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

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

Welcome to the vibrant community of On Top Of The World in Florida, where an exceptional lifestyle awaits you. This sought-after subdivision offers an array of amenities and a prime location for those looking to embrace active living in a beautiful setting.

Homes in On Top Of The World are designed to cater to residents seeking a balance of comfort and outdoor enjoyment. With the unique feature of Trails Amenities, residents can enjoy the convenience of exploring nature right at their doorstep. Whether you prefer a leisurely stroll or an invigorating hike, these trails provide the perfect opportunity to stay active and connect with the natural surroundings.

Living in On Top Of The World means having access to a well-rounded community that values both relaxation and recreation. From well-maintained homes to picturesque outdoor spaces, this subdivision offers a welcoming environment for residents to call home.

Discover the charm and convenience of On Top Of The World in Florida, where every day brings new opportunities for adventure and relaxation. Experience the best of active living in this exceptional community that truly lives up to its name.

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

9818 Sw 99th Loop, Ocala
$269,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
MOVE-IN READY SOLAR SMART HOME! Beautiful 2019 Rimon model in Crescent Ridge 3 at On Top of the World. This 2-bedroom, 2-bath home features a 2-car garage, split-bedroom floor plan, and unique second-floor flex room/den accessed through the garage. Energy-efficient features include 13 solar panels and natural gas, with an average monthly electric bill reported under $39. Upgrades include 18-inch ceramic tile, gourmet kitchen with quartz countertops, gray cabinetry, glass backsplash, gas convection range, and large island. Spacious primary suite offers two walk-in closets and an en-suite bath with custom-tiled accessible shower. Additional features include a guest bath with custom tile, interior laundry room with washer, dryer, and utility sink, screened lanai, premium corner lot with no home directly behind, and whole-house water softener. Enjoy the outstanding On Top of the World lifestyle with 4 pools, fitness centers, 23 pickleball courts, tennis, more than 200 clubs, and numerous recreational amenities. Golf cart-friendly community with access to three shopping centers. HOA includes basic internet, roof repair, exterior maintenance, landscaping, trash and recycling, and more. Don't miss this move-in-ready home! Be sure to take a look at the Matterport 3D Tour to explore the property from the comfort of your home.

9818 Sw 99th Loop, Ocala
10418 Sw 92nd Place Road, Ocala
$399,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
PRIVACY, EXTENSIVE UPGRADES & EXCEPTIONAL LIVING! Tucked away on a private homesite in the gated Long Leaf Ridge neighborhood of On Top of the World, this beautifully enhanced Livingston model blends refined finishes, thoughtful improvements, and inviting indoor-outdoor living. Featuring 2 bedrooms, 2 bathrooms, and a versatile flex room, this home offers over $80,000 in upgrades designed to elevate everyday comfort and style. The kitchen is both beautiful and functional, featuring quartz countertops, a cabinetry-wrapped center island, built-in oven and microwave, cooktop, stainless steel appliances, and a coordinating tile backsplash. Soft-close and soft-open cabinetry, along with lighting above and below the cabinets, adds an elegant finishing touch. Luxury vinyl plank flooring and crown molding enhance the home's polished interior. The open living area flows through a three-panel sliding glass door to a screened lanai with three ceiling fans, creating a welcoming space to relax and enjoy the Florida lifestyle. Beyond the lanai, an expansive paver patio offers generous room for entertaining, outdoor dining, and relaxing. Approximately 13' x 30' of the patio is covered and features two ceiling fans. The surrounding yard is beautifully landscaped with curbed planting beds and decorative stone, while the private backdrop offers no homes directly behind you! The primary suite provides a comfortable retreat with a walk-in closet featuring custom built-ins and an ensuite bathroom with a tiled, glass-enclosed walk-in shower. A hot water loop provides the convenience of quicker hot water delivery. The flex room features custom built-ins and a sliding door, creating a versatile space that can effortlessly transition from a stylish home office to a comfortable third bedroom with the built-ins serving as closet space. Additional features include a well-appointed laundry room with upper and lower cabinetry and a utility sink, plus a new washer and dryer (2025). A solar tube brings additional natural light into the home, while gutters, custom window treatments, and a transferable home warranty add further value. The spacious 2.5-car garage features a motorized screen, ceiling fan, and overhead storage for added convenience. Ideally located within walking distance of The Summit and The Arbors! With extensive upgrades, generous outdoor living space, and a private setting in Long Leaf Ridge, this Livingston model offers an appealing blend of comfort, convenience, and Florida living. Located in On Top of the World's premier 55+ active adult community, residents enjoy an impressive selection of amenities, abundant social opportunities, and convenient golf-cart access to nearby shopping, dining, and everyday essentials.

