Clearwater Homes with Trail(s) Amenities

Clearwater Homes with Trail(s) Amenities

Welcome to Clearwater, a vibrant city located in Pinellas County, Florida. Known for its stunning beaches, lively downtown area, and endless outdoor recreational opportunities, Clearwater offers a fantastic lifestyle for residents of all ages.

One of the many amenities that make Clearwater such a desirable place to live is the Homes with Trail(s) feature. Imagine living in a community where you can step outside your door and enjoy a leisurely stroll or invigorating jog along scenic trails. These trails not only promote an active lifestyle but also provide a beautiful backdrop for your daily routine.

Whether you're a nature enthusiast, fitness buff, or simply enjoy the serenity of a peaceful walk, Clearwater's Homes with Trail(s) amenity caters to your needs. You can explore the natural beauty of the area, meet neighbors while out for a walk, or simply unwind after a long day.

With a variety of real estate options available, including homes with trail access, Clearwater provides the perfect setting for your next chapter. Come experience the charm and convenience of living in a city that values both community and outdoor enjoyment. Find your dream home in Clearwater and start living the Florida lifestyle you've always dreamed of.

Newest Clearwater Homes with Trail(s) Amenities

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
2220 Swedish Drive Unit 56, Clearwater
$184,750
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Step into this light-filled 2-bedroom, 2-bath condo on the West Side of Clearwater’s highly desirable On Top of the World 55+ Golf Community. This Eldorado model is Located on the second floor, as you walk in this home immediately impresses with its Vaulted ceilings, Updated HURRICANE Impact resistant windows creating a bright, open, and airy atmosphere. Vinyl plank flooring throughout adds a clean, modern finish. The spacious gathering room is ideal for relaxing or entertaining, enhanced by updated windows that flood the space with natural light. The TV is already mounted for your convivence, The kitchen includes a new refrigerator, and the convenience continues with an in-unit washer and dryer. The 2017 A/C offers reliable comfort and peace of mind. The primary bedroom features an en' suite bath with a bidet, providing privacy and comfort. Just outside your front door, enjoy a charming sitting area—perfect for morning coffee or evening breezes—along with beautiful views that make this location feel special. BRING ALL REASONABLE OFFERS. Additional storage in the core of the building gives you extra room for seasonal items or personal belongings. Situated on the west side of the community, you’ll appreciate being close to Harbor Lake, scenic walking trails, the dog park and all the amenities that make OTOW such a sought-after lifestyle—golf, clubs, activities, and more. If financing 35% down is required. Proof of Funds for Cash

2220 Swedish Drive Unit 56, 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
2320 Brisbane Street Unit 44, Clearwater
$168,000
2 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 33763 Zip Code
Looking for the perfect move-in ready condo? This is it. This beautifully updated home features new windows, modernized bathrooms, a refreshed kitchen, and a updated air conditioning system. Enjoy easy-maintenance flooring throughout the kitchen, dining area, and hallways, along with comfortable, plush carpeting in the bedrooms and living room. Nestled in the highly desirable 55+ community of On Top of the World, you’ll enjoy an active, worry-free lifestyle with unlimited amenities. Residents have access to two golf courses, two recreation centers, tennis courts, lawn bowling, a lapidary studio, social clubs for every interest, hosted dances, and live shows. Centrally located, you are just a short drive to world-famous Clearwater Beach, major shopping centers, convenient transportation options, and two international airports. Between the pristine condo, the active association, and the prime location, this property has everything you need to live your ideal lifestyle!

