Gulfport Homes with Trail(s) Amenities

Gulfport Homes with Trail(s) Amenities

Welcome to Gulfport, Florida – a charming coastal gem nestled in Pinellas County. Known for its vibrant arts scene, friendly community, and stunning waterfront views, Gulfport offers a unique blend of small-town charm and modern amenities. This picturesque city is a haven for those seeking a laid-back lifestyle, with its colorful bungalows, quaint shops, and delightful eateries lining the streets.

One of the standout features of Gulfport is its commitment to outdoor living and recreation. Homes in this area often come with access to beautiful trails, perfect for walking, jogging, or biking. Imagine waking up in your cozy abode, stepping outside, and enjoying a refreshing morning stroll along scenic paths that wind through lush landscapes and tranquil parks. The interconnected trails not only promote an active lifestyle but also provide a sense of community, as residents and visitors alike enjoy the natural beauty that surrounds them.

Gulfport’s waterfront parks, such as the popular Gulfport Beach and the serene Clam Bayou Nature Park, offer additional opportunities for relaxation and recreation. Here, you can soak up the sun, engage in water sports, or simply unwind while watching the sunset over the horizon.

Whether you’re a first-time homebuyer or looking to retire in a peaceful paradise, Gulfport’s homes with trail amenities provide the perfect backdrop for a fulfilling lifestyle. Embrace the charm of this coastal city, where every day feels like a vacation, and the trails lead you to new adventures and cherished memories. Come discover your dream home in Gulfport, where life is truly a walk in the park!

Newest Gulfport Homes with Trail(s) Amenities

1 Beds ⋅ 1 Baths ⋅ Bermuda Bay Beach Condo SubDv. ⋅ 33711 Zip Code

Welcome to Bermuda Bay Beach & Racquet Club, a gated waterfront community on the shores of Boca Ciega Bay where resort-style amenities, beautiful sunsets, and an exceptional St. Petersburg location come together. This well-maintained second-floor, one-bedroom, one-bath condominium offers a comfortable and efficient layout designed to make the most of every square foot. The residence features a built-in Murphy bed for overnight guests, a brand-new washer and dryer, and a spacious rear porch overlooking lush tropical landscaping and the beautifully maintained courtyard. Bermuda Bay offers an impressive collection of amenities, including a private sandy beach, two heated swimming pools, a jacuzzi, lighted tennis and pickleball courts, racquetball, a putting green, shuffleboard, a gazebo, playground, kayak and canoe storage, beachside BBQ grills, two laundry facilities, and an active clubhouse with regular social events and activities. Residents often gather along the waterfront to enjoy afternoon cocktails and unforgettable Florida sunsets. The community also offers flexible rental options with a one-month minimum rental period, making this property an excellent choice for a primary residence, seasonal getaway, or second home. The HOA includes cable TV, internet, community pools, escrow reserves, exterior maintenance, on-site management, pest control, security, private roads, sewer, trash, water, and insurance. Ideally located next to Clam Bayou Nature Preserve, Bermuda Bay provides convenient access to everything St. Petersburg has to give. Downtown St. Pete is approximately 10 minutes away, St. Pete Beach is about 15 minutes away, and Tampa International Airport is approximately 20 minutes away. Gulfport Beach, restaurants, shopping, hospitals, entertainment, and major highways are all nearby. Enjoy waterfront living, outstanding amenities, and the relaxed Florida lifestyle at Bermuda Bay Beach & Racquet Club. Schedule your private showing today.

3730 42nd Way S Unit H, St Petersburg

1 Beds ⋅ 1 Baths ⋅ West Shore Village SubDv. ⋅ 33711 Zip Code

Welcome to West Shore Village! St. Petersburg’s best-kept secret and an outdoor adventurer’s paradise. This 1st level NON-Flood Zone 1 bedroom, 1 bath villa with a garage, has loads of storage and a beautiful garden view. The garage features a refrigerator and storage closet. There is a beautiful patio with Florida friendly plants where you can sit and watch the sunset, and the butterflies with a glass of wine. As you enter the home with its open floor plan, the living room has lots of natural light and space. The dining area has 2 additional closets for a pantry or storage. The kitchen is to the right with plenty of cabinets, and storage with the laundry closet. The bedroom has a walk-in closet, and ensuite bath with tub/shower. This Property is close to the heated (winter) and cooled(summer) pool and club house. The WSV community hosts monthly events in the club house, that include a kitchen, and restrooms with showers, Pool table room and library. Residents can rent the club house for family/ personal events. The tennis/ pickle ball, shuffleboard courts and horseshoes pit are around the corner. This 32-acre park like gated community is located next to the Pinellas Trail and Clam Bayou with its walking, biking, bird viewing, fishing, kayaking and paddleboarding. It is a fantastic location near downtown St Petersburg (10 minutes), with its art museums, music, restaurants and festivals. Top rated beaches and Ft. Desoto Park are under 8 miles away. Come to your Sunshine escape and unlock Florida Living at its best.

