Gulfport Homes with Trail(s) Amenities

Gulfport Homes with Trail(s) Amenities

Welcome to Gulfport, Florida – a hidden gem nestled in the heart of Pinellas County! This vibrant coastal city is renowned for its stunning waterfront views, charming arts district, and a laid-back lifestyle that beckons both families and retirees alike. With its warm, sunny climate and friendly community, Gulfport offers the perfect blend of relaxation and recreation.

One of the standout features of Gulfport is its commitment to outdoor living, particularly through its extensive trail systems. Homes in this delightful city often come with access to scenic trails that wind through lush parks and along the picturesque coastline. Imagine stepping out of your front door and onto a winding path that leads you to the stunning shores of Boca Ciega Bay, where you can enjoy leisurely walks, bike rides, or even a morning jog as the sun rises over the water.

Gulfport is not just about beautiful homes and trails; it’s also a community that thrives on culture and creativity. The city hosts numerous art festivals, farmers' markets, and live music events throughout the year, making it easy to engage with neighbors and enjoy the local scene. Whether you’re exploring the eclectic shops of the historic downtown area or savoring fresh seafood at waterfront eateries, Gulfport offers a lifestyle that is both enriching and enjoyable.

If you’re looking for a home that combines comfort with outdoor adventure, Gulfport’s trail-accessible properties are a perfect fit. Embrace the coastal lifestyle and discover the charm of Gulfport – where every day feels like a vacation!

Newest Gulfport Homes with Trail(s) Amenities

$325,000
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
$164,900
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
$650,000
2 Beds ⋅ 2 Baths ⋅ Osprey Pointe At Dolphin Cay SubDv. ⋅ 33711 Zip Code
Resort-Style Coastal Living at Dolphin Cay. With 2 Bedrooms, 2 Bathrooms, a Den/Bonus Room, as well as Under-Building Garage Parking. Welcome to paradise in the highly sought-after, 24-hour guard-gated resort community of Dolphin Cay. Offering an unparalleled blend of natural beauty and upscale amenities, this beautifully laid-out condo delivers the ultimate Florida lifestyle. Step inside and let your eyes be drawn directly to the outdoors. This residence features a full-length balcony spanning the entire width of the unit, accessible via 3 separate sets of sliding glass doors, the perfect spot for catching gentle coastal breezes. Take in tranquil views of the community pond, lush nature preserves, Boca Ciega Bay, Downtown Gulfport, and glimpses of St. Pete Beach. For ultimate peace of mind, the covered porch of the balcony has a screen hurricane shutter. The Living Space is a bright, open-concept living room and dining area featuring durable, easy-to-maintain tile flooring throughout the main areas. The Kitchen provides a countertop workspace, a breakfast bar, stainless steel appliances, and an abundance of storage. The Primary Suit: A spacious retreat featuring a large walk-in closet and its own private sliding glass door entry to the expansive balcony. The en-suite bathroom is beautifully equipped with dual sinks, a walk-in shower, and a separate bathtub. The Guest Wing & Bonus Space: Looking for a potential home office, hobby space, or extra room for hosting visitors? The versatile den/bonus room is the perfect answer. It sits directly across from the guest bathroom and adjacent to the guest bedroom, which offers excellent privacy and a window looking out toward the breezy, open-air hallway. Dolphin Cay is situated on 88 lushly landscaped acres that double as a wildlife preserve. Living here feels like being on a permanent vacation with access to top-tier resort amenities: 3 swimming pools and spas. A fully equipped fitness center and a beautiful clubhouse complete with billiards and card rooms. As well as Lighted tennis courts, a fishing pier, kayak storage/launch, and boardwalk nature trails private beach access, on Boca Ciega Bay. You are just minutes away from some of the country’s top-rated beaches, including Pass-A-Grille, Fort De Soto State Park, and St. Pete Beach. When you crave culture, fine dining, and nightlife, the vibrant energy of Downtown St. Petersburg is just a short drive away, and quick access to I-275 makes travel a breeze. Don't miss your chance to own a piece of paradise in one of St. Petersburg’s premier waterfront communities!

4801 Osprey Drive S Unit 103, St Petersburg
$199,000
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
$239,000
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
$179,873
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
$4,495,000
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
$825,000
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
$3,350,000
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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