Longboat Key Homes with Maintenance Free Community Extras

Longboat Key Homes with Maintenance Free Community Extras

Welcome to Longboat Key, Florida—an idyllic slice of paradise nestled between the sparkling waters of the Gulf of Mexico and Sarasota Bay. Known for its stunning sunsets, pristine beaches, and vibrant community, Longboat Key offers an unparalleled lifestyle that seamlessly blends relaxation with recreation. Whether you’re strolling along the beach, indulging in gourmet dining, or exploring the lush landscapes of local parks, this charming barrier island promises a life filled with beauty and adventure.

One of the standout features of Longboat Key is its array of homes within maintenance-free communities. Imagine waking up each day in a beautifully designed residence where the worries of yard work and exterior upkeep are a thing of the past. These homes come equipped with community extras that enhance your living experience, allowing you to focus on what truly matters—enjoying life. From pristine pools and tennis courts to fitness centers and social clubs, these communities foster a sense of camaraderie and connection among residents.

Longboat Key is not just a place to live; it’s a lifestyle. With access to world-class amenities, including boutique shopping, art galleries, and cultural events, every day offers something new to explore. Whether you’re looking for a seasonal retreat or a permanent residence, Longboat Key’s maintenance-free homes provide the perfect blend of luxury and convenience, allowing you to immerse yourself in the vibrant coastal lifestyle. Come discover why so many are captivated by this enchanting destination—your dream home awaits!

Newest Longboat Key Homes with Maintenance Free Community Extras

$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 condo offers two bedrooms and two baths. Walking in, your breath is taken away by an unobstructed view of the water. The story only gets better: 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, and 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 of the renovated clubhouse, or cook a nice meal in the outdoor BBQ 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 current 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
$425,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Easy access and docking at this 75 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina on D-dock. Located on the West side of the marina. Ample turning radius between piers, so lots of room to maneuver. Direct access to Sarasota Bay and the ICW; 15 minutes to the Gulf. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village and restaurants, shopping (close to Publix, CVS, and other shops), recreational and social activities, on-site maintenance and concierge services. Each slip includes wifi, water, pump out and metered electric, along with trash pick up and dockhands to assist. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 70 LOA, usable beam is 23 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the marina by submitting a current photo and boat specs.

2800 Harbourside Drive Unit D-16, 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
$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
$1,349,000
3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code
Virtually Staged. Set within Grand Bay on Longboat Key, this renovated 3BR/3.5BA residence offers panoramic views of Sarasota Bay, the Harbourside golf course and the city skyline. With 2,250 square feet, walls of glass bring the scenery into nearly every main living space, creating an inviting blend of comfort, openness and relaxed Bay Isles elegance. Floor-to-ceiling windows with plantation shutters frame the views, while tile flooring, neutral tones and recessed lighting create a warm, understated setting. The living room opens to a view overlooking the golf course, a tranquil pond and Sarasota Bay - ideal for quiet mornings or entertaining. The kitchen flows easily into the living areas and features white cabinetry, stone countertops and backsplash, and stainless-steel appliances. The primary suite offers warm wood flooring and a spacious bath with dual vanities, a makeup area and a large walk-in shower. Two guest suites each include a private en suite bath. An in-residence laundry room and one covered parking space complete the home. Grand Bay residents enjoy a clubhouse, designer-appointed lobby, two pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Bay Isles privileges include gated entry, scenic walking paths and access to the private Gulf-front Bay Isles Beach Club, featuring white sand, an attended entrance, covered picnic and entertaining areas, tiki huts, barbecue grills, restrooms, changing rooms and beach-equipment storage. Optional membership is also available at the Longboat Key Club. Amenities vary by membership category and include 45 holes of championship golf, 20 Har-Tru tennis courts, private beach and pool facilities, spa and fitness facilities, restaurants and lounges, club events and marina access.

3040 Grand Bay Boulevard Unit 225, Longboat Key
$425,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Seeking an opportunity to enjoy the Longboat Key lifestyle? This turnkey, two-bedroom, two-bath residence overlooks the Intracoastal Waterway and offers 1,072 square feet of living space. The view out the back of the condominium is simply magical. Sparkling water, beautiful sunsets, and, of course, manatees. This residence comfortably sleeps six, has direct access to the Harbour walking path, and also includes an in-home washer and dryer. Longboat Harbour offers an extensive collection of resident amenities, including a dedicated parking space, sauna, outdoor pools, putting green, kayak and paddleboard launch with storage, pickleball and tennis courts. Boat docks are available on a first-come, first-served basis for less than $600 annually, subject to availability. Residents also enjoy a recreation center with activities including poker, table tennis, billiards, arts and crafts, woodcarving and grilling areas. A deeded, private beach provides convenient access to the Gulf, along with storage, restrooms and showers. The condominium association has completed new roofing, providing added peace of mind. If you've been waiting for the right way to live, I think you just found it.

