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$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

$3,375,000
5 Beds 4 Baths SubDv. 33707 Zip Code
Must-see Italian Riviera-style villa offering exceptional coastal living in the amazing gated community of Pasadena Yacht & Country Club! This spectacular 5-bedroom, 4-bath residence offers 4,895 square feet of living space and is one of the largest one-story homes in the community. Set on one of the neighborhood’s largest lots at nearly half an acre, the highly desirable U-shaped design provides exceptional privacy while creating a seamless connection between the spacious interior and remarkable outdoor spaces. The resort-style backyard is truly an entertainer’s dream. The expansive area features a heated saltwater lap pool (resurfaced in 2024), Jacuzzi, outdoor kitchen, gas fire pit and abundant space for entertaining, dining, or simply relaxing and enjoying the Florida lifestyle. From the moment you enter the inside the impressive scale of the home is immediately apparent. The open floor plan features an elegant living room, formal dining area, and beautifully appointed wet bar. The bar includes an ice maker, quartz countertops, peninsula with seating space, two refrigerators and abundant cabinetry. The adjacent living room features beautiful wood flooring and soaring cathedral ceilings. The formal sunken dining area is framed by dramatic ceilings rising more than 20 feet and is complemented by a dedicated wine room with a Thermador wine cooler. Movie nights become an experience in the state-of-the-art media room, complete with a huge screen and surround sound. The gourmet kitchen is equally impressive, featuring a Sub-Zero refrigerator, Wolf gas range with double ovens, granite countertops, large island, peninsula with seating, and an abundance of cabinetry. Just off the kitchen is a SECOND dining area and living room, giving multiple spaces for privacy or to entertain guests in. Next to that also includes a versatile bedroom that can easily function as a children’s playroom, home office, library, or family room. The private south wing is dedicated to the primary suite and additional bedrooms. The enormous primary retreat features his-and-her closets with custom organizers, dual sinks with powder area, and a whirlpool tub overlooking the marina. An indoor shower and separate outdoor shower add a distinctive resort-style touch. Two additional generously sized bedrooms on this wing provide comfortable accommodations for family and guests. A spacious three-car garage offers ample storage, an epoxy-coated floor, and dedicated work area. Other upgrades include: full-home generator, hurricane-impact windows/sliders/doors, block home, full-home security system, water softener, irrigation/sprinkler system, dual HVAC systems, central vacuum, ceiling-mounted sound system, laundry room, large driveway, pest-control service. Pasadena Yacht & Country Club offers an exceptional private-club lifestyle with 18-hole championship golf course, tennis and pickleball courts, Olympic-size swimming pool, fitness center, and an active calendar of social events. The club is planning a new state-of-the-art fitness center as well as updates to the golf course and marina in 2027. New owners have the ability to bypass the current membership waitlist, which is reportedly more than two years long. Close to downtown St. Pete, St. Pete Beach, easy drive to Tampa, Bradenton, and Sarasota, and walking distance to charming downtown Gulfport. Home never flooded during the seller’s ownership and sits notably higher than many surrounding homes.

