Gulfport Homes with Sailboat Water Water Frontage

Gulfport Homes with Sailboat Water Water Frontage

Welcome to Gulfport, Florida – a hidden gem nestled in Pinellas County, where the charm of a quaint seaside town meets the vibrancy of coastal living. Known for its eclectic arts scene, friendly community, and stunning waterfront views, Gulfport offers a unique blend of relaxation and excitement. With a rich history and a laid-back atmosphere, this city is perfect for those seeking a peaceful retreat while still enjoying the perks of modern amenities.

One of the most sought-after features in Gulfport is its beautiful homes with sailboat water frontage. Imagine waking up to breathtaking views of the shimmering waters, where your boat is just steps away from your back door. These properties not only offer direct access to the Gulf of Mexico but also provide a lifestyle filled with adventure and leisure. Whether you’re an avid sailor or simply enjoy the tranquility of waterfront living, Gulfport’s sailboat-friendly homes are a dream come true.

The community is vibrant and welcoming, with local shops, art galleries, and delightful eateries lining the streets. The monthly Gulfport Art Walk showcases the talents of local artists and fosters a sense of community that is hard to find elsewhere. With parks, beaches, and recreational activities all around, residents can enjoy an active outdoor lifestyle year-round.

Discover the allure of Gulfport, where charming homes with sailboat water frontage await you. Experience the magic of coastal living in this picturesque Florida town, where every day feels like a vacation. Come and find your slice of paradise in Gulfport today!

Newest Gulfport Homes with Sailboat Water Water Frontage

4501 37th Street S, St Petersburg
$1,295,000
3 Beds ⋅ 2 Baths ⋅ Broadwater SubDv. ⋅ 33711 Zip Code
Waterfront living in Broadwater simply does not get much better than this. Immaculate inside and out, this 3-bedroom, 2-bath home with a 2-car garage sits along one of the widest and largest canals in the area, surrounded by gardens and landscaping that have been cared for with extraordinary attention to detail. Out back, the reason people move to Florida becomes immediately clear. A beautiful dock and deck with boat lift puts the water just steps from your door. Launch the boat for an easy afternoon on Tampa Bay, head out early for a morning of fishing, or simply stay home and enjoy the frequent visits from playful dolphins and manatees right off the end of your dock. The outdoor spaces feel more like a private tropical retreat than a backyard. A sparkling swimming pool is surrounded by custom paver patios and walkways, while the screened lanai provides a comfortable place to relax throughout the year. A wonderful cedar gazebo with a metal roof creates an inviting setting for outdoor dining, morning coffee, cocktails with friends, or a quiet dinner overlooking the pool and waterfront. Inside, the home reflects the same level of care. The kitchen was remodeled in 2022, and new sliding glass doors connect the interior living spaces beautifully with the pool, lanai and waterfront beyond. Three bedrooms and two bathrooms offer a comfortable, practical floor plan, while the 2-car garage and additional paver driveway provide exceptional parking for family and guests. Equally impressive is the extensive list of improvements. In 2025, the home received a new HVAC system, new water heater, new garage floor epoxy and fresh exterior paint. A new variable-speed pool pump was added in 2024. Improvements in 2023 included new dock pilings, an extended deck, additional paver driveway, updated electrical panel, new pool heater and new rear screened enclosure and lanai. In 2022, the owners added new stainless boat-lift cables, remodeled the kitchen, installed new sliding glass doors and replaced the garage door. The home was repiped with new water-supply lines in 2018, when the pool interior and solar panels were also added. And then there is the location. Broadwater is one of South St. Petersburg's most desirable waterfront communities, right in the heart of the thriving Skyway Marina District. You can spend the morning on the water, the afternoon along the award-winning Gulf Beaches, and the evening enjoying the restaurants, arts, culture and energy of vibrant Downtown St. Petersburg, all within minutes of home. Beautifully maintained, thoughtfully improved and surrounded by an outdoor environment that captures the very best of Florida waterfront living, this is more than a house with a pool and a dock. It is a home designed around the reasons people choose to live in St. Petersburg in the first place.