10418 Sw 92nd Place Road, Ocala
9737 Sw 100th Avenue Road, Ocala
$365,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
Virtually Staged. Single-level living in Crescent Ridge, built in 2022 and finished well beyond the standard Ginger plan. You get 1,746 sq ft under air (2,618 total), 2 bedrooms, 2 baths, a den that works as an office or guest space, and a 2-car garage. Diagonal porcelain tile, tray ceilings, and crown molding carry through the main living areas. The kitchen is set up for people who actually cook: a gas range, an apron-front sink, Preston Maple cabinets in Drift, wine storage, and a large island with a second sink. Every room is wired for Cat5 data and has TV outlets in place, so moving in is simple. The primary bath has dual sinks, quartz counters, and grey porcelain tile with a mosaic accent. The guest bath has a tub/shower combo. Have coffee on the front porch in the morning and grill on the covered lanai in the evening, using the gas line that’s already in place. Plantation shutters, a paver driveway and walkway, and a 50-year shingle roof round out the exterior. You also won’t be mowing. Lawn care is included in the monthly community fee, so your weekends stay yours. Life in On Top of the World includes golf, pools, fitness centers, tennis and pickleball, on-site dining, and a full calendar of clubs and activities. This is a 55+ community, and at least one resident per household must be 55 or older. Good to know: this is a leasehold property, and financed purchases in OTOW require at least 20% down. Ask for the leasehold guide and full fee breakdown. Schedule your private showing today.

9737 Sw 100th Avenue Road, Ocala
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
8618 Sw 91st Place Unit D, Ocala
$185,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
Welcome to this exceptionally clean and beautifully updated 2-bedroom, 2-bath Philadelphian villa in On Top of the World, offering 1,375 sq. ft. of comfortable, easy-care living. Thoughtfully maintained, this home has many of the improvements buyers are looking for already completed. The updated kitchen features new cabinetry, granite countertops and newer appliances, while updated flooring creates a fresh, cohesive feel throughout. Both bathrooms have been updated, including the shower in the primary bath. The enclosed lanai adds valuable living space, perfect for relaxing, entertaining or creating a comfortable flex space. Just beyond, a screened room overlooking the backyard offers another inviting place to enjoy Florida living. Major improvements include a 2021 roof, 2020 HVAC and 2015 windows, offering added peace of mind. The 1.5-car garage features additional cabinetry for convenient storage, giving you plenty of room to keep things organized. Beyond the home, enjoy everything that makes On Top of the World such a popular 55+ community, with swimming pools, fitness centers, golf, pickleball, tennis, walking trails, clubs, classes, entertainment and plenty of opportunities to stay active and social. Everyday conveniences are close by, too, with Publix, shopping, restaurants, pharmacies, medical offices and healthcare services all easily accessible by golf cart. With so many big-ticket updates already completed, this move-in-ready villa offers a wonderful combination of comfort, convenience and the On Top of the World lifestyle. Move in, settle in and start enjoying it!

8618 Sw 91st Place Unit D, Ocala
8683 Sw 93rd Lane Unit D, Ocala
$204,990
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
Here is an extended Bostonian you will not want to miss! Relax and enjoy your retirement in a large, open home where everything has been done for you. There are no neighbors in front as you enjoy the large front porch and park like views. Walk in through the front door and you will see a lovely living room/dining room combo. The generous master en suite and spare bedroom is off of this room. Continue further into the home and you will see the open kitchen and great room. The kitchen has so many cabinets, you will have problems filling them all. A cooks dream! Beyond there is the bonus/sitting room, where the backyard views are stunning. There is a porch off the back for you to enjoy quiet time in nature. This home has style! Roof 2018, HVAC 2026, newer hot water heater, newer kitchen cabinets, 2 solar tubes, newer windows, new guest bathroom toilet, new clothes dryer, new outdoor fitures and ceiling fans in every room. Make your appointment today!