6320 Pasadena Point Boulevard, Gulfport

$400,000
3 Beds 2 Baths SubDv. 33707 Zip Code
Welcome to **1714 55th Street S, Gulfport, FL 33707**, where comfort, convenience, and the Florida lifestyle come together in one exceptional opportunity. Whether you're searching for a primary residence, seasonal retreat, or investment property, this move-in-ready **3-bedroom, 2-bath home** offers outstanding value with **no deed restrictions**, giving you the flexibility to truly make it your own. From the moment you arrive, you'll appreciate the peace of mind that comes with major updates already completed. The **roof was replaced in 2021**, a **4-point inspection has just been completed**, and for added confidence, the seller is including a **one-year home warranty** for the new owner's protection. Best of all, this home is **ready for immediate occupancy**, allowing you to move in and start enjoying the Florida lifestyle right away. Inside, you'll find a functional floor plan with comfortable living spaces, generous bedrooms, and two full bathrooms designed to accommodate families, guests, or those who simply appreciate extra space. Natural light fills the home, creating a warm and inviting atmosphere that's ready for your personal touches. One of this home's greatest advantages is its incredible location in the heart of Gulfport. Known for its vibrant arts community, welcoming small-town charm, and beautiful waterfront, Gulfport has become one of Pinellas County's most desirable places to live. Spend your weekends strolling along the Gulfport Marina, exploring the eclectic shops and local art galleries, dining at award-winning waterfront restaurants, or enjoying live music and community festivals that take place throughout the year. The city's famous Tuesday Fresh Market and First Friday Art Walk create an atmosphere unlike anywhere else on Florida's Gulf Coast. Outdoor enthusiasts will appreciate the nearby parks, walking trails, pickleball and tennis courts, kayak launches, and waterfront recreation opportunities. Enjoy spectacular sunsets over Boca Ciega Bay, launch your boat from nearby public ramps, or simply relax along the scenic waterfront while watching dolphins play. Beach lovers will appreciate being just a short drive from some of Florida's most beautiful white-sand beaches, including **St. Pete Beach, Treasure Island, Pass-a-Grille, Madeira Beach, and Fort De Soto Park**. Whether you enjoy boating, fishing, paddleboarding, or simply soaking up the sun, you'll have endless opportunities just minutes from your front door. The location also provides quick access to vibrant **Downtown St. Petersburg**, where you'll enjoy world-class restaurants, rooftop bars, museums, breweries, shopping, waterfront parks, entertainment venues, and professional sports. Visit the renowned Salvador Dalí Museum, catch a Tampa Bay Rays game, explore Beach Drive, or enjoy concerts and events at the St. Pete Pier—all just a short drive away. Commuters will appreciate convenient access to I-275, making travel to Tampa, Clearwater, and both Tampa International and St. Pete-Clearwater International Airports simple and convenient. With **no HOA or deed restrictions**, valuable recent improvements, immediate availability, and an unbeatable location close to Gulfport's waterfront, Downtown St. Petersburg, and the Gulf beaches, this home offers an incredible opportunity to enjoy everything Florida's Gulf Coast has to offer. Schedule your private showing today and discover why so many people are proud to call Gulfport home.

1714 55th Street S, Gulfport

$100,000
1 Beds 1 Baths SubDv. 33707 Zip Code
Reduced for a quick sale!! Highly regarded first floor condo unit within Town Shores Chatham building with included covered assigned parking! Experience Florida coastal living at its finest in the highly desirable town Shores community- A vibrant active adult (55+) neighborhood perfectly situated in the shores of Boca Ciega bay in charming Gulfport. Amenities include four heated swimming pools, tennis, pickle ball, shuffleboard courts, and billiard rooms. A large clubhouse with fitness center, arts and crafts room, card and game rooms. This unit features New kitchen cabinets and countertops, Stainless Appliances, fresh paint throughout, New AC unit (condenser and air handler), New vinyl flooring in bedroom alongside a new modern bathroom and shower. HOA fee includes almost everything except electric; Water, internet, cable, trash, sewer, ground maintenance, etc. Unit is nearing completion by hired contractors-Front and rear doors are in unit and ready to be installed in line with other items. Don't miss your opportunity to live a short stroll from historic downtown Gulfport, where you’ll find eclectic shops, art galleries, dining, nightlife, and cultural events — all just minutes from beautiful Suncoast beaches and close to St. Petersburg’s vibrant urban amenities. DISCLOSURE: Some photos have been virtually staged to give buyers perspective and visualize space.

3018 59th Street S Unit 111, 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

$630,000
2 Beds 2 Baths SubDv. 33711 Zip Code
MUST SEE this dream home with 2 Bedrooms/2 Full Baths and In-Ground Pool in the heart of Gulfport’s Marina District! HVAC just replaced! Enjoy a morning coffee on the front porch! Relax with the family around the living room fireplace! Entertain friends in the huge sitting area next to pool or Fire-Pit space in the back yard! Enjoy separate living and family rooms, each designed for comfort and style! You’re going to fall in love with all the options! Other highlights include: Cabana bath leading to the huge lanai/pool, block home, large bedrooms, spacious living room, separate dining room, gorgeous hard wood floors, oversized (552 sq ft) 2 car garage with workshop area/home gym/loft and storage! Steps to Boca Ciega Bay, Gulfport Municipal Marina, Yacht Club, Clam Bayou Nature Park, the Pinellas Trail, Bars and Restaurants! Quick drive to Beaches, I275, downtown Saint Pete, Tampa, Bradenton and Sarasota. Florida's laidback lifestyle at its best! Don't miss out on the chance to call this gem your home!