4501 37th Street S, St Petersburg
43 Bayview Court S Unit A, St Petersburg
$1,210,000
3 Beds ⋅ 4 Baths ⋅ Pointe At Marina Bay Condo The SubDv. ⋅ 33711 Zip Code
NEW PRICE! Exceptional waterfront value in gated Marina Bay. This newly renovated luxury residence offers nearly 2,900 square feet of coastal-modern living PLUS a highly coveted 30-foot deeded boat slip that conveys with the property—no separate purchase and no waiting list. Seller is motivated and ready for the next owner to enjoy the Florida waterfront lifestyle. A secure key-access elevator opens directly to your private foyer, revealing soaring 11-foot ceilings, elegant tray ceilings, 8-foot doors, expansive impact-rated windows and doors, and an open-concept floor plan filled with natural light. The spacious layout includes three generous ensuite bedrooms, three full baths plus a powder room, chef's kitchen with custom wood cabinetry, abundant storage, gas fireplace, and an expansive wraparound balcony overlooking the waterfront. For boaters, Marina Bay's protected marina offers convenient docking and easy access to Boca Ciega Bay, the Intracoastal Waterway, Tampa Bay and the Gulf of Mexico. Your deeded 30-foot slip makes spontaneous sunset cruises, fishing and waterfront dining part of everyday life. Recent renovations, along with a new community roof and freshly painted exterior in 2026, create a true turn-key, lock-and-leave residence. Residents enjoy two swimming pools, two spas, a waterfront fishing pier, fitness center, clubhouse, secure under-building parking and beautifully maintained grounds. Ideally located near Eckerd College and just minutes from vibrant Downtown St. Petersburg, St. Pete Beach, Fort De Soto Park, the Pinellas Trail, Stetson University College of Law, waterfront dining, museums, championship golf, premier marinas and Tampa International Airport. Some waterfront homes simply offer a view. This one offers the freedom to step aboard your boat and go.

43 Bayview Court S Unit A, St Petersburg
3896 42nd Avenue S, St Petersburg
$2,475,000
3 Beds ⋅ 3 Baths ⋅ Broadwater SubDv. ⋅ 33711 Zip Code
Your boat gets a 20,000-pound lift. You get the Broadwater lifestyle to match. On an 80 x 140 Broadwater lot with deep-water channel access, this updated single-story home puts Boca Ciega Bay and the Gulf minutes off the dock: sunrise fishing runs, sandbar afternoons, dinner by boat, and back before the sunset cocktails need refreshing. The composite dock is built for serious boating, with lighting, shore power, fresh water, and a kayak launch, all backed by a seawall updated in 2017. Inside, 2,957 square feet across 3 bedrooms and 2.5 baths are designed for people who entertain well and cook even better. The 2026 kitchen is the centerpiece: quartzite counters and backsplash, a Wolf 48-inch dual-fuel range with griddle and grill under a 48-inch Wolf hood, paneled Sub-Zero column refrigeration (30" refrigerator, 24" freezer, and dedicated wine column), a plumbed Miele coffee system, Cove dishwasher, and a wet bar with a Scotsman pellet ice maker. A hidden walk-in pantry keeps the counters gallery-clean. The party moves easily outdoors. A covered lanai with motorized roll-down screens opens to a solar-heated saltwater Pebble Tec pool, a new pool bath, and a full outdoor kitchen with a Blaze 36-inch grill and Azure wine fridge, finished with turf, landscape lighting, and a fire pit for late evenings by the water. Back inside, a large living room and second sitting area give guests room to spread out. The split floor plan gives the primary suite real privacy, with a spa-style walk-in shower, Toto washlet, and double custom walk-in closets. Two guest bedrooms share a beautifully updated hall bath. The big-ticket items are handled: updated electrical and plumbing, 2026 laundry remodel, 2025 AC, 2019 roof, 2018 tankless water heater, whole-house water softener and filtration, and owned (paid-off) solar panels to help offset energy costs. Turnkey, polished, and ready for the next owner to tie up and stay awhile.

