Longboat Key Homes with Pool Community Features

Longboat Key Homes with Pool Community Features

Welcome to Longboat Key, Florida—a hidden gem nestled along the stunning Gulf Coast. This idyllic barrier island is celebrated for its pristine beaches, vibrant sunsets, and a laid-back lifestyle that attracts both residents and visitors alike. With its lush tropical landscapes and charming neighborhoods, Longboat Key offers a unique blend of luxury and tranquility, making it the perfect place to call home.

One of the standout features of this beautiful community is its array of homes with pools, providing residents with the ultimate luxury of enjoying sun-soaked days right in their backyards. Imagine hosting family gatherings or relaxing with a good book by your private pool, all while surrounded by the soothing sounds of nature. Many properties boast modern designs and high-end finishes, ensuring that your home is not only comfortable but also a stylish retreat.

In addition to the stunning homes, Longboat Key offers a wealth of amenities to enhance your lifestyle. Residents can enjoy world-class golf courses, exclusive beach access, and a variety of dining options that cater to every palate. The nearby Longboat Key Club provides additional leisure opportunities, including tennis, fine dining, and wellness programs.

Whether you’re looking for a permanent residence or a vacation getaway, Longboat Key’s homes with pools are an invitation to embrace the Florida lifestyle. With its charming community spirit and breathtaking surroundings, it’s no wonder that so many choose to make Longboat Key their home. Come discover the beauty and serenity that awaits you in this coastal paradise!

Newest Longboat Key Homes with Pool Community Features

$689,000
2 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Turnkey-Furnished Longboat Key Condo with Dock Access & Rental Potential. Discover effortless coastal living in this beautifully furnished turnkey condo on desirable Longboat Key. Enjoy rare short-term rental flexibility, a bright and stylish interior, and immediate move-in or income potential. Relax by the waterfront dock that is perfect for sunsets and kayaking. Enjoy close access to Gulf beaches, dining, shopping, and island amenities. An ideal Longboat Key vacation retreat or rental investment.

5310 Gulf Of Mexico Drive Unit 16, Longboat Key
$1,200,000
2 Beds ⋅ 2 Baths ⋅ Castillian The SubDv. ⋅ 34228 Zip Code
It doesn't get better than this ... sweeping gulf and beach views, the soothing sound of waves, and instant relaxation at The Castillian on Longboat Key. Residences here rarely become available, so all that's left to do is embrace the casual laid-back lifestyle. The condo's centerpiece is a beautifully renovated open kitchen featuring solid wood cabinetry, granite countertops, GE Monogram appliances, a large stainless steel sink, and a stylish built-in desk area. Both bathrooms have also been updated. The owner's suite, guest bedroom, and great room all open to the balcony, which is equipped with a hurricane shutter for added peace of mind. The Castillian consists of two 30-residence buildings and offers assigned under-building parking, a private storage closet, a heated pool and spa, an outdoor grilling area, and a tennis/pickleball court. This pet-friendly community is conveniently located near Publix and just minutes from the restaurants and shops of St. Armands Circle.

4545 Gulf Of Mexico Drive Unit 311, Longboat Key
$725,000
2 Beds ⋅ 2 Baths ⋅ Bay Harbour Apts SubDv. ⋅ 34228 Zip Code
Location! Location! Location! Awesome, Spectacular Bay views from the kitchen, dining room, living room and primary bedroom! One Bridge to the Gulf! No wait list boat slip! Longboat Key is the place you want to be for the quiet solitude of a gulf front key condo with easy access to the culture and services of Sarasota! This two bedroom, two bathroom Condo in the bay side community of Bay Harbour, has its own private marina with no wait list, and is just one bridge to the Gulf! Beach access is within minutes from several locations on Longboat, Lido and Anna Maria Island. With a Base Flood Elevation of 10 Ft, this unit was High and Dry during the storms of 2024. It has been exquisitely redesigned with upscale quartz and Cambria counter tops, ceramic and porcelain tile flooring and Bosch Appliances. There is plenty of storage available with the pantry and built in closets. Bay Harbour is a South Longboat Key community of 39 units in two buildings with a private pool, easily accessible pool baths, community room and fitness center. Each unit has assigned carport parking and separate storage. A well-managed and well-maintained community with reserves; the condo fees are among the lowest on the gulf!

