Clearwater Homes with Trail(s) Amenities

Clearwater Homes with Trail(s) Amenities

Welcome to Clearwater, Florida – a sun-soaked paradise known for its stunning beaches, vibrant culture, and welcoming community. Nestled along the Gulf Coast, Clearwater boasts some of the most beautiful waterfront views in the state, with its famous Clearwater Beach often ranked among the best in the nation. The city is not just a haven for beach lovers; it also offers a rich tapestry of parks, recreational activities, and a bustling downtown area filled with shops, restaurants, and entertainment options.

For those seeking the perfect home in Clearwater, you’ll find a fantastic selection of properties that come with trail amenities, making it an ideal choice for outdoor enthusiasts and families alike. Homes with trail access offer the perfect blend of comfort and nature, allowing residents to enjoy leisurely strolls, invigorating jogs, or serene bike rides right from their doorstep. Imagine waking up to the sound of rustling leaves and birds chirping, with scenic trails winding through lush landscapes just waiting to be explored.

Clearwater’s commitment to outdoor living is evident in its extensive network of trails, which connect neighborhoods to parks and natural preserves. Whether you’re looking for a cozy single-family home or a modern townhouse, Clearwater’s real estate market has something for everyone. Embrace the Florida lifestyle where every day feels like a vacation, and make your dream of living in a community with trail amenities a reality. Come discover the charm of Clearwater and find your perfect home today!

Newest Clearwater Homes with Trail(s) Amenities

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

2 Beds ⋅ 2 Baths ⋅ Grand Bellagio At Baywatch Condo SubDv. ⋅ 33764 Zip Code

Virtually Staged. YOUR BOAT. YOUR SLIP. JUST STEPS FROM YOUR FRONT DOOR. Welcome to 2741 Via Cipriani, where luxury waterfront living feels like a year-round resort vacation. This exceptional two-bedroom, two-bath townhome features two private primary suites—one downstairs and one upstairs—providing comfort, privacy, and a flexible layout that is perfect for homeowners and guests. This residence offers a rare combination that is difficult to find: its own boat slip, an attached two-car garage, and the convenience of walking directly from your garage into your home—then stepping outside and being just feet from your boat. Imagine beginning your morning with a peaceful kayak or canoe ride, spending the afternoon cruising on your boat, and returning home to grill by the water and enjoy the evening with neighbors. This is not simply a place to live—it is a waterfront lifestyle and a true sense of community unlike any other. Located within the prestigious, gated waterfront community of The Grand Bellagio at Baywatch, residents enjoy resort-style amenities including a 24-hour guard gate, clubhouse, fitness center, sauna, resort-style pool, community dock, waterfront walking areas, outdoor grilling stations, three dog parks, and regularly scheduled community events. The community fee also includes access to the amenities, Spectrum internet, basic television service, and convenient valet trash pickup. Whether you are an avid boater, enjoy kayaking and canoeing, or simply want to relax beside the water, this residence delivers luxury, security, convenience, and an unmatched connection to the Florida waterfront lifestyle. This is more than a townhome—it is resort-style waterfront living at its finest. Schedule your private showing and experience it for yourself.

2741 Via Cipriani Unit 916A, Clearwater

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

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

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

REDUCED! 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

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

2 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

Virtually Staged. Move-In Ready 2-Bedroom Condo in Desirable On Top of the World! NEW 2 TON HVAC SYSTEM IN 2026. 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

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

Looking for one of the BEST VALUES in On Top of the World? This BEAUTIFULLY UPDATED 2-BEDROOM, 2-BATH condo offers approximately 1,400 square feet in one of Clearwater's premier 55+ communities. Perfectly positioned DIRECTLY ACROSS FROM THE GOLF COURSE, this third-floor residence enjoys ONE OF THE MOST PRIVATE AND SERENE REAR VIEWS IN ON TOP OF THE WORLD, overlooking a semi-wooded setting with mature trees that provide exceptional privacy and a peaceful backdrop. PET FRIENDLY with NO WEIGHT OR NUMBER RESTRICTIONS for dogs, a rare feature among 55+ communities. Inside you'll find UPDATED TRAVERTINE AND PREMIUM STRAND-WOVEN BAMBOO FLOORING, an UPDATED KITCHEN featuring QUARTZ COUNTERTOPS, modern appliances, and a thoughtfully designed pantry cabinet that keeps the microwave at convenient counter height while preserving valuable countertop space. UPDATED BATHROOMS include a renovated guest bath with a comfort-height commode, and the home also offers the convenience of an IN-UNIT WASHER & DRYER. For added peace of mind, Seller will pay for a HOMEOWNER'S WARRANTY. The $561 monthly condo fee includes WATER, SEWER, TRASH, HIGH-SPEED FIBER OPTIC INTERNET, 120 BASIC CABLE CHANNELS, BUILDING INSURANCE, exterior maintenance, and maintenance of the community's outstanding amenities, including UNLIMITED GOLF on both the 9-hole and 18-hole golf courses at no additional cost. Residents enjoy two heated pools, tennis, pickleball, a remodeled fitness center and cardio gym, hobby studios, a woodshop, library, dog park, fishing, kayaking, daily shuttle service, Good Karma Café, and an active calendar of clubs, classes, and entertainment. Conveniently located just minutes from Clearwater Beach, downtown Dunedin, shopping, dining, and medical facilities, this exceptional home offers the perfect opportunity to enjoy Florida's active adult lifestyle in one of Clearwater's most desirable 55+ communities.

