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

2401 Franciscan Drive Unit 39, Clearwater
$150,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World 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 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 (MLS TB8495481) 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 luxury vinyl 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 39, Clearwater
2255 Philippine Drive Unit 45, Clearwater
$190,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Welcome to one of the better priced, updated, 1400 sqft condo in the Top of the World. It's a 2/2, 3rd floor unit (nobody above you), that combines comfort & resort style living. It has a desirable floor plan & is move in ready. The kitchen features new hardware, wood cabinets, new granite counter tops, a new under counter sink & faucet, new back splash, a new range top, stainless steel refrigerator/dishwasher/microwave, butler station, lament flooring, plus plenty of countertop space & cabinets. The Florida room has added counter tops/cabinets, large pantry closet, double pane windows, & lament flooring. The master bedroom has luxury vinyl tile and an approved 2020 stack washer/dryer closet (which conveys). The ensuite bathroom has a stand-alone shower, new toilet, new vanity sink/cabinet w/ a marble top, lighted mirror, and luxury vinyl tile. The 2nd/guest bathroom has a shower/tub combo w/ hand grip, new sink/vanity, & luxury vinyl tile. The 2nd/guest bedroom has Berber carpet. The front windows are hurricane impact. The main living area has lament flooring. The entry way has a new storm door. All rooms have recently been painted, all flooring is recent, all rooms but the kitchen/bathrooms have ceiling fans. The water heater is new, and the ac system is 2018 (well maintained & serviced yearly). Newer blinds throughout. Assigned parking. This pet friendly 55+ community has 2 activity centers/club houses, 2 heated pools, 2 golf courses (9 & 18 holes), jacuzzi, computer center, gym/exercise room, fenced dog park, hobby studio/wood shop, billiards, shuffleboard, tennis, horseshoes, lawn bowling, picnic areas, entertainment, classes, clubs, cards, library, dancing, the on-site Good Karma Cafe, & more. Your HOA covers all the amenities, 120 channel basic cable/high speed internet, water/sewer, trash, and everything outside the walls. This unit is fee simple. HOA approval is required & if financing, there is a min down payment requirement. You will be close to everything, the beach, airports, the mall, shopping, entertainment, health facilities, restaurants, pet care, hairdressers, banking, downtown Dunedin/Safety Harbor, Honeymoon Island, & more. All rooms sizes are approximate.

2255 Philippine Drive Unit 45, Clearwater
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
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
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
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
2451 Canadian Way Unit 29, Clearwater
$105,000
2 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Virtually Staged. Significant Price Improvement on this Move-In Ready 2-Bedroom Condo in Desirable On Top of the World! NEW 2 TON HVAC SYSTEM IN 2026 AND UPGRADED ENERGY-EFFICIENT WINDOWS THROUGHOUT! Probate process will be complete with the sale of this condo. COE on YOUR timetable. Welcome home to this bright and inviting 2-bedroom, 1-bath condominium in Clearwater's sought-after On Top of the World 55+ community. Offering approximately 1,100 square feet of comfortable living space, this well-maintained residence is vacant and move-in ready, making it an excellent opportunity for year-round living or a seasonal Florida retreat. The thoughtful floor plan features spacious living and dining areas, generous bedroom sizes with plenty of closet storage space, and the convenience of both front and rear entrances. Updated energy efficient windows with coverings included, allowing you to settle in immediately and add your own personal touches over time. Unit is located on 2nd floor and conveniently adjacent to community laundry facility. Residents of On Top of the World enjoy an active, resort-style lifestyle with an impressive array of amenities. The community offers multiple swimming pools, fitness facilities, tennis and pickleball courts, shuffleboard, lawn bowling, hobby studios, a woodworking shop, billiards, card rooms, library, and numerous clubs and social activities. Golf enthusiasts will appreciate access to the community's golf courses, while pet owners can enjoy the on-site dog park. Beautiful walking paths, scenic ponds, and mature landscaping create a peaceful setting throughout the neighborhood. Ideally located, you'll be just minutes from Clearwater's award-winning Gulf beaches, shopping, dining, medical facilities, cultural attractions, and both Tampa International and St. Pete-Clearwater International airports. The monthly HOA fee of $500.23 provides exceptional value and includes a wide range of community amenities, helping you enjoy a carefree Florida lifestyle. Whether you're looking for a full-time residence or a winter getaway, this inviting home offers comfort, convenience, and the vibrant lifestyle that has made On Top of the World one of Clearwater's most popular active adult communities.

2451 Canadian Way Unit 29, Clearwater
2284 Philippine Drive Unit 39, Clearwater
$123,900
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
2192 Swedish Drive Unit 26, Clearwater
$264,000
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
2456 Ecuadorian Way Unit 38, Clearwater
$100,000
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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