Location: Boca Grande
Do Not Show Listings
367 NIGHT HERON DR, BOCA GRANDE, FL 33921
$4,600,000470 Days on yellowkey MLS ID: D6140022
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$16,565
Elementary School: The Island School
High School: Lemon Bay High
Tax Year: 2025
Middle School: L.A. Ainger Middle
Remarks: This unique bayfront home offers stunning sunrises and moonscapes over Charlotte Harbor. The spacious open main floor begins with an entry leading into the two-story living room with hand painted coffered ceiling. This space is accented by the hand painted staircase, custom tera cotta tile floors and a fireplace surrounded by a hand carved pecky cypress mantle. The adjoining dining room continues into the heart of the home providing quiet dining and harbor views. Step down into the kitchen and open family room. The kitchen is completely updated with stainless appliances, granite countertops and a spacious island with a second sink. Both rooms feature cherry flooring, custom woodwork and designer cabinetry with storage features. Adjacent to the kitchen and family room, a waterfront sunroom spans the width of the home, leading to a custom, window filled stairwell to the first-floor storerooms, doubled garage spaces and a garden patio. The property finishes with a garden view leading to the mangrove coastline. There are two large main level guest rooms, one en-suite and a second with an adjacent full bath. The upstairs primary suite welcomes you with built-in shelving and desk, vaulted ceiling and expansive windows facing Charlotte Harbor. The open Roman bath, large walk-in closet and laundry room complete the space. Open the large French doors in the primary bedroom to enter a private deck with amazing harbor views. To complete the deck, a circular staircase leads to a widow's walk with a panoramic view of Gasparilla Island and beyond. Additional highlights include a finished elevator to the first floor, impact glass on all windows and doors, a new metal roof installed in 2023 and all interior walls freshly painted. This North Bay gem, in the amenity rich Boca Bay community, is a true sanctuary combining location, style and natural beauty.
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)
Listing Agent: Carol Stewart (941-276-1162)
260 GILCHRIST AVE, BOCA GRANDE, FL 33921
$5,750,00077 Days on yellowkey MLS ID: D6146072
Bed: 7 Bath: 4.0 Liv Area Sq Ft: 3902 Built: 1925 Tax: $10,992 (2025)Community: Boca GrandeSingle Family
Taxes:$10,992
Remarks: Offered for the first time since 1962, 260 Gilchrist Avenue presents a rare opportunity to acquire a true Boca Grande legacy estate, defined by provenance, architectural presence, and the enduring romance of Old Florida. Built in 1925 and thoughtfully stewarded for generations, this storied residence reflects a time when homes were crafted with intention, scale, and permanence. Sited on an exceptional 100' x 150' in-town parcel, the property is ideally positioned in downtown Boca Grande, just moments from the Village, beaches, dining, and boutiques, yet remarkably private, with a sense of prominence befitting its lineage. The home spans over 3,900 square feet under air, offering seven bedrooms and four bathrooms, with gracious proportions designed for multigenerational living and extended coastal stays. Vaulted ceilings lend volume and elegance, while two original fireplaces anchor the interiors with warmth and authenticity. Original wood floors remain intact, and the home’s cypress walls speak to the craftsmanship and character of an earlier era. A newly completed kitchen introduces a refined modern counterpoint, thoughtfully executed to meet today’s standards for daily living and entertaining while remaining respectful of the home’s historic architectural character. Recent improvements include new HVAC, electrical, and plumbing systems, delivering modern reliability while preserving the home’s timeless soul. A driveway permit is already in place, and the estate is accompanied by a current certified survey. A dedicated local historic specialist has also been engaged to outline the full architectural potential of this exceptional property. Rarely does a Gilchrist Avenue residence of this scale, significance, and authenticity come to market. 260 Gilchrist Avenue is a once-in-a-generation offering rich in history, exceptional in presence, and ideally positioned for thoughtful restoration or inspired reimagination. A true Boca Grande heritage estate, ready for its next distinguished chapter.
Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)
Listing Agent: Jamie Curry (941-716-1018)
3547 GASPARILLA RD, BOCA GRANDE, FL 33921
$2,750,000178 Days on yellowkey MLS ID: D6144543
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2260 Built: 1987Monthly Fee: $14 Tax: $27,145 (2025)Community: Gasparilla IslandSingle Family
Taxes:$27,145
Elementary School: Vineland Elementary
Remarks: SIGNIFICANT PRICE REDUCTION — DEEDED BEACH ACCESS — Attractively priced 3-bedroom, 2-bath home offering easy island living with strong value. Sold turnkey furnished (inventory available), this property is move-in or rental ready. The open floor plan features high ceilings, great natural light, and a spacious living area with a wood-burning fireplace. A bright sunroom provides flexible space, and the separate dining area flows well for everyday use or entertaining. The kitchen includes new appliances, highlighted by a Wolf dual fuel gas range with griddle, plus ample cabinet and counter space. Additional updates include newer AC and impact-rated hurricane doors and windows. Outdoor features include a large Timberline deck, heated pool and spa (resurfaced in 2023), new pool pump and heater, and an authentic chickee hut for outdoor living. A 2023 metal roof adds long-term value. Strong rental history adds to the appeal. Boat Slip #5 at Boca Grande North is available separately, featuring a 10,000 lb lift with a new motor (MLS ID #D6143184). A well-maintained property with deeded beach access and a recent price improvement—ready for immediate enjoyment or income.
Listing is courtesy of: PARSLEY BALDWIN REAL ESTATE (941-964-2700)
Listing Agent: Nancy Hyde (941-539-9616)
847 BELCHER RD, BOCA GRANDE, FL 33921
$4,499,999110 Days on yellowkey MLS ID: D6145524
Bed: 5 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 3063 Built: 2026 Tax: $14,104 (2025)Community: Boca GrandeSingle Family
Taxes:$14,104
Elementary School: None
High School: None
Middle School: None
Remarks: Custom new construction coastal cottage located on the southernmost point of sought-after Boca Grande — just steps from the pristine beaches and emerald-green waters of Gasparilla Island State Park. This thoughtfully designed residence features 5 bedrooms, 4.5 bathrooms, and over 3,000 square feet of living space, highlighted by 13-foot vaulted tongue-and-groove ceilings throughout the main living areas. Built with exceptional quality and efficiency, the home includes spray foam insulation, Andersen impact windows and front door, durable Hardie board siding, and Azek trim for long-lasting coastal performance and peace of mind. The gourmet kitchen is beautifully appointed with a gas Thermador range, panel-ready appliances, and cabinetry offering abundant storage — ideal for both everyday living and entertaining. Each bedroom on the main living level features vaulted tongue-and-groove ceilings, walk-in closets, and private en suites, creating a true retreat for family and guests alike. The 13-foot board-and-batten vaulted hallway serves as a stunning architectural focal point and a statement of craftsmanship. The first floor offers a full-over-full bunk room, a guest bedroom, and a spacious family room, providing flexible living and gathering spaces. Step outside to your shellstone pool deck, where you’ll enjoy a resort-style pool with a waterfall and linear fire feature, all overlooking the outdoor living area complete with a custom stone kitchen — perfect for sunset dinners and coastal entertaining. This tastefully designed coastal cottage blends refined luxury with relaxed island living — just steps from the beach and breathtaking sunsets. Request your private showing today
Listing Agent: Christina Sexton (941-270-2154)
14 GROUPER HOLE DR, BOCA GRANDE, FL 33921
$10,825,000133 Days on yellowkey MLS ID: N6141937
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 6207 Built: 1997 Tax: $56,560 (2025)Community: East Shore AcresSingle Family
Taxes:$56,560
Remarks: 2 DEEP-WATER DOCKS AND A COVERED 7,000 LB LIFT. 5 BEDROOMS AND 5.5 BATHROOMS. MYRTHA POOL. INDOOR GUN RANGE. NO FIXED BRIDGES TO GULF WATERS. ROOF 2017. Welcome to a true Sportsman’s Paradise at 14 Grouper Hole Drive on Gasparilla Island in Boca Grande, Florida. This exceptional waterfront estate offers an unparalleled lifestyle, where breathtaking views of the Gasparilla Sound greet you the moment you step through the grand double doors. Designed for both adventure and relaxation, this residence seamlessly blends refined elegance with world-class amenities. The main living area is on the second floor, accessible by a three-stop elevator. A bright foyer leads into the expansive living room, which is open to the third floor, creating an impressive sense of space with soaring ceilings. The dining area flows effortlessly into the kitchen, where a beautiful bay window breakfast nook offers the perfect setting to enjoy morning coffee with stunning water views. The kitchen features a WOLF gas stove, a Sub-Zero paneled refrigerator, a