3216 39th Street Unit C, St Petersburg

1 Beds ⋅ 2 Baths ⋅ Seapointe Terrace Condo SubDv. ⋅ 33711 Zip Code

Wake up to breathtaking, unobstructed Tampa Bay views, spectacular sunrises, playful dolphins, and the waterfront lifestyle you’ve been dreaming of. From the moment you step inside, your eyes are drawn through the residence to the expansive waters of Tampa Bay beyond. Thoughtfully designed, this beautifully updated 1-bedroom, 2-bath condominium maximizes its 890 square feet with an open layout, two private patios, and water views from both the living room and the primary bedroom. Hurricane-impact sliding glass doors open to a covered waterfront patio with unobstructed Tampa Bay views, while a second set of impact sliders off the kitchen leads to a private front patio, creating inviting outdoor living on both sides of the home. Recent updates include remodeled bathrooms, new cabinetry, new appliances, an upgraded electrical panel, newer HVAC, and a convenient laundry closet in the second bath. Located in highly desirable Seapointe Terrace, this residence features one of the lowest HOA fees in the community at just $788 monthly. The HOA includes insurance, water, sewer, trash, cable, high-speed internet, building reserves, and resort-style amenities including a heated waterfront pool, tennis and pickleball courts, a fishing pier, kayak launch, kayak and bike storage, and additional community storage. The milestone inspection has been completed, and the association has fully funded reserves, offering added peace of mind. Ideally located with quick access to I-275, downtown St. Petersburg, Fort De Soto Park, and the Gulf beaches, you’re also just a short walk to the newly popular SkyBeach Resort, the marina, and waterfront dining. Whether you’re searching for a full-time residence or the perfect Florida retreat, this move-in-ready waterfront home offers exceptional updates, outstanding amenities, and an unbeatable Tampa Bay location.

7530 Sunshine Skyway Lane S Unit T30, St Petersburg

2 Beds ⋅ 2 Baths ⋅ Bermuda Bay Beach Condo SubDv. ⋅ 33711 Zip Code

Welcome to the waterfront, gated community of Bermuda Bay Beach & Racquet Club, where resort-style living meets incredible value! This spacious second-floor, 2-bedroom, 2-bath condominium offers approximately 1,100 square feet of comfortable living space and is ready for your personal touch. A new HVAC system installed in 2025 provides peace of mind, while newer laminate wood flooring runs throughout the home. In-unit full-size washer and dryer make living at the beach easy and convenient. The kitchen has been opened to create a unique café-style layout with a charming coffee bar, offering an inviting gathering space and endless possibilities for customization and renovation to your own taste. Whether you're searching for a full-time residence, seasonal getaway, or investment opportunity, this versatile property checks all the boxes. Bermuda Bay allows 30-day minimum rentals, making it ideal for generating income or enjoying a combination of personal use and vacation rental flexibility. Residents enjoy an exceptional array of amenities, including a private sandy beach on Boca Ciega Bay with breathtaking sunsets, two swimming pools, a hot tub, clubhouse, tennis and pickleball courts, racquetball, shuffleboard, horseshoes, kayak storage, and beautifully landscaped grounds, all within a secure gated community. Conveniently located just minutes from Gulf beaches, downtown St. Petersburg, Gulfport, restaurants, shopping, and I-275, you'll enjoy easy access to everything the Tampa Bay area has to offer. The seller is highly motivated and willing to consider all offers. This handyman special presents an outstanding opportunity to create your own perfect retreat and enjoy the Florida lifestyle at an affordable price. Don't miss your chance to make this hidden gem your own!

