Longboat Key Homes with Pickleball Court(s) Amenities

4380 Exeter Drive Unit 101, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour Towers SubDv. ⋅ 34228 Zip Code

Virtually Staged. Investor alert. Great investment opportunity! Condominium is in great condition. Best price for two-bedroom, two-bath condominium in sought after community of Longboat Harbour. Motivated sellers, ready to have a new buyer enjoy this lovely waterfront first-floor end-unit condominium. New roof, all assessments paid, granite countertops, kitchen open to living area. All glass lanai, tile throughout main living, carpet in bedrooms were in the bedrooms but carpet removed for new flooring to be installed. A huge plus: end unit, close to the beach, washer and dryer are in the unit. Hurricane shutters on rear of unit. Additionally, the beautifully renovated recreation room overlooking the bay serves as heart of social gatherings in Longboat Harbour, hosting a variety of clubs and activities complemented by a kitchen and dance floor. The four heated swimming pools provide relaxation and enjoyment year-round. For beach lovers, a community beach pavilion across Gulf of Mexico Drive offers residents private, private deeded beach access with a cabana, parking, restrooms and dressing areas. Witness breathtaking sunrises, spot manatees and savor stunning sunsets along the Gulf beach. This exceptional opportunity offers an unparalleled lifestyle in one of Longboat Key's active, social and vibrant communities! Seize the opportunity to experience waterfront living at its finest. This condominium community was not impacted by hurricane flood waters, according to the owner. Make this beautiful community your next home!

4380 Exeter Drive Unit 101, Longboat Key

1445 Gulf Of Mexico Drive Unit 101, Longboat Key

$1,090,000

3 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code

Step into this highly desirable corner residence featuring three bedrooms, three full baths, and a 36’ x 11’ sunroom at The Players Club. Unique to this residence is a private garage, offering rare security and convenience plus an additional covered under-building parking space. You’ll immediately be drawn to the impressive 31’ balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. An open, white eat-in kitchen is designed with custom cabinetry and extra storage that flows seamlessly into the main living and dining areas. Just off the kitchen, French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The primary bedroom, a private sanctuary with an en-suite bath offers a soaking tub, separate glass-enclosed shower, dual vanities, and a fitted walk-in closet. A second bedroom functions as an additional master with a fitted walk-in closet and en-suite bath with dual sinks. A true third bedroom with two separate fitted closets and an adjacent full bathroom adds flexibility for additional guests. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves and is located Just minutes from St. Armands Circle, downtown Longboat Key, and the Longboat Key Club - with championship golf, premier tennis, and a deep-water marina. One of the largest floor plans available in the community, this residence blends privacy, convenience, and resort-style beachfront living. Offered partially furnished.

1445 Gulf Of Mexico Drive Unit 101, Longboat Key

2020 Harbourside Drive Unit 442, Longboat Key

$699,000

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2020 Harbourside Drive Unit 442, Longboat Key