spacious pantry, and a breakfast bar. French doors from the living room open onto a large screened deck—ideal for entertaining or unwinding as boats pass by. The second floor hosts three guest bedrooms, each with nearly floor-to-ceiling windows and en-suite bathrooms. A half bath and a well-appointed laundry room are also on this level. A striking catwalk on the third floor, adorned with a sculptural iron railing, overlooks the living space below while offering sweeping views of the Sound. The luxurious primary suite is a serene retreat, with private access to an open-air deck to enjoy the waterfront breeze. The en-suite bath features dual vanities, a walk-in shower, and a separate soaking tub. A generous walk-in closet with custom shelving provides ample storage. An additional sitting area with a bay window offers yet another breathtaking vantage point. A well-appointed fifth bedroom, also with mesmerizing water views and an en-suite bath, is located opposite the primary suite. The estate’s crown jewel is the extraordinary sports pavilion, seamlessly connected to the main home. Designed for ultimate recreation, it features an indoor/outdoor sitting and dining area with a retractable mosquito screen and fire pit. Inside, a stylish living space and fully equipped kitchen boast Viking appliances, Kendall Cambria Quartz countertops, a built-in bar refrigerator, and an ice machine. At its heart is the Myrtha Ozone Pool—one of Florida’s most advanced residential pools. Competition-length, with stainless steel bolted technology for durability, it features a European lighting system, the only one of its kind in North America. Exceptionally pure, the water is free of chlorine and salt, making it pristine enough to drink. The pool is both heated and cooled for year-round enjoyment, with a standalone hot tub nearby. Remote controlled hurricane shutters add to piece of mind. The sports pavilion also includes a private, air-conditioned Pilates studio and areas for ping pong and pool. For shooting enthusiasts, the state-of-the-art gun range features two dedicated lanes—one for archery and one for firearms. Equipped with a high-tech camera system for precision accuracy, a retractable target retrievals, advanced bullet entrapment, and sound suppression, this range ensures top tier performance.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
204 WATERWAYS AVE, BOCA GRANDE, FL 33921
$6,450,00077 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)
158 CARRICK BEND LN, BOCA GRANDE, FL 33921
$4,595,000212 Days on yellowkey MLS ID: D6144009
REDUCED by $100,000 (2.1%) on 04/03/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3210 Built: 1993Monthly Fee: $183 Tax: $22,520 (2024)Community: North Village SubSingle Family
Taxes:$22,520
Tax Year: 2024
Remarks: Nestled in the exclusive gated community of Boca Bay's North Village, this stunning 3-bedroom, 3-bathroom home offers over 3,200 square feet of beautifully updated living space with breathtaking lake views. Thoughtfully designed with high-end finishes and modern upgrades, this home is perfect for those seeking both luxury and comfort. The renovated chef’s kitchen is a showpiece, featuring quartz countertops, a shiplap ceiling, Thermador appliances (oven, microwave, and gas stove), a WiFi-enabled Monogram refrigerator, and a built-in ice machine. An eat-in dining area provides a warm and inviting space. The living room impresses with vaulted ceilings, an eye-catching fireplace, and a built-in bar, all enhanced by Sonos surround sound throughout, creating an ideal setting for entertaining or unwinding. Hurricane-impact windows and doors, a newer standing seam metal roof, and plantation shutters throughout provide both elegance and peace of mind. The primary suite is a private retreat, featuring French oak engineered wood flooring, a spacious loft/living area with a private office, and a spa-inspired bathroom with a copper tub and sophisticated accents. Each bathroom has been beautifully updated, adding to the home’s refined feel. Designed for seamless indoor-outdoor living, the expansive lanai offers breathtaking lake views, making it the perfect place to enjoy your morning coffee or entertain guests. A private outdoor shower adds a touch of island charm, while a Zen garden off the dining room enhances the home’s peaceful ambiance. As a resident of Boca Bay, you’ll have access to exclusive world-class amenities, including a private boat basin with slips, a croquet sports field, Har-Tru tennis courts, and four swimming pools, including a lap pool. The Gulf-front Beach Club offers a premier venue for private events, while the community fishing pier provides a serene waterfront escape. Additionally, members have access to the prestigious Pass Club, featuring exceptional dining and social opportunities in an unparalleled waterfront setting. This is a rare opportunity to own a luxurious lakefront home in one of Boca Grande’s most coveted communities. Schedule your private showing today!