448 Gulf Of Mexico Drive Unit A104, Longboat Key
$499,900
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Welcome to your slice of paradise on beautiful Longboat Key. Priced to sell and offered fully furnished, this beautifully maintained two-bedroom condominium is truly move-in ready. Combining breathtaking Sarasota Bay views with exclusive deeded beach access, this exceptional residence offers the perfect blend of waterfront serenity, resort-style amenities, and effortless coastal living. Wake each morning to spectacular sunrises over Sarasota Bay as dolphins, manatees, and coastal birds provide an ever-changing natural backdrop from your enclosed lanai. Inside, you’ll find a move-in-ready residence featuring granite countertops, plantation shutters, automatic living room blinds, tile flooring throughout, a newer roof, a three-year-old air conditioning system still under warranty, hot water heater and kitchen appliances covered under warranty through February 2027. What truly sets this property apart is the exclusive private beach experience. Imagine leaving your condo and taking a short stroll across Gulf of Mexico Drive to your deeded Gulf-front beach pavilion—a rare luxury on Longboat Key. This private beach oasis offers direct access to miles of pristine sand and the crystal-clear waters of the Gulf of Mexico, without the crowds of public beach access points. Spend your mornings collecting seashells, your afternoons soaking in the Florida sunshine, and your evenings watching unforgettable Gulf Coast sunsets paint the sky in vibrant shades of orange, pink, and gold. The private beach pavilion enhances every visit with convenient showers, restrooms, and dedicated beach chair storage, making spontaneous beach days effortless. Whether you’re taking a peaceful sunrise walk, enjoying a refreshing swim, or simply listening to the waves with your feet in the sand, this exclusive beach access transforms everyday living into a permanent vacation. Beyond the beach, Longboat Harbour delivers an unmatched resort-style lifestyle. Residents enjoy four heated swimming pools with loungers and umbrellas, a fitness center, art studio, game room, clubhouse with banquet facilities, two lighted fishing piers with fish-cleaning stations, kayak and paddleboard launches with storage, a scenic waterfront walking path, deeded covered parking, additional guest parking, and extra storage. For boating enthusiasts, boat slips accommodating vessels up to 34 feet are available via waitlist for an incredibly affordable annual fee, offering direct access to Sarasota Bay and endless days on the water. Whether you’re searching for a full-time residence, seasonal escape, or investment in the Longboat Key lifestyle, this is more than a condominium—it’s an invitation to experience the very best of waterfront and beachfront living in one extraordinary location. Bay views. Private beach. Resort amenities. Endless sunsets. Welcome to paradise.

4340 Falmouth Drive Unit 104, Longboat Key
$589,000
2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code
There is a certain ease to life on Longboat Key, where mornings can begin with a walk to the beach, afternoons unfold by the pool or on the tennis court, and dinner beside the water is never far from home. Set within Cedars East at Cedars Tennis Resort & Club, this beautifully maintained three-level townhome offers a refined way to experience one of Florida’s most desirable barrier-island lifestyles. Natural light is one of the first things you notice. An abundance of windows fills the home with sunshine, creating a bright, calm, and serene atmosphere that feels perfectly suited to its coastal surroundings. New luxury vinyl plank flooring extends through the entry and main living level, giving the home a fresh, cohesive look, while carpeting along the staircase and throughout the third-floor bedroom level adds warmth and comfort to the private spaces. The second floor brings the kitchen, dining, and living areas together in an easy, welcoming flow designed for relaxed everyday living and effortless entertaining. Just beyond the living room, the screened balcony creates a peaceful outdoor retreat for morning coffee, casual dining, quiet reading, or unwinding at the end of the day. A convenient half bath completes this level. Upstairs, the primary suite offers a private ensuite bath with dual sinks and a comfortable sense of separation from the main living areas. The second bedroom features a walk-in closet and is positioned near the full guest bath and upstairs laundry closet. The washer and dryer are approximately three months old and are included with the home. Thoughtful improvements add both style and confidence, including a roof replaced in 2024, a 2024 HVAC system serviced in April 2026, updated interior paint, refreshed flooring, newer toilets, faucets, light fixtures and vents, and a new garage door. Garage parking adds welcome convenience along with room for bicycles, beach equipment, and additional storage. Life at Cedars Tennis Resort & Club is centered around the outdoors and the relaxed sophistication of Longboat Key. Enjoy tennis and pickleball, spend the afternoon by the heated community pool, stay active in the fitness facilities, or gather for a meal without leaving the neighborhood. Nearby beach access makes Gulf days easy to enjoy, while waterfront restaurants, island cafés, marinas, biking routes, and the natural beauty of Longboat Key are all close at hand. For buyers considering investment potential, the property has a strong short-term rental history and is already heavily booked from December through June 2027, offering the advantage of established demand and reservations already in place. All rentals remain subject to current association rules, approval requirements, and the terms of existing reservations. From fresh seafood and sunset dinners to quiet mornings near the shore, this location places the best of Longboat Key within easy reach. St. Armands Circle, Anna Maria Island, and the cultural attractions of Sarasota are also nearby, allowing you to enjoy the island’s peaceful atmosphere without feeling removed from everything the area has to offer. Whether envisioned as a full-time residence, seasonal retreat, or income-producing coastal getaway, this is an opportunity to enjoy thoughtful updates, abundant natural light, resort-inspired amenities, garage parking, and the unmistakable lifestyle of Longboat Key. ¤ Please see 3D Tour and Video ¤

