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$399,900
2 Beds ⋅ 2 Baths ⋅ TB8507494 MLS
This newly remodeled, 2-bedroom, 2-full bathroom solid block bungalow offers the perfect blend of historic charm and modern luxury in the heart of Gulfport’s vibrant Art District. Positioned on a picturesque, hand-laid brick street, this home places you steps away from the eclectic Tuesday Fresh Market, lively festivals, and famous Boca Ciega Bay sunsets. This home has been completely updated with fresh interior and exterior paint, giving it a crisp, turn-key feel. The open living space flows into a fully updated kitchen featuring brand-new stainless steel appliances. With two full, completely renovated bathrooms, this home ensures modern comfort and style in every corner. The spacious outdoor patio is a true standout, offering a versatile space for entertainment or your latest creative projects. After a day at the nearby beach, enjoy a refreshing rinse in the private outdoor shower. The fully fenced yard provides a safe sanctuary for pets, and don't forget to grab a fresh mango! Start your mornings on the sweet front porch, a classic feature perfect for sipping coffee and greeting neighbors on one of Gulfport's iconic historic brick-lined streets. Whether you are looking for a creative retreat or a coastal sanctuary, this bungalow captures the very best of Florida’s most artful community. Note: Roof 2018. AC 2018. Electric & plumbing 2025. All permits & inspections completed & receipts available.

2920 57th Street S, South Pasadena
$389,900
2 Beds ⋅ 1 Baths ⋅ TB8496629 MLS
This charming retreat is located in the vibrant downtown area of Gulfport just a few blocks from Beach Boulevard where you’ll discover eclectic shops, art galleries, lively restaurants/bars plus the popular Tuesday Fresh Market. Enjoy unbeatable proximity to the Gulfport Pier, marina, beach, parks, playgrounds, recreation center, theatre & library. With year-round events & activities plus quick access to downtown St. Petersburg & the Gulf beaches, this location truly offers the best of Florida living. Step inside this elevated, vintage 2 bedroom, 1 bath home & be greeted by a spacious enclosed front porch perfect for morning coffee or evening wine. The bright living room features hardwood floors flowing into a dining area & galley kitchen. Both bedrooms fit queen size beds with the larger bedroom offering a walk-in closet for added convenience. There is a detached studio with a bathroom & laundry room. The fully fenced yard backs up to an alley & includes a storage shed along with ample off-street parking via a long brick driveway. Newer roofs, A/C and main water heater. Recent termite treatment with a transferable warranty. Located in the AE flood zone. Fantastic investment opportunity, vacation home or winter escape. Furnishings & décor are negotiable. Don’t miss your chance to own this unique, vintage Gulfport gem.

2907 Clinton Street S, South Pasadena
$1,210,000
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
$739,000
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
$2,698,000
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
$445,000
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
$1,500,000
5 Beds ⋅ 7 Baths ⋅ TB8357835 MLS
BIG PRICE DROP! Newer construction modern coastal style home right in the heart of Gulfport. One block from the water and mere steps from all of the local favorites on Beach Drive. This three-level block construction home is a fortress with impact rated windows and doors. The oversized garage and corner lot provide ample parking for cars, golf carts, boats, and anything else you can think of. All five bedrooms have their own ensuite and each floor boasts a separate powder room. The open concept kitchen stuns with quartz countertops, soft close shaker cabinetry, high end Samsung appliances, and luxury lighting fixtures. Surrounding the entire second floor is a beautiful wrap around porch with marvelous water views that provide the perfect space for entertaining and taking in the Florida sunsets. The water views are further amplified off the third floor balcony beyond the loft and wet bar. Your own private elevator connects each floor making this residential masterpiece functionally flawless. Smart home features include a complete home security system, cameras, MyQ garage doors, and a Schlage smart lock. Other amazing features are the luxury vinyl flooring throughout, Eemax tankless hot water heater, recessed energy efficient LED lighting, and it can come fully furnished. For the investor looking to add a crown jewel to their portfolio please inquire about the financials and pro forma projections. Call today and be the envy of family, friends, and neighbors!

5402 31st Avenue S, South Pasadena
$275,000
1 Beds ⋅ 1 Baths ⋅ TB8325207 MLS
LAST PRICE DROP! LESS THAN LAND VALUE. Hurry this Mixed use property in the heart of down town Gulfport wont last. Step into the charm of this enchanting cottage located in the heart of Gulfport! While the home requires some TLC (Flood damage from Helene), it offers endless possibilities to create your dream space. The expansive outdoor living area is a true showstopper, featuring mature landscaping and a spacious deck perfect for entertaining or enjoying a quiet retreat. Nestled just a short distance from downtown Gulfport, you’ll enjoy easy access to the city’s vibrant scene of activities, restaurants, and entertainment. Whether you’re an investor or looking to personalize your own oasis, this property is your canvas to bring new life to a Gulfport gem. Don't miss the opportunity to embrace the Gulfport lifestyle—schedule a showing today! Home was affected by Hurricane Helene and has been substantially damaged - Buyer is fully responsible for verifying all permitting information, and the potential for the property with the City of Gulfport, county, and/or FEMA officials. Seller makes no warranties. Sold "AS-IS" with right to inspect.

3022 56th Street S, South Pasadena