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Welcome to a turnkey, income-producing coastal retreat in the heart of Gulfport's Historic Waterfront Arts District. This Key West-inspired residence offers 4 bedrooms, 2.5 bathrooms, and 3,804 square feet of light-filled living space with sweeping views of Boca Ciega Bay and Veterans Park just steps from the front door. Currently operating as a successful short-term rental, the home is being sold fully furnished and rental-ready — a rare opportunity to step into an established, cash-flowing vacation rental from day one. Existing bookings, guest reviews, and operating history are available to qualified buyers upon request, making this an ideal acquisition for investors, 1031 exchange buyers, or second-home owners seeking offset income. Inside, soaring cathedral ceilings, a spacious great room, warm wood flooring deliver the elevated finishes today's guests and homeowners expect. Multiple porches and balconies showcase the water views and capture Gulf breezes, while the layout comfortably sleeps a full group without sacrificing privacy. Location is everything: a one-minute walk to Veterans Park and the Gulfport waterfront, minutes to the shops, restaurants, art galleries, and live music of Beach Boulevard, and a quick drive to St. Pete Beach, downtown St. Petersburg, and Tampa International Airport — the exact walkability and lifestyle that keep this property booked. Whether you're expanding a short-term rental portfolio or looking for a coastal residence that pays for itself between visits, 5433 Essex Ave S is a rare turnkey offering in one of Florida's most sought-after small-town waterfront communities. STR certificate and licenses in place and transferable subject to city approval.

4 Beds ⋅ 3 Baths ⋅ SubDv. ⋅ 33707 Zip Code

Welcome to a turnkey, income-producing coastal retreat in the heart of Gulfport's Historic Waterfront Arts District. This Key West-inspired residence offers 4 bedrooms, 2.5 bathrooms, and 3,804 square feet of light-filled living space with sweeping views of Boca Ciega Bay and Veterans Park just steps from the front door. Currently operating as a successful short-term rental, the home is being sold fully furnished and rental-ready — a rare opportunity to step into an established, cash-flowing vacation rental from day one. Existing bookings, guest reviews, and operating history are available to qualified buyers upon request, making this an ideal acquisition for investors, 1031 exchange buyers, or second-home owners seeking offset income. Inside, soaring cathedral ceilings, a spacious great room, warm wood flooring deliver the elevated finishes today's guests and homeowners expect. Multiple porches and balconies showcase the water views and capture Gulf breezes, while the layout comfortably sleeps a full group without sacrificing privacy. Location is everything: a one-minute walk to Veterans Park and the Gulfport waterfront, minutes to the shops, restaurants, art galleries, and live music of Beach Boulevard, and a quick drive to St. Pete Beach, downtown St. Petersburg, and Tampa International Airport — the exact walkability and lifestyle that keep this property booked. Whether you're expanding a short-term rental portfolio or looking for a coastal residence that pays for itself between visits, 5433 Essex Ave S is a rare turnkey offering in one of Florida's most sought-after small-town waterfront communities. STR certificate and licenses in place and transferable subject to city approval.

