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5433 Essex Avenue S, Gulfport
$1,200,000
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

6010 17th Avenue S, Gulfport
$1,680,000
4 Beds ⋅ 6 Baths ⋅ Pasadena Estates Sec G SubDv. ⋅ 33707 Zip Code
Perched high above sea level in a non-flood zone, (approximately 15’), this exceptional 1923 Spanish Mediterranean Revival Estate sits on nearly one Acre in the heart of Gulfport. The property features two structures with a combined 4 bedrooms and 5.5 bathrooms, including a beautifully preserved 3BR/3.5BA main residence, a versatile two-story carriage house, and a detached 2-car carport showing preserved wood rarely seen in the area. The main home showcases original hardwood floors, exposed wood-beam ceilings, graceful arches, two gas fireplaces, and hurricane-impact windows throughout. First floor layout includes formal living room with gas fireplace, formal dining room with large windows, a sunlit family room, a quaint powder bath and an en-suite guest bedroom or first floor primary with a fireplace! In the well appointed gourmet kitchen you will find heart-of-pine floors, gas range with 6-burner gas range with griddle, stainless steel appliances, a step-down walk-in pantry and more arches! Upstairs, a spacious primary en-suite features a walk-in dressing room, and access to the quintessential Spanish-style balcony. The guest bathroom comes with separate shower & claw foot tub, while the third bedroom enjoys the possibility of having its own future south-facing private balcony. The detached carriage house includes a guest en-suite, laundry room, two-car garage, one-car carport, and an upstairs flex room equipped with a full bath ideal as a home office, a studio, a gym, or a play room, you decide! Outdoor living is exceptional with a magnificent Resort-Style heated saltwater pool and spa with built-in self cleaning system, and lush fully fenced grounds. Encompassing an entire block from north to south, the extensive south-facing rear backyard with gate access, provides additional parking for large vessels - RV or boat, as well endless possibilities for a tennis, pickleball or basketball court for memorable outdoor entertaining. Conveniently located just minutes from Gulfport's vibrant waterfront district, award-winning beaches, downtown St. Petersburg, Tampa, and Sarasota, this remarkable Estate presents a rare opportunity to own a 1920’s classic that perfectly balances timeless charm, and modern comfort.

6010 17th Avenue S, Gulfport

2719 52nd Street S, Gulfport
$695,000
3 Beds ⋅ 3 Baths ⋅ Veteran City SubDv. ⋅ 33707 Zip Code
If you’re looking for historic Gulfport beach house charm combined with thoughtful modern upgrades, this fully renovated POOL home must be seen to be believed. Located in the art district, just a five minute walk to Beach Boulevard dining and shops, properties like this rarely come on the market. The original pine hardwood floors and portico ceilings have been beautifully restored. The interiors feature granite countertops, all new kitchen cabinetry, and updated lighting and fixtures. The property has been extensively upgraded with new electrical wiring, updated internal plumbing, heat pump and central A/C units, and a whole house water softener. Home had no storm damage and No flood insurance required! Solar panels installed on both the house and back building keep utility costs extremely low. Current Duke bills average approximately $35 per month, the minimum charge monthly. An electric vehicle charging station means fuel is free for your electric car. A stunning, natural garden at the back of the fully vinyl-fenced property features a generous, shaded entertainment lanai (20’ x 30’) with grilling pad and a prep kitchenette in the back building. Travertine pavers create elegant walkways and an easy-care surface for parties. A fountain and mature plantings make this a haven for birdwatching. A second screened dining lanai offers access to the saltwater swimming pool and the main kitchen. Brick pavers surround the pool, front driveway, and rear garage parking pad. All have been power-washed, re-sanded and sealed this year. Low-maintenance landscaping supported by a well and irrigation system, period-appropriate metal awnings above the front doors, and a metal storage shed add practicality to beauty. The spacious primary bedroom with ensuite bath opens into the back lanai and could also serve as an art studio, writer’s retreat, guest quarters, or home office. The home also includes a laundry room that doubles as a pantry and staging area for entertaining, complete with refrigerator, washer, dryer, granite counters, and storage cabinets. Major improvements have been made for storm protection and insurance savings. All duplex windows have been replaced with hurricane impact windows, hurricane shield covers protect the side doors and rear structure, and roof repair and strapping have been completed to qualify for full wind mitigation discounts. A great find for multi-generational families, friends looking for a compound or even the versatility of a rental. If you sleep on this one, you won’t sleep in it.