4814 Del Rio Way S, Gulfport

$519,000
2 Beds 2 Baths SubDv. 33707 Zip Code
Down payment assistance or lender paid rate buy down available for qualified buyers with preferred lender. Introducing this charming 2 bed, 2 bath home nestled in the heart of Gulfport, FL. This beautifully maintained residence offers the perfect blend of modern comfort and coastal charm. Featuring a spacious floor plan with abundant natural light, a split floor plan, a well-appointed kitchen with new stainless steel appliances and quartz countertops, and a cozy dining nook. All the windows in the home have been upgraded to ensure energy savings and weather protection. Brand NEW Roof. In the back of the home you'll find the enclosed Florida room perfect for year round use. Step outside to a large backyard, ideal for entertaining or gardening. The one car garage offers plenty of space for your toys and golf-cart. This property does NOT require flood insurance. House has been recently tented and is 4pt ready. HVAC system is 2019. Large tree in front of house was recently removed due to insurance concerns. Enjoy the vibrant Gulfport community, with its eclectic shops, restaurants, and easy access to the beach. This home is a true gem, offering the Florida lifestyle you've been dreaming of.

2320 59th Street S, Gulfport

$?
3 Beds 3 Baths SubDv. 33707 Zip Code
Seller financing available! 2332 SF town home with custom accents and 3 BR/2 1/2 BA/ 2 Car Garage! Separate entry foyer leads to spacious open floor plan with dining area defined by elegant columns and tray ceiling with subtle back-lighting. Perfect for entertaining, the kitchen displays beautiful wood cabinets, solid surface countertops and stainless steel appliances. An expansive master bedroom suite on the 2nd floor includes two large walk-in closets, private balcony,and deluxe bath area with dual sinks, large soaking tub & separate shower stall. Built in 2003, the gated community of Villas Del Verde is adjacent to Pasadena Yacht & country Club and very centrally located - close to shopping, grocery stores, restaurants, beaches, Stetson College of Law, artsy Gulfport and downtown St Petersburg - everything a family needs for today's active lifestyle. Come home to Villas Del Verde, grill out on your covered patio, relax on your master suite balcony overlooking the tranquil pond and fountain, or work out in the fitness room at the Clubhouse, followed by a dip in the heated pool & spa!

6304 Vista Verde Drive W, Gulfport

$?
2 Beds 2 Baths SubDv. 33707 Zip Code
Enjoy your "home in the sky" in this recently painted Penthouse condo at Pelican Bay. Located in the gated community of Pasadena Yacht and Country Club communities this 2 bedroom/2 bath condo offers an expansive south facing view and encompasses the city skyline to the Skyway Bridge and beach. The interior has been redesigned for todays living with an open living/dining room and kitchen plan. Additionally the kitchen offers a glass backsplash, tons of storage, including rollout shelving and "pot drawers" plus a bar sink to make entertaining easy.Special features included in this home are your entrance hallway with gallery lighting and chair rail, full size washer/dryer, walk-in fitted closets, space saving pocket doors and storm shutters for your peace of mind. The two condo buildings share a pool, with hot tub and clubhouse. This building is pet friendly. Need more to do, join Pasadena Yacht and CC and enjoy golf, dining, tennis and more. Whatare you waiting for....

5940 Pelican Bay Plaza S Unit Ph-C, Gulfport

$339,000
3 Beds 1 Baths SubDv. 33707 Zip Code
Great Price for cottage on large lot with GORGEOUS WATER VIEWS! Recently renovated old Key West style cottage. Pergola porch to relax and watch the boats go by. Across from Mariner's Cove High and Dry. Bay views from several rooms. Crossstreet to your boat! Restored wide plank hardwood floors. Vaulted ceilings with beautiful beams. Cute little fireplace. Completely renovated kitchen with hand painted cabinetry and cottage shelves for country beach cottage appeal. New kitchen appliances. Original bead board walls and ceilings. Ceramic tile in bathroom and kitchen. Unique floor plan bright/open. Landscaped with brick gardens, new sod, brick walk and pergola. Every kind of tropical plant grows easily here! Newirrigation system, sod throughout entire property. Room for large pool and/or addition. Furniture & accessories negotiable. Walk to marina,beach restaurants and shops. Part of Pink Flamingo Tour. The cutest house in Gulfport everyone says.One of a kind! Historic home tax credit possible. $45k under appraisal. Rented seasonal now $2500 mo.

Gulfport