Location: Boca Grande
Keyword(s): L.A. Ainger Middle
Keyword(s) Middle School: L.A. Ainger Middle
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)
6030 BOCA GRANDE CSWY #B21, BOCA GRANDE, FL 33921
$1,375,00071 Days on yellowkey MLS ID: D6146964
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1683 Built: 1985 Tax: $12,732 (2025)Community: Boca Grande North Ph BSpa: YesCondo
Taxes:$12,732
Remarks: One or more photo(s) has been virtually staged. Rare by design. Exceptional by location. Only six 3-bedroom, 3-bathroom residences exist at Boca Grande North, and this is the only one currently on the market. Enjoy expansive living spaces and sweeping views of both the Gulf of Mexico and Gasparilla Sound—an extraordinary combination that rarely becomes available 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 Sound 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 Sound-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 (941-214-3111)
Listing Agent: Cheryl Hayek, Llc (732-539-5777)
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 is courtesy of: BOCA GRANDE REAL ESTATE, INC. (941-964-0338)
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)
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)
6020 BOCA GRANDE CSWY #43 Boat Slip, BOCA GRANDE, FL 33921
$215,00014 Days on yellowkey MLS ID: D6147879
Bed: Bath: 0.0 Built: 2012Monthly Fee: $180 Tax: $2,043 (2024)Community: Boca Grande North Marina CondoDock-Rackominium
Taxes:$2,043
Tax Year: 2024
Remarks: Boca Grande North Marina Boat Slip #43 includes a 10,000-pound capacity boat lift. All docks are made of composite materials. The Boat Slip is deeded, and you do not need to be a Boca Grande North condominium owner to purchase! The boat lift can fit either a pontoon boat or "V" hull boat as aluminum bunkers are in place. Deepwater with no bridges and only minutes to the ICW and Gulf!
Listing is courtesy of: THE BRC GROUP, LLC (941-964-8180)
Listing Agent: John Corcoran (941-716-4741)
6040 BOCA GRANDE CSWY #11 Boat Slip, BOCA GRANDE, FL 33921
$190,000199 Days on yellowkey MLS ID: D6145288
Bed: Bath: 0.0 Built: 2012 Tax: $2,161 (2025)Community: Boca Grande North Marina CondoDock-Rackominium
Taxes:$2,161
Remarks: Price decrease! Boca Grande North Marina Boat Slip #11 includes a 10,000-pound boat lift. All docks are made of composite materials. The Boat Slip is deeded, and you do not need to be a Boca Grande North condominium owner to purchase! Deep water with no bridges and minutes to the Gasparilla Sound and the Gulf. Well maintained boat lift and recent service invoices available upon request.
6040 BOCA GRANDE CSWY #03 Boat Slip, BOCA GRANDE, FL 33921
$185,000184 Days on yellowkey MLS ID: D6145421
REDUCED by $10,000 (5.1%) on 06/23/2026
Bed: Bath: 0.0 Built: 2012 Tax: $2,693 (2025)Community: Boca Grande North Marina CondoDock-Rackominium
Taxes:$2,693
Remarks: Priced to sell! Motivated Seller! Boca Grande North Marina Boat Slip #03 includes an 8,000-pound boat lift. All docks are made of composite materials. The Boat Slip is deeded, and you do not need to be a Boca Grande North condominium owner to purchase! Deep water with no bridges and minutes to the Gasparilla Sound and the Gulf. Well maintained boat lift.
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.
Listing Agent: Maryjo Pigott (941-961-0630)
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)
290 GULF BLVD #14, BOCA GRANDE, FL 33921
$2,795,000248 Days on yellowkey MLS ID: D6144562
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1408 Built: 1979Monthly Fee: $292 Tax: $21,673 (2025)Community: Lighthouse Residence 14Half Duplex
Taxes:$21,673
Remarks: BEACH LOVER'S DREAM IN BOCA GRANDE Imagine waking up to the gentle sound of waves and breathtaking Gulf views right from your window. This charming 3-bedroom, 2-bathroom townhouse offers 1,408 square feet of beachfront living at its finest. Just steps from the sand, this turnkey property lets you embrace the coastal lifestyle immediately. Enjoy your morning coffee on the screened porch while watching dolphins play in the Gulf waters. The townhouse has a new roof, a newly installed HVAC system, updated flooring, and new appliances that add modern convenience to this beach retreat. With an open floor plan and three bedrooms there is ample space for family and friends. Location? Simply perfect! A short golf cart ride delivers you to the Historic Village of Boca Grande with its charming shops and restaurants. Beach enthusiasts will appreciate the direct beach access – no streets to cross, just a sandy path leading straight to paradise. The lower level offers a large, shaded area to congregate after fun at the beach, for grilling, or golf cart or car parking. The townhome has a robust rental history that makes this an attractive investment opportunity when you're not enjoying it yourself.
420 GULF BLVD #6, BOCA GRANDE, FL 33921
$2,450,000230 Days on yellowkey MLS ID: D6144829
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1328 Built: 1981Monthly Fee: $477 Tax: $19,991 (2025)Community: Sundown ColonyTownhouse
Taxes:$19,991
Remarks: Experience breathtaking sunsets and the soothing sound of waves just steps from your door. This beautiful two-bedroom, two-and-a-half-bathroom townhome offers the perfect blend of comfort and coastal living, located directly on the Gulf of Mexico and conveniently close to downtown, restaurants, and the community center. Step out your backdoor to immerse yourself in the serene beauty of the Gulf and the surrounding nature. Features include granite countertops, screened lanais with durable Trex decking, and access to a community pool for relaxation. Don't miss this opportunity to own a slice of paradise!
Listing Agent: Don Lutz (941-456-9614)
5850 GASPARILLA RD #M4, BOCA GRANDE, FL 33921
$495,00053 Days on yellowkey MLS ID: D6147496
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 686 Built: 1981 Tax: $8,565 (2025)Community: Marina Village Ph 01Spa: YesCondo
Taxes:$8,565
Remarks: Experience the ultimate in carefree island luxury with this elevated, top-floor 1-bedroom, 1-bathroom condo in Marina Village at the Boca Grande Club, offering stunning views of Gasparilla Sound and Uncle Henry’s Marina. This charming coastal retreat provides exceptional peace of mind with hurricane impact glass windows and doors throughout, a durable metal roof, newer siding and soffits, and newer 2023 HVAC system and hot water heater for enhanced comfort and efficiency. The open-concept interior flows seamlessly to a private balcony, creating the perfect outdoor setting to watch boats glide across the water while enjoying gentle breezes off the Sound. As part of the exclusive, gated Boca Grande Club, residents enjoy unparalleled access to world-class Gulf-front amenities, including miles of pristine white-sand beaches, Gulf-front dining at the Clubhouse with some of the best views on the Island, premier tennis facilities, and two resort-style Gulf-side pools, in addition to the sparkling pool just steps away within Marina Village. The Club also features a state-of-the-art fitness center with personal training services available, along with a vibrant social calendar filled with activities such as yoga and water aerobics. Enhancing the effortless island lifestyle, Marina Village offers a private golf cart gate providing convenient and discreet access into town while bypassing the main road entirely. Representing exceptional value as either a turnkey investment property or private island getaway, this top-floor residence captures the very best of the Boca Grande lifestyle.
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