508 Forest Way Unit 508, Longboat Key
$1,575,000
2 Beds ⋅ 2 Baths ⋅ Sea Gate Club SubDv. ⋅ 34228 Zip Code
Welcome to unit 1B at Sea Gate Club on beautiful Longboat Key. This is the gorgeous, newly remodeled Beachfront walkout unit that you've been waiting for! Do you prefer to live like a single family home, no elevator, and walk straight out to the sandy beach in less than 100 steps? Then this is the One! Perfectly positioned near mid-island, and close to shopping at Publix or CVS. 2 bedrooms with direct Gulf views, plus 2 lovely bathrooms, open floor plan with split bedrooms on opposite sides of the unit. New kitchen cabinets, new quartz countertops, all new appliances. Lives like a single family home as you don't have to ride an elevator, or cover up to go to the beach. Just an easy walk-in/out of your private patio to get to the beach and pool. Sea Gate Club condos are comprised of 89 units, spread across 15 floors. The building has been extensively updated over the past few years. Recent updates include a new pool and hot tub, new roof, newer hurricane rated windows, newer exterior stucco and paint, new elevator doors, climate-controlled bike storage, and paddleboard/kayak storage. Now is the perfect time to buy in this beautiful building, as there are NO current or pending assessments! Hurry before it's gone, this one is beautiful.

2425 Gulf Of Mexico Drive Unit 1B, Longboat Key
$975,000
2 Beds ⋅ 2 Baths ⋅ Tiffany Plaza SubDv. ⋅ 34228 Zip Code
Longboat Key living has never been easier than with this beachfront property facing the Gulf. This turnkey, 1,456-square-foot condominium offers two bedrooms and two baths. Entering, your breath is taken away by an unobstructed view of the water. The story only gets better as you enjoy a private balcony where you can take in the sights and sounds of the crashing waves and unwind to unforgettable sunsets over the Gulf. It comes fitted with hurricane shutters, a renovated sliding door, a washer and dryer hookup, and the kitchen and baths were remodeled in 2012. Plus, you'll have a reserved parking spot to call your own. Get acquainted with the easygoing neighbors, take the family for a swim in the pool at the renovated clubhouse, or cook a nice meal in the outdoor barbecue area, all set among beautifully landscaped grounds. And if the pool isn't your style, that's okay, you can get acquainted with nature firsthand! The owners note frequently sighting dolphins treading the water and sea turtle nests right outside their door.