2719 52nd Street S, Gulfport

5850 27th Avenue S, Gulfport
$425,000
3 Beds ⋅ 2 Baths ⋅ Caldwells Rep SubDv. ⋅ 33707 Zip Code
Tucked into a quiet residential street and directly adjoining Wood Ibis Park, this thoughtfully updated Gulfport home brings a rare combination of location, privacy, connection to nature and flexible living. The home’s split layout creates an easy flow. Two bedrooms off the front hall are complemented by the inviting living room and ample kitchen with L-shaped quartz counters and new cabinetry. The home features wood-grain luxury vinyl flooring throughout. A light-filled dining room opens through French doors to a generous screened lanai, leading to a lush private garden and fenced back yard. At the rear of the home, a versatile bedroom suite features a vaulted ceiling, walk-in closet, private bath, and its own kitchenette, along with a private entrance and dedicated off-street parking. The space works well as a primary retreat, guest suite, creative studio, multigenerational living quarters, rental opportunity, or work-from-home solution. The home provides peace of mind with new HVAC - 2025, roof (hurricane clips and attic insulation) - 2023, solar panels - owned, impact windows, vinyl siding, new fridge and dishwasher; electric bills are minimal. After storm-related flooding in 2024, the seller used the necessary repairs as an opportunity to make meaningful upgrades, resulting in modernized systems, finishes, and energy performance. Appliances, solar, all convey. (The mailbox does not...the exception...) Mature trees and abundant birdlife create a calm, restorative setting where it’s easy to forget you’re in a metro area, convenient to everything. Native landscaping minimizes water use, while permeable pavers, a private rear driveway, alley access, and a spacious storage shed add everyday practicality. The verdant back garden opens directly onto Wood Ibis Park with its lake and walking trails. Stroll to the Pearl Restaurant or downtown Gulfport’s waterfront, art scene, dining, and community events—an eclectic, open-hearted community and one of Florida’s most sought-after small cities.

5850 27th Avenue S, Gulfport

2714 52nd Street S, Gulfport
$790,000
4 Beds ⋅ 3 Baths ⋅ Veteran Park SubDv. ⋅ 33707 Zip Code
Paradise found! Wonderful home located on a double lot in historic Art District of Gulfport. The interior of this home has been extensively remodeled with a coastal modern flair. The main house has an open floor plan with a formal foyer and grand hall, perfect for displaying art. Dining and living rooms features a triple sliding glass door with access to a private patio. The stylish kitchen has solid-wood cabinetry with soft-close drawers, quartz and maple butcher-block countertops, upgraded stainless appliances including a gas range with Euro-style vent hood. The original bead-board ceiling was kept intact adding charm to the modern kitchen. The generously sized, light filled primary suite is to die for and features a wall of built in closet space, large bath with huge shower, dual vanities, and a real laundry room. The two guest rooms share an updated hall bath. Recent updates include gorgeous White Oak luxury vinyl, solar system, updated electric & plumbing, tankless gas water heater, plantation shutters, impact windows & sliders, spray foam insulation, and all new fans and light fixtures. Backyard stamped concrete patio and screened porch are perfect for all season dining and entertaining. Studio apartment is perfect for your guests or an art studio with its attached bath and bonus room that would make a perfect kitchenette. On the south side of the home, there is plenty of parking including a newly built oversized 2 car garage with workshop area- a paved driveway & non-paved areas for 7 vehicles, or even a boat or RV. The huge 1/4 acre fenced yard will be your private oasis with lots of space to relax, play, or BBQ - and there is room for a pool! NO FLOOD INSURANCE REQUIRED. Stroll to Beach Blvd with its casual & fine dining, fun shops, bars, & boutiques, and Tuesday morning fresh market; or walk to the park, waterfront, Pier, library & more! Our best Gulf beaches are a 9 minute drive, 2 International airports within 30 minutes, and downtown St Pete just 12 minutes!