3580 41st Lane S Unit I, St Petersburg

2 Beds ⋅ 3 Baths ⋅ Bermuda Bay Beach Condo SubDv. ⋅ 33711 Zip Code

Welcome to Bermuda Bay Beach & Racquet Club — where every day feels a little more like vacation and a little less like reality. Tucked quietly in the heart of this gated waterfront paradise, this charming 2-bedroom, 2.5-bath townhouse offers 1,280 square feet of comfort, character, storage galore, and the kind of laid-back Florida lifestyle everyone chases. Let’s start with the rare stuff… because Bermuda Bay residents know: storage is basically waterfront gold. This floor plan is famous for its smart use of space and endless storage options, including a huge double-length walk-in closet in the primary suite, oversized guest room walk-in closet, under-stair storage, oversized pantry, attic access, and even an outdoor storage closet for beach gear, bikes, holiday decorations, or that paddleboard you swear you’re going to use every weekend. The layout is warm, comfortable, and move-in ready, with ceramic tile downstairs, hardwood flooring upstairs, newer windows, in-unit laundry, and room to personalize and update at your own pace — already priced accordingly so you can add your own style without paying for someone else’s questionable design choices from 2007. One of the standout features? The gorgeous, brand-new screened lanai completed last year with nearly $9,000 invested, creating the perfect private outdoor retreat surrounded by lush greenery and peaceful landscaping. Morning coffee, evening wine, lazy Sunday naps… this is the spot. Upstairs, the spacious primary suite features an updated vanity area, large corner walk-in shower with glass surround, and a built-in dressing/makeup area that feels delightfully tucked away from the world. Some furnishings are negotiable, making your move even easier. And then there’s Bermuda Bay itself — one of St. Petersburg’s best-kept hidden gems. Residents enjoy a private beach on Boca Ciega Bay with sunset views that honestly make you stop mid-sentence, two sparkling pools, a hot tub, tennis & racquet courts, clubhouse, kayak storage, shuffleboard, beautifully maintained grounds, and a private gated connection directly to the Pinellas Trail for biking, jogging, dog walks, or nature-filled strolls through nearby bird sanctuary areas. Despite feeling worlds away, you’re just minutes to Gulfport, downtown St. Pete, beaches, restaurants, nightlife, shopping, and easy highway access for commuting or airport runs. This is the sweet spot buyers wait for: private, peaceful, affordable waterfront community living with room to make it your own. Whether you’re looking for a full-time residence, seasonal escape, or investment opportunity, this Bermuda Bay townhouse delivers the Florida lifestyle with comfort, charm, and just enough tropical magic to make your friends jealous.

3595 41st Lane S Unit D, St Petersburg

2 Beds ⋅ 3 Baths ⋅ West Shore Village One SubDv. ⋅ 33711 Zip Code

Beautifully updated 2-bedroom, 2.5-bath townhome located in the gated community of West Shore Village in South St. Petersburg. This spacious residence offers 1,180 square feet of comfortable living space featuring an open-concept layout, updated finishes, and a bright Florida room perfect for a home office, additional living space, or relaxing year-round. Both bedrooms are generously sized, each with ample closet space and private bath access, while the additional half bath downstairs adds convenience for guests. Enjoy a prime location just minutes from downtown St. Pete, Gulf beaches, shopping, dining, and easy access to I-275 and the Skyway Bridge. Community amenities include a pool, tennis courts, shuffleboard, and beautifully maintained grounds. Don’t miss the opportunity to enjoy Florida living in one of St. Petersburg’s most convenient locations!

3267 39th Street S Unit B, St Petersburg

2 Beds ⋅ 2 Baths ⋅ Bermuda Bay Beach Condo SubDv. ⋅ 33711 Zip Code

Welcome to your slice of paradise in Bermuda Bay—where coastal vibes meet easy, everyday living. This nicely updated 2-bedroom, 2-bath second-floor condo offers 1,050 square feet of bright, open living space designed for both comfort and style. From the moment you walk in, you’ll notice the seamless flow of tile and wood-look flooring—durable, modern, and perfect for that laid-back Florida lifestyle (sand happens… this place can handle it). The updated kitchen features contemporary finishes and plenty of workspace, making it as functional as it is inviting, while both bathrooms have been tastefully refreshed for a clean, move-in-ready feel. No projects, no stress—just bring your suitcase and your favorite beach chair. One of the standout features? A brand-new screened-in lanai—your private spot for morning coffee, evening wine, or pretending you’re going to read a book while watching the palm trees sway instead. You’ll also love the convenience of a stacked, front-load washer and dryer right in the unit—because hauling laundry anywhere in Florida heat should be illegal. Located in the sought-after Bermuda Bay community, you’re surrounded by lush landscaping, waterfront access, and resort-style amenities that make every day feel like a getaway. Whether you're looking for a full-time residence, seasonal escape, or investment opportunity, this is a value-packed property that checks all the boxes. Move-in ready, stylishly updated, and priced to make sense—this one won’t sit around waiting.

3795 41st Lane S Unit H, St Petersburg

4 Beds ⋅ 4 Baths ⋅ Marina Bay Ph I & Ii SubDv. ⋅ 33711 Zip Code

THIS HIGH AND DRY PROPERTY HAS NEVER FLOODED! This home has an ADDITIONAL FULL BATH DOWNSTAIRS making this a 4 bedroom, 4 1/2 bath home. This gorgeous unpermitted, all wet, bathroom is handicap accessibile with a mini-split air handler, handmade italian marble tiles, dual shower-head, bidet toilet and back-lit mirror. This exceptional residence offers DEEP WATER open views across Maximo Channel, a private boat dock & lift, pool/hot tub & custom outdoor kitchen. Additionally, there's a customized automated audiovisual system with home theatre/stereo entertainment, security & indoor/outdoor/garage integration. Experience elevated waterfront living in the exclusive gated community of Marina Bay. This resort-style indoor/outdoor living at its finest, designed for both relaxation and entertaining!