2430 Florentine Way Unit 56, Clearwater

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

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

You'll be delighted you didn't miss this beautifully maintained ~ diamond in the rough condo featuring an updated A/C and located in one of the most sought-after sections of the renowned On Top of the World community. The spacious El Dorado floor plan offers the perfect blend of comfort and functionality, ideal for both entertaining guests and enjoying easy everyday living. Conveniently situated directly across from the West Activity Center, you'll have exceptional amenities just steps from your door, including a 12-table billiards room, heated lap pool, 13-jet spa, card room, and a large party room complete with a full kitchen. When you're ready to explore, you're just minutes from the soft sands of Clearwater Beach and a short drive from the dining, entertainment, and cultural attractions of Tampa. Enjoy nearby shopping at three major malls, browse unique antique shops, or stroll the charming downtown districts of Safety Harbor and Dunedin. With so much to see and do, every day can be an adventure—or simply a chance to sit back, relax, and enjoy the tropical Florida lifestyle.

2284 Philippine Drive Unit 39, Clearwater

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

Welcome to your top-floor oasis in the highly desirable, gated On Top of the World 55+ golf community. This beautifully FULLY FURNISHED updated two-bedroom, two-bathroom Antigua penthouse offers 1,210 square feet of bright, maintenance-free living. Enjoy this condo with NEW WASHER & DRYER, NEW A/C, NEW DISHWASHER, NEW RANGE, and NEW HOT WATER TANK Inside, you will find vaulted ceilings, luxury vinyl plank and ceramic tile flooring, built-in shelving, and a massive twelve-by-fifteen eat-in kitchen with a pantry. The primary suite features a large bedroom, ceiling fan, and a spacious walk-in closet, while an in-unit washer and dryer add everyday convenience. Situated on the third floor of an elevator-equipped building, this home offers total ease of access.The monthly condo fee covers internet, cable TV, water, sewer, trash, pest control, twenty-four-hour guarded security, and complete exterior maintenance. As a resident, you gain access to an unmatched resort lifestyle featuring two private golf courses, two pools, an in-ground spa, a fitness center, tennis courts, a dog park, an on-site restaurant, and a community boat ramp with lake access. This pet-friendly condo allows up to two pets and is perfectly located in Clearwater near world-class beaches, dining, and shopping. It serves as an ideal year-round residence or seasonal retreat with a flexible six-month minimum lease period. Schedule your private showing today to experience premier Florida active 55+ living.

2209 Utopian Drive E Unit 307, Clearwater

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

Welcome to a bright and breezy 3rd-floor end unit in Clearwater’s beloved On Top of the World community—where every day feels a little lighter. This unit fully furnished and located on a quiet cul-de-sac featuring 2-bed, 2-bath home that offers 1,100 sq ft of easy living, framed by Double-Pane updated windows that bring in soft natural light and peaceful green-space views. The well-maintained Refurbished A/C keeps things cool year-round, while the interior blends luxury vinyl plank flooring and Ceramic Tile in the main living areas with cozy carpeted bedrooms, all wrapped in a calm, neutral décor that instantly feels relaxing. Start your mornings with coffee overlooking the greenery with a sitting area right outside your door, spend afternoons enjoying the community’s endless amenities, and end your evenings in a home that’s move-in ready and designed for a low-maintenance, active lifestyle. This is the kind of place where comfort meets convenience—and where every day feels like a fresh start, right outside your front door is a small sitting area. This building has an elevator, but in case you are a fitness aficionado the parking place for #51 is at the bottom of the stairs. This unit is Located within a vibrant and active 55+ community, residents enjoy an unmatched lineup of amenities designed to elevate everyday living. Spend your days on two private golf courses (9- and 18-hole), relax at two heated pools, or take part in endless activities at the community’s two full activity centers. Stay energized in the remodeled cardio gym, join fitness classes, dance groups, clubs, cards, or billiards—there’s always something happening. Pet owners appreciate the fenced dog park with shaded seating, while hobbyists love the dedicated craft studios and full woodshop for hands-on creativity. For added convenience, the on-site Good Karma Café offers quick snacks and “take & bake” meals. All of this is just minutes from Clearwater’s beaches, shopping, dining, entertainment, and transportation, making it easy to enjoy the best of Florida living.

2461 Rhodesian Drive Unit 51, Clearwater

Start Your Search