Location: Boca Grande
Keyword(s): L.A. Ainger Middle
Keyword(s) Middle School: L.A. Ainger Middle
Do Not Show Listings
40 SEAWATCH LAKE DR, BOCA GRANDE, FL 33921
$4,750,000Listed 05/01/2026 4:43PM 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)
5700 GULF SHORES DR DR #A-117, BOCA GRANDE, FL 33921
$1,450,0001 Day on yellowkey MLS ID: D6147220
0 Days Off yellowkey (back on 5/1/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1411 Built: 1980 Tax: $12,324 (2025)Community: Sea Oats Of Bocal GrSpa: YesCondo
Taxes:$12,324
Elementary School: Vineland Elementary
Remarks: Experience effortless coastal living in this beautifully updated 2-bedroom, 2-bathroom first-floor beachfront end-unit, perfectly positioned for unobstructed Gulf views and seamless indoor-outdoor living. This rare corner residence is filled with natural light, offering an open and inviting layout designed to maximize both comfort and scenery. Step out from your living space and enjoy the convenience of ground-level access—no stairs needed—while still benefiting from the building’s elevator for easy guest access. The thoughtfully updated interior features a bright, coastal-inspired design with modern finishes, creating a relaxed yet refined retreat. The spacious primary suite offers a peaceful escape, while the guest bedroom provides ample room for family or visitors. Residents enjoy a well-rounded suite of amenities, including a sparkling community pool just steps away, tennis courts for active afternoons, and both gas and charcoal grilling areas ideal for entertaining. A dedicated golf cart charging area adds convenience for island-style living. This meticulously maintained community ensures a tranquil environment with a strict no-pet policy for both owners and rental guests, preserving the serene atmosphere. Whether you're seeking a full-time residence, seasonal getaway, or investment opportunity, this Gulf-front gem delivers unmatched accessibility, amenities, and breathtaking coastal views in one exceptional package.
Listing is courtesy of: BOCA GRANDE REAL ESTATE, INC. (941-964-0338)
Listing Agent: Don Lutz (941-456-9614)
312 BAILY ST, BOCA GRANDE, FL 33921
$3,250,0003 Days on yellowkey MLS ID: D6147192
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2572 Built: 2003 Tax: $38,895 (2025)Community: Golden BeachSingle Family
Taxes:$38,895
Remarks: Under contract-accepting backup offers. Welcome to 312 Baily St — a charming 3-bedroom, 3-bath home in the Golden Beach neighborhood on the south end of Boca Grande, just one block from the Gulf of Mexico. Built in 2003, this custom 2,572 sq ft home offers an open floor plan with a third-level bonus room featuring expansive island views. Inside, vaulted ceilings, hardwood floors, oversized windows, and a skylight bring in natural light throughout, with a tucked-away reading nook for relaxed afternoons. The kitchen offers a gas cooktop, ample counter space, and a breakfast bar for casual meals and gathering. The primary suite includes a private deck, office space, and a spacious bath with soaking tub, walk-in shower, and double sinks. A large screened porch overlooks the oversized, beautifully landscaped lot, offering a private, quiet setting. A three-car garage provides ample space for vehicles, golf carts, storage, and beach gear, so parking is never a concern. This property boasts concrete block construction at the ground level, along with an elevated structure, Hardiplank siding, and a metal roof for lasting durability. Close to the beach, the village of Boca Grande, the lighthouse, and the Gasparilla Inn & Club, the property’s location makes it easy to enjoy everything the island has to offer. Nearby amenities include pickleball and tennis courts, a local farmers market, and a dog park. Comfortable coastal living in one of Boca Grande’s most desirable neighborhoods. Don’t miss your chance to call Boca Grande home.
Listing Agent: Angela Steffan (941-855-1277)
6030 BOCA GRANDE CSWY #B21, BOCA GRANDE, FL 33921
$1,375,0003 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. 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 Bay 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 Bay-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)
767 S HARBOR DR #1B, BOCA GRANDE, FL 33921
$2,249,00088 Days on yellowkey MLS ID: D6145871
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1770 Built: 1997Monthly Fee: $348 Tax: $16,986 (2025)Community: Harborside/Boca BaySpa: YesCondo
Taxes:$16,986
Remarks: Stunning 3-bedroom, 2 1/2-bath waterfront residence on the shores of Charlotte Harbor, offering exceptional bay views and unforgettable sunrises. Located in a beautifully landscaped community featuring a pool and spa, fishing pier, and resort-style amenities, this home is designed for both comfort and coastal living. The open-concept living area allows you to take in sweeping water views while cooking, dining, or relaxing in front of the TV. Interior highlights include solid-surface countertops, crown molding, and a spacious primary suite with dual closets and dual vanities. Step out onto the lanai to enjoy morning sunrises, waterfront meals, and the daily parade of passing boats. The residence is in excellent condition and features impact-resistant windows, doors, and sliders, along with electric shutters for added peace of mind. Additional conveniences include a private garage, direct elevator access into the unit, and a large ground-level storage room. Ownership includes access to all Boca Bay amenities, including tennis courts, a fitness facility, four community pools, the Pass Club restaurant, and more. $ 50,000 and $ 20,000 one time membership fees are due at closing.