Listing Agent: Shawna Wagar (941-307-0712)
160 1ST ST E, BOCA GRANDE, FL 33921
$4,500,000130 Days on yellowkey MLS ID: D6145289
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4039 Built: 2003 Tax: $22,368 (2025)Community: Acreage & UnrecSingle Family
Taxes:$22,368
Remarks: Custom-built by McHugh Porter Builders and designed by historic preservation architect Henry Browne, this 4BR/4.5BA waterfront home offers timeless architecture within the historic district of Boca Grande. Located on a no-bridge boating canal, this property features yellow pine floors, cathedral ceilings with beams, a first-floor primary suite and guest suite, open kitchen, and spacious waterfront porch. Two additional bedrooms and a family room loft with full bath were added in 2011. Xeriscape landscaping, Hardiplank siding, 2022 Metal roof, and a private dock with a 10,000-lb lift complete this exceptional coastal property.
164 1ST ST E, BOCA GRANDE, FL 33921
$4,995,000207 Days on yellowkey MLS ID: D6143872
1 Days Off yellowkey (back on 4/1/2026)
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 5036 Built: 2018 Tax: $33,771 (2024)Community: Acreage & UnrecSingle Family
Taxes:$33,771
Remarks: Under contract-accepting backup offers. Welcome to an extraordinary coastal residence in the historic village of Boca Grande. This meticulously crafted home has an impressive 5,036 square feet, five bedrooms (the first-floor bedroom could be a den or office with direct access to a screened porch), and five bathrooms. This sturdy and elevated home on the natural “crown” of the island has not suffered any hurricane damage from wind or water. The home and the setting epitomize small island living. This remarkable home features an open floor plan, custom woodwork and oak flooring. The gourmet kitchen features professional-grade appliances including a Subzero refrigerator, a 4 burner Wolf stove with griddle, Miele wall steam oven, and an Asko dishwasher. A custom-designed breakfast bar, walk-in pantry, and an innovative Miele coffee bar cater to both daily living and elegant entertaining. This home features an 11’ curved “live edge” tiger maple bar with a bar sink, refrigerator, ice machine and custom cabinetry. Wine connoisseurs will appreciate the 100+ bottle custom chilled wine closet. The bar and adjoining lounge areas have LED “star constellation” lighting for a clean and enchanting ambiance. The bar and lounge look out through large disappearing sliding-glass doors to the coral stone patio, outdoor wood fireplace and canal, inviting seamless indoor-outdoor living with highly desirable southern exposure. Practical luxury abounds with an elevator, impact glass windows and doors, Hardi Plank siding, and a metal roof ensuring both comfort and security. The oversized garage accommodates both vehicles and a golf cart, perfect for exploring the charming village surroundings. The private den/office/bedroom, separate formal dining room, library, and bonus room offer versatile spaces for work and leisure. The home features a formal dining room that could be used alternatively as a music conservatory or a large, sunny office. There is a “bonus” room on the midlevel that has a full laundry with folding table and drying closet, a number of cleverly hidden spaces for storage, and a vaulted ceiling central space for work or leisure. The second floor features a gallery hallway and library with access to an outdoor balcony. For sailing or powerboat enthusiasts, the property's 80’ dock and 10,000-pound boat lift provide direct, deep-water access to Florida's pristine waters, without height-restrictive bridges. The home's location on the nearest canal to the center of town, offers boaters optimal convenience and privacy. The dock itself has a swim ladder and a custom-designed pivoting platform for safely launching small crafts like paddle boats, kayaks and SUP boards. Snook and other game fish can be caught right off the sunny dock, and the dock has a fish-cleaning station. Thoughtful additions include electric screens, a hidden wall safe nook, custom closet wooden built-ins, pocket doors, Plantation shutters, motion detection lighting, and innovative storage solutions demonstrate the meticulous attention to detail throughout this exceptional property. This residence stands as a testament to luxurious coastal living, where every element has been carefully considered to create an unparalleled living experience.
