Location: Boca Grande
Do Not Show Listings
5850 GASPARILLA RD #M7, BOCA GRANDE, FL 33921
$699,00042 Days on yellowkey MLS ID: D6146400
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 686 Built: 1981 Tax: $8,223 (2025)Community: Marina Village Ph 01Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,223
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Enjoy a front row view of Charlotte Harbor! This one bedroom, one bath end unit was beautifully renovated in 2022. It boasts all new kitchen cabinets, custom built in bench seating with hidden locked owners’ storage, ocean beige dolomite kitchen counters( harder than marble and more heat resistant than quartz). The bathroom has Pompeii iscle quartz countertop. New AC in 2023! Hurricane impact windows and doors, tile floors, and updated lighting. Sit on your screened in lanai and watch dolphins, manatees, wildlife and yachts. Wake up to majestic sunrises! The Boca Grande Club is rich in amenities including private beach access, tiki bar pool side, 8 tennis courts, state of the art fitness center and 1st class Club House dining with panoramic beach views. Marina Village is a serene and all embracing community. Own your piece of paradise right here!
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)
Listing Agent: Janie Vaughan (941-855-9234)
5000 GASPARILLA RD #BC204, BOCA GRANDE, FL 33921
$1,097,000160 Days on yellowkey MLS ID: D6144569
1 Days Off yellowkey (back on 3/3/2026)
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1984 Tax: $14,972 (2025)Community: Beach Chalet Bld GSpa: YesCondo
Taxes:$14,972
Elementary School: Vineland Elementary
High School: Lemon Bay High
Middle School: L.A. Ainger Middle
Remarks: Under contract-accepting backup offers. Admire the gorgeous Gulf of Mexico views from this desirable beachfront, one bedroom two bathroom condo in the Boca Grande Club, a private, gated beachfront community. This beautifully renovated second floor condo with elevator access features a redesigned kitchen featuring white cabinetry, a stunning granite countertop and stainless steel appliances. The owner suite has fabulous gulf views and enlarged bathroom featuring double sinks and additional storage cabinets. The glass enclosed lanai provides extended living space with large impact sliders and a living room picture window enhances the stunning sunset views. Offered fully furnished with a coastal ambiance, it is the perfect retreat for relaxing and peaceful island living. Located close to all the luxurious amenities of the Boca Grande Club including: a recently renovated gulf front restaurant and Tiki bar, three swimming pools, state of the art fitness center, fitness classes, 8 tennis courts and player clinics. Please inquire for membership details and cost.
Listing is courtesy of: GULF TO BAY SOTHEBY'S INTERNAT (941-964-0115)
Listing Agent: Kristin O'Connor (941-457-9553)
320 GASPARILLA ST, BOCA GRANDE, FL 33921
$2,775,00042 Days on yellowkey MLS ID: D6146411
2 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1741 Built: 1959 Tax: $20,479 (2025)Community: Golden BeachSpa: NoSingle Family
Taxes:$20,479
Elementary School: The Island School
Remarks: Discover 320 Gasparilla Street located just south of the village in Golden Beach. This 3-bedroom, 2-bathroom pool home offers comfortable living with a desirable one-level layout, situated on a large, south facing lot. The main living areas feature a living and dining room combination, complemented by a glassed-in Florida room that fills the home with natural light. The kitchen is clean and functional, and the bedrooms are generously sized. The fully fenced backyard includes a freshwater pool and a tiki-style bungalow, creating a private outdoor haven. Conveniently located near a beach access, the property offers the laid-back coastal lifestyle Boca Grande is known for. Whether as a primary residence, seasonal getaway, or investment property, this presents a wonderful opportunity to own on Gasparilla Island.
Listing Agent: Carol Stewart (941-276-1162)
5856 GASPARILLA RD #M31, BOCA GRANDE, FL 33921
$1,195,000776 Days on yellowkey MLS ID: D6135181
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1065 Built: 2007 Tax: $12,423 (2023)Community: Marina Village Ph 02Condo
Taxes:$12,423
Tax Year: 2023
Remarks: No damage from Hurricane Milton! Exquisitely furnished 2 bedroom 2 bath condominium overlooking Charlotte Harbor. This property affords views of dolphins, manatees and many flora and fauna. The sunrises are spectacular creating a blessed feeling for another beautiful day in paradise. The lakes to the west and the glorious sunsets are an added bonus to a beautiful location. The Boca Grande Club is an amenity rich community with several pools, beach side tiki bar, private beach access, world class dining, 8 Har-Tru tennis courts and state of the art fitness center. There's no place like home.
