Treasure Island Homes with Two Story Style

Treasure Island Homes with Two Story Style

Welcome to Treasure Island, a charming city located in Pinellas County, Florida. Known for its stunning beaches, vibrant community, and endless recreational opportunities, Treasure Island offers a unique blend of coastal living and small-town charm.

If you're looking for a home with a two-story style, Treasure Island has a variety of options to choose from. Two-story homes in this area often boast spacious layouts, modern amenities, and beautiful views of the surrounding landscape. Whether you're looking for a cozy beach cottage or a luxurious waterfront property, you're sure to find the perfect two-story home to suit your lifestyle in Treasure Island.

Living in Treasure Island means enjoying year-round sunshine, pristine beaches, and a laid-back coastal atmosphere. Residents have easy access to a wide range of outdoor activities, including boating, fishing, and watersports. The city also offers a vibrant dining scene, eclectic shops, and a calendar full of events and festivals for residents to enjoy.

If you're dreaming of living in a two-story home in a picturesque coastal city, look no further than Treasure Island. With its unbeatable location, friendly community, and endless recreational opportunities, Treasure Island is the perfect place to call home. Explore the real estate options in Treasure Island today and start living the beachside lifestyle you've always wanted.

Newest Treasure Island Homes with Two Story Style

$2,000,000
4 Beds ⋅ 4 Baths ⋅ TB8535661 MLS
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, Treasure Island
$3,250,000
5 Beds ⋅ 3 Baths ⋅ W7888215 MLS
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
TB8529647 MLS
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, Treasure Island
$1,699,000
6 Beds ⋅ 4 Baths ⋅ TB8531341 MLS ⋅ Waterside BLDG.
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, Treasure Island
$395,000
3 Beds ⋅ 2 Baths ⋅ TB8530824 MLS ⋅ 20 BLDG.
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 ⋅ TB8515640 MLS
Deep-water waterfront living with direct Gulf access in the heart of St. Pete Beach. Just four blocks from the sand and three blocks from the shops, restaurants, and Sunday Market of historic Corey Avenue, this beautifully renovated Boca Ciega Bay residence offers the rare combination of boating convenience, walkability, and luxury coastal living. Positioned on deep water with direct access to the Gulf of Mexico, this exceptional property is designed for buyers who want to enjoy the Florida waterfront lifestyle to its fullest. The composite dock features a 10,000-pound boat lift, making it easy to spend your days fishing, island hopping, waterfront dining, or exploring the Gulf waters. Inside, the 2,268-square-foot floor plan is both elegant and functional, featuring 3 bedrooms, 3 bathrooms, and a versatile second-story studio with a full bath, ideal as a home office, fitness space, guest suite, or creative retreat. Each bedroom enjoys access to its own bath, while the split-bedroom design offers privacy and comfort for family and guests. From the moment you step through the front door, sweeping water views take center stage. The open-concept living area flows seamlessly into a chef-inspired kitchen complete with GE Café Series appliances, shaker cabinetry, granite countertops, pantry storage, and a stylish coffee bar, all designed to complement the home's waterfront setting. The primary suite serves as a private sanctuary overlooking the bay, featuring direct patio access, dual closets, and a spa-inspired ensuite bath. Outdoor living is equally impressive, with a covered waterfront patio perfect for dining al fresco and a spectacular 40-foot second-story balcony where you can enjoy breathtaking sunrises over Boca Ciega Bay. Spend your evenings watching dolphins and manatees from your dock, launch your boat for a sunset cruise, or take a short golf cart ride to the beach, local restaurants, and entertainment. Few properties offer this level of accessibility both on the water and on land. Built for peace of mind, the home also features hurricane-impact windows and doors, a 50-year metal roof, indoor laundry, generous garage storage, Halo fingerprint entry locks, Nest thermostat, Ring security cameras, and updated appliances, fixtures, and major mechanical systems. Whether you're seeking a full-time waterfront residence, luxury vacation home, or boater's paradise, this turnkey St. Pete Beach property delivers the ultimate Florida lifestyle with deep water, direct Gulf access, and world-class beaches just moments away.

7025 Boca Ciega Drive, Treasure Island
$1,495,000
4 Beds ⋅ 3 Baths ⋅ TB8527052 MLS
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 ⋅ TB8520828 MLS
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, Treasure Island
$3,900,000
TB8523225 MLS
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, Treasure Island
$2,300,000
3 Beds ⋅ 3 Baths ⋅ TB8513872 MLS
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, Treasure Island
$675,000
5 Beds ⋅ 4 Baths ⋅ TB8506601 MLS
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
$3,250,000
5 Beds ⋅ 3 Baths ⋅ W7885505 MLS
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
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