Listing Agent: Angela Steffan (941-855-1277)
12 SEAWATCH DR, BOCA GRANDE, FL 33921
$3,250,00031 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 GrandeSingle 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.
Listing Agent: Ralph Dilena, Jr. (941-380-0878)
1660 16TH ST E, BOCA GRANDE, FL 33921
$6,500,000114 Days on yellowkey MLS ID: D6145442
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4511 Built: 1991 Tax: $19,645 (2024)Community: Boca GrandeSingle Family
Taxes:$19,645
Remarks: Positioned in a secluded and private corner of Boca Grande, this exceptional estate boasts prime deep-water dockage, with direct access to Charlotte Harbor and no bridges to the Gulf of Mexico. Expansive canal frontage and outstanding boat dockage with an 8,000 lb boat lift provides ample space for a large yacht and multiple smaller vessels. Immerse yourself in magnificent views of the bay, bayou, and Gulf from numerous rooms, porches, and balconies. With over 4,500 sq.ft. of living space, the home features 4 bedrooms, 4.5 baths, and a variety of sitting and study rooms. The grand living areas include soaring ceilings, formal dining, family, and breakfast rooms, and a master suite that is nothing short of enormous. Upstairs, you'll find an additional family room perfect for relaxation. The Victorian-style design is filled with intricate architectural details such as columns, corbels, large coral stone wood burning fire place, Venetian glass chandeliers, and stained-glass windows and doors. Restored cypress cabinetry and built-in loft beds in one of the guest bedrooms add unique custom touches to the interior. Just a short stroll or golf cart ride to the legendary Gasparilla Inn, the village of Boca Grande, renowned restaurants, and shops, or across the street to miles of pristine sandy beach. This paramount boating location is a dream for both anglers and pleasure cruisers, with world-class backwater and tarpon fishing right at your fingertips. Charming island destinations, including Don Pedro and Cabbage Key, are also just a short pleasure cruise away. The property includes the submerged land behind the home, which allows for tremendous flexibility if redesigning the dock.
252 WATERWAYS AVE, BOCA GRANDE, FL 33921
$5,495,00055 Days on yellowkey MLS ID: D6146498
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!
Listing Agent: Maryjo Pigott (941-961-0630)
5010 GROUPER HOLE CT, BOCA GRANDE, FL 33921
$4,500,000115 Days on yellowkey MLS ID: D6145351
Bed: 4 Bath: 2.5 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)
208 HARBOR DR, BOCA GRANDE, FL 33921
$7,295,000172 Days on yellowkey MLS ID: D6143951
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 1718 Built: 1994 Tax: $31,828 (2023)Community: Boca Grande AddSingle Family
Taxes:$31,828
Tax Year: 2023
Remarks: RARE OPPORTUNITY OF PURCHASING A CUSTOM WATERFRONT HOME WITH PRIVATE “MARINA” WHICH INCLUDES 3 DEEPWATER SLIPS, 2 OF WHICH ARE UP TO 100 FEET IN LENGTH, IN THE HEART OF BOCA GRANDE! Located with easy access to the ICW from the Millers Marina Channel this is a one of a kind property. Offering deepwater, long slip lengths and housing for the owner and/or the crew! Of the two covered slips, one is 60ft x 18 1/2ft and the other slip is 100ft x 18 1/2ft. Both boat covers are a work of art and engineered with concrete 45 ft long driven pilings, metal roof detailed with a yellow pine underside and galvanized aluminum. The center slip is 100ft x 20ft and is equipped with a lift. A tackle room is conveniently located adjacent to the dock for easy access. Designed by architect George Palermo and built by Pat Ball of Ball Construction originally on a 50 ft wide lot in 1994 then added on in 1999 when a 25ft adjacent lot was purchased for a combined 75ft of prime waterfront. The home consists of 4 bedrooms, 4.5 baths, a comfortable kitchen and living area, loft, large screened deck overlooking the water and boat docks plus a roof top deck. The house can be used as a primary or vacation home as well as staff for crew and team members. The main house has a kitchen and living area with sliders and a screened lanai overlooking the water and docks. The master bedroom has a queen bed and an en suite bathroom with a stall shower. There is also a guest bedroom with a queen-sized bed, both bedrooms have sliders to enjoy the view, with electric hurricane shutters for extra protection. A loft area overlooks the living area and water with a trundle bed but is also perfect for an office! The “Lighthouse” is accessed via a rear entrance to a bedroom with an en suite full bath, then up a set of stairs to a loft with built-in bunk beds and a full bath. There is a special rooftop deck with a custom copper topped light with access via pull down stairs. Call now for a private showing of this special piece of Boca Grande, Florida.
