Treasure Island Homes with Two Story Property Description

4 Beds ⋅ 4 Baths ⋅ Brightwater Beach Estates 1st Add SubDv. ⋅ 33706 Zip Code

The hard part is already done. Deep-water access on Boca Ciega Bay, on Brightwater Beach, a 90x110 waterfront lot in Brightwater Beach Estates, and a 3,513 SF residence taken to a clean, professionally remediated shell. New roof (2025). New seawall and dock (2022) permitted marine construction, the most expensive and slowest component on any waterfront property. Complete new electrical. New HVAC. Full interior demolition and remediation, permitted and closed. Pool, spa, and mature landscaping in place. Those are the line items that break budgets and blow schedules here they’re finished, and roughly a year of timeline never comes out of your calendar. What’s left: your kitchen, baths, millwork, and finishes, in the layout you choose. 4BR/3.5BA, three-car garage, Gulf beaches minutes away. Waterfront in this pocket doesn’t arrive cleared and permit-current. This one does.

423 55th Avenue, St Pete Beach

$3,250,000

5 Beds ⋅ 3 Baths ⋅ Coney Island SubDv. ⋅ 33706 Zip Code

Own one of Treasure Island's rarest beachfront compounds. Featuring The Pink Flamingo and The Blue Dolphin—two fully renovated Gulf-front homes generating nearly $300,000 in annual gross rental income—this turnkey legacy property offers the perfect blend of luxury living, proven cash flow, and irreplaceable direct beach frontage. Celebrated for their distinctive 1950s retro coastal theme, The Pink Flamingo and The Blue Dolphin have become iconic beachfront destinations, where vintage Old Florida charm meets modern comfort. Every detail has been thoughtfully designed to capture the nostalgia of a bygone era while providing today's guests with the quality and amenities they expect. The result is a truly memorable experience that has earned nothing but 5-star reviews and a loyal base of repeat visitors who return year after year. Behind the timeless aesthetic lies a property that has been meticulously updated for peace of mind and long-term value. Both homes feature impact-rated windows and doors, combining enhanced storm protection with energy efficiency, quiet interiors, and abundant natural light—all while preserving their unique character and curb appeal. With an established rental business, proven financial performance, and nearly $300,000 in annual gross revenue, you'll step into immediate cash flow while enjoying the flexibility to use the property however you choose. Live in one home and rent the other, continue operating both as premier vacation rentals, or create the ultimate multi-generational beachfront retreat for family and friends. The Pink Flamingo offers spacious accommodations, vibrant retro-inspired décor, and breathtaking Gulf views that make every stay unforgettable. Just steps away, The Blue Dolphin complements the experience with its own distinctive personality and inviting atmosphere, creating the perfect pairing for larger groups, extended families, or dual rental opportunities. Together, they form a one-of-a-kind beachfront compound that simply cannot be replicated. Step outside and the Gulf of Mexico becomes your backyard. Spend your mornings with coffee overlooking the water, your afternoons with your toes in the sugar-white sand, and your evenings watching spectacular sunsets from your private beachfront oasis. It's the quintessential Florida lifestyle that guests rave about and one that few properties can truly offer. For investors, the value extends well beyond the real estate itself. You're acquiring an established hospitality business with a proven operating history, exceptional guest satisfaction, and a recognizable identity that sets it apart in a competitive market. The combination of all 5-star ratings, repeat clientele, and turnkey operations provides a solid foundation for continued success from day one. Perfectly situated in the heart of Treasure Island, you're just minutes from waterfront dining, shopping, boating, entertainment, and John's Pass while still enjoying the privacy and tranquility of direct beachfront living. Properties offering two separate Gulf-front homes, a proven six-figure income stream, distinctive branding, modern upgrades, and an irreplaceable location are extraordinarily rare. The Pink Flamingo and The Blue Dolphin are more than vacation rentals—they are beloved destinations that blend nostalgia, luxury, and investment potential into one unforgettable opportunity. Note - There is also a second lot included that is in front of the lot with the houses.

