Location: Boca Grande, Boca Grande
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40 SEAWATCH LAKE DR, BOCA GRANDE, FL 33921
$4,750,00070 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$45,656
Elementary School: The Island School
High School: Lemon Bay High
Tax Year: 2025
Middle School: L.A. Ainger Middle
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)
17 SEAWATCH DR, BOCA GRANDE, FL 33921
$3,900,000240 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)
1600 JEAN LAFITTE DR, BOCA GRANDE, FL 33921
$8,500,000206 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)
36 SEAWATCH DR, BOCA GRANDE, FL 33921
$2,650,000248 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
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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 is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)
Listing Agent: Marcy Davis (941-685-5005)
1669 JOSE GASPAR DR, BOCA GRANDE, FL 33921
$7,500,00077 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)
12 SEAWATCH DR, BOCA GRANDE, FL 33921
$3,250,000101 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.
350 GILCHRIST AVE, BOCA GRANDE, FL 33921
$4,975,000398 Days on yellowkey MLS ID: TB8392464
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2049 Built: 1956 Tax: $34,467 (2024)Community: Boca GrandeSingle Family
Taxes:$34,467
Elementary School: Vineland Elementary
Remarks: LOCATION LOCATION LOCATION-Walk to everything from this truly exquisite 3 bedroom, 2 ½ bathroom Gilchrist Cottage in the heart of the “Historic District”. Loaded with mid-century charm, updated professionally with modern coastal contemporary influence throughout, all nestled onto a deep 50’ by 150’ lot. The property is being beautifully remodeled nearly new and will be delivered Designer furnished for immediate use! This delightful home offers a very private swimming pool area tucked behind privacy fencing covered with fragrant Jasmine, among just planted new lush and additional landscaping. A standing seam metal roof protects the Cottage along with back-alley access to a large, covered carport. The main living area provides a Great Room concept with Philippine Shellstone flooring throughout and a comfortably spacious 10’ by 28’ old fashioned front porch facing the Gulf of Mexico! Estate Wall, extensive pavers, and luminous night lighting offers a very special ambiance at this superb location. A rare opportunity to own in this very limited heart of the Village
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)
Listing Agent: Robert Melvin (941-380-8891)
208 HARBOR DR, BOCA GRANDE, FL 33921
$7,295,000242 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)
760 E RAILROAD AVE, BOCA GRANDE, FL 33921
$5,450,000185 Days on yellowkey MLS ID: D6145439
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3075 Built: 2012 Tax: $19,906 (2025)Community: Boca GrandeSpa: YesSingle Family
Taxes:$19,906
Remarks: Nestled in the heart of Boca Grande's charming historic district, just steps from downtown amenities, this impeccable custom-built home offers the epitome of luxury island living. Constructed in 2012, architecture by T.A. Krebs with unparalleled craftsmanship and attention to detail, this move-in-ready home exudes timeless elegance and modern sophistication. Upon entering, you are immediately captivated by the soaring 24-foot cupola and exquisite 6-inch tongue-and-groove board ceilings, setting a grand tone for the open and inviting interior. The home features three spacious bedrooms and four and a half well-appointed bathrooms, providing ample space for family and guests. Cozy up by one of two stunning brick fireplaces—one gracing the living room and the other in the serene primary bedroom. Throughout, luxurious travertine and wood flooring flows seamlessly, complemented by granite countertops in the gourmet kitchen. Equipped with top-of-the-line Wolf and sub-zero appliances, a convenient garden sink, gas stove, gas oven, and generous pantry, this kitchen is a chef's dream. French doors seamlessly connect the interior to the outdoor oasis: a brick-paved patio overlooking a heated pool and spa and a dedicated pool bathroom for ultimate convenience. Additional highlights include a large upper-level bonus room ideal for extra sleeping or living area or relaxation, durable Hardy board siding, all impact-resistant glass windows and doors for peace of mind, a 2+ car garage, and lush, mature landscaping that envelops the property in privacy and natural beauty. Truly a rare gem in the heart of Boca Grande, this exceptional home blends historic charm with contemporary luxury—ready for you to call it your own.
1627 GASPAR DR S, BOCA GRANDE, FL 33921
$5,300,000130 Days on yellowkey MLS ID: D6146322
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2715 Built: 1990Monthly Fee: $222 Tax: $19,277 (2025)Community: Boca Grande IslesSingle Family
Taxes:$19,277
Remarks: Located in the gated community of Boca Grande Isles, this well-maintained, 3 bedroom, 3 bathroom, waterfront home is a boater’s dream with direct access to Charlotte Harbor and no bridges to the Gulf of Mexico. The 2,715 sq. ft. residence features an open floor plan with vaulted open-beam ceilings, hardwood floors, custom built-ins, plantation shutters, and impact sliding glass doors framing serene canal views and leading to a screened lanai. The remodeled kitchen is appointed with quartz counters, Sub-Zero refrigerator, Wolf gas range, ample workspace, and a dumbwaiter. The living and dining areas flow effortlessly to a 48’ x 10’ screened outdoor space overlooking the water. The spacious primary suite offers canal views, patio access, a generous walk-in closet with washer/dryer, and a renovated bath with quartz counters, dual sinks, soaking tub, and separate rain shower. Outdoors, enjoy a composite dock with a 16,000-lb boat lift, 110’ seawall, two-car garage, golf cart garage, paved circular driveway, and plenty of backyard space with room to add a pool. An air-conditioned storage/workout room offers added versatility. This exceptional canal-front property delivers premier island living and easy Gulf cruising from your own dock.
260 GILCHRIST AVE, BOCA GRANDE, FL 33921
$4,950,000147 Days on yellowkey MLS ID: D6146072
REDUCED by $800,000 (13.9%) on 05/06/2026
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 Agent: Jamie Curry (941-716-1018)
1660 16TH ST E, BOCA GRANDE, FL 33921
$6,500,000184 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.
Listing Agent: Carol Stewart (941-276-1162)
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