8683 Sw 93rd Lane Unit D, Ocala
8847 Sw 104th Circle, Ocala
$394,788
3 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
Some homes simply have to be experienced—and this extraordinary Ariana is one of them! Beautiful sunsets, peaceful views, and designer touches throughout make this 2020-built home an exceptional opportunity. Built for entertaining and thoughtfully upgraded for everyday comfort, it offers two bedrooms plus a versatile flex room, two beautifully appointed bathrooms, a 3-car tandem garage, and an incredible bonus sunroom—all for less than $400,000! The open living and dining areas flow into a stunning kitchen featuring quartz countertops, stainless steel appliances, and a gorgeous backsplash. From intimate dinners to lively gatherings, this home makes entertaining feel effortless. The split floor plan provides privacy for the primary suite, creating a relaxing retreat with an upgraded en suite bath and a completed California Closet system. The spacious laundry room connects directly to the primary suite and includes a washer and dryer, abundant storage, a large utility sink, and additional California Closet organization. The versatile flex room offers space for a home office, mancave, creative studio, or hobbies. A true standout is the bonus 320-square-foot sunroom with heating and air conditioning, hurricane windows, blinds, and abundant natural light. Create a second living room, game room, craft space, or home office while enjoying peaceful views of open green space and the retention pond. Step outside to the separate screened lanai, where beautiful sunsets provide the backdrop for relaxing evenings overlooking the fenced backyard. The outdoor grilling patio adds another inviting setting for casual meals and gatherings with friends. The 3-car tandem garage includes a 4-foot extension and a Lifestyle garage door screen, providing generous space for vehicles, a golf cart, storage, and projects. A widened driveway and the home’s position farther back on the lot add parking convenience. Located in On Top of the World in Ocala, this home comes with a lifestyle worth celebrating. Enjoy swimming, pickleball, tennis, fitness activities, walking trails, clubs, cards, creative pursuits, and lifelong learning. Golf, dining, entertainment, and community gatherings offer even more ways to enjoy your days and connect with friends. The HOA package adds convenience with lawn care, internet, exterior painting every seven years, roof care for 25 years, trash service, common-area maintenance, community amenities, and HOA-provided insurance coverage. Owners carry their own condo insurance policy—giving you more time to enjoy your home and the Florida lifestyle. Owner financing is available with 50% down, subject to mutually agreed terms. The motivated seller is flexible, creative, and welcomes all offers. BUYER INCENTIVE: Qualified buyers may receive a lender-paid, one-year interest rate buydown—one percentage point below the note rate during the first year—with an eligible Conventional or FHA purchase loan for a primary residence. Ask for complete details and qualification requirements. Photos include actual property photographs and AI-generated, virtually staged images illustrating furnishing possibilities. Virtual furnishings are for illustration. This Ariana is anything but ordinary. Come experience the views, the upgrades, the entertaining spaces, and the exceptional value for yourself. Schedule your private showing today—your next chapter could begin here!

8847 Sw 104th Circle, Ocala
8519 Sw 91st Street Unit F, Ocala
$189,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
END-UNIT AUGUSTA VILLA | 2 BEDROOMS + LARGE DEN | UPDATED THROUGHOUT Enjoy spacious living in this Augusta model, the largest villa floor plan, featuring 2 bedrooms, 2 bathrooms, a large den, and an oversized 2-car garage. Wood trim around doors, fresh interior paint, new luxury vinyl plank flooring in common areas , and new lighting fixtures and ceiling fans create a fresh, inviting feel. The generous great room and dining area feature a vaulted ceiling, and bay window that brings in abundant natural light, adding to the home's open, airy feel. Built-in bookshelves make the large den ideal for a home office, craft room, or reading retreat. The kitchen offers a spacious pantry and appliances replaced in July 2026. An extended, enclosed Florida room connects to the kitchen at the same floor level and is under air conditioning, expanding the home's living and entertaining space. The primary suite features a walk-in closet and an ensuite bathroom with a double-sink vanity. The split-bedroom layout provides privacy, with the guest bedroom located away from the primary suite and conveniently beside the second bathroom. Additional updates include a 2021 roof, a 2022 water heater, and a 2020 Tempstar 3.5-ton, 14-SEER heat pump. With its generous layout, updated finishes, and desirable end-unit location, this Augusta villa offers plenty of room to relax, entertain, and enjoy!

