Clearwater Homes with Trail(s) Amenities

Clearwater Homes with Trail(s) Amenities

Welcome to Clearwater, Florida – a vibrant coastal gem nestled in the heart of Pinellas County. Renowned for its stunning white-sand beaches and crystal-clear waters, Clearwater offers a unique blend of relaxation and adventure, making it a perfect destination for families, retirees, and everyone in between. With a rich cultural scene, delightful dining options, and a plethora of outdoor activities, this city is not just a place to live; it’s a lifestyle.

One of the standout features of Clearwater is its commitment to outdoor living, particularly for those who appreciate a life intertwined with nature. The homes in Clearwater often come equipped with trail amenities, providing residents with easy access to beautiful walking, jogging, and biking paths. Imagine waking up to the gentle sound of waves and stepping outside to stroll along scenic trails that wind through lush landscapes and picturesque parks. Whether you're an avid runner or prefer a leisurely evening walk, these trails enhance the quality of life, encouraging an active and healthy lifestyle.

In addition to its natural beauty, Clearwater boasts a thriving community spirit, with events and festivals that bring neighbors together. From the world-famous Clearwater Beach to the charming downtown area filled with boutiques and eateries, there’s always something happening in this dynamic city.

Explore the homes of Clearwater, where trail amenities are just one of the many features that make living here truly special. Embrace the sunshine, the sea, and the sense of community that awaits you in this enchanting Florida paradise!

Newest Clearwater Homes with Trail(s) Amenities

$269,000
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
$175,000
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
$114,000
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! 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, and the convenience of both front and rear entrances. Window coverings are included, allowing you to settle in immediately and add your own personal touches over time. 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
$174,900
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 $535 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
$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
$114,000
2 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Rated AAA...!!! Attractive, Affordable, Available NOW! Price Improvement! 3rd floor condo in the fabulous community of On Top of the World. This 2 Bed / 1 Bath unit has been upgraded where it really matters. Beautiful, easy-care laminate flooring throughout. New Modern Step-In Shower and Vanity in the Bathroom. Top of the Building means no noise from above. The Newer Windows are energy-efficient insulation against the Florida heat, lowering your A/C bill. Your Internet is included in your monthly fee, a $150.00 Value. Both Bedrooms are large with ample closet space. The Florida Room can be used as an office, another media room, craft space or lounge. Located near the elevator, offering easy access to your home, with less walking. Tucked into the corner with all the privacy one could want. Neighbors are only on one side. On Top of the World is the Nation's largest 55+ Active Community. There is something for everyone here. Located minutes from the Country's Best Beaches, Sports Venues, Performing Arts Centers, you'll find many ways to Live Your Best Life. Put this condo on your itinerary. Clearwater Florida is Centrally Located. Explore the Fabulous Shopping and Dining nearby. Take an easy Day-Trip to Tarpon Springs, Safety Harbor or Dunedin. These charming towns are easy to navigate to and are a pleasure! Commuting to Tampa, Saint Petersburg or Coastal Towns is also easy to do from here. On Top of the World boasts 2 Golf Courses that are FREE for Owners to Play anytime! There are 2 pools, Billiards, Travel Clubs, a Fitness Center with modern equipment, Walking Trails, Dances, Concerts and More. Design your own Jewelry in the On-Site Studio, Paint and Draw or learn the Ukelele. Seriously! On Top of the World is solidly built in a Non-Evacuation / Non-Flood Zone. No worries! Underground Utilities, Wide Streets, lots to do. Make this one to see.