5433 Essex Avenue S, Gulfport

$5,400,000

A rare offering along the iconic shores of Clearwater Beach, this exceptional Gulf-front estate embodies timeless coastal sophistication, remarkable craftsmanship, and an unparalleled waterfront lifestyle. Situated within the most coveted Mandalay neighborhood, this custom residence occupies an irreplaceable Gulf-front homesite with approximately 60 feet of direct beachfront, delivering unobstructed views across the Gulf of A and some of Florida's most spectacular sunsets. Behind its impressive façade lies approximately 3,559 square feet of meticulously designed living space where elegant architecture meets modern luxury. Every room reflects thoughtful attention to detail, from soaring ceilings and extensive custom millwork to rich hardwood floors, natural stone finishes, multiple fireplaces, and expansive windows that showcase breathtaking Gulf vistas throughout the home. Designed with both elegance and functionality in mind, the residence offers beautifully appointed formal and informal living spaces that effortlessly accommodate intimate gatherings as well as grand-scale entertaining. The gourmet kitchen features premium appliances, custom solid wood cabinetry, stone countertops, wine refrigeration, abundant storage, and seamless integration with the surrounding living spaces. The private owner's retreat is a sanctuary overlooking the Gulf of America, complete with a fireplace, luxurious spa-inspired bath, generous walk-in closets, and private outdoor spaces designed to capture the beauty of the coastline. Spacious guest accommodations, including a private in-law suite, provide exceptional flexibility for family and visitors. A private elevator connects multiple levels, while advanced climate systems, humidity control, impact-rated windows, integrated security features, and thoughtful accessibility enhancements further elevate everyday living. Outside, expansive terraces, wraparound porches, beautifully landscaped grounds, outdoor kitchen, private courtyards, and multiple waterfront entertaining areas create an extraordinary extension of the home's luxurious interior. One of the property’s most extraordinary features is the private rooftop retreat-over 1,500 square feet of elevated outdoor living, accessed directly by the elevator. Designed for unforgettable entertaining, it offers breathtaking 360-degree panoramic views spanning Clearwater Beach, the Gulf of America and the Intracoastal Waterway. A dedicated gas fireplace hookup provides the perfect setting for elegant evenings under the stars. Completing this exceptional residence is an oversized tandem garage with ample space for two vehicles, plus a golf cart or exotic sports car-a rare luxury in beachside living! Located directly on one of the top award-winning beaches - Clearwater Beach, upscale dining, marinas, shopping, and vibrant coastal attractions, this distinguished residence represents far more than a home—it is a legacy property in one of Florida's most desirable waterfront destinations. Combining an irreplaceable Gulf-front setting, enduring architectural appeal, exceptional construction, and an unrivaled location, this is a truly rare opportunity to own one of Clearwater Beach's premier luxury waterfront estates.

3 Beds ⋅ 5 Baths ⋅ SubDv. ⋅ 33767 Zip Code

A rare offering along the iconic shores of Clearwater Beach, this exceptional Gulf-front estate embodies timeless coastal sophistication, remarkable craftsmanship, and an unparalleled waterfront lifestyle. Situated within the most coveted Mandalay neighborhood, this custom residence occupies an irreplaceable Gulf-front homesite with approximately 60 feet of direct beachfront, delivering unobstructed views across the Gulf of A and some of Florida's most spectacular sunsets. Behind its impressive façade lies approximately 3,559 square feet of meticulously designed living space where elegant architecture meets modern luxury. Every room reflects thoughtful attention to detail, from soaring ceilings and extensive custom millwork to rich hardwood floors, natural stone finishes, multiple fireplaces, and expansive windows that showcase breathtaking Gulf vistas throughout the home. Designed with both elegance and functionality in mind, the residence offers beautifully appointed formal and informal living spaces that effortlessly accommodate intimate gatherings as well as grand-scale entertaining. The gourmet kitchen features premium appliances, custom solid wood cabinetry, stone countertops, wine refrigeration, abundant storage, and seamless integration with the surrounding living spaces. The private owner's retreat is a sanctuary overlooking the Gulf of America, complete with a fireplace, luxurious spa-inspired bath, generous walk-in closets, and private outdoor spaces designed to capture the beauty of the coastline. Spacious guest accommodations, including a private in-law suite, provide exceptional flexibility for family and visitors. A private elevator connects multiple levels, while advanced climate systems, humidity control, impact-rated windows, integrated security features, and thoughtful accessibility enhancements further elevate everyday living. Outside, expansive terraces, wraparound porches, beautifully landscaped grounds, outdoor kitchen, private courtyards, and multiple waterfront entertaining areas create an extraordinary extension of the home's luxurious interior. One of the property’s most extraordinary features is the private rooftop retreat-over 1,500 square feet of elevated outdoor living, accessed directly by the elevator. Designed for unforgettable entertaining, it offers breathtaking 360-degree panoramic views spanning Clearwater Beach, the Gulf of America and the Intracoastal Waterway. A dedicated gas fireplace hookup provides the perfect setting for elegant evenings under the stars. Completing this exceptional residence is an oversized tandem garage with ample space for two vehicles, plus a golf cart or exotic sports car-a rare luxury in beachside living! Located directly on one of the top award-winning beaches - Clearwater Beach, upscale dining, marinas, shopping, and vibrant coastal attractions, this distinguished residence represents far more than a home—it is a legacy property in one of Florida's most desirable waterfront destinations. Combining an irreplaceable Gulf-front setting, enduring architectural appeal, exceptional construction, and an unrivaled location, this is a truly rare opportunity to own one of Clearwater Beach's premier luxury waterfront estates.