Listing is courtesy of: THE BRC GROUP, LLC (941-964-8180)
Listing Agent: Dawn Havens (941-504-7845)
1671 JOSE GASPAR DR, BOCA GRANDE, FL 33921
$3,995,00030 Days on yellowkey MLS ID: D6146862
REDUCED by $400,000 (9.1%) on 04/30/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2301 Built: 1988Monthly Fee: $188 Tax: $11,368 (2025)Community: Boca Grande IslesSpa: NoSingle Family
Taxes:$11,368
Remarks: Experience waterfront living in this recently updated Boca Grande residence, ideally positioned along the serene shores of Gasparilla Sound. This four-bedroom, four-bath pool home blends timeless coastal charm with thoughtful modern upgrades, starting with its inviting curb appeal and welcoming entry. Inside, elegant shiplap detailing enhances the interior walls, adding warmth and character throughout. The home features an updated kitchen and breakfast room with stunning water views. The second-floor primary suite serves as a private retreat, complete with a updated bath and its own waterfront deck. Three additional bedrooms, two en suite, offer private entrances off the pool, creating a perfect setup for guests or extended family. Storm-resistant doors and windows flood the home with natural light while providing peace of mind and added protection. Step outside to embrace the ultimate waterfront lifestyle. The expansive pool area overlooks the water, complemented by a private boardwalk and dock—ideal for kayaks, paddleboards, fishing, or simply enjoying breathtaking sunsets. This exceptional property is a perfect opportunity to own an island home in Boca Grande —where comfort, and coastal beauty come together seamlessly.
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)
Listing Agent: Carol Stewart (941-276-1162)
460 GULF BLVD #4, BOCA GRANDE, FL 33921
$2,800,000191 Days on yellowkey MLS ID: TB8437810
REDUCED by $195,000 (6.5%) on 04/29/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1131 Built: 1978Monthly Fee: $242 Tax: $20,143 (2024)Community: Gulf DunesTownhouse
Taxes:$20,143
Tax Year: 2024
Remarks: Spectacular Southern exposure corner beach front villa that has been impeccably rebuilt featuring expanded, incredible, open beachfront sunning deck maximizing the Gulf of America sunset views! The main level includes an open and spacious living room, dining area, and all new stainless GE appliances, custom wood cabinetry and beautiful Marble countertops throughout the home. Meticulously crafted wood finishes, plank tile, maintenance free floors throughout, looks exactly like wood. Additional features include; refined wood staircase, cable railing, custom lighting, subway tile backsplash and much more! Gulfside screened porch out to the newly added spacious open deck on the beach! The Southern exposure and Westerly Sunsets are breathtaking. Top floor is comprised of the guest ensuite bedroom and bath, Gulfside Master ensuite bedroom and bath...complete with screened porch and floating Teak deck. The ground level, out of the sun patio features a fully enclosed outdoor shower, all leading to the pristine beach. The newer enclosed garage is air conditioned and offers back of the enclosed space french doors for south side access for the golf cart and a Hurricane Rated garage door for your SUV. The revamped exterior features; 2021 metal roof, impact glass throughout, Trex decking with soffits, trim and composite siding. HOA approved plans to add an ensuite bedroom with modified entry. Excellent rental history if desired. A complete, like new, beautiful Townhome...come and visit this almost completely rebuilt - only 10 home - beachfront development!
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)
Listing Agent: Robert Melvin (941-380-8891)
5000 GASPARILLA RD #BC306, BOCA GRANDE, FL 33921
$1,150,00024 Days on yellowkey MLS ID: D6146747
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 828 Built: 1984 Tax: $13,139 (2025)Community: Beach Chalet Bld GSpa: YesCondo
Taxes:$13,139
Remarks: Experience effortless coastal living in this beautifully appointed one bedroom, two bath condo, perfectly positioned on the desirable 3rd floor with sweeping Gulf of Mexico views. Offered fully furnished, including a built in queen Murphy bed for guest, and ready for immediate enjoyment or rental income potential. Located within the exclusive Boca Grande Club, residents enjoy an array of resort style amenities, including three sparkling pools, a gulf front private restaurant, a lively tiki bar, a state-of-the-art fitness center, and eight Har-Tru tennis courts. A premier tennis program with professional instruction, along with on site rental management and housekeeping services, ensures both convenience and exceptional lifestyle appeal. Just a short golf cart ride away, you’ll find the charming Village of Boca Grande, offering boutique shopping, dining, and Old Florida charm. Whether you’re seeking a serene getaway or a smart investment opportunity, this exceptional beachfront condominium delivers the best of both worlds. Membership fees apply for ownership. Please inquire for cost.
