH DR, BOCA GRANDE, FL 33921
$2,650,000247 Days on yellowkey MLS ID: D6144560
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2914 Built: 1991Monthly Fee: $708 Tax: $14,896 (2024)Community: Seawatch Boca GrandeSingle Family
Taxes:$14,896
Tax Year: 2024
Remarks: Charming Seawatch Home – Beachside Elegance in Boca Grande Discover the ultimate in coastal luxury with this beautifully appointed 3-bedroom, 3-bathroom home in the exclusive gated beachfront community of Seawatch on Boca Grande. Set along 1,000 feet of pristine, private Gulf-front shoreline, Seawatch offers an unparalleled island lifestyle with two community pools, three tennis courts, and lush tropical landscaping—all just minutes from Boca Grande’s charming village. Designed with both elegance and comfort in mind, this residence features a bright, open floor plan with soaring cathedral ceilings and panoramic water views from nearly every room. The spacious master suite serves as a serene retreat, offering a private balcony overlooking the Gulf, two walk-in closets, and a spa-like bath with dual vanities, a soaking tub, separate shower, and private water closet. Two additional bedrooms provide ideal accommodations for family and guests, including one with its own ensuite bath for added privacy. This home has been thoughtfully updated for modern coastal living with high-impact windows, a durable standing seam metal roof, ultraviolet (UAV) air purification system, whole-home surge protection, upgraded electrical, and a complete water treatment system, ensuring comfort, safety, and peace of mind. Enjoy peaceful moments in the top-level Seawatch, where you can savor morning coffee at sunrise or take in the breathtaking Gulf sunsets. A cozy loft area provides the perfect spot for a home office, reading nook, or quiet retreat surrounded by island beauty. The screened lanai invites you to relax and unwind while enjoying gentle sea breezes and tranquil water views. Practical features complement the home’s elegance, including a spacious lower-level garage and workshop—perfect for vehicles, golf carts, and beach gear. From this ideal location, you’re just moments away from Boca Grande’s boutique shops, fine dining, biking and walking paths, and world-class beaches. Don’t miss this rare opportunity to own a piece of paradise in one of Boca Grande’s most coveted communities. Experience Seawatch—where luxury meets the laid-back rhythm of island life.
Listing Agent: Marcy Davis (941-685-5005)
319 PILOT POINT LN, BOCA GRANDE, FL 33921
$3,995,000446 Days on yellowkey MLS ID: TB8375836
REDUCED by $200,000 (4.8%) on 06/22/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3384 Built: 1991Monthly Fee: $100 Tax: $40,069 (2024)Community: North BaySingle Family
Taxes:$40,069
Remarks: THIS IS YOUR OPPORTUNITY – Remodeled and walk-in ready! Come explore the exceptional panoramic sparkling water views from this well-maintained residence nestled on the shores of Charlotte Harbor in the “North Bay” neighborhood of Boca Bay. The home is beautifully updated with new furniture and is being offered Turn-Key for immediate use. Featuring stunning wood floors and coastal contemporary updates to the bathrooms and kitchen – including new cabinets, lighting, and more. Offering four bedrooms (including a bunk room) and four full bathrooms, all clean and inviting, with excellent bonus space throughout. The metal roof, clapboard siding, and spectacular rooftop deck (that never misses a sunset) all contribute to that timeless Old Florida charm. All impact glass windows and sliding glass doors are already in place for added peace of mind. Mother Nature at her best with exceptional views from every level! For the fisherman, paddle boarder, or kayaker, you can walk out and wade the nearby grass flats and sand bars, which offer some of the best fishing in and around Boca Grande. As part of the Boca Bay community, this property enjoys access to community pools, the exclusive Pass Club, and available boat dockage – offering a complete coastal lifestyle. This residence represents a terrific value for an open bay view / bayfront home. Come and explore this enchanting opportunity.