2714 52nd Street S, Gulfport

6138 11th Avenue S, Gulfport
$605,000
3 Beds ⋅ 3 Baths ⋅ Pasadena Estates Sec F SubDv. ⋅ 33707 Zip Code
Welcome to this charming Gulfport retreat, where timeless character meets thoughtful updates located in a NO FLOOD ZONE. Upon entering the home you feel the instant warm with all the natural light through the huge windows and amazing details. The converted front porch and living room welcomes you and flows into the gorgeous updated kitchen. The shaker cabinets are 2 tone wood complemented with sparkling quartz counters. The beautiful black backsplash is such a great statement and pieces it all together. There are adequate cabinets for all your storage needs including a pantry. The large dining room is located just off from the kitchen and is the perfect spot to gather with your family and friends. The main home offers two spacious bedrooms and one-and-a-half baths. Main bedroom does have added closet space which is a rare find. The garage has been transformed into a fully permitted THIRD BEDROOM SUITE with its own bath. This is perfect for guests, a private office or an INVESTMENT RENTAL. Step outside to your private backyard oasis where lush landscaping, multiple patios, new turf grass and a sparkling SCREENED IN POOL provide endless options for relaxing or entertaining! The custom painting on the side of the converted garage is one of a kind and adds a great vibe. The home has new exterior paint and new lush landscaping. The home has beautiful luxury vinyl and tile throughout for easy cleaning. The home is located just a bike ride or short drive from Gulfport’s vibrant restaurants, shops, parks, Stetson Universtiy and the beaches. This home truly combines everyday convenience with the laid-back charm of coastal living.

6138 11th Avenue S, Gulfport

1604 58th Street S, Gulfport
$464,900
4 Beds ⋅ 2 Baths ⋅ Pasadena Gardens Gulfview Sec SubDv. ⋅ 33707 Zip Code
DUPLEX ALERT! Welcome to 1604 58th Street S, a vibrant mid-century duplex in the heart of Gulfport that’s full of charm, character, and income potential. This solid block property comes fully furnished and offers two separate 2-bedroom, 1-bath units, each with its own private entrance, unique style, and artistic flair. The front unit features bold colors, stained concrete floors, a retro kitchen, and a vintage tiled bath. The back unit has a cozy cottage vibe with mid-century pink cabinetry, wood-paneled walls, and an updated bathroom with a walk-in shower. Both units are bright and spacious, featuring a newer roof (2023), central HVAC (2017), newer on-demand water heaters (2018), and have ample storage. The fully fenced yard offers space to relax, garden, or entertain, and there’s a long driveway for off-street parking. Each unit is separately metered, with shared laundry and multi-family zoning, making it perfect for house-hacking, long-term tenants, or short-term rental use. Located just minutes from Gulfport Beach, the waterfront district, art walks, and downtown St. Pete, this is your chance to own a truly unique income property in one of Pinellas County’s most beloved neighborhoods. If you're looking for a property that’s anything but cookie-cutter, 1604 58th Street S delivers style, soul, and serious income potential. Schedule your showing today and step into a slice of Florida charm that’s bursting with possibility.

1604 58th Street S, Gulfport

6325 9th Avenue S, Gulfport
$359,000
3 Beds ⋅ 2 Baths ⋅ Pasadena Estates Sec C SubDv. ⋅ 33707 Zip Code
SELLERS ARE ACCEPTING BACK UP OFFERS - UNDER CONTRACT BUT WE ARE ACCEPTING ALL BACK UP OFFERS!!! PRICE IMPROVEMENT ON THIS HOME BY $24,000.00 - SELLERS HIGHLY MOTIVATED. Welcome to your bright and breezy Gulfport retreat! Ideally located just minutes from downtown Gulfport, the waterfront, Stetson University, and the Pinellas Trail, this home offers the perfect blend of comfort, convenience, and classic Florida charm. Step inside to find a light-filled living room with easy-care ceramic tile flooring, throughout the home, seamlessly flowing into the open modernized, custom kitchen and expansive great room – perfect for relaxing or entertaining. The home features two spacious bedrooms with large windows, and a full bathroom. The generous great room and dining area have an open-concept layout ideal for gatherings, leading to a screened-in porch that invites year-round indoor-outdoor living. Outside, the backyard is just waiting for you to make it your private oasis, complete with decking and a charming pergola. A standout feature of this property is the detached in-law apartment with a private entrance. This one-bedroom, one-bath unit includes tile flooring and a compact kitchen – great for guests, extended family, or rental potential. Additional features include a utility shed, easy access to US-19, Tyrone Square Mall, and vibrant downtown St. Petersburg. Roof replaced in 2005; A/C updated in 2011. Don't miss your chance to own this unique Gulfport gem – schedule your tour today!