2320 Brisbane Street Unit 44, Clearwater
2741 Via Cipriani Unit 916A, Clearwater
$499,000
2 Beds ⋅ 2 Baths ⋅ Grand Bellagio At Baywatch Condo SubDv. ⋅ 33764 Zip Code
Virtually Staged. ONE BOAT SLIP WOULD BE NICE… BUT HOW ABOUT TWO? YES, YOU READ THAT RIGHT — TWO PRIVATE BOAT SLIPS, INCLUDING A BOAT LIFT, JUST STEPS FROM YOUR FRONT DOOR! Welcome to 2741 Via Cipriani, Unit 916A, where waterfront living gets an upgrade. This exceptional 2-bedroom, 2-bath townhome offers something truly unique within The Grand Bellagio at Baywatch: TWO private boat slips, including a boat lift, paired with an attached 2-car garage and direct access from your garage into your home. There is no other residence in the community with this setup. Walk from your garage, through your home, and out to your boats just steps away. Keep both slips for your own watercraft, or enjoy the flexibility and potential value that comes with owning an additional slip. For the serious boater, this is the kind of setup that is incredibly difficult to duplicate. And the lifestyle doesn’t stop at the docks. Inside, you’ll find two private primary suites—one downstairs and one upstairs—creating a flexible layout ideal for homeowners, guests, or multigenerational living. Imagine starting your morning with a kayak or canoe ride, spending the afternoon cruising Tampa Bay, then pulling back into your own slip and walking straight home. Grill by the water, relax along the waterfront, or enjoy an evening with neighbors. Your boat. Your slips. Your garage. Your home. All just steps apart. Located within the gated waterfront community of The Grand Bellagio at Baywatch, residents enjoy a 24-hour guard gate, resort-style pool, clubhouse, fitness center, sauna, waterfront walking areas, outdoor grilling stations, three dog parks, community dock, and regularly scheduled community events. The community fee also includes Spectrum internet, basic television service, valet trash pickup, and access to the community amenities. Whether you’re an avid boater, kayaker, paddleboarder, or simply want to wake up every day surrounded by the Florida waterfront lifestyle, 2741 Via Cipriani offers a combination you simply won’t find anywhere else in the community. Two boat slips. A boat lift. A 2-car garage. Two primary suites. And your boats just steps from your front door. There’s waterfront living—and then there’s this. Schedule your private showing and experience it for yourself.

2741 Via Cipriani Unit 916A, Clearwater
19029 Us Highway 19 N Unit 26-204, Clearwater
$247,000
2 Beds ⋅ 2 Baths ⋅ Imperial Cove 14 SubDv. ⋅ 33764 Zip Code
Discover waterfront Florida living at 19029 US Hwy 19 N #204, Clearwater, FL 33764, a beautifully maintained and tastefully renovated 2-bedroom, 2-bath condo located in the highly sought-after gated 55+ community of Imperial Cove. Situated in Association 14, Building 26, this building is a longtime community favorite for its convenient location and substantial construction. Originally engineered to be structurally sound for an additional three floors, Building 26 was built “tank strong,” with the additional stories ultimately not constructed. Unit #204 offers an exceptional combination of comfort, convenience, thoughtful updates, and beautiful views. Enjoy quick elevator access just steps from your front door, in-unit laundry, one dedicated covered parking space, and plenty of guest parking. Relax on the lanai and take in beautiful Florida sunsets, while the front porch and balcony areas provide additional views of this incredible waterfront community. Dolphin and manatee sightings are a regular part of life here! Inside, the condo has been tastefully updated and renovated with quartz countertops, a glass tile backsplash, an eat-in kitchen area, formal dining space, and a large living area perfect for entertaining. A reverse osmosis water system was installed in 2026, adding another thoughtful upgrade to the home. The primary bathroom features a tiled walk-in shower with glass doors, while the guest bathroom has been totally remodeled with a new tub. Additional improvements include a new refrigerator and stove in 2026, new ceiling fans in 2026, updated electrical panel in 2026, reverse osmosis water system in 2026, HVAC replaced in 2024, and water heater replaced in 2022. Imperial Cove offers an impressive active-adult lifestyle with a gated entrance, active clubhouse/community room, billiards rooms, fitness center/gym, sauna and showers, shuffleboard courts, putting greens, outdoor grilling areas, library, fishing pier, and a heated saltwater swimming pool. A lighted walking path winds through the community and along the waterfront, offering gorgeous Tampa Bay views and opportunities to see dolphins, manatees, and spectacular Florida sunsets. Even better, this unit enjoys the lowest HOA fee in Imperial Cove while providing access to the community's outstanding amenities. Association fees include water, sewer, trash, exterior maintenance, grounds maintenance, roof and more. Centrally located in Pinellas County, you're minutes from shopping, dining, entertainment, Clearwater, St. Petersburg, Tampa, area beaches, airports, and everything the Tampa Bay area has to offer. If you're searching for a move-in-ready 55+ Clearwater condo with elevator access, in-unit laundry, covered parking, waterfront amenities, extensive community activities, beautiful views, and an unbeatable Central Pinellas location, #204 at Imperial Cove deserves to be at the top of your list. Come experience the Imperial Cove lifestyle and see why Building 26 is such a community favorite!