12609 Sunshine Lane, Treasure Island

$1,699,000

St Petersburg Beach Replat SubDv. ⋅ 33706 Zip Code

Virtually Staged. An exceptional opportunity to own a fully furnished, turnkey four-unit property in the heart of St. Pete Beach, just moments from the sugar-white sands of the Gulf. Beautifully updated throughout, this versatile property features two two-bedroom residences, two one-bedroom residences—including a detached studio—and private kitchens, dining areas, and modern finishes in every unit. Luxury vinyl plank flooring, thoughtfully renovated interiors, and a cohesive coastal aesthetic create an inviting experience for guests or residents alike. This property offers outstanding flexibility for rental income, while also lending itself to multi-generational living, seasonal use, or a combination of personal enjoyment and investment potential. Offered fully furnished, it's truly ready to begin generating income from day one. Outside, the spacious lot provides even more opportunity. In addition to four dedicated parking spaces, there's ample room to create an outdoor entertainment area with grilling, dining, fire pit seating, or additional parking, allowing future owners to further enhance the property's appeal. Ideally located just blocks from the beach, residents and guests can easily enjoy Corey Avenue's restaurants, boutiques, Sunday Market, waterfront dining, and all that vibrant St. Pete Beach has to offer, while downtown St. Petersburg is just a short 20 minute drive away. Whether you're seeking rental income, creating a family compound, or looking for a rare coastal property with exceptional flexibility, this is a unique opportunity in one of Tampa Bay's most sought-after beach communities.

644 72nd Avenue, St Pete Beach

$1,699,000

6 Beds ⋅ 4 Baths ⋅ St Petersburg Beach Replat SubDv. ⋅ 33706 Zip Code

Virtually Staged. An exceptional opportunity to own a fully furnished, turnkey four-unit property in the heart of St. Pete Beach, just moments from the sugar-white sands of the Gulf. Beautifully updated throughout, this versatile property features two two-bedroom residences, two one-bedroom residences—including a detached studio—and private kitchens, dining areas, and modern finishes in every unit. Luxury vinyl plank flooring, thoughtfully renovated interiors, and a cohesive coastal aesthetic create an inviting experience for guests or residents alike. This property offers outstanding flexibility for rental income, while also lending itself to multi-generational living, seasonal use, or a combination of personal enjoyment and investment potential. Offered fully furnished, it's truly ready to begin generating income from day one. Outside, the spacious lot provides even more opportunity. In addition to four dedicated parking spaces, there's ample room to create an outdoor entertainment area with grilling, dining, fire pit seating, or additional parking, allowing future owners to further enhance the property's appeal. Ideally located just blocks from the beach, residents and guests can easily enjoy Corey Avenue's restaurants, boutiques, Sunday Market, waterfront dining, and all that vibrant St. Pete Beach has to offer, while downtown St. Petersburg is just a short 20 minute drive away. Whether you're seeking rental income, creating a family compound, or looking for a rare coastal property with exceptional flexibility, this is a unique opportunity in one of Tampa Bay's most sought-after beach communities.

644 72nd Avenue, St Pete Beach

$395,000

3 Beds ⋅ 2 Baths ⋅ Sun Ketch Condo SubDv. ⋅ 33706 Zip Code

This charming very rare Three (3)-bedroom, two-bath, condo-townhome-style end unit in Sun Ketch II community, in the Isle of Capri, one of the most desirable islets of Treasure Island, offers the perfect blend of comfort and convenience, just a short walk to Treasure Islands beautiful sandy beaches (lots of activities through the year), restaurants, supermarket, public transportation and bars along the cozy boardwalk for gathering and to enjoy the sunset. Unit has been updated throughout newer kitchen, granite counter, stainless steel appliances, tile in kitchen, laminate flooring throughout the rest of the unit, master bath beautifully renovated, super clean. 2021 Roof and skylights, AC and water heater approximately 2018, newer water purification system and new blacktop roads recently completed. Unit is ready for your personal touch. Soaring cathedral ceilings with two skylights enhance the home’s space and bring in natural light; inside utility room with washer & dryer and screened balcony. The oversize garage easily accommodates 3+ cars and still has lots of space for all your toys and storage. This is a great place for downsizing family, starting family, second home or investment property. A 30-day minimum lease (up to 6 times a year); it is pet friendly (1 small dog & 2 cats) are allowed; no age restriction; buyer and renter approval is required. The lower condo fee of $735 p/mo includes Cable TV, Internet, Maintenance of the Exterior, Water, Sewer, Garbage Collection, Maintenance of the Grounds, Pest Control, Insurance of the outside of the building, Flood Insurance, Pool and Escrow Reserve Fund. The community offers a variety of amenities along with large-heated pool, Roselli Park includes, Dog Park, tennis courts, playground, baseball field, pickleball courts, shuffleboard and ball field. The unit comes furnished, for convenience of the seller. Sale is "AS IS" condition, with right to inspect. Easy access to Tampa International Airport & Clearwater St. Pete Airport.