3896 42nd Avenue S, St Petersburg
4379 44th Street S, St Petersburg
$1,400,000
4 Beds ⋅ 3 Baths ⋅ Broadwater Unit 2 Blk P SubDv. ⋅ 33711 Zip Code
Welcome to waterfront living at its finest in the highly sought-after Broadwater neighborhood of St. Petersburg. Situated on an oversized 11,278-square-foot lot with 80 feet of waterfront frontage, this beautifully updated 4-bedroom, 3-bathroom residence offers 2,505 square feet of thoughtfully designed living space and a lifestyle that is second to none. Best of all, this home has never flooded, providing peace of mind while enjoying all the benefits of waterfront living. Inside, you'll find spacious living areas filled with natural light and designed to maximize the stunning water views. At the heart of the home is a chef's kitchen featuring premium Wolf appliances including double ovens and a Wolf microwave/oven combination, along with Sub-Zero refrigeration. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating the perfect setting for both everyday living and entertaining. Step outside and discover your own private waterfront resort. The expansive backyard is anchored by a massive pool overlooking the canal and surrounded by multiple seating and gathering areas, offering countless places to relax, entertain, and enjoy the view. The covered outdoor kitchen is a true showpiece, complete with an Alfresco grill, Alfresco cooktop, Sub-Zero refrigerator, Sub-Zero ice maker, and Perlick wine refrigerator, creating the ultimate outdoor entertaining experience. Boating enthusiasts will appreciate the private dock, dedicated jet ski platform, and recently installed 14,000-pound boat lift. With 80 feet of seawall frontage and quick access to Boca Ciega Bay, you'll enjoy easy access to waterfront dining, fishing, sandbars, and sunset cruises right from your backyard. Additional updates include a new roof in 2022, updated sliding door in 2020, plumbing improvements, and the addition of the boat lift in 2023. Located in one of St. Petersburg's premier boating communities, Broadwater offers a convenient location just minutes from Gulf beaches, downtown St. Petersburg, shopping, dining, and entertainment. Whether you're hosting family and friends poolside, preparing dinner in the gourmet indoor or outdoor kitchen, or heading out for a day on the water, this exceptional property offers the very best of Florida waterfront living.

4379 44th Street S, St Petersburg
17 Franklin Court S Unit C, St Petersburg
$1,389,000
3 Beds ⋅ 2 Baths ⋅ Marina Bay Garden Villas SubDv. ⋅ 33711 Zip Code
Elevated, FORTIFIED Gold™ Certified and perfectly positioned in Marina Bay, 17C Franklin offers resilient construction, peaceful nature and water views, and the ease of single-level living. This fee-simple townhome is not a condo, so there is no condo assessment. Built of all-block construction with all living areas on the second level and accessed by private elevator, the home combines storm-ready peace of mind with everyday comfort. Overlooking a protected nature sanctuary with tranquil water views and no direct water exposure, the setting is both private and serene. Inside, the 2,334-square-foot floor plan features open-concept living, 10-foot vaulted ceilings, and seamless indoor-outdoor flow to upper and lower screened lanais. The gourmet kitchen is centered around a quartz island and includes a new Bosch dishwasher (2025). The primary suite offers dual walk-in California Closets and a spacious spa-like bath. Additional features include impact-rated windows, doors, and garage, reinforced roof-to-wall connections, a 22-kilowatt whole-house Generac generator, fully integrated HIVE smart home system, Klipsch surround sound, Hunter Douglas electronic blinds, and whole-house water purification. A rare bonus is the approximately 2,300-square-foot climate-controlled garage with epoxy floors, dedicated HVAC, retractable screen, and custom cabinetry, ideal for collectors, storage, or workshop space. Marina Bay amenities include two pools, including one geothermal pool, spas, fitness center, and deepwater marina. Elevated, engineered, and designed for easy living, this is a rare opportunity in Marina Bay.