Listing is courtesy of: THE BRC GROUP, LLC (941-964-8180)
Listing Agent: Brian Corcoran (941-626-3439)
38 SEAWATCH LAKE DR, BOCA GRANDE, FL 33921
$2,250,000422 Days on yellowkey MLS ID: D6141118
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3057 Built: 1988Monthly Fee: $707 Tax: $14,249 (2025)Community: Seawatch Boca GrandeSingle Family
Taxes:$14,249
Remarks: One or more photo(s) has been virtually staged. This waterfront Seawatch residence in Boca Grande offers over 3,000 sq. ft. of living space showcasing stunning views of Lake Gasparilla and its abundant birdlife. This spacious home features three bedrooms, three bathrooms, and multiple bonus areas that could become your office or library. Expansive glass sliding doors lead to a large open porch with unhindered lake views. The eat in kitchen was recently outfitted with new stainless appliances and has plenty of counter space and a roomy pantry. The top floor leads to an en-suite main bedroom with updated bath, a private, open deck, and an upper-level “Seawatch” room. This property has impact, storm rated doors and windows, hardwood floors, updated fixtures and much more. As part of the popular, gated Seawatch community, residents enjoy two pools, three tennis courts, and private beach access to the islands best beach.
858 GRANDE PASS WAY, BOCA GRANDE, FL 33921
$7,995,0001331 Days on yellowkey MLS ID: D6127374
1 Days Off yellowkey (back on 3/25/2026)
Bed: 4 Bath: 5.5 Liv Area Sq Ft: 5433 Built: 2024Community: Hill Tide EstatesSingle Family
Taxes:
Tax Year:
Remarks: Under contract-accepting backup offers. Brand New Construction*** Another Luxury Model Home at Hill Tide Estates is now complete and turnkey ready! The ‘fully furnished’ Sunny Isles Model presented by Seagate Development Group & Theory Design features a unique blend of elegance and precision craftsmanship. The multi-level floor plan offers panoramic water views of Boca Grande Pass and sunsets over the Gulf of Mexico. Theory Design’s custom décor furniture package offers convenience and instant gratification for the most selective Buyer. The second level / main floor features a spacious Master Suite with an additional VIP Suite that will be enjoyed by your special guests. Seagate's showcase custom kitchen is tastefully appointed with beautiful wood cabinetry, Thermador built in appliances, massive quartz dining island, and a cocktail cabinet with beverage cooler & ice maker. Outdoor living will be the focal point of this model as the elevated custom saltwater pool & spa is conveniently accessed off the main level. Elegant waterfalls gently spill over into main pool complemented with custom spa and sun shelves. The spacious covered lanai features remote screens, custom double sided fireplace, and an outdoor summer kitchen. The top / third level offers 2 additional bedroom ensuites, and a captivating sunset room with additional beverage & ice maker for entertaining. Hill Tide Estates or the “Jewel of Boca Grande” is majestically positioned along the shores of Boca Grande Pass. This 19-luxury home site development offers panoramic seascape unmatched anywhere else on Gasparilla Island. The gated community features a private tiered beach, and a unique private fishing / observation pier in Boca Grande Pass exclusive for the 19 homeowners.