6325 9th Avenue S, Gulfport

5021 24th Avenue S, Gulfport
$1,075,000
5 Beds ⋅ 4 Baths ⋅ SubDv. ⋅ 33707 Zip Code
Price improvement! The price of this exceptional home has been thoughtfully adjusted to align with the latest market conditions. This is an opportunity to own one of Gulfport’s most spectacular properties, located outside the flood zone on 3.5 lots, and with a turn-key, income producing casita, offering an incredibly attractive value to the future owner. Welcome to Sea Grape Cottage, a stunning ONE-OF-A-KIND property nestled in the heart of the vibrant and eclectic Historic Gulfport Art District. Spanning an impressive 3,686 sqft (342.4 m²) on one of the largest combined lots in Gulfport (NOT in a flood zone), this grand home blends vintage architectural details with modern updates and offers an incomparable “must see” price/sqft value. The first floor features a Great Room showcasing a magnificent wood-burning fireplace and perfect for entertaining, along with the spacious primary suite, an additional bedroom with walk-in closet, and a large office / bedroom. There is also an enclosed Florida room, perfect for relaxation. Upstairs you'll find another bedroom suite with generous closet space and a writing nook. The home boasts high ceilings, extensive areas for displaying art, and bamboo floors throughout the main living areas, adding warmth and elegance to the space. The fully renovated kitchen (with breakfast nook and pantry) delights with new cabinets, quartz countertops, recessed and pendant lighting, and top-of-the-line appliances. The large dining room, lovingly known as the “Boat Room", features a unique wooden ceiling, nautical design and a separate boat bench sitting area. Off the kitchen is a large private courtyard patio for al fresco dining. Attached to the home, with its own private entrance, is a FULLY FURNISHED charming one bedroom Casita, or mother-in-law suite, providing a perfect retreat for guests or potential turn-key rental income. There is also an attached oversized one-car garage with a sink and space for a work bench and storage. Recent updates include a new roof with wind mitigation features and new gutters, a new Trane 5-ton HVAC system, and several new appliances. The exterior has been thoughtfully updated, with a large main driveway providing ample parking, restored block wall along street perimeter, refreshed vintage paver walkways, a separate driveway for Casita access / RV parking, and gardens featuring fruit trees and ornamental plants. The property also includes an outdoor covered seating area, a well, and storage shed. Encompassing 3.5 lots, this property offers plenty of space for additional development, including a FULLY CLEARED LOT that is ready for your expansion ideas, such as a future pool or guest/rental house. The home is walking distance to Gulfport's lively art scene, acclaimed restaurants, shops, marina, and a variety of recreational options, including beaches, pickleball/tennis courts, parks, and more. With its exceptional charm, unique history, and proximity to the best of Gulfport, St Petersburg, Tampa and airports, Sea Grape Cottage is a truly unmatched property.

5021 24th Avenue S, Gulfport

1106 Freemont Street S, Gulfport
$357,500
2 Beds ⋅ 1 Baths ⋅ Pasadena Estates Sec H SubDv. ⋅ 33707 Zip Code
One or more photo(s) has been virtually staged. Now MOVE IN READY COME SEE THE IMPROVEMENTS! True Florida home with all the new improvements and today’s modern amenities. Walk up the gradual steps to a wide entry porch large enough to hold chairs and place to greet your neighbors that walk by your home in the morning or evening hours. Opening the front door you will be greeted with original hardwood flooring, ample hurricane graded windows that bring in the light and the large space to entertain friends and family. The kitchen will delight you with real wood cabinets, stainless steel appliances and lots of storage including a panty with pull out shelving. Enjoy your convection oven, microwave and beautiful granite counters. Lots of storage for all your kitchen dishes and appliances. Updates include new roof, new windows, complete bathroom with Jacuzzi soaking tub and farm house bathroom sink. Step next into the dining area with a huge window and nice space that adjoins a very large screened in porch, great place to relax after a meal. The porch opens up to a deck with composite decking and above ground pool. Beautiful landscaping enhances the area and adds a mild sweet aroma to the air. Around the corner is an outdoor bathroom and shower great after a swim in the pool or use as a guest bath for company. A separate entry off the deck to the bonus room with a wardrobe could be used as a 3rd bedroom has an adjoining room to use as a hobby area, office or walk-in closet. That room leads to the 2nd bedroom with closet. This beautiful Florida home truly rambles and the large yard is an open pallet for your dreams.buyers are responsible for veriflying the accuracy off all information