19 Bayfront Court S, St Petersburg

2 Beds ⋅ 2 Baths ⋅ Dolphin Cay Antigua SubDv. ⋅ 33711 Zip Code

One or more photo(s) has been virtually staged. Discover breathtaking waterfront living from this elegant 5th-floor residence overlooking the open waters of Boca Ciega Bay in the sought-after gated community of Dolphin Cay. Wake each morning to expansive water views and the calming rhythm of the bay from your large, covered veranda, where year-round sunsets, passing boats, and the occasional dolphin or manatee create a constantly changing coastal panorama. Inside, the open-concept floor plan is designed to maximize both natural light and water views. Floor-to-ceiling windows and 8-foot sliding glass doors bring the outdoors in, filling the living and dining areas with natural light. The kitchen is perfectly positioned for entertaining, featuring granite countertops, a generous counter bar, and ample cabinetry, The primary suite is a peaceful waterfront retreat, offering stunning views of Boca Ciega Bay, a custom-designed walk-in closet, and a spa-style bath. The guest suite provides privacy and comfort, complete with a convenient Murphy bed and easy access to the adjacent guest bath and laundry area. A versatile bonus room offers exceptional flexibility and can serve as a third bedroom, home office, or media room depending on your needs. Additional features include hurricane shutters, updated windows, a private storage closet, and a reserved in garage parking space. Located within the guard-gated 88-acre waterfront community of Dolphin Cay, residents enjoy a resort-style lifestyle surrounded by lush tropical landscaping and protected nature areas. Community amenities include: Private beach and fishing pier, Three heated waterfront pools and spa, Three Har-Tru lighted tennis courts, Kayak launch and waterfront walking trails, Fitness center and clubhouse with billiards and library, two-acre private beach, and On-site management and 24-hour gated entry. Perfectly positioned just 10 minutes from the vibrant restaurants, museums, marinas, and cultural venues of Downtown St. Petersburg, while also minutes from the Gulf beaches of St. Pete Beach and Pass-a-Grille. Tampa International Airport and St. Pete-Clearwater International Airport are both easily accessible. An exceptional opportunity to experience peaceful waterfront living in one of St. Petersburg’s most beloved gated coastal communities.

4717 Dolphin Cay Lane S Unit 507, St Petersburg

6 Beds ⋅ 6 Baths ⋅ Dolphin Cay-Phase 1 SubDv. ⋅ 33711 Zip Code

Welcome to 4930 Sandpiper Lane, a stunning estate nestled within the sought-after, gated community of Dolphin Cay in St. Petersburg. This expansive, meticulously maintained home on a beautifully manicured double lot offers the perfect blend of luxury, functionality, and Florida lifestyle. Boasting 6,140 heated sq ft of living space with 6 spacious bedrooms, 4 full bathrooms, and 2 half baths, this home provides ample space for family and guests alike. The thoughtfully designed floor plan includes a dedicated office and an impressive theater room, perfect for working from home or enjoying movie nights in style. Outdoors, the private backyard retreat features a sparkling swimming pool, a basketball court, and lush mature landscaping — ideal for entertaining or simply relaxing under the Florida sun. A detached 3-car garage offers added convenience and storage. Peace of mind updates include a new roof in 2018, and a majority of the AC being replaced in 2024. Dolphin Cay is one of St. Pete’s premier gated waterfront communities, offering amazing sunset views to the West and Gulf of Mexico, an elegant community center with billiard/casino room, library, two community pools (one adult only), three Har-tru lighted tennis courts, private pier, health and fitness center, spa, private grilling area, storage & launch area for kayaks, plus a private 2 acre beach. Dolphin Cay is situated on 88 acres of lushly landscaped property with over 4 miles of boardwalks and nature trails that meander through a 24 acre wildlife preserve and around Spoonbill Lake. The Pinellas Bike Trail runs right in front of this complex and leads to miles of biking & walking trails throughout Pinellas County. All of this within minutes of downtown St. Petersburg, world-class dining, shopping, and the Gulf beaches. This is a rare opportunity to own a truly special property in a secure, amenity-rich neighborhood. Schedule your private showing today and experience the best of coastal living.

4930 Sandpiper Lane S, St Petersburg

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