Listing Agent: Kristin O'Connor (941-457-9553)
5020 GROUPER HOLE CT, BOCA GRANDE, FL 33921
$4,675,00087 Days on yellowkey MLS ID: D6145898
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 2951 Built: 2002 Tax: $71,279 (2025)Community: East Shore AcresSpa: NoSingle Family
Taxes:$71,279
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)
340 PALM AVE, BOCA GRANDE, FL 33921
$3,295,0005 Days on yellowkey MLS ID: TB8502017
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1080 Built: 1906 Tax: $18,178 (2025)Community: Betton Hill Add 12Spa: NoSingle Family
Taxes:$18,178
Remarks: Nestled in the heart of Boca Grande’s coveted “Historic District”, this enchanting two-bedroom, two-bathroom, plus bunkroom Palm Cottage built in 1906 has been thoughtfully reimagined with refined designer finishes and modern conveniences throughout. As you walk up to the property you are greeted by lush tropical landscaping, offering both privacy and vivacious natural beauty. Inside, the front sitting room and dining area is bathed in natural light, creating an inviting space equally suited for tranquil mornings or intimate gatherings with family and friends. At the center of the home, the living room and kitchen blend effortless comfort with understated sophistication. An open-concept design is enhanced by custom built-ins, a charming reading nook, and a generous central cooking island – ideal for entertaining. Overhead, a beautifully crafted tongue-and-groove stained wood ceiling adds warmth and architectural character. The primary suite serves as a serene retreat, complete with a spacious walk-in closet and a spa-inspired en-suite bath featuring a beautifully appointed shower. French doors open directly to the rear porch, inviting seamless indoor-outdoor living. The backyard presents a rare opportunity to curate your own private oasis, with ample space to envision a pool, pavilion, or thoughtfully designed entertaining terrace. This exceptional cottage captures the essence of Boca Grande living – timeless, relaxed, and effortlessly elegant. Both an addition and pool/spa have been professionally designed for the Property. The Cottage is Rental Ready and has excellent rental history! Schedule your private showing today and experience this Cozy Cottage firsthand.
6040 BOCA GRANDE CSWY #5, BOCA GRANDE, FL 33921
$200,000282 Days on yellowkey MLS ID: D6143184
Bed: Bath: 0.0 Liv Area Sq Ft: 330 Built: 2012 Tax: $2,423 (2024)Community: Boca Grande North Marina BoatDock-Rackominium
Taxes:$2,423
Remarks: Lowest priced Boca Grande North slip w/ 10,000 lb lift. | Direct Gulf access | No fixed bridges | Fits ~26-27 ft | Rentable. Enjoy direct Gulf access with no fixed bridges and deep water, ideal for serious boaters. Accommodates approximately 26-27 ft vessel (buyer to verify). Cruise the back bays or head straight to the Gulf — some of Southwest Florida's best fishing waters are just minutes away. Features include a 10,000 lb lift with newer motor, electric, water, and a fish cleaning station, all set on recently rebuilt composite docks for low-maintenance ownership. Ownership is not contingent on residence in this community, offering flexibility for both local and off-island buyers. Slips may be rented, providing an opportunity for seasonal income or offsetting ownership costs. A standout value for buyers seeking a well-equipped slip without the need for additional improvements. Easy to show.