12223 Sun Vista Court E, Treasure Island

$1,450,000

3 Beds ⋅ 4 Baths ⋅ Bayside Add To St Pete Beach SubDv. ⋅ 33706 Zip Code

Experience the pinnacle of St. Pete Beach living! This exquisitely renovated, contemporary waterfront home on Boca Ciega Bay is offered for the discerning buyer. This beautifully designed 2,268 sq. ft. home includes 3 bedrooms, 3 bathrooms, and a second-story studio complete with a 4th bathroom. Use the studio for a fitness room or a home office. The home interior features a private bath for each bedroom and split floor plan for maximum livability. Take in the sunrise from the private, 40' long second-story balcony deck or enjoy a relaxing evening on your dock while watching dolphins and manatees. This home is beautifully designed and very well maintained. Stunning waterfront views greet you as you enter the foyer and open-concept common area. The chef's dream kitchen includes high-end shaker cabinets, GE Café Series appliances, granite countertops, a pantry, and a modern coffee bar. View the water from your Primary bedroom complete with spa-like ensuite, his and hers closets, and back patio access. The covered back patio is ideal for outdoor dining and includes a storage closet for boat gear. The composite wet dock includes a 2020 boat lift, accommodating up to a 10,000-pound vessel. Take advantage of the extra hanging storage in the two-car garage. This amazing home is conveniently located 4 blocks from St. Pete Beach (voted #5 in the world by Trip Advisor), a boat ride to numerous waterfront venues, and within 3 blocks of historic Corey Ave and its Sunday Market. Everything you need is a short walk or golf cart ride away! Hurricane impact windows/doors, 50-year metal roof, indoor laundry, and more. All kitchen appliances, fixtures, and major mechanical appliances are new (2026). All entry doors have Halo fingerprint locks to be configured by the new owner. New Nest Thermostat as well as new Ring security cameras, all in their original boxes, are waiting for you to install. Truly turn-key! Call today for your private tour. Buyer or buyer's agent to verify all measurements.

7025 Boca Ciega Drive, St Pete Beach

$1,495,000

4 Beds ⋅ 3 Baths ⋅ Capri Isle SubDv. ⋅ 33706 Zip Code

Completely updated 4 bedroom, 3 full-bath residence in the prestigious Isle of Capri. This home is a boater’s dream. Leave your deep-water dock and you are less than 5 minutes to the Intracoastal Waterway. Then, it’s a short trip to John’s Pass and the Gulf. The open floor plan in this spacious home features water views from almost every room. The high ceilings with 3 large sliding doors make this home ideal for indoor/outdoor entertaining. This home boasts 2 open living areas, one upstairs and one downstairs. Both overlook the water. Take your pick of a primary bedroom suite on each floor, with stunning water views from both suites. The first-floor suite leads out to the pool area and has plenty of closet space. The 2nd, 3rd and 4th bedrooms are located upstairs, and all are comfortably sized with plenty of closet space, including a large walk-in closet in the 2nd floor suite. The large open kitchen features all new appliances and a pass-through to the outdoor patio. This home includes many extras such as impact windows and sliding glass doors, laundry chute, large 2-car garage, and circular driveway. The Isle of Capri neighborhood has a park, playground, racquetball courts, ball field, and dog park. Enjoying the award-winning Treasure Island Beaches, great restaurants and shops make you feel like you’re on vacation year-round. Outstanding value for a waterfront home with so much to offer.

775 Capri Boulevard, Treasure Island

$1,199,900

4 Beds ⋅ 3 Baths ⋅ Don Ce-Sar Place SubDv. ⋅ 33706 Zip Code

Welcome to your own private Don Cesar Place tropical oasis in the heart of St. Pete Beach! Tucked away on an oversized, lushly landscaped lot, this beautifully updated 3-bedroom, 2-bath main residence is paired with a large and separate 1-bedroom, 1-bath guest house, creating the perfect coastal retreat for family, guests, multigenerational living, or additional income potential. Rich with Old Florida character, this property was originally developed by the Don Cesar’s own Thomas Rowe. The main home features original architectural details, an inviting fireplace, abundant natural light, and spacious living areas that seamlessly blend timeless charm with modern updates. The remodeled kitchen showcases shaker cabinetry, stone countertops, stainless steel appliances, and opens to the dining and living spaces, making it ideal for entertaining. Upstairs, the oversized primary suite offers a private retreat complete with an en-suite bath, bonus room, and generous closet space. Step outside into your own boutique resort-style backyard where a sparkling pool is surrounded by mature tropical landscaping, creating exceptional privacy and the perfect setting for relaxing or entertaining. The detached guest house provides its own living space, kitchen, bedroom, bath, and laundry room, making it ideal for visitors, extended family, or private home office. Located just minutes from the sugar-sand beaches of St. Pete Beach, waterfront dining, marinas, shopping, and everything the Gulf Coast lifestyle has to offer, this unique property offers the rare combination of character, flexibility, and outdoor living that's increasingly difficult to find. Whether you're searching for a primary residence, vacation home, or investment opportunity, this one-of-a-kind tropical turn key compound is ready to impress.