17 Franklin Court S Unit C, St Petersburg
21 Crescent Place S, St Petersburg
$1,250,000
3 Beds ⋅ 2 Baths ⋅ College Landings Rep SubDv. ⋅ 33711 Zip Code
Set along the picturesque waters of Boca Ciega Bay is the coveted community of Marina Bay - a 60-acre tropical oasis nestled among Bayview Isles, Eckerd College, and Tierra Verde - where you will discover the artistic masterpiece of coastal living that is 21 Crescent Place. This 2000 square-foot, 3-bedroom, 2-bath residence offers a serene water view of the Bay with a private marina just steps away. The property is designed with exceptional flow, abundant light, and a seamless blend of indoor and outdoor spaces. This elevated, one-level home, complete with a private elevator and a whole-house natural gas 22kW GENERAC generator, offers luxurious seaside living with absolute peace of mind. Step inside to admire beautifully restored light oak floors and the exquisitely remodeled (2024) open-concept interior, where natural light and picturesque water views fill the space. Custom features, luxury finishes, and exceptional details abound, including bespoke lighting throughout, oversized windows, crown molding, and a modern staircase with stainless steel balusters. The heart of the home is the newly designed gourmet kitchen, equipped with smart-enabled appliances, a gas cooktop, custom cabinetry, an electronics drawer, quartz countertops, and a breathtaking waterfall island, making it a culinary enthusiast's paradise. Retreat to the owners' suite, a private sanctuary featuring built-in custom storage and a spa-like ensuite bath with a double vanity, a spacious tiled walk-in shower, and modern jetted soaking tub. Two additional bedrooms and a fully remodeled bath with a walk-in shower offer ample space for guests or family. All living spaces are on one level, served by a private elevator with access to the expansive 2,000 sq. ft., 4-car garage—perfect for vehicles, recreational equipment, a workshop, gym, or game room. The garage, complete with sink, is presently outfitted with a vintage darkroom, showcasing not only the versatility of the space but the owners’ artistic flair. Additional upgrades to the property include impact windows, a new tile roof (2021), a tankless hot water heater, mini-split in garage and whole house HVAC (2024). In addition to the lush tropical trees and plants surrounding the property, the landscaping and numerous lakes throughout Marina Bay enhance the beauty of this home. Watch osprey, herons, egrets, ibis, and ducks, along with pelicans diving for fish and dolphins and manatees playing in Boca Ciega Bay beside the community’s deep-water marina. Additional amenities include two pools (one with geothermal heat for year-round swimming), two spas, a fitness center, a community clubhouse, and a fishing pier adjacent to the docks. Marina Bay is a pet-friendly community, just 10 minutes from downtown St. Pete, 25 minutes from Tampa Airport, and a short bike ride along the protected bike paths of Pinellas Trail to Pass-a-Grille and St. Pete Beach. Deep water boat slips are available for purchase.