Listing is courtesy of: PARSLEY BALDWIN REAL ESTATE (941-964-2700)
Listing Agent: Nancy Hyde (941-539-9616)
1669 JOSE GASPAR DR, BOCA GRANDE, FL 33921
$7,500,0008 Days on yellowkey MLS ID: D6147162
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: 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)
5700 GULF SHORES DR #C143, BOCA GRANDE, FL 33921
$1,150,000180 Days on yellowkey MLS ID: D6144570
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1334 Built: 1979Monthly Fee: $1,408 Tax: $15,986 (2024)Community: Sea Oats Bldg CCondo
Taxes:$15,986
Remarks: Call Penny for Gate Code. Now's your chance to own a piece of paradise! Breathtaking, pool and GULF views from the extra large enclosed lanai! Renovated down to the studs in 2017 this 2 bed, 2 bath has a completely new layout! Kitchen has new appliances and elegant quartz countertops. Custom Starmark cabinetry with hidden hinges and flush inset doors along with Kohler and Brizo hardware are found both in the kitchen and baths. Primary has large walk-in shower. New light fixtures and recessed ceiling lights. Tile floor throughout looks like wood but durable and easy to clean! Plantation shutters and impact glass on windows and lanai doors. New electric, plumbing and HVAC. Not a detail was missed in this must see condominium! Unit includes a parking space, storage closet and use of golf cart lot. Resort - like amenities include a large heated swimming pool, lighted tennis courts, patios for BBQ's and elevators for easy access. Enjoy walks on Boca Grande's coveted white sandy shoreline, take a golf cart ( included in sale) to the nearby bike path and head downtown to enjoy the many restaurants and shopping or simply relax and watch the sunset from your lanai.
Listing Agent: Penny Oudheusden (203-550-3882)
281 SEABREEZE CT, BOCA GRANDE, FL 33921
$2,400,00074 Days on yellowkey MLS ID: D6146199
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1504 Built: 1987 Tax: $6,045 (2025)Community: SeabreezeSingle Family
Taxes:$6,045
Remarks: REDUCED PRICE - Welcome to your private tropical retreat offering relaxed coastal living just minutes from convenient beach access. This residence captures the charm and style of Boca Grande without the premium price. Surrounded by lush palms and mature landscaping, the home features expansive outdoor living areas designed for year-round enjoyment. An oversized upper deck provides a serene setting for entertaining or unwinding, while the beautifully paved lower-level pool and spa area creates an additional private gathering space. Multiple outdoor options make this home ideal for hosting and embracing the Florida lifestyle. Inside, natural light fills the thoughtfully designed interior. Warm wood floors upstairs add character and comfort. The bathrooms have been tastefully updated with spa-inspired finishes, including frameless glass showers, stone accents, and a freestanding soaking tub. A spacious laundry area with cabinetry adds everyday convenience. This home appeals to buyers seeking the charm and style of Boca Grande without the premium price — offering comfort, flexibility, and exceptional outdoor living in a highly desirable location near the beach.
350 GILCHRIST AVE, BOCA GRANDE, FL 33921
$4,975,000329 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
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
4190 LOOMIS AVE, BOCA GRANDE, FL 33921
$2,755,000303 Days on yellowkey MLS ID: D6142937
Bed: 4 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4608 Built: 1999 Tax: $12,335 (2025)Community: East Shore AcresSingle Family
Taxes:$12,335
Remarks: One or more photo(s) has been virtually staged. 200 Palms- a custom retreat bordering nature preserve positioned on 1.35 acres at the end of a quiet cul-de-sac and backing to a serene nature preserve, this custom-built home blends warm, natural elements with thoughtful design. Soaring Douglas Fir vaulted ceilings crown the expansive great room, where rich cherry cabinetry, Viking and Sub-Zero appliances, and an oversized kitchen island that seats eight create a comfortable space for gathering. The home’s two main levels feature 10-foot-wide, fully screened wraparound decks—ideal for enjoying the peaceful, private setting. Multiple sets of double French doors create seamless indoor-outdoor flow from nearly every room. With four spacious bedrooms, three full bathrooms, and an additional office or fifth bedroom with a half bath, the layout is both flexible and functional. The ground floor, with 4 car garage and workshop, is accessible—like all three levels—via a private elevator. Additional updates include a new metal roof (July 2021), fresh carpeting, and two recently replaced air conditioning units. This home offers a rare combination of craftsmanship, privacy, and modern comfort—perfect for relaxed island living.