4325 Gulf Of Mexico Drive Unit 402, Longboat Key
$1,195,000
3 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code
Behind the gates of Bay Isles, this beautifully updated waterfront townhome in Fairway Bay offers the rare convenience of a private deepwater dock accommodating vessels up to 40’. From here, Sarasota Bay, waterfront dining and the Gulf are only minutes away by boat, while peaceful water views become part of the backdrop to everyday living. A stepped walkway welcomes you inside, where more than 2,100+/- sq. ft. unfolds across two thoughtfully designed levels. The moment you enter, soaring 2-story ceilings create an immediate sense of openness, while warm wood flooring, soft neutral tones and carefully selected finishes create an inviting atmosphere throughout. The living room centers around a striking linear fireplace, creating a natural gathering place for relaxing or entertaining. Nearby, the dining area transitions effortlessly into the reimagined kitchen, where white cabinetry with glass panel accents, stone countertops, tile backsplash, breakfast bar and a dedicated coffee station combine beauty with everyday function while keeping the space connected to the surrounding living areas. The primary suite offers a peaceful retreat with its own private terrace overlooking the bay, while the spa-inspired bath features an oversized soaking tub, rainfall steam shower and abundant natural light from an overhead skylight. Two additional bedrooms, along with flexible bonus areas for hobbies, fitness or music, provide comfortable accommodations for family and guests. Multiple terraces throughout the home create inviting places to enjoy the waterfront setting from sunrise through evening. A popular, bayfront and pet-friendly community, Fairway Bay offers a heated pool, spa, fitness center, clubhouse, tennis courts and scenic walking and biking paths. Optional membership to the Longboat Key Club provides access to championship golf, dining, tennis and an exceptional collection of island amenities.

1906 Harbourside Drive Unit 304, Longboat Key
$549,000
2 Beds ⋅ 2 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code
This well-maintained 2BR/2BA residence in Grand Bay features a large, full-width terrace with views of Sarasota Bay. Floor-to-ceiling glass and multiple terrace access points bring in natural light and make the outdoor space a true extension of the living area. Large-format ceramic tile, high ceilings and a neutral color palette create a bright, comfortable interior. The open living and dining area overlooks the bay, while the oversized terrace provides ample space for outdoor dining, entertaining or relaxing among the tropical landscaping. Double doors lead to the galley-style kitchen, which includes white cabinetry, stone countertops, a tray ceiling, a paneled refrigerator and a window for additional natural light. The primary suite offers generous proportions and corner sliding doors opening directly to the terrace. Its en-suite bath features dual vanities and a spa tub. The spacious guest suite includes a walk-in closet and direct outdoor access. An in-residence laundry room adds convenience - two under-building parking space. Grand Bay residents enjoy a clubhouse, fitness center, two Har-Tru tennis courts, two heated swimming pools and spa. Bay Isles ownership also includes deeded access to the private Bay Isles Beach Club on the Gulf of Mexico, with an on-site attendant, covered gathering areas, grills, changing rooms, restrooms and showers. Separate, optional membership in the Longboat Key Club is also available. Depending on the membership selected, members may enjoy access to 45 holes of golf, tennis and pickleball facilities, a private beach, fitness and wellness programs, a full-service spa, dining, marina amenities and year-round social activities.

3080 Grand Bay Boulevard Unit 512, Longboat Key
$1,299,000
2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code
Welcome to an extraordinary Gulf-front residence where timeless coastal elegance meets uncompromising craftsmanship. Completely reimagined from top to bottom, this impeccably furnished two-bedroom, two-bath condominium offers an unparalleled blend of luxury, comfort, and breathtaking natural beauty. Perfectly positioned on the second floor, this architectural gem enjoys panoramic, unobstructed views of the Gulf of Mexico with spectacular year-round sunsets and direct beach access just steps away. A 26-foot private lanai creates the perfect setting for morning coffee, alfresco dining, or simply soaking in the soothing sounds of the waves. Designed with understated coastal luxury in mind, the open-concept great room seamlessly connects the living, dining, and kitchen spaces while showcasing mesmerizing Gulf views from virtually every room. Nine-foot ceilings, Brazilian walnut flooring, elegant crown molding, plantation shutters, abundant natural light, and a sophisticated Lutron automated lighting system create an atmosphere that is both warm and refined. The chef-inspired culinary kitchen is a true showpiece, featuring custom furniture-grade cabinetry, Caesarstone quartz countertops, premium Miele and Sub-Zero appliances, and exceptional attention to every detail. A built-in office nook, high-speed Google Mesh Wi-Fi, integrated premium sound system, tankless water heater, and convenient in-unit laundry add modern functionality to this exceptional home. The thoughtfully designed split-bedroom floor plan offers two private suites, each with its own luxurious bath and spacious walk-in closet, ensuring maximum privacy for owners and guests alike. Constructed of solid concrete block with durable stucco construction, this residence also offers outstanding peace of mind. Hurricane-impact windows and doors and an elevated second-floor location provide exceptional resilience and protection. The impeccably maintained beachfront community has completed significant recent improvements, including a new roof, renovated stairways and entryways, and lush tropical landcaping. Financially strong with well-funded reserves, the association offers residents carefree ownership and outstanding amenities, including a heated resort-style swimming pool, tennis courts, and miles and miles of gorgeous beach. The vibrant, socially active community offers owners and guests a welcoming coastal atmosphere, with frequent gatherings at the beach, pool, and barbecue area. For pet owners, you'll also appreciate that your pets are welcome, too, in this pet-friendly community. Whether you’re searching for a coastal beachfront retreat, a full-time residence, or an exceptional investment in one of Florida’s most coveted Gulf-front locations, this remarkable home delivers an unmatched combination of sophisticated design, premium finishes, modern technology, and one of the most spectacular waterfront settings imaginable.