5850 GASPARILLA RD #M1&3, BOCA GRANDE, FL 33921
$1,700,000719 Days on yellowkey MLS ID: D6136229
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1568 Built: 1981 Tax: $17,488 (2023)Community: Marina Village Ph 01Condo
Taxes:$17,488
Remarks: No damage from Hurricane Milton ! This first floor all one level beautifully furnished property was originally 2 units that were combined to afford an open floor plan and an extra bonus room that serves as a 3rd bedroom if so desired! Full view harbor waterfront where dolphins and manatees are often present! Enjoy majestic sunrises with expansive views in this special property. Boca Grande Club is an amenity rich community with several pools, private beach access, 8 tennis courts, state of the art fitness center and the best private restaurant on the island! Enjoy an end of day cocktail at the poolside Tiki bar, overlooking the beach and a glorious sunset. One time Club Initiation fee of $50,000.00 and one time Capital Improvement Fee of $15,000.00 upon membership.
1644 TREASURE LN, BOCA GRANDE, FL 33921
$10,650,000179 Days on yellowkey MLS ID: D6144295
0 Days Off yellowkey (back on 4/12/2026)
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4964 Built: 1996Monthly Fee: $208 Tax: $92,663 (2024)Community: Boca Grande IslesSpa: YesSingle Family
Taxes:$92,663
Tax Year: 2024
Remarks: Welcome to your island paradise on Boca Grande Isles. With 100 feet of waterfront and direct access to the Intracoastal Waterway, this stunning modern take on West Indies architecture residence has been completely renovated and offers an island sanctuary. Key features to this four bedroom, five and one-half bath residence spans 4,900+ square feet of meticulously updated living with unparalleled sophistication. The spectacular great-room is a masterpiece, boasting a wood beam ceiling, porcelain tile and wood flooring, crown molding with intricate detailing, built-in bar area with wine cooler, a decorative fire-place, and an expansive wall of glass overlooking Gasparilla sound offering an abundance of natural light. This cozy serene space connects by a wall of expansive sliding glass doors to an open-air porch with breathtaking water views. This home is crafted with the finest materials and finishes, seamlessly blending modern elegance with durability. The open-concept kitchen and breakfast area create a versatile floor plan perfect for daily living. The gourmet kitchen features quartz countertops, soft-close cabinets and drawers, Bosch appliances, 6-burner gas range located on the center island, and a Sub-Zero cabinet-faced refrigerator. The expansive primary suite, on the main living level, serves as a luxurious escape, featuring a sprawling walk-in closet and a spa-like bathroom with high-end finishes, dual vanities, a soaking tub, and an oversized shower. The upper level offers three additional bedrooms, each offering its own unique charm and character. Outside, embraces the epitome of island living. Beautiful mature landscaping, a two-car garage, a captivating pool, and a cozy fire pit create an idyllic haven for relaxation under starlit skies. With deep sailboat water access, and a 16k lb boat lift, nest in this beautiful island waterside home.
Listing Agent: Jeff Moore (941-855-0737)
5000 GASPARILLA RD #BC306, BOCA GRANDE, FL 33921
$1,150,0006 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.
894 HILL TIDE LN, BOCA GRANDE, FL 33921
$16,850,000791 Days on yellowkey MLS ID: D6134942
Bed: 6 Bath: 7.5 Gar: 3 Liv Area Sq Ft: 8100 Built: 2025Monthly Fee: $1,583 Tax: $41,468 (2023)Community: Hill Tide EstatesSpa: YesSingle Family
Taxes:$41,468
Remarks: Brand New Construction Now Complete***Quite possibly the most unique waterfront location ever offered for sale in Southwest Florida! Sunrises and Sunsets will be enjoyed here in the winter months together with 180 degrees of Gulf to Bay cerulean waterscape, pristine beaches, nostalgic lighthouse view, and the Historic Boca Grande Pass – AKA ‘The Tarpon Capital of the World’! This exquisite BCB Homes custom built estate offers 8,100 square feet of living space and nearly 3,000 square feet of additional outdoor & garage accommodations. The generous floor plan headlines two magnificent Master / VIP mega suites which is a must see even for the most selective Buyer along with three additional luxurious bedroom ensuites, and a bonus room with full bath that could serve as the sixth guest quarters. In addition, the home showcases a waterfront club room for entertaining, an elegant dining room with decorative ceiling details, and the captivating Sea Watch lounge on second level overlooking the heart of Boca Grande Pass. The well appointed kitchen and family room combination will certainly be a popular gathering place offering panoramic water views and convenient access to the outdoor lanai, pool / spa, and waterfront garden. There is also a spacious den conveniently located off the main entry with a picturesque window overlooking the front garden. The interior finishes were thoughtfully selected by owner to ensure the highest of quality. Ruffino custom Maple cabinetry will be presented in nearly every room together with