Clearwater Homes with Pickleball Court(s) Amenities

Clearwater Homes with Pickleball Court(s) Amenities

Welcome to Clearwater, Florida – a coastal paradise nestled in Pinellas County, known for its stunning beaches, vibrant culture, and year-round sunshine. With its picturesque waterfront views and a lively arts scene, Clearwater is the perfect blend of relaxation and recreation. Whether you’re strolling along the famous Clearwater Beach or enjoying a sunset at Pier 60, this city offers an unparalleled lifestyle that attracts residents and visitors alike.

For those who appreciate an active lifestyle, Clearwater is home to a unique selection of properties featuring pickleball courts. As one of the fastest-growing sports in the United States, pickleball combines elements of tennis, badminton, and ping-pong, making it a fun and engaging activity for all ages. Imagine stepping out of your beautifully designed home and onto your private pickleball court, ready to enjoy a game with friends or family in the warm Florida sun.

These homes with pickleball court amenities not only promote a healthy lifestyle but also foster a sense of community. Residents can join in on friendly matches or host neighborhood tournaments, creating lasting memories and friendships. Additionally, many of these properties are conveniently located near Clearwater’s top attractions, dining, and shopping, ensuring that you’re never far from the action.

If you’re looking for a home that offers both luxury and leisure, Clearwater’s pickleball-equipped properties are the perfect choice. Embrace the vibrant lifestyle that awaits you in this charming coastal city and discover your dream home today!

Newest Clearwater Homes with Pickleball Court(s) Amenities

2386 Sumatran Way Unit 44, Clearwater
$125,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
This well-maintained 2BR/2BA unit on the 2nd floor is move in ready. The unit features updated windows in the Florida Room and Master bathroom, a washer/dryer, and the AC was replaced in 2021. The kitchen has an updated built in oven, extra cabinets and counter tops and a dual basin stainless steel sink. Assigned parking. The 55+ community has two activity centers, and two private golf courses with 9 and 18 holes, free exclusively for resident owners. There are two swimming pools; one is heated. The remodeled Cardio Gym has the latest exercise equipment. A very pet-friendly community, there is a fenced dog park with covered seating. There are hobby studios, and a wood shop for the exclusive use of the residents. Activities include fitness classes, dancing, clubs, cards, billiards, entertainment, classes, and much more. The on-site Good Karma Café has take & bake meals and snacks. Close to beaches, transportation, shopping, entertainment, and fine dining. All room sizes, floor plans and square footage are approximate. This property is being transferred by a leasehold estate deed. Association approval is required. If financing, 35% down is required.

2386 Sumatran Way Unit 44, Clearwater
2221 Swedish Drive Unit 53, Clearwater
$179,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Virtually Staged. Beautiful 3rd-floor 2-bedroom, 2-bath partially furnished El Dorado model offering 1,370 sq ft of bright, open living on the highly sought-after West Side of On Top of the World’s golf community—just steps from Harbor Lake. Complete with a charming sitting area at the front entry perfect for enjoying your morning coffee or relaxing after a day of activities, you will see this sets the tone before you step inside. The spacious interior features ceramic tile flooring throughout the main living areas, granite kitchen countertops, newer appliances, and a new disposal. The home includes updated windows in front (2008); back windows are hurricane-impact (2025) providing added protection and efficiency. Major mechanicals are already updated with a (2025) water heater and Trane A/C (2018). The primary bedroom offers new soft carpeting, creating a comfortable retreat. The guest bedroom is carpeted and is a blank canvas. This desirable El Dorado layout delivers generous room sizes, abundant natural light, and a smooth, easy-living flow. Located on OTOW’s premier West Side, residents enjoy close proximity to golf, pools, fitness centers, clubs, and endless activities—all within a vibrant 55+ community and minutes from shopping, dining, and Clearwater’s beautiful beaches.

