Clearwater Homes with Trail(s) Amenities

Clearwater Homes with Trail(s) Amenities

Welcome to Clearwater, Florida – a vibrant coastal city nestled in Pinellas County, renowned for its stunning beaches, crystal-clear waters, and a year-round sunny climate. Clearwater offers a unique blend of relaxation and adventure, making it a prime destination for both residents and visitors alike. The city is famous for its picturesque waterfront, bustling downtown, and an array of recreational activities, ensuring there’s always something exciting to explore.

For those seeking a home in this idyllic setting, Clearwater boasts a variety of properties that come with exceptional amenities, particularly for nature enthusiasts and outdoor lovers. Homes with trail amenities are a standout feature in Clearwater, providing residents with direct access to scenic walking and biking trails that wind through lush landscapes and along the beautiful coastline. Imagine starting your day with a peaceful morning stroll or an invigorating bike ride against the backdrop of breathtaking sunsets and tranquil waters.

The community in Clearwater is warm and welcoming, with a rich cultural scene that includes art galleries, music festivals, and an array of dining options ranging from casual beachside cafes to upscale restaurants. Families will appreciate the top-rated schools and parks, while retirees will find a vibrant social scene and plenty of opportunities to stay active.

Whether you’re looking for a cozy beach bungalow or a modern family home, Clearwater’s properties with trail amenities offer the perfect blend of comfort, convenience, and a lifestyle that embraces the great outdoors. Come discover your dream home in Clearwater and experience the best of Florida living!

Newest Clearwater Homes with Trail(s) Amenities

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
2333 Feather Sound Drive Unit A401, Clearwater
$269,000
2 Beds ⋅ 2 Baths ⋅ Crystal Bay Condo SubDv. ⋅ 33762 Zip Code
BEAUTIFULLY REMODELED CORNER UNIT FACING THE GOLF COURSE AND RESORT STYLE AMENITIES! This move in ready condo features a freshly remodeled kitchen with granite countertops and under cabinet lighting, two beautifully updated bathrooms, one with a bathtub and the other with a walk in shower, and gorgeous polished porcelain flooring throughout. Decorative granite stone accent walls frame the patio doors, adding a distinctive touch. Additional upgrades include new hurricane rated windows, excluding the bathrooms and sliding patio door, plus an A/C system and water heater that are both approximately two years old. Enjoy the privacy of a desirable corner unit and a screened in back porch overlooking the private golf course, with mature trees providing a peaceful natural buffer between the building and the green. Experience resort style living with a heated pool, jacuzzi, fully equipped fitness center, saunas, clubhouse, game room, pool table, ping pong, four commercial grills, and a spacious poolside patio. The clubhouse features a kitchen and can be reserved at no additional charge for private gatherings. Additional amenities include a dog park, playground, walking trails, assigned parking, guest parking, and storage. The HOA includes water, sewer, trash, internet, cable, grounds maintenance, and storage, providing exceptional convenience and value. Conveniently located near St. Pete Clearwater International Airport and Tampa International Airport, just minutes from I275 with easy access to downtown Tampa, downtown St. Petersburg, shopping, dining, and Gulf Coast beaches. Beautiful upgrades, peaceful golf course views, and outstanding amenities make this condo an exceptional opportunity to enjoy the Florida lifestyle. Schedule your private showing today!

2333 Feather Sound Drive Unit A401, 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
2220 Swedish Drive Unit 42, Clearwater
$174,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Welcome to 2220 Swedish Drive #42, located in the highly desirable 55+ community of On Top of the World in Clearwater! Offering 1,440 square feet of living space, this spacious 2-bedroom, 2-bathroom condo combines comfort, functionality, and an exceptional maintenance-free lifestyle. Step inside to discover an inviting living and dining area featuring beautiful wood flooring, while porcelain tile adds a stylish and durable touch to the kitchen and sitting area. The generously sized kitchen offers plenty of room for cooking and entertaining, with windows overlooking lush green space that bring in natural light and peaceful views. The versatile sitting area provides additional space to relax, read, or entertain guests. Enjoy the convenience of an IN-UNIT WASHER AND DRYER, a highly desirable feature that adds to the home’s everyday comfort. Beautiful green space views create a tranquil setting, while one assigned parking space adds convenience. The charming Colonial-style building features an ELEVATOR for easy access. Beyond your front door, On Top of the World offers an incredible array of amenities designed for an active and social lifestyle! Residents can enjoy TWO SWIMMING POOLS, two activity centers, golf courses, a fitness center, tennis and pickleball courts, shuffleboard, lawn bowling, billiards, woodworking facilities, walking trails, a dog park, and an on-site café. With numerous clubs, organized activities, and social events, there’s always something to enjoy! Conveniently located near shopping, restaurants, medical facilities, and the beautiful Gulf Coast beaches, this community offers the perfect combination of relaxation, recreation, and convenience. Whether you’re looking for a full-time residence or a seasonal Florida retreat, this spacious condo offers an opportunity to enjoy the best of Clearwater’s active adult lifestyle. Schedule your private showing today! This property is being transferred via a leasehold estate deed, requires Association approval, and necessitates a 35 percent down payment if financing.

2220 Swedish Drive Unit 42, 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
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
$478,000
2 Beds ⋅ 2 Baths ⋅ Grand Bellagio At Baywatch Condo SubDv. ⋅ 33764 Zip Code
Live like you are on vacation every day at the prestigious Grand Bellagio at Baywatch—one of Clearwater’s premier waterfront communities. This is a rare opportunity to own a fully remodeled 2-bedroom, 2-bath townhome with an attached 2-car garage, a private boat slip, and a boat lift, all just steps apart. The community now features a brand-new dock and brand-new slips, with the applicable new-slip warranty transferring to the buyer. A second boat slip may also be available for separate purchase. This exceptional residence offers the garage-to-home-to-boat lifestyle that boaters dream about. Park inside your private 2-car garage, enter directly into your home, then walk outside and be on your boat within minutes. Head out for fishing, cruising, kayaking, or paddleboarding; stop for waterfront dining at AJ’s Dockside Bar & Grill; or refuel at the nearby boat fuel dock at Cove Cay Marina. When the day is over, return to your own slip and walk straight home—no trailering, off-site storage, marina commute, or searching for parking. The beautifully remodeled interior is designed for comfort, privacy, and flexibility. Two spacious primary suites—one upstairs and one downstairs—each provide their own private retreat and beautifully updated bathroom. The layout is perfect for hosting guests, multigenerational living, or creating a private executive office while still maintaining a separate bedroom suite. Grand Bellagio offers the atmosphere and amenities of an upscale waterfront resort. Residents enter through a 24-hour guarded gate and enjoy a resort-style waterfront pool, elegant clubhouse, fitness center, sauna, waterfront walking paths, outdoor grilling areas, three dog parks, valet trash service, community events, and direct access to the water. The HOA fee provides exceptional value by including building and flood insurance, water, sewer, trash and valet trash service, pest control, exterior maintenance, Spectrum cable and internet, and access to the community’s extensive amenities. Here, the services, security, waterfront setting, and resort-style lifestyle give you far more than an ordinary community. This is not simply a place to live—it is the complete Clearwater waterfront lifestyle: a fully remodeled home, private 2-car garage, brand-new dock, private boat slip with lift, resort amenities, and the freedom to step outside and be on the water. Few properties can offer this entire combination in one remarkable location.

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
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