On Top Of The World Homes with Trail(s) Amenities

On Top Of The World Homes with Trail(s) Amenities

Welcome to On Top Of The World, a vibrant and welcoming community nestled in the heart of Clearwater, Florida, in beautiful Pinellas County. This enchanting subdivision is a true gem, offering an unparalleled lifestyle that combines relaxation, recreation, and a sense of belonging.

On Top Of The World is renowned for its charming homes that embody both comfort and style. Each residence is designed with modern living in mind, featuring spacious layouts, inviting interiors, and beautiful outdoor spaces. Whether you’re looking for a cozy retreat or a larger family home, this community has something to suit every taste and need.

One of the standout features of On Top Of The World is its exceptional amenities, particularly the extensive trails that weave throughout the neighborhood. These scenic pathways provide residents with the perfect opportunity to enjoy leisurely strolls, invigorating bike rides, or peaceful morning jogs while soaking in the lush surroundings. The trails are ideal for those who appreciate an active lifestyle and wish to connect with nature right outside their door.

In addition to the stunning homes and trails, residents of On Top Of The World enjoy access to a host of community amenities, including recreational facilities, social clubs, and organized events that foster a strong sense of community spirit. Here, neighbors become friends, and every day feels like a vacation.

If you’re seeking a vibrant community with a perfect blend of comfort, convenience, and outdoor adventure, On Top Of The World in Clearwater is the ideal place to call home. Come discover the beauty of this remarkable subdivision and make it your own!

Newest On Top Of The World 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
$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
$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
$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
$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
$265,000
2 Beds ⋅ 3 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Virtually Staged. Gorgeous 2 bed 2.5 bath in Clearwater's premier 55+ community, On Top of the World. This unit is in one of the rare 2 story buildings and offers an OPEN FLOOR PLAN, VAULTED CEILINGS and a bright, sunny feel. The building is surrounded by luscious greenery, walking trails and a nearby lake that adds to the abundance of the area's feeling of nature. Upon entering the unit you will be greeted with the bright, open floor plan which features LUXURY VINYL PLANK FLOORING in the living and formal dining spaces. The tiled kitchen features STAINLESS STEEL APPLIANCES, a TILED BACKSPLASH and a WATER FILTRATION SYSTEM. The living space adjacent to the kitchen has a BAY WINDOW with a gorgeous view that floods the area with Florida sunshine. This unit has a dedicated UTILITY ROOM with a washer and dryer and a newer AC (2021). The primary bedroom is an EN SUITE with generously sized with DOUBLE WALK IN CLOSETS. The second bedroom is also an EN SUITE with an ADDITIONAL WALK IN CLOSET and a soothing walk-in, WHIRL POOL STYLE TUB. On Top of the World delivers resort-style living with TWO EXCLUSIVE GOLF COURSES, 9 and 18 holes, TWO HEATED SWIMMING POOLS, tennis, pickleball, a fitness center, DOG PARK, horseshoe pits, lawn bowling, and shuffleboard. A grand ballroom hosts live music and events, and an on-site café offers take-and-bake meals. On Top of the World has over 100 clubs and activities. Ideally located near Dunedin’s beaches, Clearwater Beach, upscale shopping, healthcare, and Tampa International and St. Pete/Clearwater Airports. Seize this chance for luxurious, active living in a vibrant community, SAFELY OUTSIDE FLOOD AND EVACUATION ZONES. 35% down required by OTOW if financing. Schedule your showing today

2192 Swedish Drive Unit 26, Clearwater
$187,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Discover this Well-Maintained home Located on the desirable West Side of On Top of the World - Clearwater's 55+ Premier Golf Community Step into this 2nd-floor condo that features soaring cathedral ceilings that enhance the spacious feel of the open kitchen and gathering-room concept—perfect for everyday living and entertaining. The 2-bedroom, 2-bath layout includes easy-care laminate flooring, an in-unit washer and dryer, NEWER APPLIANCES and a solid foundation ready for your personal touches. A/C 2013. BRING ALL REASONABLE OFFERS. Just steps from an aerated pond and Harbor Lake, the setting offers a peaceful backdrop for morning walks and sunset views. An elevator in the building adds convenience, making this a comfortable and accessible home in a vibrant 55+ community. Experience this vibrant, amenity-rich lifestyle the community is known for. This building's central features include an elevator, additional washers and dryers, and secure storage for owners. Community & Location Living in this gated community provides access to extensive resort-style amenities, many of which are included in your monthly fees: Free Golf: Resident owners enjoy access to two private golf courses (9 and 18 holes) at no extra cost. Active Lifestyle: The nearby East Activity Center features a fitness center, heated swimming pools, tennis and pickleball courts, and over 175 social clubs. Prime Convenience: The building is close to the East Activity Center for easy access. On-site services include a cafe, dog park, woodworking shop, and even free shuttle bus service to major shopping malls and grocery stores. Central Location: Just minutes from the award-winning Clearwater Beach, top-tier dining, and healthcare facilities. Experience maintenance-free 2026 living in one of Florida's

2220 Swedish Drive Unit 36, Clearwater
$105,000
2 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Yay! We have cleared probate and are ready to sell. 2 Bedroom/1 Bathroom Condo offered for Sale in On Top of the World. 1100sq.ft. 55+. Once you enter, you will notice this condo just feels good. Carpeted for comfort. The East-West exposures bathe the rooms in light. The Living/Dining Room combination allows for larger furniture pieces. Both Bedrooms are good sized & will easily accommodate Queen sized bed sets. Easy-care Luxury Vinyl Tiles are underfoot in the in the Kitchen & Florida Room. The expansive Florida Room is situated for more casual seating as well as less formal dining. It's perfect to use as an Office, Media or Craft room. Located conveniently on the 2nd floor just off the elevator. With a Back Door, you can easily bring in groceries or your laundry, which, by the way, is mere steps away. It's like having your own laundry room, yet no heat, lint or space lost! On Top of the World is a community that offers boundless activities and resort style amenities. The Condo is equipped with High-Speed Fiber-Optic Internet included in the monthly maintenance fee. A $150/mo. value! This condo is high & dry! Located in a non-flood zone and non-evacuation zone. Are you a new "Snowbird" looking to escape the northern winters? You can use this condo in the winter months, then rent it for the Summer to "pay for itself" until you make a full time move. There is no waiting time to rent! Most of the Furniture is included. This Clearwater location is perfect to use as "Home Base". Close to the Best Beaches in the Country! Excellent Shopping, Dining & superb Medical Facilities are nearby. There are Performing Arts Centers, Sports Venues, International & Regional Airports close by & a breeze to navigate to. Check out the small-town flavors of Dunedin, Safety and Palm Harbors. Tarpon Springs, St. Petersburg and Tampa are all an easy commute and are worthy daytrips. On Top of the World boasts 2 golf courses that are FREE for Owners to play. Play 9 holes on the short course or a full 18-hole round. The property has walking trails, Tennis and Pickleball courts, 2 Pools, a well-appointed gym, and clubs galore. Take the water aerobics, yoga or line dancing classes. Learn to play the Ukelele! This community is what you make of it. Bring your large dog, there is no size limit. There's even a Dog Park here. Come for a tour of this condo and the community and start living the Real Florida Lifestyle.

2456 Ecuadorian Way Unit 38, Clearwater
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