PRIME LOCATION in the heart of Gulfport's vibrant waterfront district, this exceptional 5 unit commercial property presents a rare turnkey opportunity for investors seeking to capitalize on the area's thriving vacation rental market. Just STEPS from Gulfport Beach and Boca Ciega Bay, guests can enjoy a walkable coastal lifestyle surrounded by waterfront dining, boutique shopping, art galleries, fishing, boating, and year-round community events. Recently renovated with a fresh coastal aesthetic, the property features 5 attractive units showcasing luxury vinyl plank flooring, updated kitchens and bathrooms, contemporary fixtures, and bright, open living spaces designed to appeal to today's travelers. Tropical landscaping, charming curb appeal, and ample on-site parking further enhance the property's welcoming beach-town atmosphere. One of Gulfport's greatest attractions is its unique blend of Old Florida charm and vibrant local culture. Guests can stroll to the popular Tuesday Fresh Market, enjoy waterfront events at the Historic Casino Ballroom, explore nearby walking trails and nature preserves, or spend the day kayaking, paddleboarding, and fishing along Boca Ciega Bay. The area's lively arts scene, independent restaurants, and welcoming small-town feel continue to draw visitors seeking an authentic Florida experience. Ideally located just MINUTES from St. Pete Beach, Downtown St. Petersburg, and many of Tampa Bay's premier attractions, this beautifully renovated 5 unit property offers an exceptional opportunity to generate short-term rental income in one of Pinellas County's most sought-after waterfront destinations.

5 Beds ⋅ 5 Baths ⋅ TB8522343 MLS

PRIME LOCATION in the heart of Gulfport's vibrant waterfront district, this exceptional 5 unit commercial property presents a rare turnkey opportunity for investors seeking to capitalize on the area's thriving vacation rental market. Just STEPS from Gulfport Beach and Boca Ciega Bay, guests can enjoy a walkable coastal lifestyle surrounded by waterfront dining, boutique shopping, art galleries, fishing, boating, and year-round community events. Recently renovated with a fresh coastal aesthetic, the property features 5 attractive units showcasing luxury vinyl plank flooring, updated kitchens and bathrooms, contemporary fixtures, and bright, open living spaces designed to appeal to today's travelers. Tropical landscaping, charming curb appeal, and ample on-site parking further enhance the property's welcoming beach-town atmosphere. One of Gulfport's greatest attractions is its unique blend of Old Florida charm and vibrant local culture. Guests can stroll to the popular Tuesday Fresh Market, enjoy waterfront events at the Historic Casino Ballroom, explore nearby walking trails and nature preserves, or spend the day kayaking, paddleboarding, and fishing along Boca Ciega Bay. The area's lively arts scene, independent restaurants, and welcoming small-town feel continue to draw visitors seeking an authentic Florida experience. Ideally located just MINUTES from St. Pete Beach, Downtown St. Petersburg, and many of Tampa Bay's premier attractions, this beautifully renovated 5 unit property offers an exceptional opportunity to generate short-term rental income in one of Pinellas County's most sought-after waterfront destinations.