2457 Ecuadorian Way Unit 73, Clearwater
$148,900
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
$149,000
2 Beds ⋅ 2 Baths ⋅ Eastwood Shores 3 SubDv. ⋅ 33760 Zip Code
Virtually Staged. One or more photo(s) has been virtually staged. * HIGH DESIRED EASTWOOD SHORES 3 COMMUNITY WITH THE LOWEST HOA ** WELCOME TO THE LONGBROOKE NEIGHBORHOOD! ** NEVER FLOODED OR DAMAGED FROM NEITHER HURRICANES! PET FRIENDLY, WELCOME TO ALL THE AGES, RENTAL ALLOWED.PRICE TO SELL ON THE WATER! ACCESS TO FISHING PIER & DOCK WITH THE WALKING TRAIL. Located along the SHORES OF TAMPA BAY, COVE CAY GOLF CLUB is home to a beautiful, coastal-style offering abundant opportunities to spot wildlife. Is open to the public and you can get a membership. HOA FEES $526/MONTHLY, INCLUDES WATER, TRASH, SEWER, CABLE TV EXTERIOR MAINTENANCE, BUILDING INSURANCE, LANDSCAPING & EXTERIOR PEST CONTROL, NO ASSESSMENTS. This lovely TOWNHOME around 900 sq ft offers 2-BEDROOM, 1.5 BATHS 1-CAR GARAGE access & the COVERED PORCH perfectly situated on BACK OF THE PRIVATE FENCE COURTYARD. THIS END UNIT IS MOVE IN READY AND HAS MANY UPGRADES and offers a nice OPEN FLOOR PLAN with no neighbors on the top. IT FEATURES, wood finished kitchen cabinets with new hardware, STAINLESS-STEEL APPLIANCES. NEW LIGHT FIXTURES, NEW CEILING FAN, HVAC (2021) WATER HEATER (2021), NEWER WASHER / DRYER, NEW INSTALLED LUXURY VINYL FLOORS, NEW FAUX WOOD BLINDS, NEW CARPET UPSTAIRS, FRESHLY PAINTED. The primary bedroom features a WALK IN CLOSET AND has the SECOND BUILD IN CLOSETS, second bedroom has also double built in closets. You'll appreciate having your own laundry closet with washer, dryer inside the garage and additional storage, plus convenient access to one assigned parking spot in the garage and on the driveway. From the kitchen you can directly access the garage. Located in a non-age-restricted community, you'll also have access to, POOL, TENNIS COURT, A COMMUNITY DOCK, PRIVATE FISHING PIER all covered by the affordable HOA fee, Eastwood Shores is a park-like complex of all ages, Pet Lovers, (2 PETS) are allowed in this complex. walking distance from Cove Cay Golf Course which is open to the public and MARINA. HOA FEES HAVE BEEN CONSISTENT IN LAST 10 YEARS, strong reserves, financing is allowed. Super location close to shopping and St. Pete Clearwater, Airport and Tampa International. Easy access to Roosevelt Blvd for commuters going to Tampa and St. Pete. Snowbirds can leave a car in the garage when they return north.! Flood Insurance $685 per year . Less than 10 min drive to Clearwater Beach, the Clearwater Aquarium, and the vibrant downtowns of Dunedin and Tampa. Ideally situated between Tampa and St. Petersburg is just minutes from world-class dining, vibrant shopping, pristine beaches, and the convenience of St Pete With effortless access to major highways, everything you need is within reach. NEW WOLFORD RD WAS JUST COMPLETED BY THE CITY, which gives a direct and shorter route to downtown to Tampa & St. Pete. Don’t miss your opportunity to call this move-in ready gem. Schedule a tour today and experience Eastwood Shores living at its finest!

2935 Lichen Lane Unit C, Clearwater
$225,000
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 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
$139,000
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
$150,000
2 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 33763 Zip Code
Located in On Top of the World, a premier 55+ adult condominium community on over 300 acres offers resort-style living with two golf courses that are free to the residents, pickleball courts, shuffleboard/lawn bowling, 4 tennis courts, horseshoe pits, two recreation centers with events that include live bands and balls, over 60 active clubs, billiards room, craft room, café, fitness center with 13 exercise classes, wood working and craft rooms, dog park, two pools including one heated pool with hot tub, lakes with fishing pier, picnic areas with grills, ponds and lakes with walking trails, and more. There is a free resident shuttle that operates 5 days a week to local grocery stores and the malls. **The $565 monthly HOA fee includes Cable TV, Internet, Water/Sewer/Trash, Exterior Maintenance, Grounds Maintenance, Building Insurance, Roof, and community amenities. ** This is a rare opportunity to purchase up to two units next door to create one large home, multi-generational living, or a live-in caregiver. Your home also has one reserved parking space, plus there is adjacent guest parking. This top-floor second-story unit is located in a prime location adjacent to the golf course and only 1,800 feet from the recreation center and pool. The windows were upgraded to impact-resistant windows, and the floors are a combination of carpet, parquet, and tile. The spacious open floor plan has a large living room and dining room in front of the home, and a kitchen with a dinette, plus a large 300-foot Florida room. There are also two additional bedrooms with two bathrooms. A stacked Washer/Dryer combo is included with the home, plus there is a laundry facility down the hallway. There is also an outdoor breezeway with room for a table in front of the home. Minutes to Clearwater Beach, Dunedin, shops, restaurants, and easy access to Tampa International Airport.

2401 Franciscan Drive Unit 41, Clearwater
$97,000
1 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
This gem is ready for you to simply unpack and start living! Bright and inviting, this charming 1-bedroom, 1-bath retreat offers a bonus sun-room — perfect spot for morning coffee or a quiet afternoon read. Low-maintenance laminate flooring flows throughout, while the kitchen features granite countertops, a tile backsplash and a new dishwasher. Well-maintained 2017 HVAC and a new 2026 water heater ensure piece of mind. Beyond your front door, life at On Top of the World (OTOW), an active, 55+ community, offers two private golf courses — an 18-hole and a 9-hole — completely free to resident owners with an activity card. Cool off or unwind in one of two heated outdoor pools. Stay active with tennis and pickleball courts, shuffleboard, horseshoes and lawn bowling or take your fitness to the next level at the state-of-the-art East Activity Center, featuring top-tier cardio and strength equipment alongside an aerobics studio for yoga, Tai Chi and more. Creative souls will love the woodshop and artistic studios, while social butterflies can explore over 175 resident-led clubs, gather in the grand ballroom and auditorium, browse the community library or catch up with neighbors at The Good Karma Café. Outside, enjoy two freshwater fishing piers, a dedicated dog park and beautifully landscaped grounds with paved paths for walking and biking. This is more than a home — it's a lifestyle upgrade waiting for you!

2043 Denmark Street Unit 39, Clearwater
Start Your Search