19029 Us Highway 19 N Unit 26-204, Clearwater
2370 Jamaican Street Unit 30, Clearwater
$145,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Tucked into the sought-after On Top of the World 55+ community, this well-maintained 2-bedroom, 2-bath residence offers 1,100 square feet of comfortable living space with a layout that feels open, functional, and easy to enjoy. The spacious living and dining areas flow naturally together, creating plenty of room for quiet evenings at home or gathering with friends and family. The kitchen offers abundant cabinetry, generous counter space, a ceiling fan, and a dedicated eat-in area for casual meals or morning coffee. The primary suite provides a private place to unwind, complete with ample closet space and an en suite bath. A second bedroom and full bath offer flexibility for overnight guests, a home office, hobby space, or whatever best fits your lifestyle. One of the home's standout features is the enclosed Florida room, adding valuable extra space that can be enjoyed throughout the year. Use it as a reading room, sitting area, game room, craft space, or simply a comfortable spot to relax and enjoy the Florida lifestyle. Living in On Top of the World means more than just having a place to call home. Residents enjoy an active, resort-style community with golf, swimming pools, fitness facilities, walking areas, clubhouses, social clubs, activities, and recreation designed for a wide range of interests. Whether you're looking for a full-time residence, seasonal escape, or an easy-to-maintain home in an established 55+ community, 2370 Jamaican Street, Unit 30 offers a comfortable setting, versatile living space, and access to one of the area's most popular active-adult lifestyles.

2370 Jamaican Street Unit 30, Clearwater
2380 World Parkway Boulevard Unit 40, Clearwater
$249,999
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Welcome to this stunning corner-unit condo offering 2 bedrooms and 2 bathrooms, beautifully updated with luxury vinyl flooring throughout. Filled with natural light, this bright and inviting home features an open-concept kitchen that flows seamlessly into the living and dining areas, creating the perfect space for everyday living and entertaining. With approximately $47,000 in upgrades, this home has been thoughtfully enhanced for both style and peace of mind. The kitchen is equipped with stainless steel appliances installed in 2023, while updated hurricane-impact windows provide added security and energy efficiency. The water heater was replaced in 2025, and the primary bathroom has been tastefully renovated with modern finishes. The location is exceptional situated just steps from the clubhouse and pool, you'll enjoy easy access to community amenities. Relax from the comfort of your home with front-row views of clubhouse activities or simply walk over and join the fun. This move-in-ready residence combines modern updates, abundant natural light, and an unbeatable location.

2380 World Parkway Boulevard Unit 40, Clearwater
2054 Sunset Point Road Unit 38, Clearwater
$167,400
2 Beds ⋅ 1 Baths ⋅ Woodlake 1 Condo SubDv. ⋅ 33765 Zip Code
Welcome home to this well-maintained 2-bedroom, 1-bath condominium in the established Woodlake community, where pride of ownership shines through after being lovingly cared for by the same family for more than 40 years. Offering a clean, functional layout and durable tile flooring throughout, this residence is ready for its next chapter. Enjoy peace of mind with several important updates already completed, including a new HVAC system (March 2026), refrigerator, dishwasher, microwave, and washing machine (2024), toilet (2023), electrical panel (2009), and tub surround (2009). Woodlake offers residents beautifully maintained grounds along with amenities that include a community pool, tennis courts, clubhouse, and recreational areas. The community is centrally located in Clearwater, providing convenient access to shopping, dining, parks, medical facilities, Downtown Dunedin, Safety Harbor, Tampa International Airport, and the world-famous Gulf beaches. Whether you're searching for a primary residence, seasonal getaway, or low-maintenance Florida lifestyle, this home offers an excellent opportunity in one of Clearwater's well-established condominium communities.