3101 Beach Boulevard S Unit 1-5, South Pasadena

Listing courtesy of MIHARA & ASSOCIATES INC.. 813-960-2300

$1,210,000

JUST REDUCED $90,000! Exceptional Value Meets Income-Producing Potential in Gulfport's Historic Waterfront District. A rare opportunity to own a fully furnished, Key West-inspired coastal retreat offering short-term vacation rental potential, breathtaking Boca Ciega Bay views, and one of the most walkable locations in Gulfport's Historic Art District. Whether you're searching for a high-performing Airbnb/VRBO investment, second home, or full-time waterfront residence, this turnkey property delivers an unmatched combination of lifestyle, luxury, and exceptional value. Just steps from Gulfport's charming downtown, you'll enjoy award-winning restaurants, art galleries, boutique shopping, waterfront parks, marinas, live entertainment, and the beloved Tuesday Fresh Market. This is Florida coastal living at its finest. Designed to maximize indoor-outdoor living, the home features multiple private balconies and expansive outdoor entertaining spaces overlooking Veterans Park and Boca Ciega Bay—perfect for morning coffee, sunset cocktails, or simply soaking in the waterfront atmosphere. Inside, an open-concept floor plan is filled with natural light and thoughtfully designed for entertaining. The gourmet kitchen showcases stone countertops, abundant cabinetry, generous prep space, and premium finishes that make hosting effortless. The luxurious primary suite offers a peaceful retreat with a professionally designed walk-in closet and a spa-inspired ensuite featuring dual vanities, a whirlpool soaking tub, and an oversized walk-in shower. Two additional guest bedrooms each enjoy private balconies with beautiful water views and refreshing coastal breezes. Built for long-term durability and low-maintenance ownership, this exceptional home includes an elevator, impact-rated windows, Hardie plank siding, Trex decking, synthetic turf landscaping, and a whole-home solar system that helps keep utility costs remarkably low. The oversized two-car garage offers abundant storage for vehicles, kayaks, paddleboards, golf carts, bicycles, and all your beach gear. Located just minutes from Downtown St. Petersburg, award-winning Gulf beaches, championship golf, marinas, and Tampa Bay's premier attractions, this move-in-ready residence is equally suited as a luxury primary home, seasonal escape, or income-producing investment. With a recent $90,000 price improvement, this is an exceptional opportunity to own one of Gulfport's premier waterfront homes at an incredible new value. Schedule your private showing today.

4 Beds ⋅ 3 Baths ⋅ TB8457726 MLS

JUST REDUCED $90,000! Exceptional Value Meets Income-Producing Potential in Gulfport's Historic Waterfront District. A rare opportunity to own a fully furnished, Key West-inspired coastal retreat offering short-term vacation rental potential, breathtaking Boca Ciega Bay views, and one of the most walkable locations in Gulfport's Historic Art District. Whether you're searching for a high-performing Airbnb/VRBO investment, second home, or full-time waterfront residence, this turnkey property delivers an unmatched combination of lifestyle, luxury, and exceptional value. Just steps from Gulfport's charming downtown, you'll enjoy award-winning restaurants, art galleries, boutique shopping, waterfront parks, marinas, live entertainment, and the beloved Tuesday Fresh Market. This is Florida coastal living at its finest. Designed to maximize indoor-outdoor living, the home features multiple private balconies and expansive outdoor entertaining spaces overlooking Veterans Park and Boca Ciega Bay—perfect for morning coffee, sunset cocktails, or simply soaking in the waterfront atmosphere. Inside, an open-concept floor plan is filled with natural light and thoughtfully designed for entertaining. The gourmet kitchen showcases stone countertops, abundant cabinetry, generous prep space, and premium finishes that make hosting effortless. The luxurious primary suite offers a peaceful retreat with a professionally designed walk-in closet and a spa-inspired ensuite featuring dual vanities, a whirlpool soaking tub, and an oversized walk-in shower. Two additional guest bedrooms each enjoy private balconies with beautiful water views and refreshing coastal breezes. Built for long-term durability and low-maintenance ownership, this exceptional home includes an elevator, impact-rated windows, Hardie plank siding, Trex decking, synthetic turf landscaping, and a whole-home solar system that helps keep utility costs remarkably low. The oversized two-car garage offers abundant storage for vehicles, kayaks, paddleboards, golf carts, bicycles, and all your beach gear. Located just minutes from Downtown St. Petersburg, award-winning Gulf beaches, championship golf, marinas, and Tampa Bay's premier attractions, this move-in-ready residence is equally suited as a luxury primary home, seasonal escape, or income-producing investment. With a recent $90,000 price improvement, this is an exceptional opportunity to own one of Gulfport's premier waterfront homes at an incredible new value. Schedule your private showing today.