walnut engineered flooring, meticulously hand crafted cypress and poplar wood finished 12 foot + ceilings, Pompeii quartz & quartzite countertops, and hand laid Walker Zanger tile & stone flooring. Other interior selections will include Sub Zero & Wolf appliances, Lutron lighting control / audio surround, and a custom elevator cabin servicing all floors. The outdoor space is exceptional offering 184 feet of water fronting beachscape and direct access to the inclusive East Beach and Pier. Enjoy entertaining and cooking out in your well equipped outdoor kitchen poolside with convenient remote control shutters and bug screens for added protection against all elements. Exterior construction is just as impressive with storm security being the focal point. The all concrete block structure is fortified with Anderson 400 hurricane rated windows and doors together with a hand etched concrete stucco finish for superior strength and durability. Other exterior construction upgrades include remote hurricane rated shutters, Englert standing seam metal roof, and Clopay hurricane rated garage doors. Multiple outdoor terraces will enhance the exterior profile combined with custom decorative shutters, and the prominent Cupola representing the Architects vision of elegance. All current selections and finishes will be available upon serious inquiries. Hill Tide Estates is majestically positioned along the shores of Boca Grande Pass, Charlotte Harbor, and the Gulf of Mexico. The Gated Community features a private tiered beach, and a unique private fishing / observation pier exclusive for the 19 homeowners.***The photos containing furniture have been virtually staged for visual demonstration.
Listing is courtesy of: BOCA GRANDE REAL ESTATE, INC. (941-964-0338)
Listing Agent: Heath Seckel (863-207-2586)
261 SEABREEZE CT, BOCA GRANDE, FL 33921
$4,250,00088 Days on yellowkey MLS ID: D6145605
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2420 Built: 2016 Tax: $45,691 (2025)Community: SeabreezeSingle Family
Taxes:$45,691
Remarks: Experience relaxed coastal living in this beautifully decorated McHugh-Porter custom home, offered turnkey and thoughtfully designed for comfort and ease. This one-level residence centers around a light-filled great room and a well-appointed chef’s kitchen with Caesarstone countertops, ideal for both entertaining and everyday living. Clean, modern lines extend seamlessly through impact-glass sliders to a private outdoor retreat. The outdoor space is intentionally scaled for low-maintenance enjoyment, featuring a heated pool nestled among mature trees and a fenced yard that provides rare privacy. Whether it’s a quiet morning swim or an evening unwind, the setting feels peaceful and secluded. The home offers four bedrooms, a private office, and inviting porches that capture the gentle Florida breezes. Located on a quiet cul-de-sac south of the village, you’re just moments from direct beach access, tennis, pickleball, and the dog park. A whole-house generator and dehumidified 2.5-car garage complete this meticulously maintained home—where thoughtful design meets easy coastal living. This is a must see!
Listing Agent: Ralph Dilena, Jr. (941-380-0878)
5000 GASPARILLA RD #VH20, BOCA GRANDE, FL 33921
$2,450,00040 Days on yellowkey MLS ID: D6146472
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1640 Built: 1987Monthly Fee: $29 Tax: $27,657 (2025)Community: Village Boca Grande ClubCondo
Taxes:$27,657
Remarks: Fully renovated Village Home in the gated Boca Grande Club, offering 3 bedrooms, 3 baths plus a fourth kids’ room and over 1,600 square feet of living space, including approximately 400 square feet of thoughtfully added living area. Designed with a coastal-contemporary aesthetic, the home features an open-concept layout with vaulted ceilings, abundant natural light, enclosed sunrooms, and a striking new fireplace that anchors the main living space. The gourmet kitchen showcases premium LG appliances, quartz countertops, and designer fixtures, seamlessly blending style and functionality. The reimagined primary suite offers a spacious walk-in closet and a spa-inspired bath with dual vanities and a large walk-in shower. The loft level has been expertly transformed to include a private bedroom and full bath, creating an ideal retreat for guests or family. Throughout the home you’ll find designer tile, new hardwood flooring, updated doors, trim, and hardware, along with modern conveniences including a full-size in-home washer and dryer and outdoor elevator lift. Significant upgrades include impact windows, Hardie siding, Trex decking, a newer roof, open-air lift, and a 2017 HVAC system, ensuring both durability and peace of mind. Enjoy west-facing outdoor living with beautiful sunset views and glimpses of the Bay and Gulf, along with a garage and private garden area. Located just steps from the secluded beach, this home offers the perfect blend of privacy and coastal lifestyle. Residents of the Boca Grande Club enjoy an exceptional amenity package including Gulf-front dining, three pools, tiki bar, fitness center, yoga and water aerobics, eight tennis courts, and gated security.