Listing Agent: Heath Seckel (863-207-2586)
2021 20TH ST W, BOCA GRANDE, FL 33921
$7,950,00067 Days on yellowkey MLS ID: D6146286
Bed: 8 Bath: 7.0 Liv Area Sq Ft: 5792 Built: 1998Community: Acreage & UnrecSingle Family
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.
1000 E RAILROAD AVE, BOCA GRANDE, FL 33921
$9,995,000132 Days on yellowkey MLS ID: D6145234
Bed: 5 Bath: 6.0 Liv Area Sq Ft: 6417 Built: 1975Community: Boca GrandeSingle Family
Remarks: Extraordinary legacy estate in the heart of Boca Grande’s Historic District is a true West Indies–inspired sanctuary where timeless architecture, artisan craftsmanship, and tropical elegance converge. Expansive estate lot, 6,417-sq ft residence offers complete privacy and an undeniable sense of discovery—with enchanting architectural moments revealed around every corner. Natural stone, rich woods, and refined detailing of understated luxury. Custom mahogany and cypress accents, intricate ceiling designs, sculpted wood columns, and expansive French doors define the home’s open, flowing footprint. Impact-rated windows and doors flood each room with natural light, while it is notable that none of the living areas experienced water intrusion during past hurricanes. Dominican coral stone extends across both exterior and interior surfaces, architectural continuity reinforces the home’s island character. Designed for effortless gatherings of any size, offers an exceptional array of indoor and outdoor entertaining spaces. Expansive living and dining areas flow seamlessly to beautifully appointed patios, covered lounges, and inviting courtyard retreats. Multiple conversation areas and a well-equipped kitchen make hosting intimate dinners and large celebrations easy. Outdoors, resort-style amenities create a private backdrop for poolside afternoons, evening cocktails, and unforgettable events—an entertainer’s dream. Over 4,000 sq ft of space that opens to a breathtaking courtyard oasis, where cascading waterfalls, lush landscaping and ambient lighting transform the grounds into a private retreat. Stunning heated pool & spa, glass-tile sunshelf complemented by an outdoor kitchen, mosquito-misting system, and whole-property landscape lighting for effortless living year-round. The chef’s kitchen boasts river granite countertops, island, custom cabinetry, premium appliances, and multiple bar areas. Modern technology integrates discreetly with the whole-home Sonos sound system and automated Lutron lighting control. Curated living and entertaining spaces include a gracious dining room, expansive living areas, a dedicated home office, and an upper-level media/entertainment room. The private owner’s wing is an intimate sanctuary with a vast bedroom offering tranquil views across the pool and gardens. The spa-inspired bath offers a luxurious retreat with an oversized walk-in shower, oversized jacuzzi tub, exotic stonework, dual vanities, and elegant lighting. Dual walk-in closets provide generous storage and customization. This 5-bedroom, 6-bath estate offers four additional guest suites, each beautifully appointed with its own ensuite bath, spacious closets, and custom finishes. For boating enthusiasts, the property’s location is second to none—moments from premier local marinas, effortless access to Gasparilla Sound and the Gulf. Enjoy a day of island hopping, world-class fishing, or a sunset cruise, and every adventure begins with ease. Privately enclosed and secured by dual power-operated gates and a paver driveway with decorative turf inlays and a fully gated perimeter for exceptional security and privacy. For pet lovers, dedicated spaces, conveniences, and secure landscaped outdoor areas provide room to roam. Perfectly equipped for pets to enjoy the luxury lifestyle right alongside their owners. The estate is just a golf cart ride from Boca Grande’s world-renowned beaches, shopping, dining, and historic village center—yet feels worlds away.