161 1ST ST E, BOCA GRANDE, FL 33921
$4,995,000185 Days on yellowkey MLS ID: D6145389
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2548 Built: 1983 Tax: $27,417 (2024)Community: Harbor Drive WaterwaysSpa: NoSingle Family
Taxes:$27,417
Remarks: Discover this beautifully renovated cottage nestled in the Historic Village of Boca Grande, where old-world charm meets modern convenience. This 4-bedroom, 3-bathroom home spans 2,548 square feet and showcases thoughtful upgrades throughout, including a durable metal roof, Hardie plank siding, improved kitchens and bathrooms, and stunning wide plank wood flooring. The heart of the home features an open living area with custom wood ceilings, a cozy gas fireplace, a charming cupola that fills the space with natural light and flows to a large 335 sqft screened porch looking over the canal for true indoor-outdoor living. The primary bedroom and additional bedrooms provide comfortable accommodations, while an in-law suite with kitchenette on the lower level offers flexible living options. You will enjoy the lower-level outdoor living space from the shade of a covered porch or sunbathe around the custom in-ground heated pool and hot tub that create the perfect setting for relaxation. Your waterfront lifestyle includes an impressive 80-foot dock with a covered 20,000-pound boat lift on the Harbor Drive Waterways canal just steps from your back door. Practical amenities abound with dual garages equipped with electric vehicle charging stations, a golf cart charging station, and a convenient laundry room. The circular driveway features classic Chicago brick pavers, while mature landscaping and fencing complete the picturesque setting. Location is everything here – in minutes you can hop on your boat and be cruising Charlotte Harbor; or enjoy a short golf cart ride to the pristine Gulf beaches, charming shops and restaurants of Historic Boca Grande. The renowned Gasparilla Inn, exceptional golf courses, local marinas, and even Coral Creek private airport are all nearby, making this the perfect blend of peaceful retreat and convenient access to island attractions.
Listing Agent: Angela Steffan (941-855-1277)
1669 JOSE GASPAR DR, BOCA GRANDE, FL 33921
$7,500,00076 Days on yellowkey MLS ID: D6147162
0 Days Off yellowkey (back on 6/18/2026)
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 4475 Built: 2001Monthly Fee: $208 Tax: $77,571 (2025)Community: Boca Grande IslesSpa: NoSingle Family
Taxes:$77,571
Remarks: Under contract-accepting backup offers. Located in the Beautiful Boca Grande Isles, 1669 Jose Gaspar Drive is a striking example of Bermuda-style architecture, seamlessly blending timeless elegance with relaxed coastal living. Constructed of solid concrete with a durable concrete tile roof, the home features a classic stucco exterior and signature stepped rooflines—designed for both aesthetic appeal and resilience—capturing the essence of refined island design. Inside, light-filled interiors create an airy, sophisticated atmosphere. Expansive living spaces flow effortlessly, offering the perfect setting for both entertaining and everyday comfort. Thoughtful architectural details and curated finishes evoke understated luxury, while French doors and large windows and open layouts invite in natural light and gentle harbor breezes. Spanning approximately 4,500 square feet, the home features a gourmet kitchen complete with a sitting and casual dining area, along with a spacious great room anchored by a stunning shell stone fireplace—ideal for gatherings. The residence includes five bedrooms and six and a half baths, many with serene harbor views. An unfinished bonus room above the garage provides flexibility for a home office, studio, or additional bedroom. Outdoors, a beautifully elevated pool and patio create a private oasis, perfectly complementing the home’s stately presence within the Boca Grande Isles. Surrounded by lush tropical landscaping and some of the island’s finest fishing, the property offers a private retreat just moments from Boca Grande’s pristine beaches, charming village center, and scenic bike paths. This exceptional Bermuda-style residence embodies coastal sophistication and island luxury—an outstanding opportunity to experience the beauty and serenity of Boca Grande living.
12 SEAWATCH DR, BOCA GRANDE, FL 33921
$3,250,000100 Days on yellowkey MLS ID: D6146794
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3088 Built: 1989Monthly Fee: $867 Tax: $47,320 (2025)Community: Seawatch Boca GrandeSpa: NoSingle Family
Taxes:$47,320
Middle School: SKY Academy Englewood
Remarks: 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.