21 Crescent Place S, St Petersburg
3807 48th Avenue S, St Petersburg
$1,049,000
3 Beds ⋅ 2 Baths ⋅ Maximo Moorings SubDv. ⋅ 33711 Zip Code
Experience refined waterfront living in this fully reimagined residence located in the coveted Maximo Moorings of St. Petersburg’s Skyway Marina District. Perfectly positioned on a tranquil canal with direct access to open water, this exceptional 3-bedroom, 2-bath home offers a private boat dock with lift, a resort-style pool, and an expansive paver patio designed for effortless indoor-outdoor living. The thoughtfully redesigned interior showcases an open, flowing floor plan that seamlessly connects the living room, dining room, family room, and kitchen—ideal for both refined entertaining and relaxed coastal living. At the heart of the home, the chef-inspired kitchen impresses with new quartz countertops, new rich wood cabinetry, premium new appliances, a breakfast bar, an oversized pantry closet, and a pass-through window to the patio for seamless alfresco dining. Every detail has been elevated with new baths, new flooring, new doors, extensive upgrades throughout, and lush new landscaping. A new A/C system (2025) and new washer and dryer provide modern efficiency and peace of mind. The desirable split-bedroom layout offers privacy and tranquility. The elegant primary suite features a walk-in closet, spa-like en suite bath, and sliding glass doors opening directly to the pool and patio. Two generously sized guest bedrooms provide ample closet space, while the beautifully appointed guest bath doubles as a convenient pool bath. Both the dining room and family room open to the outdoor living area through sliding doors, enhancing the home’s seamless connection to its waterfront setting. Whether lounging poolside, entertaining under the stars, or cruising directly to open water from your backyard, this extraordinary home captures the essence of luxury Florida waterfront living.

3807 48th Avenue S, St Petersburg
4200 46th Avenue S, St Petersburg
$1,299,000
3 Beds ⋅ 2 Baths ⋅ Maximo Moorings SubDv. ⋅ 33711 Zip Code
New Price! Welcome to this beautifully renovated, move-in-ready waterfront retreat in the highly desirable Broadwater neighborhood, featuring underground utilities and effortless coastal living. This 3-bedroom, 2-bath residence is offered fully furnished, making it ideal as a primary home, second home, or investment opportunity. Designed for true Florida waterfront living, the property features two private boat lifts (12,000 lb & 13,000 lb capacities), offering easy access to Tampa Bay and the Gulf. Enjoy seamless indoor-outdoor living with a screen-enclosed pool and freestanding hot tub, perfect for relaxing or entertaining year-round. Ideally located just minutes from downtown St. Petersburg, pristine beaches, and only 30 minutes to Tampa International Airport, this home delivers the ultimate blend of luxury, convenience, and coastal lifestyle.

4200 46th Avenue S, St Petersburg
18 Jefferson Court S, St Petersburg
$1,099,000
3 Beds ⋅ 2 Baths ⋅ College Landings Rep SubDv. ⋅ 33711 Zip Code
ELEVATED with no previous storm impact or flooding, this home has hurricane impact windows and doors, a full house generator and wind-rated remote power screens on lanai. Perfectly situated 10 minutes to vibrant downtown St. Petersburg and a 5-minute drive to the Gulf (you can even ride your bike or walk from the neighborhood to the beach along a wide biking/pedestrian path!) and 25 minutes to Tampa International airport, this home provides easy access to the best of coastal and city living. Minutes from top rated golf courses and water activities, this home offers exceptional storage, even room for a boat! Step inside to discover cathedral ceilings and a bright, open floor plan featuring luxury vinyl plank flooring throughout. Architectural designed with expansive outdoor living create a home that feels larger and more distinctive than a typical townhome. The updated kitchen and baths shine with modern finishes, complimented by designer lighting, fresh paint, and upgraded plumbing. Every detail has been thoughtfully considered, including plantation shutters and custom closets for added functionality. Enjoy relaxing or entertaining on the screened porch and expansive lanai(25x17) with spectacular views of the Boca Ciega Bay, Maximo Channel and lush gardens. A 3+ car epoxy garage and tankless water heater add extra convenience and peace of mind. This architecturally stunning property truly has it all-modern updates, prime location, and stunning surroundings. Marina Bay amenities include 2 pools (1 geothermal heated for year-round swimming), large spa overlooking pond and fountain, gym and community room. Day slips available at community marina. A private fishing pier, perfect for casting a line at sunset. Don't miss this opportunity to call this one home!