8519 Sw 91st Street Unit F, Ocala
2426 Persian Drive Unit 64, Clearwater
$135,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Don’t miss this beautifully furnished, move-in-ready condo! This charming condo features two completely furnished bedrooms, thoughtfully decorated with elegance and flair, making it easy to settle in and start enjoying the Florida lifestyle right away. The bright Florida room provides the perfect setting for a lovely dining area, with plenty of space to relax, entertain, or simply unwind while enjoying the sunshine. Recent updates include replacement windows in 2013 and a new A/C system installed in 2021, giving you added comfort and peace of mind. Best of all, there’s nothing left to do but move in and enjoy everything On Top of the World’s 55+ community has to offer. Residents can take advantage of an incredible array of amenities, including two heated pools, 9- and 18-hole golf courses, a state-of-the-art fitness center, billiards, sauna, jacuzzi, lapidary and ceramics facilities, and so much more. With a wide variety of clubs and activities, there’s always something to look forward to. Enjoy Monday night bingo, social dances, entertaining shows, and even opportunities to take the stage and share your own talents! Come discover the joy of living your best life in this wonderfully maintained, thoughtfully designed community. Move in, make yourself at home, and start enjoying everything this exceptional lifestyle has to offer!

2426 Persian Drive Unit 64, Clearwater
2220 Swedish Drive Unit 56, Clearwater
$184,750
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Step into this light-filled 2-bedroom, 2-bath condo on the West Side of Clearwater’s highly desirable On Top of the World 55+ Golf Community. This Eldorado model is Located on the second floor, as you walk in this home immediately impresses with its Vaulted ceilings, Updated HURRICANE Impact resistant windows creating a bright, open, and airy atmosphere. Vinyl plank flooring throughout adds a clean, modern finish. The spacious gathering room is ideal for relaxing or entertaining, enhanced by updated windows that flood the space with natural light. The TV is already mounted for your convivence, The kitchen includes a new refrigerator, and the convenience continues with an in-unit washer and dryer. The 2017 A/C offers reliable comfort and peace of mind. The primary bedroom features an en' suite bath with a bidet, providing privacy and comfort. Just outside your front door, enjoy a charming sitting area—perfect for morning coffee or evening breezes—along with beautiful views that make this location feel special. BRING ALL REASONABLE OFFERS. Additional storage in the core of the building gives you extra room for seasonal items or personal belongings. Situated on the west side of the community, you’ll appreciate being close to Harbor Lake, scenic walking trails, the dog park and all the amenities that make OTOW such a sought-after lifestyle—golf, clubs, activities, and more. If financing 35% down is required. Proof of Funds for Cash

2220 Swedish Drive Unit 56, Clearwater
8625 Sw 94th Street Unit G, Ocala
$194,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
END UNIT | RENOVATED | PRIME LOCATION This beautifully renovated 2-bedroom, 2-bath Montgomery villa with a 2-car garage is designed for buyers with refined tastes. Both bathrooms have been thoughtfully remodeled with stylish vanities, tile surrounds, and sleek barn-style glass enclosures. Carrera marble-look tile flooring flows through the living spaces, complemented by NO popcorn ceilings, elegant chair rail and wainscoting, and shiplap accents in the primary bedroom. The bright white kitchen features new appliances and cabinetry that extends into the adjacent flex room, ideal for a coffee station, hutch, or creative workspace. Plantation shutter blinds add style, privacy, and timeless appeal throughout the home. The garage is truly a standout, finished with epoxy floors, painted walls, new cabinetry, and appliance stands, both functional and visually impressive. Major updates include a newer roof (2016), windows (2015), HVAC (2014), and a new garage door in 2025. Perfectly positioned beside open green space, this end unit offers added privacy while remaining conveniently close to shopping, dining, banking, and the Health and Recreation Center amenities. Enjoy Florida living year-round from the eastern facing, three-season lanai, enhanced with with new windows installed in 2016. Located in On Top of the World, Ocala's premier 55+ active adult community, residents enjoy a resort-style lifestyle with golf cart access to three shopping centers, championship golf courses, and an abundance of amenities. Seller is offering one year home warranty.

8625 Sw 94th Street Unit G, Ocala
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
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