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

$750,000

3 Beds ⋅ 2 Baths ⋅ Club Longboat Beach & Tennis SubDv. ⋅ 34228 Zip Code

Welcome to effortless Gulf-front living at Club Longboat Beach & Tennis Resort, one of Longboat Key’s sought-after beachfront communities. This beautifully updated three-bedroom, two-bath residence is offered turnkey furnished, making it an exceptional opportunity for a full-time residence, coastal retreat or potential income-producing investment. In desirable Building 1, this spacious first-floor residence offers approximately 1,484 square feet of comfortable, thoughtfully designed living space with the rare convenience of no elevators or long walks. The open, split-bedroom floor plan features wide-plank flooring, a light and inviting coastal palette, and an easy flow for everyday living and entertaining. The updated kitchen features crisp white cabinetry, stainless steel appliances, under-cabinet lighting, a glass tile backsplash and a large center island with seating. Floor-to-ceiling sliders in the great room open to a private, lushly landscaped patio, extending the living space outdoors and creating a peaceful place to enjoy the Longboat Key lifestyle. The spacious primary suite offers direct patio access, a beautifully updated bath with walk-in glass shower and generous closet space. Two additional bedrooms provide flexibility for family and guests, including a den/third bedroom with Murphy bed. The current owner recently updated a second full bath and the laundry room, which has full-size washer and dryer and additional laundry cabinetry. The unit's abundant storage throughout completes the interior. Just outside your front door is a private storage room and covered parking space, with ample additional guest and resident parking throughout the community. Club Longboat offers approximately 750 feet of direct Gulf-front beach and an exceptional resort-style lifestyle. Amenities include eight Har-Tru tennis courts, several lighted for evening play, an on-site tennis professional, pickleball, two heated swimming pools including separate adult and family pool areas, spa/whirlpool, sauna, beach chairs and umbrellas, grilling areas, bocce, fishing, on-site management and an active social calendar. An updated clubhouse with fitness and social spaces is also planned as part of the community’s exciting improvements ahead. Owners enjoy a welcoming community with regular social events, including Friday happy hours and seasonal celebrations. Club Longboat is also pet-friendly for owners and offers exceptional rental flexibility, with a 30-day minimum and up to 12 leases per year. For buyers looking to offset ownership costs, this residence offers a proven rental history. There are currently future bookings of $59k for 3rd Qu 2026 through April 2027. Full details and rental history available upon request. The combination of a three-bedroom floor plan, turnkey furnishings, direct Gulf access and flexible leasing has made this an exceptionally desirable rental. Ideally on the Gulf side of Longboat Key, you are minutes from outstanding dining, boating, golf and recreation, with the shops and restaurants of St. Armands Circle and the arts and culture of downtown Sarasota just a short drive away. Whether you are searching for a turnkey beach home, seasonal escape or investment property, this beautifully furnished Club Longboat residence offers the combination buyers want most, direct gulf access, resort-style amenities, three bedrooms, rental flexibility and unmistakable lifestyle of Longboat Key. Simply arrive, unpack and head to the beach.

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

4545 Gulf Of Mexico Drive Unit 311, Longboat Key

$1,095,000

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

$574,900

2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

NEW AND IMPROVED PRICE! 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, Longboat Key

1095 Gulf Of Mexico Drive Unit 303, Longboat Key

$650,000

2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code

Experience everything coastal luxury living has to offer in one of Longboat Key's most sought-after waterfront communities. This beautifully updated 2 bedroom, 2 bathroom condominium offers peaceful pond and fountain views, direct access to the pristine Gulf of America beaches, and an unbeatable location just minutes from St. Armands Circle and downtown Sarasota. Inside, engineered flooring flows throughout the open-concept floor plan, creating a seamless blend of comfort and style. The spacious living and dining areas open to a private balcony overlooking the tranquil pond and fountain, providing the perfect setting to enjoy morning coffee or unwind with breathtaking Florida sunsets. The well-appointed kitchen features granite countertops, stainless steel appliances, a breakfast bar, and abundant natural light, making it ideal for both everyday living and entertaining. The generous primary suite offers serene water views, ample closet space, and an en-suite bathroom with dual vanities and a walk-in shower. A spacious guest bedroom and nearby full bath provide privacy and comfort for family and visitors. Experience everything coastal luxury living has to offer in this exceptional Longboat Key residence. Residents enjoy resort-style amenities including an Olympic-sized heated swimming pool and spa overlooking the Gulf of America, private beach access, a fitness center, tennis and pickleball courts, community grills, beautifully landscaped tropical grounds, covered parking, secure building access, and the peace of mind of a 24-hour gated entrance with guard. Cable, internet, water, sewer, trash, and exterior maintenance are all included in the condominium fees, providing exceptional value and effortless ownership. Just minutes from the boutiques and award-winning dining of St. Armands Circle and the cultural attractions of downtown Sarasota, this is Florida waterfront living at its finest.