1671 JOSE GASPAR DR, BOCA GRANDE, FL 33921
$4,500,00012 Days on yellowkey MLS ID: D6146862
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.
150 1ST ST E, BOCA GRANDE, FL 33921
$6,995,00053 Days on yellowkey MLS ID: D6146257
0 Days Off yellowkey (back on 4/1/2026)
Bed: 6 Bath: 6.0 Gar: 1 Liv Area Sq Ft: 3848 Built: 2020 Tax: $58,023 (2025)Community: Acreage & UnrecSingle Family
Taxes:$58,023
Remarks: Under contract-accepting backup offers. Located in the heart of the Village within the historic charm of Boca Grande, this exceptional 6-bedroom, 6-bath coastal retreat artfully blends timeless architecture with modern craftsmanship. Designed by Stofft Cooney Architects and built in 2020 by the island’s premier builder, Safety Harbor Construction, the residence offers over 3,800 square feet under air, including two beautifully appointed sunrooms, and was thoughtfully conceived for refined entertaining and seamless indoor–outdoor living. A custom mahogany front door opens to a classic “Gasparilla Inn” inspired sun porch with green high-gloss painted wood floors, introducing interiors rich with antique wormy chestnut reclaimed flooring, tongue-and-groove ceilings with decorative beams, and a striking Isokern Magnum wood-burning fireplace. The open-concept kitchen is a chef’s showpiece, appointed with leathered Taj Mahal quartzite countertops, dual dishwashers, WOLF and Monogram appliances, and a fully equipped butler’s pantry with ice maker, beverage drawers, wine refrigerator, and generous storage. A beautifully integrated dry bar in the living area features a copper countertop, additional beverage drawers, and an ice maker. British-inspired Origin bi-fold aluminum doors fully recess to transform the living space into an open-air sanctuary, complemented by a remote-controlled screen at the touch of a button. The outdoor kitchen is anchored by a custom built-in Kalamazoo Gourmet Fire Grill, designed to cook with wood, charcoal, or gas, with additional space for preferred appliances. The main-level primary suite captures serene outdoor views and features a private, spa-like bath with dual vanities, walk-in closet, and a full-size laundry room. Two additional guest suites complete the main level, including one reimagined as a den inspired by BZ’s Lounge at the iconic Gasparilla Inn. Upstairs, a cozy TV room provides an inviting setting for movie nights and game time. Three additional guest suites include one transformed into a bright craft room with charming views of Palm Avenue, along with a convenient second-floor laundry closet. Set on 81 feet of deepwater canal frontage with direct, no-bridge access to the Harbor and Gulf, the property is a boater’s dream. The private dock features over 600 square feet of Azek decking, a 20,000-pound boat lift (2020), and a 10,000-pound lift added in 2023. The main living level is elevated over 11 feet and constructed on a solid concrete base for peace of mind. A residential elevator services all floors from the extended one-car garage with golf cart side entry and additional storage. Andersen impact windows, Boral exterior siding, a corrugated metal roof, solid wood soffits, and a whole-home Reme Halo air purifier complete this impeccably built residence, offering the rare union of Village character, architectural integrity, and exceptional boating and beach access.
Listing Agent: Jamie Curry (941-716-1018)
5000 GASPARILLA RD #12B, BOCA GRANDE, FL 33921
$1,945,00032 Days on yellowkey MLS ID: D6146553
1 Days Off yellowkey (back on 4/7/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1323 Built: 1979Monthly Fee: $183 Tax: $25,830 (2025)Community: Boca Grande Club Ph 01Spa: NoCondo
Taxes:$25,830
Remarks: Under contract-accepting backup offers. Welcome to luxury living at the prestigious Boca Grande Club! This top-floor condominium offers an unparalleled coastal lifestyle with breathtaking Gulf front views. Meticulously remodeled, this residence boasts 2 bedrooms, 2 bathrooms, and an inviting upstairs loft for added flexibility. Upon entering, the allure of this residence is immediately evident with the abundance of natural light due to its southern end-unit location. The impact glass windows and doors seamlessly connect the interior to the captivating Gulf panorama. The entire space has been expertly curated by an interior designer, ensuring a harmonious blend of sophistication and comfort. No detail has been overlooked in the customization of this condo. Elegant moldings and a stunning expansive white oak ceiling contribute to an ambiance of refined opulence. The custom window treatments, as well as designer wallpaper and lighting fixtures add an extra layer of style, creating a unique visual in every room. The kitchen features quartzite countertops, a large island with barstool seating, and custom cabinetry that blends style with functionality. The bathrooms are equally impressive, showcasing elegant finishes and fixtures. The master suite, with its Gulf views, provides a serene retreat for relaxation. Residents enjoy access to the exclusive host of amenities of the Boca Grande Club. Several pools, private beach access, a members-only Gulf-front restaurant, a fitness center, tennis courts, and a tiki bar provide a wealth of leisure options. This condo's location in close proximity to the main pool and Gulf-front restaurant adds an extra layer of convenience, ensuring you can fully embrace the unparalleled lifestyle offered by the Boca Grande Club.