2031 SHORE LN, BOCA GRANDE, FL 33921
$11,300,000467 Days on yellowkey MLS ID: D6139748
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4342 Built: 2016 Tax: $78,305 (2023)Community: Shore Lane - See SurveySingle Family
Taxes:$78,305
Tax Year: 2023
Remarks: Truly a one-of-a-kind location rarely presented on exclusive Shore Lane will now be offered for purchase! Located just one estate off the Historic District and the closest in proximity to the downtown Village of Boca Grande, this prominent beachfront treasure will surely take your breath away. Built in 2016 with the owner’s vison for entertaining family and guests while creating a secluded tropical oasis unique to anything else on Gasparilla Island. This influenced Caribbean architectural gem encompasses a majestic courtyard offering the ultimate blend of solitude and spa like atmosphere. The 5-star resort style split plan lives exceptionally featuring a VIP beachside ensuite with three additional ensuite guest quarters connected by a charming covered breezeway lined with Bahama shutters and Brazilian Ipe wood hallways. Designed specifically to capture the azure seascape and green flash sunsets from nearly every room, this luxurious interior layout features an exquisite common living area with wood cladded vaulted ceilings, massive fixed-glass impact windows and doors, and a stunning dual faced coral stone handmade fireplace that commands your attention. The chef’s kitchen exudes elegance and is complimented by white oak wood cabinetry, a chic mosaic tiled mural backsplash, and a marble prep galley with cooking island & breakfast bar all being serviced by Wolf and Sub-Zero appliances. Enjoy the comfortable family and dining room concept with convenient access to the enclosed lanai operated with electric screens or relax on the open veranda with a cocktail secured by reinforced modern glass railings. The VIP master Gulfside wing features an integrated media room accompanied by a lovely terrace overlooking the courtyard pool in addition to a private covered sea watch lanai awarding the best views imaginable. Escape to the lush VIP bath enclave offering custom double wood and marble vanities, a beautiful free standing tub, and the showcase walk in marble laid shower with rain head controls. The guest wing quarters are just as impressive highlighted by a discrete office, and a unique bonus room that could serve as the 5th bedroom if needed. All the guest ensuites are complimented with white oak wood flooring, subway tiled showers, stone countertops, and each having its own personal Juliet balcony positioned prominently over the courtyard garden. Exterior storage is fantastic with over 4,000 square feet of space on lower level for all the beach toys and fishing equipment, and not to mention the additional 2 car detached twin bay garages for vehicles with convenient access to elevator. Whether spending the day basking in the sun next to the lap pool in your private courtyard or taking a swim in the warm cerulean waters of the Gulf of Mexico, this once in a lifetime setting will create a legacy retreat for family & guests that will be enjoyed for many generations to come.
Listing Agent: Heath Seckel (863-207-2586)
5000 GASPARILLA RD #BC105, BOCA GRANDE, FL 33921
$799,000132 Days on yellowkey MLS ID: D6145227
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 730 Built: 1984 Tax: $11,320 (2025)Community: Boca Grande ClubSpa: YesCondo
Taxes:$11,320
Remarks: With breathtaking gulf views and direct beach access, this condo is the perfect retreat for those seeking tranquility and beachfront relaxation. Natural light, tasteful beach decor and a screened lanai create an island oasis. This easy to maintain condo not only offers your own slice of paradise, but also grants access to a host of exclusive amenities. Enjoy a world class tennis facility, state of the art fitness center, three swimming pools, Tiki bar and a fantastic gulf front restaurant. All within the Boca Grande Club, a private, gated community located on the Gulf of Mexico. Initiation fees and yearly Club dues apply. Please inquire for cost.
319 PILOT POINT LN, BOCA GRANDE, FL 33921
$4,195,000378 Days on yellowkey MLS ID: TB8375836
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.
739 S HARBOR DR #2, BOCA GRANDE, FL 33921
$2,450,00015 Days on yellowkey MLS ID: D6146999
0 Days Off yellowkey (back on 4/18/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1655 Built: 1997Monthly Fee: $348 Tax: $19,392 (2025)Community: Harborside At Boca Bay CondoSpa: YesCondo
Taxes:$19,392
Remarks: Under contract-accepting backup offers. Live the pinnacle of Boca Grande waterfront living in this exceptional three-bedroom, two and a half bath Harborside condominium. Perched on the top floor with an enviable end-unit location, this residence delivers sweeping, unobstructed views of Charlotte Harbor that captivate from sunrise to moonrise. Step inside to discover an elegant open-concept floor plan bathed in natural light, where soaring ceilings, crown molding, plantation shutters throughout the home, and marble tile flooring create a refined sense of space and sophistication. The gourmet kitchen features stainless steel appliances and granite countertops, while the expansive glassed lanai serves as the heart of the home—an idyllic setting for morning coffee, sunset cocktails, or simply marveling at the ever-changing panorama of azure waters, abundant wildlife, and graceful boating activity. Additional peace of mind comes from electronic hurricane roll-down shutters, ensuring effortless protection during storm season. Designed for effortless coastal living, this lock-and-leave retreat offers the perfect blend of privacy and convenience with its private garage, dedicated storage, and elevator access. The community of Boca Bay surrounds you with a resort-style lifestyle: four sparkling swimming pools, a private bayside beach, a fishing pier, seven clay tennis courts, a state-of-the-art fitness center, and exclusive access to the world-class Boca Bay Pass Club for casual gulf-side dining.
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