1095 Gulf Of Mexico Drive Unit 303, Longboat Key

4390 Exeter Drive Unit 107, 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

5260 Gulf Of Mexico Drive Unit 413, 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

4234 Gulf Of Mexico Drive Unit M1, Longboat Key

$649,000

2 Beds ⋅ 2 Baths ⋅ Pelican Harbour & Beach Club SubDv. ⋅ 34228 Zip Code

COMMUNITY BOAT SLIP AVAILABLE! It really is all about the location- and of course the view! Situated on gorgeous Sarasota Bay, this lovely two bedroom, two bath first floor condo offers a walk out to the sculpted grounds of Pelican Harbour and great water views of the bay from your private screened lanai. Recently professionally renovated in tasteful coastal chic, this beautifully updated condo boasts new hurricane impact windows, designer Samsung kitchen appliances, ceramic tile flooring, an island kitchen with granite countertops and white shaker wood cabinets, ceiling fans, plantation shutters, closet built-ins, washer and dryer, and new window treatments. New AC (2025). Pelican Harbour and Beach Club is a pet friendly community and offers world class amenities including private gulf beach access, a heated resort-style pool, kayak and bike storage, day dock, tennis, and pickleball. This well-maintained community has successfully completed its milestone inspection, has fully-funded reserves, and has no special assessments. Association fees include building maintenance, landscaping, building insurance, cable, water, sewer, trash, professional management, and pest control. The community has covered reserved carports, new roofs and a composite day dock that is perfect to enjoy a cup of coffee while catching those stunning Florida sunrises over water. At this writing, community has two 30 ft boat slips available at $600 per year. Pelican Harbour is centrally located mid key, with convenient access to St. Armands Circle, Bayfront Park, Publix, and fine dining at a number of outstanding restaurants. Your unique opportunity to enjoy the Longboat Key lifestyle awaits!

4234 Gulf Of Mexico Drive Unit M1, Longboat Key

$2,150,000

3 Beds ⋅ 2 Baths ⋅ Longboat Key Estates SubDv. ⋅ 34228 Zip Code

Escape to your own waterfront haven at 617 Rountree Drive, a hidden gem nestled in the luxurious Longboat Key Estates community! Tucked away on a tranquil street, this 3-bedroom, 2-bathroom home offers an exceptional coastal lifestyle along with strong investment upside in an area surrounded by multi-million-dollar modern updates. Step directly into your backyard to take in serene canal views outside stretching toward Sarasota Bay and the Intracoastal waterway, complete with 100 feet of upgraded seawall (2022) and a 16,000-lb boat lift (2022)—saving you massive upfront capital costs and offering immediate, bridge-free water access. As a resident, you also enjoy deeded beach access to a resident-only Gulf-front beach and Tiki hut just a five-minute stroll away. Whether you choose to enjoy the existing home, customize the footprint, or build new, this generous lot provides an ideal canvas to capitalize on the neighborhood's continuing transformation. All this, just minutes from Bayfront Park's pickleball and tennis courts, kayak launches, St. Armands Circle, fine dining, downtown Sarasota, Van Wezel Performing Arts, shopping, Sarasota-Bradenton International Airport, and the wonderful Florida lifestyle!

617 Rountree Drive, Longboat Key

6700 Gulf Of Mexico Drive Unit 143, Longboat Key

$410,000

1 Beds ⋅ 1 Baths ⋅ Whitney Beach SubDv. ⋅ 34228 Zip Code

Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story condo is being offered turnkey furnished, making it completely move-in ready—just bring your suitcase and start enjoying island life. Inside, the bright living room showcases peaceful water views bringing the beauty of marine life right to your window. The kitchen features stainless steel appliances and coastal-inspired design. The home offers a relaxed, airy feel perfect for full-time living, a seasonal getaway, or an investment property. This pet-friendly and rental-friendly community is vibrant and social, offering an unmatched waterfront lifestyle. Residents enjoy private beach access, two pools, tennis and shuffleboard courts, a fitness center, and kayak launch and storage. Boating and fishing enthusiasts will appreciate the boat slips and fishing dock, while outdoor living is elevated with grill stations, picnic areas, and complimentary beach chairs. Whether you are searching for a relaxing coastal escape or an active waterfront lifestyle, this exceptional Longboat Key condo delivers the very best of Florida living with breathtaking water views, abundant amenities, and endless opportunities to enjoy the beauty of marine life and island living!

6700 Gulf Of Mexico Drive Unit 143, Longboat Key

Longboat Key Homes with Pickleball Court(s) Amenities

Newest Longboat Key Homes with Pickleball Court(s) Amenities