4390 Exeter Drive Unit 107, Longboat Key
$550,000
2 Beds ⋅ 2 Baths ⋅ Banyan Bay SubDv. ⋅ 34228 Zip Code
Move-in-ready condition, ground-floor bayside condominium with Sarasota Bay views and deeded private Gulf beach access in the sought-after Banyan Bay Club! Discover effortless coastal living in this beautifully updated 2-bedroom, 2-bath residence offering 1,155 square feet on the bayside of Longboat Key. Thoughtfully renovated throughout, this inviting home features new luxury vinyl plank flooring, new kitchen appliances, updated bathrooms with new vanities, and a bright, open floor plan designed for comfortable island living. Enjoy Sarasota Bay views from the living room, primary bedroom, and private rear patio. Step directly from your patio onto the beautifully landscaped lawn, where you can enjoy your morning coffee, watch boats and dolphins pass by, observe abundant coastal wildlife, and welcome beautiful Florida sunrises. The convenient ground-floor location offers effortless access and seamlessly blends indoor and outdoor living. Residents of this pet-friendly community enjoy the best of both worlds with deeded private Gulf beach access and outstanding amenities, including a heated pool, clubhouse, pickleball, tennis, fishing pier, kayak storage and launch, and assigned parking. Whether you enjoy boating, kayaking, fishing, shelling, or relaxing on the beach, this community offers the quintessential Longboat Key lifestyle. Ideally located near championship golf, waterfront dining, marinas, boutique shopping, St. Armand's Circle, and downtown Sarasota, this exceptional residence is perfect as a primary home, seasonal retreat, or investment opportunity. Don't miss this rare opportunity to own an updated, move-in-ready, bayside condominium with Sarasota Bay views, deeded private Gulf beach access, and the relaxed elegance of island living. EASY TO SHOW. SUPRA ON storeroom door across from front door.

5260 Gulf Of Mexico Drive Unit 413, Longboat Key
$569,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
If you are looking for a tastefully upgraded Longboat Key beach house, this is it! Relax in your completely renovated coastal-contemporary, stand-alone villa, with its front pond view, private rear patio and large yard space. The uncrowded, 11-mile Longboat Key beach is directly across Gulf of Mexico Drive via Spanish Main's private deeded access. Your spacious, light-filled home welcomes you with a charming entrance foyer, open living-dining room with built-in cabinets and a large kitchen-family room area with sliding doors to the rear yard. Your bright kitchen has an island, new appliances, quartz counters, and wood cabinets with lots of storage space. Important additional benefits include a new electric hot water tank, new hurricane rated doors and rear sliders, tile roof replaced in 2017, flat roof in 2024, impact windows in 2020 and 2024, and A/C in 2022. The primary bedroom has a walk-in closet and an en suite bath with a new walk-in shower and vanity. The guest bedroom has a view of the pond and double closets. The guest bathroom has a skylight and a new walk-in shower, vanity, linen and medicine cabinets. If you want to move right in or rent it, the attractive turn-key furnishings are negotiable. Outside, there is a large side storage area for bicycles and beach toys. The front porch offers a tranquil area to relax and view the large pond with its ducks, jumping fish, and pretty night lights. Walk, bike or drive to the heated community pool, patio area, and clubhouse adjacent to the deep water marina and kayak launch. If you are a boat person, slips can be rented, as available, for an extremely reasonable cost and there is easy access to Sarasota bay and the Intracoastal Waterway with no fixed bridges. Spanish Main Yacht Club is an over-55 community, conveniently located near several restaurants, Durante Park, community tennis, pickle-ball, dog park, fitness activities and St. Armands Circle shops and restaurants. Let me show you the lifestyle that this beautiful, unique villa has to offer.

524 Spanish Drive S Unit 125, Longboat Key
$899,500
3 Beds ⋅ 3 Baths ⋅ Tangerine Bay Club SubDv. ⋅ 34228 Zip Code
Welcome to one of Longboat Key's premier bayfront communities, Tangerine Bay Club, where your days are spent like you live at a luxury resort! This three bedroom, 2 and a half bath elevated residence offers spacious living with gorgeous views of the mote style lagoon, spectacular resort style pool and Sarasota Bay. A private 2 car garage only adds to the many benefits of living here. Did we mention the day dock and pier over Sarasota Bay? The community gym overlooking the gorgeous pool? The Tennis and pickleball courts? The ability to purchase a membership at the Bay Isles Beach club for only a nominal yearly fee? This is truly island living at its best! A welcoming front entrance courtyard allows for a wonderful arrival spot just steps from the elevator yet this unit, being a corner residence, feels very private. Once inside you'll be immediately impressed with the light filled spaces that allow for you to enjoy the incredible views from multiple large windows. A balcony accessed from the great room and the Primary bedroom is a spot you'll want to enjoy every morning with your coffee and every evening with your cold beverage. Just a short distance from multiple restaurants, the Longboat Key Club, The St.Regis resort and the bridge that takes you over to St.Armands Circle and then onto the cultural mecca of downtown Sarasota....at a price that makes it easy to imagine. Whether you choose to renovate and make it your own or enjoy it just as it is, this is one you will want to see!