2221 Swedish Drive Unit 53, Clearwater
2980 Haines Bayshore Road Unit 105, Clearwater
$225,000
2 Beds ⋅ 3 Baths ⋅ Caribay Condo SubDv. ⋅ 33760 Zip Code
Welcome home to your Florida dream home. This beautiful 2- bed, 2.5-bath townhouse-style condo offers unobstructed, panoramic views of Old Tampa Bay from both levels. Caribay Condos are one of the area’s best-kept secrets—an all-ages, pet- friendly community with exceptional amenities and a true resort- like lifestyle. Community amenities include: a heated/cooled pool, tennis courts lined for pickleball, a private dock for fishing, sunbathing, birdwatching, or simply enjoying the sweeping bay views. The community also offers kayak/paddleboard storage with a private association launch area, plus a spacious clubhouse with lounge, large-screen TV, game room with pool table, kitchenette, bathrooms and showers. The open-concept main floor features a bright living and dining area with wall-to-wall sliders, a galley-style kitchen, a large interior laundry room, and generous storage areas. There are nearly 200 sq ft of enclosed porches with impact-resistant sliding doors, to ensure you don't miss the exceptional views. Upstairs, both oversized bedrooms include private en-suite bathrooms. The primary suite is a true retreat with floor-to- ceiling sunrise over the bay views that make every morning feel like vacation. Enjoy an oversized garage—perfect for storage or a vehicle—plus driveway parking for a second car. Caribay’s location is unbeatable: minutes from Tampa International and St. Pete-Clearwater airports, world-class beaches, downtown St. Pete and Tampa, dining, arts, sports, and seasonal events. The community remained unaffected by recent hurricanes, adding peace of mind. All high-ticket items have been recently updated, including a new roof (2026), AC (2024), and hot water heater (2021). The monthly maintenance fee covers internet, cable, water, sewer, trash, lawn care, mangrove trimming, maintenance and insurance of all common elements, and master association flood insurance. Perfect for full-time living, seasonal enjoyment, or a vacation escape; you will not want to miss your opportunity to experience waterfront living at its best. Schedule your private showing today.   (Some photos virtually staged.)

2980 Haines Bayshore Road Unit 105, Clearwater
420 N Bayshore Boulevard Unit 104, Clearwater
$89,000
1 Beds ⋅ 1 Baths ⋅ Harbour Towne Condo SubDv. ⋅ 33759 Zip Code
LOCATION, LIFESTYLE & FLORIDA CHARM — ALL IN ONE! Welcome to Harbour Towne Condominiums, where convenience meets the relaxed Florida lifestyle! Ideally situated along the Clearwater side of the Courtney Campbell Causeway, just minutes from charming downtown Safety Harbor, this cozy studio condo offers the perfect opportunity to enjoy everything the Tampa Bay area has to offer. LOVE THE OUTDOORS? YOU’RE IN THE RIGHT PLACE! With the scenic Ream Wilson Trail and Bayshore Boulevard nearby, walking, biking, and enjoying Florida’s beautiful weather can become part of your everyday routine. Harbour Towne offers beautifully maintained green spaces and an impressive selection of community amenities, including a sparkling swimming pool, tennis and pickleball courts, a clubhouse with kitchen, fitness center, and on-site management. LOCATION IS EVERYTHING! Enjoy easy access to Tampa, St. Petersburg, two international airports, the delightful shops and restaurants of downtown Safety Harbor, and the world-famous sugar-white sands of Clearwater Beach. Whether you’re searching for a full-time residence, seasonal Florida escape, or an investment opportunity with leasing subject to association approval, this studio offers flexibility in a fantastic location. YOUR PIECE OF FLORIDA PARADISE IS WAITING — COME EXPERIENCE THE HARBOUR TOWNE LIFESTYLE!