5429 Essex Avenue S, South Pasadena

Listing courtesy of KELLER WILLIAMS ST PETE REALTY. murraycoleman@kw.com

$739,000

Experience the best of Florida living in this stunning 2-bedroom, 2-bath coastal retreat, ideally positioned just the second house from the beach. Built in 2017 and meticulously maintained, this 2,750 sq ft residence blends modern design with relaxed Gulfport charm. The open-concept main living area is perfect for entertaining and features LVP flooring throughout, contemporary lighting, and abundant natural light. The chef’s kitchen is appointed with quartz countertops, stainless steel appliances, a center island with breakfast bar, shaker-style cabinetry with crown molding, tile backsplash, stainless range hood, and a walk-in pantry with a custom door. A dedicated dining area offers ample space for gatherings and everyday living. The spacious primary suite includes an ensuite bath with dual vanities, a large soaking tub, and an oversized tiled walk-in shower. A guest bedroom and an elegant guest bath with a large tiled shower complete the main living quarters. Enjoy outdoor living from one of two second-story balconies—one overlooking the front for coastal breezes and one in the rear with views of your private backyard oasis. The lower level features a large unfinished space, offering incredible potential for future expansion. With plenty of room to customize, the area could easily be built out to include additional bedrooms, bathrooms, a game room, home gym, or bonus living space—allowing you to design the perfect layout to fit your lifestyle. Outdoors, relax or entertain by the sparkling in-ground pool in the fenced backyard, complemented by a paved driveway and a 2-car attached garage. Located in the heart of vibrant Gulfport, this home is just steps from the sand and minutes from the city’s charming downtown, known for its colorful art district, waterfront dining, and lively community events. This move-in-ready coastal home offers a rare opportunity to live just moments from the Gulf. Schedule your private showing today.

2 Beds ⋅ 2 Baths ⋅ W7882028 MLS

Experience the best of Florida living in this stunning 2-bedroom, 2-bath coastal retreat, ideally positioned just the second house from the beach. Built in 2017 and meticulously maintained, this 2,750 sq ft residence blends modern design with relaxed Gulfport charm. The open-concept main living area is perfect for entertaining and features LVP flooring throughout, contemporary lighting, and abundant natural light. The chef’s kitchen is appointed with quartz countertops, stainless steel appliances, a center island with breakfast bar, shaker-style cabinetry with crown molding, tile backsplash, stainless range hood, and a walk-in pantry with a custom door. A dedicated dining area offers ample space for gatherings and everyday living. The spacious primary suite includes an ensuite bath with dual vanities, a large soaking tub, and an oversized tiled walk-in shower. A guest bedroom and an elegant guest bath with a large tiled shower complete the main living quarters. Enjoy outdoor living from one of two second-story balconies—one overlooking the front for coastal breezes and one in the rear with views of your private backyard oasis. The lower level features a large unfinished space, offering incredible potential for future expansion. With plenty of room to customize, the area could easily be built out to include additional bedrooms, bathrooms, a game room, home gym, or bonus living space—allowing you to design the perfect layout to fit your lifestyle. Outdoors, relax or entertain by the sparkling in-ground pool in the fenced backyard, complemented by a paved driveway and a 2-car attached garage. Located in the heart of vibrant Gulfport, this home is just steps from the sand and minutes from the city’s charming downtown, known for its colorful art district, waterfront dining, and lively community events. This move-in-ready coastal home offers a rare opportunity to live just moments from the Gulf. Schedule your private showing today.