Listing Agent: Michelle Finley (941-204-4000)
250 WHEELER RD, BOCA GRANDE, FL 33921
$3,795,000196 Days on yellowkey MLS ID: D6143946
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2552 Built: 2001Community: Acreage & UnrecSingle Family
Remarks: Perfectly located only steps to the beach and a quick bike ride to the village of Boca Grande! This thoughtfully renovated 3 bedroom, 3 1/2 bath pool home is completely updated inside and out and offered turnkey furnished! The large and inviting front porch has plenty of room for outdoor living with seating to enjoy a meal or the colorful sunsets! Built with hardi plank siding, all impact resistant windows and doors, and a newer (2022) metal roof! Enter and you will find wood floors throughout, a living room detailed with built-ins, and a large dining area. The kitchen features an island with seating for 4, gas stove, quartz countertops, tile backsplash, stainless steel appliances and a wine refrigerator. To enjoy the outdoors, there is a fenced and heated swimming pool area with an oversized pool deck offering open or covered seating areas. There is also plenty of open parking plus space under the house, as well as an enclosed golf cart garage! For the dog lover, this home is conveniently located near Lee County Park offering fenced dog parks. You can also enjoy the seasonal Boca Grande Famer’s Market, community tennis courts, and just a short walk to watch the spectacular sunsets on the Gulf waters beyond the Boca Grande range light built in 1927!
9901 NE GASPARILLA PASS BLVD, BOCA GRANDE, FL 33921
$5,575,000 MLS ID: D6146380
Bed: 5 Bath: 5.0 Liv Area Sq Ft: 4016 Built: 2025Community: Gulf Shores North 04Single Family
Remarks: One or more photo(s) has been virtually staged. Modern Coastal Luxury - NEW HOME - Just Completed! Discover one of Boca Grande’s newest and most exclusive homes on the prestigious North Shore of Gasparilla Island. This brand-new 5-bedroom, 5-bathroom estate (each bedroom featuring en-suite bathrooms) offers over 4,000+ sq. ft. designed for effortless coastal entertaining on one level. Set at the end of a private living cul-de-sac and positioned on one of the highest elevated lots on the island, the property is surrounded by masonry privacy walls and features professionally designed lush tropical landscaping. Once inside, you’ll find soaring ceilings, custom millwork, 7.5” white oak flooring, and impact-rated sliders that blend indoor and outdoor living. A unique zero-post sliding glass door system leads to an expansive covered lanai (600+ sq. ft.) featuring a retractable Phantom Screen, custom outdoor kitchen with Coyote appliances, while overlooking the elegantly designed pool and spa. The home is an entertainer's dream featuring a chef’s inspired kitchen complete with designer cabinetry, Thermador appliances, extra-large workstation sink, dual dishwashers, quartz countertops, and a 12' center island perfect for hosting. Additional highlights include a wet bar and prep area coupled with a wine chiller tower, beverage center, spacious walk-in pantry, and discreet mudroom/laundry area. The primary suite is thoughtfully designed offering a majestic view of the pool and backyard with separate walk-in closets. The primary bathroom is a serene retreat offering heated floors, an oversized shower and soaking tub, along with custom Robern medicine cabinets and designer lighting. The additional en-suite bathrooms offer their own privacy and Bedroom 2 can also serve as a den or office if desired. Guest suite bathrooms provide private comfort with curbless walk-in showers and custom designer finishes throughout. Designed by nationally recognized T.A. Krebs Architects, and crafted by preferred island builder L.J. Silva Construction, this 2025 masterpiece combines masonry block construction with energy-efficient spray foam insulation, premium concrete tile roofing, "cool touch" Shellock pool and lanai pavers, and a 24 kW Generac generator. With an attached 3-car garage, the home has ample storage for your Moke or golf cart and other outdoor island toys. Smart home technology includes an app-controlled pool/spa & fireplace lighting, irrigation, sound pre-wiring throughout and a 75" Samsung Frame Pro TV in the family room. Deeded beach access is just steps away and ownership boat dockage with lift capability (up to 65') is just across the road, for easy and quick access if desired. This estate offers both tranquility and accessibility to the island’s best amenities. Along with Coral Creek Jet Center/Airport and a Tom Fazio Signature Golf Course just across the Bridge. A few photographs are virtually staged. Experience the pinnacle of Boca Grande living - modern coastal luxury at its finest.
Listing Agent: Jeff Moore (941-855-0737)
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