420 N Bayshore Boulevard Unit 104, Clearwater
2363 Israeli Drive Unit 33, Clearwater
$107,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Step into this cheerful well cared for 2-bedroom, 2-bath condo in Clearwater’s beloved On Top of the World 55+ community, where the lifestyle is easy and the possibilities are wide open. This clean second-floor unit is partially furnished and ready for someone who wants a move-in-ready start while planning their updates. You’ll appreciate the updated windows in the back, a dependable 2013 A/C, and a layout that includes a bright Florida room—furniture included! The primary bedroom also comes furnished, and the living room’s crisp neutral couch stays, giving you a great base for your décor. The kitchen is truly turn-key, stocked with pots, pans, glasses, and dishes, plus a new 1-year-old SS refrigerator that makes settling in even easier. Just bring groceries and you’re good to go. Located steps to the elevator and the laundry room. Yes, it needs updating—but that’s your chance to make it shine. Meanwhile, you get to enjoy all the amenities OTOW is famous for: golf, pools, fitness centers, clubs, and endless activities. A clean slate, partial furnishings, and instant livability in one of Clearwater’s most social, active communities. Come make this condo your next fun project.

2363 Israeli Drive Unit 33, Clearwater
2426 Persian Drive Unit 64, Clearwater
$135,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Don’t miss this beautifully furnished, move-in-ready condo! This charming condo features two completely furnished bedrooms, thoughtfully decorated with elegance and flair, making it easy to settle in and start enjoying the Florida lifestyle right away. The bright Florida room provides the perfect setting for a lovely dining area, with plenty of space to relax, entertain, or simply unwind while enjoying the sunshine. Recent updates include replacement windows in 2013 and a new A/C system installed in 2021, giving you added comfort and peace of mind. Best of all, there’s nothing left to do but move in and enjoy everything On Top of the World’s 55+ community has to offer. Residents can take advantage of an incredible array of amenities, including two heated pools, 9- and 18-hole golf courses, a state-of-the-art fitness center, billiards, sauna, jacuzzi, lapidary and ceramics facilities, and so much more. With a wide variety of clubs and activities, there’s always something to look forward to. Enjoy Monday night bingo, social dances, entertaining shows, and even opportunities to take the stage and share your own talents! Come discover the joy of living your best life in this wonderfully maintained, thoughtfully designed community. Move in, make yourself at home, and start enjoying everything this exceptional lifestyle has to offer!

2426 Persian Drive Unit 64, Clearwater
2184 Springrain Drive, Clearwater
$414,900
3 Beds ⋅ 2 Baths ⋅ Spring Lake Of Clearwater SubDv. ⋅ 33763 Zip Code
Virtually Staged. A charming opportunity awaits! Lovely home ideally situated on a spacious corner homesite in the desirable Spring Lake community. From the moment you arrive, you’ll appreciate the curb appeal, generous yard and inviting atmosphere that make this property stand out. Inside, soaring ceilings and an open floor plan create a warm and welcoming living space. The family room centers around a beautiful wood-burning fireplace and flows seamlessly into the dining area, where French doors open to the covered patio. The spacious kitchen offers abundant cabinetry and storage, including a convenient walk-in pantry, while the adjacent dinette provides another set of French doors overlooking the backyard. The main level features two generously sized secondary bedrooms and a full bathroom with a tub/shower combination. The entire second floor is dedicated to the private primary suite, offering an expansive bedroom, multiple closets and a spacious en-suite bathroom complete with dual sinks, a soaking tub, separate shower and walk-in closet. Tile and laminate flooring throughout make the home comfortable and easy to maintain. Outside, the covered and tiled patio provides an ideal setting for entertaining, relaxing or enjoying Florida's year-round outdoor lifestyle. The large, fenced corner lot offers plenty of room for pets, gardening, play and future outdoor possibilities. The home boasts a 2023 A/C and 2021 roof bringing energy efficiency and peace of mind. Spring Lake residents enjoy an array of community amenities, including a swimming pool, tennis courts, playground, fitness center and clubhouse. The community is conveniently located near shopping, medical facilities, dining and major roadways, while offering easy access to area lakes and the Gulf beaches. A wonderful opportunity to own a spacious home with character, privacy and an excellent location in Spring Lake.