3120 Clinton Street S, South Pasadena

Listing courtesy of RE/MAX CHAMPIONS. 727-807-7887

$2,698,000

Discover a one-of-a-kind modular home steps from Boca Ciega bay with fabulous views from every level. This stunning home boasts 7 bedrooms, 7.5 bathrooms, and a spacious 5-car garage. Imagine the options afforded by this layout. Perfect for multi generational living, Airbnb or income producing potential,1031 exchange, Entrepreneurial think tank retreat,hotel or one large single dwelling. Featured RV garage, perfect for storing your work vehicle, creating a mobile office or even launching a rental business. Step into your own private retreat, featuring separate living quarters on each level. With private entrances and upscale finishes throughout, you’ll enjoy flexibility without sacrificing privacy. The top floor is a true sanctuary—your personal haven with 3 bedrooms, a beautifully designed office, and breathtaking views of Boca Ciega Bay. Bask in natural light on rich mahogany floors beneath soaring vaulted ceilings. The gourmet kitchen, equipped with a gas stove and expansive island, leads to a covered veranda where sunsets paint the sky, perfect for entertaining or evenings of relaxation. The second floor is a versatile space, currently optimized as a 2-bedroom suite and 1-bedroom executive apartment—ideal for guests or rental income. On the ground floor, a charming studio suite offers an additional escape, complemented by a well-equipped workshop and beautiful landscaping nourished by a well-water irrigation system. Every inch of this estate reflects unparalleled craftsmanship with features like hurricane-impact windows, individual climate control for each space, tankless water heaters, and a whole-house water filtration system. Designed to embrace the luxury of coastal living while providing peace of mind with CAT 5 storm resilience. This home truly stimulates everyone’s imagination. Embrace the ultimate Florida lifestyle—this exceptional property awaits your personal touch! In the heart of downtown Gulfport steps from Boca Ciega Bay.

7 Beds ⋅ 8 Baths ⋅ TB8444501 MLS

Discover a one-of-a-kind modular home steps from Boca Ciega bay with fabulous views from every level. This stunning home boasts 7 bedrooms, 7.5 bathrooms, and a spacious 5-car garage. Imagine the options afforded by this layout. Perfect for multi generational living, Airbnb or income producing potential,1031 exchange, Entrepreneurial think tank retreat,hotel or one large single dwelling. Featured RV garage, perfect for storing your work vehicle, creating a mobile office or even launching a rental business. Step into your own private retreat, featuring separate living quarters on each level. With private entrances and upscale finishes throughout, you’ll enjoy flexibility without sacrificing privacy. The top floor is a true sanctuary—your personal haven with 3 bedrooms, a beautifully designed office, and breathtaking views of Boca Ciega Bay. Bask in natural light on rich mahogany floors beneath soaring vaulted ceilings. The gourmet kitchen, equipped with a gas stove and expansive island, leads to a covered veranda where sunsets paint the sky, perfect for entertaining or evenings of relaxation. The second floor is a versatile space, currently optimized as a 2-bedroom suite and 1-bedroom executive apartment—ideal for guests or rental income. On the ground floor, a charming studio suite offers an additional escape, complemented by a well-equipped workshop and beautiful landscaping nourished by a well-water irrigation system. Every inch of this estate reflects unparalleled craftsmanship with features like hurricane-impact windows, individual climate control for each space, tankless water heaters, and a whole-house water filtration system. Designed to embrace the luxury of coastal living while providing peace of mind with CAT 5 storm resilience. This home truly stimulates everyone’s imagination. Embrace the ultimate Florida lifestyle—this exceptional property awaits your personal touch! In the heart of downtown Gulfport steps from Boca Ciega Bay.

5659 Shore Boulevard S, South Pasadena

Listing courtesy of COASTAL PROPERTIES GROUP. 727-493-1555

$445,000

Live the Gulfport life in this charming, walkable home. Embrace the vibrant, laid-back Gulfport lifestyle from this beautifully renovated bungalow. Positioned for easy strolls to the downtown area, you can enjoy the Art District, restaurants, and the waterfront just blocks from your front door. This bright and airy 2-bed, 2-bath home blends classic Florida charm with modern updates. The luminous sunroom offers a peaceful retreat, while the polished terrazzo floors add character throughout. Completely move-in ready, this property is more than a home—it's your entrance to everything Gulfport has to offer.

2 Beds ⋅ 2 Baths ⋅ TB8426104 MLS

Live the Gulfport life in this charming, walkable home. Embrace the vibrant, laid-back Gulfport lifestyle from this beautifully renovated bungalow. Positioned for easy strolls to the downtown area, you can enjoy the Art District, restaurants, and the waterfront just blocks from your front door. This bright and airy 2-bed, 2-bath home blends classic Florida charm with modern updates. The luminous sunroom offers a peaceful retreat, while the polished terrazzo floors add character throughout. Completely move-in ready, this property is more than a home—it's your entrance to everything Gulfport has to offer.

2831 Clinton Street S, South Pasadena

Listing courtesy of GULFPORT REALTY. 727-289-5500