7001 Gulf Of Mexico Drive Unit 24, Longboat Key
$1,150,000
2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code
Virtually Staged. Experience Gulf-front living at its absolute finest in this extraordinary, completely reimagined residence at Seaplace on Longboat Key. Perfectly positioned on the first floor with unobstructed, direct views of the Gulf of Mexico, this exceptional two-bedroom, two-bath condominium offers the rare opportunity to walk directly from your private covered terrace onto the beautifully landscaped grounds and pristine white sand beach. Taken down to the studs and masterfully rebuilt, every detail of this home has been thoughtfully curated with uncompromising quality and timeless coastal elegance. Wide-plank herringbone flooring flows throughout the residence, complementing the open-concept design and creating a warm yet sophisticated atmosphere. The chef's kitchen is truly stunning, featuring custom cabinetry, quartz countertops, designer tile backsplash, premium appliances, beverage refrigerator, oversized island, floating shelves, custom range hood, and abundant storage—perfect for entertaining while enjoying breathtaking Gulf views. The spacious living area is anchored by a custom-built entertainment wall complete with a sleek linear fireplace, floating shelves, ambient lighting, and extensive built-in cabinetry. Wake each morning to panoramic Gulf views from the primary suite, complete with a custom-designed walk-in closet and an elegant spa-inspired bathroom featuring dual vanities, premium fixtures, and an oversized walk-in shower. The beautifully renovated guest bedroom and bathroom provide luxurious accommodations for family and friends. Additional upgrades include: Tankless water heater, Designer lighting throughout, Custom built-ins, Impact-rated sliding glass doors and windows, Premium interior doors and trim, Covered parking, Exceptional storage throughout The expansive covered terrace becomes an extension of your living space, offering the perfect setting for morning coffee, sunset cocktails, or simply listening to the soothing sound of the waves. Just steps away are miles of sugar-white sand and turquoise Gulf waters. Residents of Seaplace enjoy 24-hour guard-gated security, two resort-style swimming pools, tennis and pickleball courts, a fitness center, clubhouse, walking trails, and 42 acres of meticulously maintained beachfront grounds. This is more than a condominium—it is a rare opportunity to own one of Seaplace's finest Gulf-front residences, where luxury craftsmanship meets one of Longboat Key's most spectacular beachfront settings.

2089 Gulf Of Mexico Drive Unit G1-104, Longboat Key
$1,349,000
2 Beds ⋅ 2 Baths ⋅ Veinte SubDv. ⋅ 34228 Zip Code
Rarely available, charming boutique style condominium community with direct panoramic views of the turquoise waters of the Gulf of America and breathtaking sunsets!  Veinte is a luxury boutique condominium community with only 20 residences and includes private under-building garage parking, bicycle storage, abundant guest parking, and resort-style amenities including a gorgeous pool facing the Gulf, tennis/pickleball court, and a BBQ area. Perfectly positioned on Longboat Key, you can walk next door to Maison Blanche for renowned Zagat and Golden Spoon award-winning dining or stroll across the street to Publix, CVS, Longboat Key Fitness personal trainers, and J.McLaughlin. Only a short distance from St. Armands, Golf Courses, boating, boutique shopping, restaurants, Opera, Ballet and many Galleries to explore.  Once entering this unique residence, you will be greeted with the beautiful white sandy beaches and azure waters of the Gulf of America. Inside, some TLC or updates will make this an incredible residence. to your own personal taste. Sit on your lanai for your morning coffee or afternoon cocktail and watch the million-dollar view and fabulous sunsets. The unit has two large bedrooms and an open concept floor plan including a large dining area, family room and spacious kitchen.

2675 Gulf Of Mexico Drive Unit 203, Longboat Key
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