350 Gulf Of Mexico Drive Unit 213, Longboat Key
$699,000
2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code
Nestled in the attractive community of Fairway Bay in Bay Isles on Longboat Key is this fabulous 2BR/2BA elevated townhouse. This tastefully decorated condo residence is on one level above the oversized 2-car garage and is an end unit. It is beautifully maintained, in great condition and offered turnkey-furnished with upscale furnishing from Robb & Stucky. The spacious living room and dining room has high ceilings, crown molding, plantation shutters, a fireplace and a wet bar with built-ins. The updated kitchen completed in 2025 is a neutral palette with new white cabinetry, white quartz countertops, a super pull-out pantry, all new appliances and washer & dryer in the past 12 months. A/C replaced in 2020 & water heater in 2021. The flooring in the entire residence was recently replaced with luxury vinyl plank flooring. A spacious shaded screened lanai offers a peaceful garden view and is a short walk to the heated pool and the bay. The bathrooms have also been updated in 2025 with new flooring, new cabinets, fixtures and shower door. The primary bedroom suite is a quiet sanctuary offering ample room for your apparel with two walk-in closets and Hunter-Douglas window blinds. This townhouse affords plenty of room for guests and a large family to stay. There is a two-and-a-half garage with a large finished air-conditioned space on the ground floor giving you extra space. Community amenities include walking paths, 2 heated pools, a fitness room, tennis & pickle ball courts and a social room. The building will soon benefit from a new roof, which the seller has paid for. Residents benefit from on-site management and 24-hour security. Ownership includes deeded access to the private Bay Isles Beach Club, featuring a Gulf front pavilion, grilling areas, and beautiful sandy beaches. Located within the Longboat Key Club, residents have the option to join golf, tennis, and social memberships, all just minutes from the boutiques and dining on world-renowned St. Armands Circle, downtown Sarasota’s cultural attractions and Harbourside Marina.

2000 Harbourside Drive Unit 1501, Longboat Key
$307,000
1 Beds ⋅ 1 Baths ⋅ Longboat Harbour Towers SubDv. ⋅ 34228 Zip Code
Price Improved! Exceptional opportunity to own a beautifully furnished waterfront residence in a gated, amenity-rich boating community. This one-bedroom unit features Hurricane-Impact Sliding Glass Doors &Windows( over $40 Value) allowing abundant natural light while providing peace of mind. Enjoy waterfront living with access to a Private Beach located at 4415 Gulf of Mexico Drive, complete with gated parking, indoor facilities, and beachside amenities. Residents have access to an impressive array of community features, including four heated swimming pools, a spacious fitness center, pickleball courts, tennis courts, kayak and bicycle storage, plus more ..and a vibrant boating community with first-come, first-served boat slips. Additional amenities include a banquet hall and numerous social and recreational opportunities. Whether you're seeking a full-time residence, seasonal retreat, or investment property, this waterfront gem offers the perfect combination of coastal lifestyle, convenience, and value. Don't Waite! Schedule your private virtual viewing today.

4350 Chatham Drive Unit 105, Longboat Key
$619,900
2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code
We are offering an exceptional investment opportunity at Bayport Beach & Tennis Club. Unit 521 is PRICED BELOW a recent June 2026 independent appraisal and currently the lowest-priced residence in the Bayport Beach & Tennis Club complex, we feel this beautifully updated condominium represents one of the best values on Longboat Key for a primary residence, seasonal retreat, vacation home, or investment property. Features include impact-resistant windows and sliding glass doors, City-permitted interior remodeling, a newer air conditioning system, covered parking, private storage, and numerous thoughtful upgrades throughout. The recent June 2026 independent appraisal, City permit records, association budget, reserve information, and HOA documents are available electronically upon request. Discover the essence of coastal resort living within Bayport's beautifully landscaped 27-acre Gulf-to-Bay community featuring 1,200 feet of private deeded Gulf of Mexico beachfront, direct Sarasota Bay access with a fishing pier and kayak launch, mature tropical landscaping, scenic walking trails, and an outstanding collection of resort-style amenities. Residents enjoy a heated Junior Olympic lap pool, four Har-Tru tennis courts, fitness center, clubhouse, community room, kayak launch and storage, professional on-site management, and one of Longboat Key's most desirable waterfront lifestyles. Conveniently located just minutes from Publix, Ace Hardware, Pickle ball facilities, waterfront dining, boating, championship golf, St. Armands Circle, The Ringling Museum, dog parks, and the cultural attractions of downtown Sarasota, Bayport offers the perfect balance of island tranquility and everyday convenience. Whether you're searching for a full-time residence, seasonal getaway, vacation home, or long-term investment, this move-in-ready residence offers exceptional value in one of Florida's premier Gulf-to-Bay communities. Experience the relaxed elegance, natural beauty, and resort lifestyle that have made Bayport Beach & Tennis Club one of Longboat Key's most sought-after addresses. Come experience why so many residents say that living at Bayport isn't just owning a home—it's embracing a year-round island resort lifestyle that others only experience on vacation.

521 Bayport Way Unit 521, Longboat Key
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