1106 Freemont Street S, Gulfport

5757 26th Avenue S, Gulfport
$875,000
Lake Butler Villa Cos Add SubDv. ⋅ 33707 Zip Code
Welcome to A HOME WITH ENDLESS POSSIBILITIES that is NOT in a flood zone. This exceptional property with its artistic flair in the heart of Gulfport offers more than meets the eye. This stunning 3-bedroom, 2-bathroom single family home with a separate 1/1 efficiency unit is a tropical paradise with updated kitchen and baths, bamboo flooring, wood burning fireplace, oversized garage, outdoor shower, and multiple sheds. The intriguing feature of this home is its versatility. Part of the main house can be closed off to create a studio w/bath that has its own separate entrance and parking, which is perfect for generating rental income, accommodating guests, or setting up a private workspace. In addition to the studio, the property also boasts a 1-bedroom, 1-bathroom rental unit with its own electric meters and a newer 2021 tankless hot water heater. Both units come fully furnished and ready to go; in the last three years they have generated over $147K in short term rental income. YTD Jan-Sep. for '23 totals are $47,933. - (Airbnb links are listed in realtor remarks, new owners will also be able to decide if they want to honor bookings scheduled Jan-Mar. '24). The home is situated on an oversized corner lot with 2 separate driveways with plenty of parking. If you have a green thumb or simply love to sit and relax surrounded by nature, the meticulously landscaped yard is an oasis with delightful local artwork around every winding path. This beautiful backyard had the honor of being featured in the 2021 Pink Flamingo Garden Tour! Just a short stroll away you will find you are in the town of Gulfport with all the charm it has to offer, including its restaurants, bars, shops, and artistic feel. Don't miss out on this one-of-a-kind property offering a perfect blend of comfortable living with proven income potential. Contact me today to experience it for yourself – this gem won't be available for long!

5757 26th Avenue S, Gulfport

5757 26th Avenue S, Gulfport
$875,000
4 Beds ⋅ 3 Baths ⋅ Lake Butler Villa Cos Add SubDv. ⋅ 33707 Zip Code
Welcome to A HOME WITH ENDLESS POSSIBILITIES that is NOT in a flood zone. This exceptional property with its artistic flair in the heart of Gulfport offers more than meets the eye. This stunning 3-bedroom, 2-bathroom single family home with a separate 1/1 efficiency unit is a tropical paradise with updated kitchen and baths, bamboo flooring, wood burning fireplace, oversized garage, outdoor shower, and multiple sheds. The intriguing feature of this home is its versatility. Part of the main house can be closed off to create a studio w/bath that has its own separate entrance and parking, which is perfect for generating rental income, accommodating guests, or setting up a private workspace. In addition to the studio, the property also boasts a 1-bedroom, 1-bathroom rental unit with its own electric meters and a newer 2021 tankless hot water heater. Both units come fully furnished and ready to go; in the last three years they have generated over $147K in short term rental income. YTD Jan-Sep. for '23 totals are $47,933. - (Airbnb links are listed in realtor remarks, new owners will also be able to decide if they want to honor bookings scheduled Jan-Mar. '24). The home is situated on an oversized corner lot with 2 separate driveways with plenty of parking. If you have a green thumb or simply love to sit and relax surrounded by nature, the meticulously landscaped yard is an oasis with delightful local artwork around every winding path. This beautiful backyard had the honor of being featured in the 2021 Pink Flamingo Garden Tour! Just a short stroll away you will find you are in the town of Gulfport with all the charm it has to offer, including its restaurants, bars, shops, and artistic feel. Don't miss out on this one-of-a-kind property offering a perfect blend of comfortable living with proven income potential. Contact me today to experience it for yourself – this gem won't be available for long!

5757 26th Avenue S, Gulfport

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