18 Jefferson Court S, St Petersburg
17B Franklin Court S, St Petersburg
$1,799,000
3 Beds ⋅ 2 Baths ⋅ Marina Bay SubDv. ⋅ 33711 Zip Code
Our NEW CONSTRUCTION Marina Bay Villas feature ELEVATED SINGLE-STORY LIVING 17'+ ABOVE SEA LEVEL --- NO IMPACT FROM HURRICANE HELENE OR MILTON FROM RISING WATER OR WIND. This former builder model home with amazing views of the lagoon and preserve is now for sale! Designed and built to FORTIFIED – Gold standards, which is superior resilient construction that far exceeds building code. Our beautifully appointed Villas in the amazing waterfront community of Marina Bay provide the ideal blend of pure luxury and practical convenience – over 2,300 SF of living space ALL ON ONE LEVEL, with an equal amount of parking and storage below providing a garage beyond compare! Featuring a modern, open floor plan with a PRIVATE ELEVATOR from the first level garage to the second floor living level. Custom features and luxury finishes in this 3 bedroom, 2 bath Villa include 10’ ceilings, dramatic vaults in the Great Room, premium appliances, WALK-IN-PANTRY, natural gas cooking, and 22kW GENERAC Natural GAS GENERATOR are standard! NO LOSS OF POWER HERE! To top it off, feel secure with all CONCRETE BLOCK construction and foam insulation for energy efficiency. Marina Bay is located on the southern tip of Pinellas County on Pinellas Bayway next to Eckerd College, just 6 minutes to downtown St. Petersburg, moments to world-class beaches and only 25 minutes to Tampa airport. This waterfront community features almost 2,000’ of intracoastal water (ICW) directly on Boca Ciega Bay. Community amenities include 2 pools, 2 spas, fitness center, clubhouse, fishing pier, direct access to Pinellas Trail, tropical landscaping, spectacular water features and fountains, an abundance of wildlife and so much more. Pet friendly, deep water boat slips available. PRIVATE, PEACEFUL, PROTECTED!

17B Franklin Court S, St Petersburg
47A Bayview Court S, St Petersburg
$2,200,000
3 Beds ⋅ 3 Baths ⋅ Marina Bay SubDv. ⋅ 33711 Zip Code
Our NEW CONSTRUCTION Marina Bay Villas feature ELEVATED SINGLE-STORY LIVING 17'+ ABOVE SEA LEVEL ---NO IMPACT FROM HURRICANE HELENE OR MILTON FROM RISING WATER OR WIND. This spectacular NEW villa in the beautiful waterfront and gated community of Marina Bay offers the ideal blend of pure luxury and practical convenience – almost 2,600 sq.ft. of living space ALL ON ONE LEVEL, with an equal amount of parking and storage below providing a garage beyond compare! The beautifully appointed Delray Grande Villa model features a modern, open floor plan and your own PRIVATE ELEVATOR from the first level garage to the second floor living level. Custom features and luxury finishes in this 3 bedroom, 2-1/2 bath Villa include 10’ ceilings, dramatic vaults in the Great Room, premium appliances, a walk-in Pantry and Laundry Room, natural gas cooking, and 22kW GENERAC Natural GAS GENERATOR. All block construction with foam insulation for energy efficiency. The spacious Kitchen features Cambria counter tops, wood cabinets, and stainless steel appliances. Marina Bay is ideally located on the southern tip of Pinellas County next to Eckerd College, just 6 minutes to downtown St. Petersburg, moments to world-class beaches and only 25 minutes to Tampa airport. This pet-friendly, waterfront community features almost 2,000’ of intracoastal water directly on Boca Ciega Bay. Community amenities include 2 pools (one with geothermal heat), 2 spas, fitness center, clubhouse, fishing pier, direct access to Pinellas Trail, lush tropical landscaping, spectacular water features and fountains, an abundance of wildlife and so much more. Deep water boat slips available. PRIVATE, PEACEFUL, PROTECTED!

47A Bayview Court S, St Petersburg
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