3310 E Maritana Drive, St Pete Beach

$1,500,000

5 Beds ⋅ 4 Baths ⋅ Phillips Div Rev Map SubDv. ⋅ 33706 Zip Code

The 1934 Historic Pineapple house is on the market and should be on your radar! This rare 92 year old Coastal Compound in the Heart of Pass-a-Grille is a one-of-a-kind property offering the perfect blend of historic island charm and modern updates with a beautifully renovated 3-bedroom, 2-bath main residence plus a second story 2-bedroom, 2-bath guest house, separated by a large solid wood and insulated conjoining door that offers the new buyer the option of having a 5-bedroom 4-bath with two kitchens, two indoor laundry locations, with endless possibilities for extended family, guests, or additional income potential. No Pass-a-Grille parking problem here as the home has a side by side two vehicle parking garage and two vehicle carport. Rich in character, the main home features soaring tongue-and-groove ceilings, exposed wood beams, original hardwood floors, and abundant natural light throughout. The updated kitchen offers shaker cabinetry, stone countertops, stainless steel appliances, and leads into the living spaces designed for relaxed coastal living. The spacious second floor primary suite is timeless and serves as a private retreat with a spa-inspired bath, and connecting bonus room perfect for a home office or coffee/wine bar. The additional guest bedrooms provide comfort for family and guests. The attached guest house has been thoughtfully updated maintaining its timeless coastal character, offering a full kitchen, spacious living area, two bedrooms, and two full baths. The exterior private and a covered entertainment area boasts a large kitchen counter, flat screen tv, and power and gas line to add outdoor refrigerator and and gas grill, perfect for gathering after a day at the beach. Located just steps from the sugar sand beaches of Pass-a-Grille, boutique shopping, waterfront dining, marinas, and historic 8th Avenue, this exceptional property offers a rare opportunity to own one of the area's classic island homes. Whether you're searching for a primary residence, vacation retreat, or an investment with exceptional flexibility, this unique coastal compound truly has it all. The 2/2 guest quarters is currently rented for $3000 a month plus renter pays utilities. Main house rents monthly between $6000 to $15,000 a month depending on the season. 24 hour notice for showings as the property is currently occupied. Currently July, August, December 2026 and January, March-April 14, 2027 are rented.

105 21st Avenue, St Pete Beach

$3,900,000

Coney Island SubDv. ⋅ 33706 Zip Code

Situated directly across the street from the sparkling Gulf Coast with 80 feet of prime road frontage on Gulf Blvd., this property puts guests steps away from the sand. Public beach access is directly across the street, along with convenient beach stores and dining options. A refreshing, temperature controlled swimming pool completes the classic Florida vacation experience; sun, sea, and relaxation at your doorstep. Owned and operated by the same family for 35 years, this beloved 11-unit boutique hotel (10 rooms plus a spacious owners apartment with office) has been a welcoming haven for generations of families, friends, and beach lovers. Its not just a business, its a legacy built on heartfelt hospitality, genuine connections, and creating memories that bring guests back year after year. This property is offered fully furnished and ready for immediate operation, while also providing the flexibility to add your own personalized touch to elevate the boutique charm for the next generation of guests. The owners apartment provides comfortable on-site living with dedicated office space for managing the property or rent out the owners apartment to maximize ROI. The intimate scale of this 11-unit boutique property makes it ideal for complete Hotel Takeovers perfect for wedding parties, milestone birthday celebrations, family reunions, and business retreats. Imagine having the entire hotel and pool to yourselves: private beach mornings, sunset gatherings by the water, and personalized service that turns your special occasion into a cherished memory. Whether it' s a beachside wedding with all guests staying on-site, a multi-day birthday celebration for the whole family, or a focused corporate retreat with team-building steps from the Gulf, this property offers a rare private-resort feel guests will remember forever. Many guests return season after season, drawn to the coastal vibe and unbeatable location. Walk or Trolley Ride just minutes to Johns Pass Village & Boardwalk, Pinellas County's #1 tourist attraction. This charming fishing village features over 100 unique merchants, waterfront restaurants, shops, a local fishing fleet, dolphin watching tours, boat rentals, and vibrant boardwalk energy. Millions of tourists visit the St. Pete-Clearwater and Madeira Beach area annually, drawn to its authentic Old Florida charm and endless activities. Florida welcomed a record 143 million visitors in 2024, with strong numbers continuing into 2026, proof of the reliable demand in this coastal chic beach town. Imagine waking up to Gulf breezes, serving guests who quickly become like family, and enjoying the lifestyle that comes with owning a slice of paradise. Whether you are an experienced hospitality operator or a family looking to continue a tradition of impeccable service, this property offers the perfect blend of established success and future opportunity. A true Florida treasure, ready for its next chapter of creating lifelong memories, one guest at a time. Do not miss this rare chance to own a piece of the Gulf Coast legacy. Call today for details and schedule a private showing.