2184 Springrain Drive, Clearwater
2287 Philippine Drive Unit 9, Clearwater
$169,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Welcome to easy Florida living in this desirable ground-floor Supreme model, ideally located on the west side of On Top of the World Clearwater! This spacious 2-bedroom, 2-bath residence offers approximately 1,070 square feet of comfortable living space with thoughtful updates throughout. Step inside to find attractive luxury vinyl flooring, ceramic tile in the kitchen, updated windows, newer doors in the bedrooms, Stainless Steel Appliances in the kitchen and updated vanities in the bathrooms and for added convenience, the kitchen also features a stackable washer and dryer, allowing you to take care of laundry right at home. Enjoy Florida outdoor living with patios in both the front and back, including a fenced rear patio that provides a private spot for morning coffee, relaxing with a good book, or simply enjoying the outdoors. The convenient ground-floor location means no stairs or elevator needed. The desirable west-side location is another bonus, offering a short walk to the community dog park and beautiful Harbor Lake. Located in the popular On Top of the World 55+ community in Clearwater, this sought-after Supreme model combines comfortable living, convenient first-floor access, numerous updates, private outdoor space, in-unit laundry, and a wonderful location—all ready for its next owner to make it home. The Buyer/Buyers Agent is to verify all information about this property, including but not limited to square footage, room sizes, condition, deed restrictions, rules, and regulations. MILESTONE COMPLETE Association approval is required. Financing requires 35% down.

2287 Philippine Drive Unit 9, Clearwater
2209 Utopian Drive E Unit 207, Clearwater
$199,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Welcome to easy Florida living in the highly desirable Active Adult community of On Top of the World! This spacious two-bedroom, two-bath condominium offers a comfortable, functional layout along with the convenience of an inside laundry—a rare and valuable feature within the community. One of the home’s best features is its location. Step outside your door and enjoy the scenic walking trail surrounding Arbor Lake, perfect for a peaceful morning walk, an evening stroll or simply taking in the natural surroundings. On Top of the World is known for its impressive selection of amenities, including two activity centers, two golf courses, swimming pools, a fitness center, tennis and pickleball courts, shuffleboard, lawn bowling, billiards, a dog park and countless clubs, classes and social activities. Whether you prefer an active lifestyle or a relaxing day by the pool, there is always something to enjoy. Ideally located near shopping, dining, medical facilities and everyday conveniences, this community also places you just a short drive from charming Downtown Dunedin, the Pinellas Trail and the sugar-sand beaches of Clearwater Beach and Honeymoon Island. Enjoy waterfront restaurants, local breweries, festivals, boating and everything the Tampa Bay lifestyle has to offer. With its spacious floor plan, rare inside laundry and exceptional location near Arbor Lake, this residence is ready for its next owner to make it home. Come experience the carefree, amenity-rich lifestyle that makes On Top of the World one of Clearwater’s most popular Active Adult communities!

2209 Utopian Drive E Unit 207, Clearwater
2350 Haitian Drive Unit 54, Clearwater
$214,999
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Welcome to this beautiful 2-bedroom, 2-bathroom home in the desirable On Top of the World community in Clearwater, Florida! This home offering comfort, style, and peace of mind for its next owner. The A/C is approximately 5 years old, and the hot water heater and appliances were upgraded in 2025. The home features an upgraded 55-gallon hot water heater, recessed can lighting in the living room, and a 220V electrical line installed for the walk-in tub. The primary bathroom has been beautifully remodeled with a new shower, vanity, quartz countertop and sink with black faucet, tile flooring, and an upgraded 19-inch tall toilet. The guest bathroom features a top-of-the-line walk-in spa tub with built-in stereo, color-changing lights, massager, heated seat, aromatherapy, micro bubbles, and handheld shower. Additional primary bathroom upgrades include a new vanity, granite countertop and faucet, tile flooring, and an upgraded 19-inch tall toilet. Additional improvements throughout the home include newly spray-painted ceilings, kitchen cabinets with a convenient corner Lazy Susan, and quartz countertops throughout the kitchen. The kitchen also features a Frigidaire Gallery dishwasher and Frigidaire Gallery microwave. A front storm door adds another nice improvement to the home. With approximately $48,000 in upgrades and improvements, this home offers an opportunity to enjoy a beautifully updated residence in the popular On Top of the World community. Come see all the thoughtful improvements and make this Clearwater home your own!