Listing Agent: Randy Wojcik (941-204-0015)
367 NIGHT HERON DR, BOCA GRANDE, FL 33921
$4,600,000453 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
Taxes:$16,565
Remarks: This unique bayfront home offers stunning sunrises and moonscapes over Charlotte Harbor. The spacious open main floor begins with an entry leading into the two-story living room with hand painted coffered ceiling. This space is accented by the hand painted staircase, custom tera cotta tile floors and a fireplace surrounded by a hand carved pecky cypress mantle. The adjoining dining room continues into the heart of the home providing quiet dining and harbor views. Step down into the kitchen and open family room. The kitchen is completely updated with stainless appliances, granite countertops and a spacious island with a second sink. Both rooms feature cherry flooring, custom woodwork and designer cabinetry with storage features. Adjacent to the kitchen and family room, a waterfront sunroom spans the width of the home, leading to a custom, window filled stairwell to the first-floor storerooms, doubled garage spaces and a garden patio. The property finishes with a garden view leading to the mangrove coastline. There are two large main level guest rooms, one en-suite and a second with an adjacent full bath. The upstairs primary suite welcomes you with built-in shelving and desk, vaulted ceiling and expansive windows facing Charlotte Harbor. The open Roman bath, large walk-in closet and laundry room complete the space. Open the large French doors in the primary bedroom to enter a private deck with amazing harbor views. To complete the deck, a circular staircase leads to a widow's walk with a panoramic view of Gasparilla Island and beyond. Additional highlights include a finished elevator to the first floor, impact glass on all windows and doors, a new metal roof installed in 2023 and all interior walls freshly painted. This North Bay gem, in the amenity rich Boca Bay community, is a true sanctuary combining location, style and natural beauty.
260 GILCHRIST AVE, BOCA GRANDE, FL 33921
$5,750,00060 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.
5700 GULF SHORES DR #B133, BOCA GRANDE, FL 33921
$998,500162 Days on yellowkey MLS ID: D6144565
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1326 Built: 1980Monthly Fee: $1,408 Tax: $16,037 (2025)Community: Sea Oats Bldg BCondo
Taxes:$16,037
Remarks: Set along one of Boca Grande’s most inviting stretches of shoreline, this beautifully updated first-floor residence offers an effortless blend of coastal charm, comfort, and island ease. Ideally located in the center of Building 3, the two-bedroom, two-bathroom condominium enjoys tranquil views of the lush tropical courtyard, the resort-style pool, and the shimmering Gulf beyond. Inside, natural light and a soft coastal palette create a calm, welcoming atmosphere. The open layout connects the tastefully updated kitchen with the living and dining areas, making the home equally suited for relaxing evenings or casual gatherings. Just off the kitchen, a flexible bonus nook provides room for an additional sleeping space or a comfortable home office. Impact-rated sliding glass doors lead to a generous screened lanai—perfect for enjoying Gulf breezes, morning coffee, and sunset skies. The primary suite is a peaceful retreat with direct lanai access and a thoughtfully refreshed bath. A well-appointed guest suite offers comfort and privacy for visiting family and friends. Additional conveniences include under-building parking, elevator access, and a private storage closet ideal for beach gear, bikes, and fishing rods. Sea Oats is a gated beachfront community known for its quiet setting, beautifully maintained grounds, and resort-style amenities, including a heated pool and spa, outdoor grilling areas, tennis courts, and direct beach access. Recent community enhancements—including new roofs, updated exterior finishes, and completed milestone structural inspections—provide both confidence and peace of mind.
3547 GASPARILLA RD, BOCA GRANDE, FL 33921
$2,750,000161 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
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
$4,499,99993 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
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
$10,825,000116 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
$6,450,00060 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 Agent: Heather Wolfe (813-240-6963)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.