11965 Gulf Boulevard, St Petersburg

$2,300,000

3 Beds ⋅ 3 Baths ⋅ Websters Map Warren SubDv. ⋅ 33706 Zip Code

Rare Pass-A-Grille Opportunity: Legal Nightly Rental Triplex + Adjacent Buildable Parcel Dreaming of a beach home in Pass-A-Grille without giving up income potential? Here's a rare opportunity to own two side-by-side properties in one of Florida's most desirable coastal communities. Purchase 107 14th Ave (MLS #TB8513816) together with 109 14th Ave (MLS #TB8513872), offered at $3,300,000 for both properties. The legal nightly rental license conveys with 109 14th Ave. The triplex features three charming accommodations—including a cottage and two flats—designed to capture the relaxed, authentic Pass-A-Grille lifestyle that keeps visitors returning year after year. The property has been successfully operated as a vacation rental with online booking and automated guest check-in and check-out systems already in place. Build your dream beach home on the adjacent parcel while maintaining an established income-producing property next door, or explore the flexibility of creating your own private coastal compound. Located just steps from the Gulf beaches, waterfront dining, boutique shopping, marinas, and the cherished Pass-A-Grille sunset tradition, this unique offering combines lifestyle, income potential, and future possibilities in an exceptional location. Whether you're seeking a proven investment, a future homesite, or the opportunity to enjoy both, opportunities like this are rarely available in Pass-A-Grille.

109 14th Avenue, St Pete Beach

$675,000

5 Beds ⋅ 4 Baths ⋅ Herrons Sub 5 SubDv. ⋅ 33706 Zip Code

Located in the heart of highly sought-after Sunset Beach, this rare tri-plex opportunity is just a 2-minute walk to the beautiful white sands of Sunset beach and surrounded by the laid-back beach lifestyle that makes Treasure Island so special. Walk to local beachfront restaurants, live music, coffee shops, bars, and entertainment, while enjoying one of the most charming and walkable beach communities on Florida’s Gulf Coast. Previously operated as a highly successful short-term rental property, this unique beach compound consists of three separate units, including a main building with two apartments plus a detached standalone efficiency unit — offering endless possibilities for redevelopment, investment, vacation use, or future income potential. The property sustained flood damage during Hurricane Helene and wind damage during Hurricane Milton and is currently vacant and in disrepair. This is being marketed primarily for its exceptional location, lot value, and redevelopment potential. Renovate and reimagine the existing structures, elevate the property approximately 12 feet to create a future coastal retreat, or start fresh with brand-new construction. Opportunities like this in Sunset Beach are increasingly rare. This location places you minutes from everything beach living has to offer — waterfront dining, boating, fishing charters, dolphin cruises, parasailing, jet ski rentals, beach bars, live entertainment, and nightly sunsets over the Gulf. Whether you envision a luxury beach getaway, income-producing investment property, or a completely new coastal development project, the potential here is truly unmatched. Bring your vision and take advantage of this incredible opportunity to create something special in one of Tampa Bay’s most beloved beach communities. Photos of the exterior were taken prior to the hurricanes. The two exterior images are virtual renderings provided for inspiration only and illustrate one possible redevelopment concept with the structures elevated approximately 12 feet. Renderings are conceptual, not existing conditions, and are subject to local approvals and building requirements.

106 E Bay Drive, Treasure Island

Treasure Island Homes with Two Story Property Description

Newest Treasure Island Homes with Two Story Property Description