810 Eldorado Avenue, Clearwater Beach

$989,000

Welcome to your private island retreat, tucked away on a quiet cul-de-sac in one of Tierra Verde's most desirable neighborhoods. This exceptional POOL HOME blends MULTI-GENERATIONAL LIVING, ENERGY EFFICIENCY, and the Florida lifestyle you've been dreaming of. Featuring 4 BEDROOMS, 3 BATHROOMS, and a 2-CAR GARAGE, the flexible split floor plan includes two bedrooms on the main level and two upstairs. The spacious upstairs retreat is ideal as a SECOND PRIMARY SUITE, PRIVATE GUEST QUARTERS, or IN-LAW SUITE, complete with pre-plumbing for a kitchenette and washer/dryer hookups. The downstairs primary suite features a spa-inspired STEAM SHOWER, while the adjacent bedroom and bath offer the opportunity to create an expansive LUXURY PRIMARY SUITE. The inviting living room showcases a dramatic stone accent wall with a WOOD-BURNING FIREPLACE, while the chef's kitchen is equipped with NEWER STAINLESS STEEL APPLIANCES, a WINE REFRIGERATOR, and pull-out refrigerator drawers. Step outside to your private tropical oasis featuring lush landscaping and a sparkling POOL, perfect for year-round entertaining and relaxation. A standout architectural feature is the charming CRAFTSMAN-INSPIRED TURRET, leading to a unique third-floor lookout surrounded by windows—ideal as a HOME OFFICE, studio, or peaceful retreat. Enjoy peace of mind with major updates including a NEW ROOF (2025), FULLY PAID-OFF SOLAR PANELS with electric bills averaging under $40/month, TWO A/C SYSTEMS (2020 & 2023), and a TANKLESS WATER HEATER. Located just minutes from marinas, waterfront dining, downtown St. Petersburg, and only 3 miles from Fort De Soto Park, you'll enjoy award-winning beaches, boating, kayaking, fishing, biking, and nature trails right outside your door. This is a rare opportunity to own an energy-efficient island home in one of Tampa Bay's most sought-after waterfront communities.

4 Beds ⋅ 3 Baths ⋅ SubDv. ⋅ 33715 Zip Code

Welcome to your private island retreat, tucked away on a quiet cul-de-sac in one of Tierra Verde's most desirable neighborhoods. This exceptional POOL HOME blends MULTI-GENERATIONAL LIVING, ENERGY EFFICIENCY, and the Florida lifestyle you've been dreaming of. Featuring 4 BEDROOMS, 3 BATHROOMS, and a 2-CAR GARAGE, the flexible split floor plan includes two bedrooms on the main level and two upstairs. The spacious upstairs retreat is ideal as a SECOND PRIMARY SUITE, PRIVATE GUEST QUARTERS, or IN-LAW SUITE, complete with pre-plumbing for a kitchenette and washer/dryer hookups. The downstairs primary suite features a spa-inspired STEAM SHOWER, while the adjacent bedroom and bath offer the opportunity to create an expansive LUXURY PRIMARY SUITE. The inviting living room showcases a dramatic stone accent wall with a WOOD-BURNING FIREPLACE, while the chef's kitchen is equipped with NEWER STAINLESS STEEL APPLIANCES, a WINE REFRIGERATOR, and pull-out refrigerator drawers. Step outside to your private tropical oasis featuring lush landscaping and a sparkling POOL, perfect for year-round entertaining and relaxation. A standout architectural feature is the charming CRAFTSMAN-INSPIRED TURRET, leading to a unique third-floor lookout surrounded by windows—ideal as a HOME OFFICE, studio, or peaceful retreat. Enjoy peace of mind with major updates including a NEW ROOF (2025), FULLY PAID-OFF SOLAR PANELS with electric bills averaging under $40/month, TWO A/C SYSTEMS (2020 & 2023), and a TANKLESS WATER HEATER. Located just minutes from marinas, waterfront dining, downtown St. Petersburg, and only 3 miles from Fort De Soto Park, you'll enjoy award-winning beaches, boating, kayaking, fishing, biking, and nature trails right outside your door. This is a rare opportunity to own an energy-efficient island home in one of Tampa Bay's most sought-after waterfront communities.

342 2nd Avenue N, Tierra Verde

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