2350 Haitian Drive Unit 54, Clearwater
4535 Great Lakes Drive S, Clearwater
$295,000
2 Beds ⋅ 2 Baths ⋅ Lakes Unit I The SubDv. ⋅ 33762 Zip Code
Price Improvement! - Welcome to The Lakes, a sought-after 55+ pet-friendly community in Pinellas Park, where comfort, convenience, and an active Florida lifestyle come together. This charming 2-bedroom, 1.5-bath home offers 1,020 square feet of living space, an inviting open floor plan, and an oversized lot with plenty of room to enjoy the outdoors. Beautifully updated and move-in ready, this home has been extensively improved since 2023, giving the next owner peace of mind. The kitchen features white cabinetry, granite countertops, and modern stainless-steel appliances, creating a bright and welcoming space for everyday living and entertaining. Updated bathrooms and double-pane windows throughout add to the home's comfort and efficiency. Step through to the spacious screened Florida Room, the perfect bonus space for morning coffee, afternoon relaxation or simply enjoying Florida's beautiful weather. The home also features a 2023 roof, HVAC system, water softener, microwave, and updated kitchen and baths. Best of all, the property is located in a non-flood zone. One of the biggest advantages of living in The Lakes is the incredible value offered by the community. HOA dues are just $305 per month and include water, sewer, trash pickup, cable, Wi-Fi internet, lawn maintenance, irrigation, clubhouse, and pool. The association is known for its strong sense of community and excellent financial health, with a recent reserve study confirming the strength of its reserve funds. Residents have access to an impressive clubhouse featuring a full kitchen, meeting rooms, library, card room, billiards, shuffleboard, raised stage area for community events, and a sparkling community pool with patio area. Whether you're looking to stay active, meet neighbors, enjoy social activities, or simply relax, The Lakes offers an inviting community atmosphere. Conveniently located in Clearwater with easy access to shopping, restaurants, medical facilities, St. Petersburg, Clearwater, and Tampa, including Tampa International Airport and St. Pete-Clearwater International Airport, this home puts everything you need within easy reach. Whether you're searching for a full-time Florida residence, seasonal getaway, or low-maintenance retirement home, this property delivers an appealing combination of comfort, updates, value, and community lifestyle. BONUS FOR QUALIFIED BUYERS: An assumable VA loan at approximately 6% is available, offering a potential financing opportunity for an eligible buyer. The seller has already purchased his next home and is ready to make his move — this home is ready for its next owner!

4535 Great Lakes Drive S, Clearwater
2000 World Parkway Boulevard Unit 20, Clearwater
$110,000
1 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
This one bedroom/one bathroom condo with bonus room is stylishly updated with quartz breakfast bar pass-through to kitchen and beautiful quartz countertops. Upgrades included a/c and hot water heater, new storm door, front door and lighting. Tile floors throughout this comfortable home right out to your Florida room with a peaceful view of the grounds. It can be used for guests, office, reading, library, etc. Lovely decorator quartz bathroom vanity and neutral paint from start to finish. Stairs lead right up from your parking space to your front door balcony with laundry room right around the corner (no elevator). Just a short walk to the East Recreation Center with pool and cardio gym. You will love this vibrant 55+ neighborhood. Golf on beautiful courses, hike scenic green spaces, play cards, dance, join clubs, attend community events, take group trips, or relax in the heated swimming pools. This is a pet friendly area and dogs will love the dedicated dog parks. You will really appreciate being close to shopping malls, dining, entertainment, healthcare facilities, and gorgeous area beaches. It's a place where comfort meets community, where everything you need is right at your doorstep.

2000 World Parkway Boulevard Unit 20, Clearwater
Start Your Search

How much is your home worth?

Get instant property value now!