2054 Sunset Point Road Unit 38, Clearwater
2451 Canadian Way Unit 29, Clearwater
$105,000
2 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Virtually Staged. Significant Price Improvement on this Move-In Ready 2-Bedroom Condo in Desirable On Top of the World! NEW 2 TON HVAC SYSTEM IN 2026 AND UPGRADED ENERGY-EFFICIENT WINDOWS THROUGHOUT! Probate process will be complete with the sale of this condo. COE on YOUR timetable. Welcome home to this bright and inviting 2-bedroom, 1-bath condominium in Clearwater's sought-after On Top of the World 55+ community. Offering approximately 1,100 square feet of comfortable living space, this well-maintained residence is vacant and move-in ready, making it an excellent opportunity for year-round living or a seasonal Florida retreat. The thoughtful floor plan features spacious living and dining areas, generous bedroom sizes with plenty of closet storage space, and the convenience of both front and rear entrances. Updated energy efficient windows with coverings included, allowing you to settle in immediately and add your own personal touches over time. Unit is located on 2nd floor and conveniently adjacent to community laundry facility. Residents of On Top of the World enjoy an active, resort-style lifestyle with an impressive array of amenities. The community offers multiple swimming pools, fitness facilities, tennis and pickleball courts, shuffleboard, lawn bowling, hobby studios, a woodworking shop, billiards, card rooms, library, and numerous clubs and social activities. Golf enthusiasts will appreciate access to the community's golf courses, while pet owners can enjoy the on-site dog park. Beautiful walking paths, scenic ponds, and mature landscaping create a peaceful setting throughout the neighborhood. Ideally located, you'll be just minutes from Clearwater's award-winning Gulf beaches, shopping, dining, medical facilities, cultural attractions, and both Tampa International and St. Pete-Clearwater International airports. The monthly HOA fee of $500.23 provides exceptional value and includes a wide range of community amenities, helping you enjoy a carefree Florida lifestyle. Whether you're looking for a full-time residence or a winter getaway, this inviting home offers comfort, convenience, and the vibrant lifestyle that has made On Top of the World one of Clearwater's most popular active adult communities.

2451 Canadian Way Unit 29, Clearwater
3062 Eastland Boulevard Unit 406, Clearwater
$147,000
1 Beds ⋅ 1 Baths ⋅ Imperial Pines Condo SubDv. ⋅ 33761 Zip Code
Welcome to Imperial Pines, one of Clearwater's most desirable gated 55+ communities. This 1-bedroom, 1-bath condominium offers comfortable, low-maintenance living in a prime location just minutes from Tampa Bay attractions. Located on the fourth floor with elevator access, this bright and inviting residence features an open floor plan with updated laminate flooring throughout the main living areas and bedroom, tile flooring in the bathroom, an updated vanity, and tile flooring on the screened balcony, creating the perfect space to enjoy your morning coffee or unwind at the end of the day. The spacious primary bedroom includes a large walk-in closet and convenient en-suite bath access. The kitchen offers ample storage with its original cabinetry and functional layout, ready for your personal touches. Imperial Pines residents enjoy a resort-style lifestyle with a heated pool and spa, sauna, fitness center, billiards room, library, clubhouse, social activities, scenic walking paths, and beautifully maintained grounds. The community also features gated access, assigned under building parking #21 right next to the elevator lobby door, guest parking, and elevator service. The monthly condominium fee includes cable TV, internet, water, sewer, trash, exterior maintenance, grounds maintenance, pool amenities, private roads, and fully funded escrow reserves for added peace of mind. Ideally located just steps from Publix, Starbucks, CVS, restaurants, banking, fitness centers, and medical offices, and only minutes from Mease Countryside Hospital, Philippe Park, downtown Safety Harbor, and Clearwater's world-famous beaches. Enjoy nearby outdoor dining, boutique shopping, local festivals, farmers markets, and community events that make this area one of Pinellas County's most sought-after destinations. Whether you're looking for a year-round residence or a seasonal Florida retreat, this move-in ready condo offers exceptional value, convenience, and the carefree Florida lifestyle you've been searching for.

3062 Eastland Boulevard Unit 406, Clearwater
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