171 DAMFIWILL ST, BOCA GRANDE, FL 33921
$3,700,00051 Days on yellowkey MLS ID: D6147406
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1050 Built: 2024 Tax: $25,417 (2025)Community: Bg Yacht Basin DamfiwillSingle Family
Taxes:$25,417
Remarks: “The Boat House” is a rare opportunity to own one of Boca Grande’s most compelling newly constructed deep-water boating properties, a refined waterfront retreat purpose-built for the avid sportfishing and boating lifestyle. Completed in 2024 by Yusk Construction and interiors masterfully curated by local designer, Sue Sligar, this custom residence delivers the increasingly rare combination of immediate Gulf access, new marine infrastructure, and elevated coastal luxury in an exceptionally efficient island footprint. Positioned along a protected deep-water canal with no fixed bridges to Charlotte Harbor or the Gulf, the property was designed for owners who prioritize quick access to open water, effortless dockage, and turnkey boating convenience. A newly constructed seawall and exceptional dock complex create a highly functional waterfront environment tailored to the serious fisherman and boating enthusiast alike. Features include a 24,000-pound Coastal Series boat lift, expansive ENDECK synthetic decking, aluminum-framed grated platform, illuminated fish-cleaning station, shore power, freshwater service, and direct deep-water access to the harbor and Gulf within minutes. Inside, the design aesthetic elevates the residence far beyond a traditional boating property. Refined coastal textures, nickel-gap shiplap walls and ceilings, designer wallpaper, curated lighting, brass stair railings, and bespoke cabinetry create interiors reminiscent of an elegant private yacht club...polished, timeless, and effortlessly luxurious. Andersen hurricane-impact windows and doors flood the home with natural light while delivering exceptional storm protection and peace of mind. The chef’s kitchen was designed for elevated entertaining after a day on the water, featuring quartz countertops, custom soft-close cabinetry, and a premium appliance suite including a Liebherr refrigerator/freezer and Bosch induction range, dishwasher, and microwave drawer. Offering two bedrooms, one full bath, and two half baths, the residence was intentionally designed to function as the ideal luxury boating retreat, guest residence, or private quarters for a captain or crew supporting a larger island estate. Elevated approximately 13’3” above base flood elevation, the structure incorporates superior construction standards including a concrete block base, advanced steel cross-frame reinforcement system, standing seam metal roof, Hardie siding and soffits, open-cell spray foam insulation, tankless electric water heater, and a 2024 HVAC system. The pull-through garage operates as a fully equipped marine utility space complete with epoxy floors, EV charging readiness, rod storage systems, additional refrigeration, full size washer and dryer, plumbing for an ice-maker, and extensive storage for fishing gear, water toys, and boating equipment. Technology and security are seamlessly integrated with an Alert 360 security system, Lutron lighting controls, multiple WiFi access points, security cameras, and SONOS surround sound anchored by an 85-inch Samsung television in the living room. For the discerning Boca Grande owner seeking state-of-the-art dockage, immediate deep-water Gulf access, and a turnkey luxury residence designed around the boating lifestyle, “The Boat House” represents an exceptionally rare island offering.
Listing Agent: Jamie Curry (941-716-1018)
5010 GROUPER HOLE CT, BOCA GRANDE, FL 33921
$3,975,000184 Days on yellowkey MLS ID: D6145351
REDUCED by $525,000 (11.7%) on 06/09/2026
Bed: 4 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 2648 Built: 1986 Tax: $5,933 (2024)Community: East Shore AcresSingle Family
Taxes:$5,933
Remarks: 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.
Listing Agent: Richard Hugger (941-270-2816)
340 PALM AVE, BOCA GRANDE, FL 33921
$3,295,00073 Days on yellowkey MLS ID: TB8502017
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1080 Built: 1906 Tax: $18,178 (2025)Community: Betton Hill Add 12Spa: NoSingle Family
Taxes:$18,178
Remarks: 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.
252 WATERWAYS AVE, BOCA GRANDE, FL 33921
$5,250,000124 Days on yellowkey MLS ID: D6146498
REDUCED by $245,000 (4.5%) on 05/22/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3500 Built: 1999 Tax: $32,023 (2025)Community: Harbor Drive WaterwaysSingle Family
Taxes:$32,023
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!
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