On Top Of The World Homes under $250,000

On Top Of The World Homes under $250,000

Welcome to On Top Of The World, a vibrant and welcoming subdivision nestled in the heart of sunny Florida! This enchanting community is designed for those who appreciate a blend of comfort, convenience, and a touch of elegance. With a variety of homes available for under $250,000, On Top Of The World offers an incredible opportunity for first-time homebuyers, retirees, and anyone seeking an affordable yet fulfilling lifestyle.

One of the standout features of On Top Of The World is its emphasis on active living. Residents enjoy access to a wealth of amenities, including beautifully landscaped parks, walking trails, and recreational facilities. Whether you're looking to take a leisurely stroll, enjoy a game of tennis, or relax by the pool, this community has something for everyone. The sense of camaraderie among neighbors fosters a warm and inviting atmosphere, making it easy to forge lasting friendships.

The homes in this subdivision are thoughtfully designed, offering modern layouts and appealing finishes that cater to a range of tastes. From cozy two-bedroom bungalows to spacious three-bedroom homes, you'll find the perfect space to call your own without breaking the bank. With prices under $250,000, On Top Of The World stands out as an ideal choice for those looking to invest in their future while enjoying the perks of Florida living.

Located conveniently near shopping, dining, and entertainment options, On Top Of The World is not just a place to live—it's a lifestyle. Come discover the charm and community spirit that awaits you in this delightful subdivision!

Newest On Top Of The World Homes under $250,000

2428 Columbia Drive Unit 36, Clearwater
$126,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
On Top of the World Condominium Community, This second-floor condominium offers several features that distinguish it from many other units in the community. According to county records, the property is located in a non-flood zone. Full eight-foot ceilings provide a comfortable, open feeling throughout the home, and elevator access makes reaching the second floor convenient. One particularly desirable feature is the two separate entrances—one through the front of the unit and another directly into the kitchen. Many condominiums in the community have only one entrance. The home features newer double-pane windows and a remodeled kitchen. While some areas retain their original finishes, they have been exceptionally well maintained. Some buyers may appreciate the retro character, while others may eventually choose to update to their personal taste. In my opinion, this condominium is exceptionally clean, well cared for, and move-in ready. The lovely rear view adds to the comfortable atmosphere. Located in the established On Top of the World community, known for its extensive amenities and active lifestyle, this property offers a combination of convenience, character, and thoughtful improvements.

2428 Columbia Drive Unit 36, Clearwater
2040 World Parkway Boulevard Unit 22, Clearwater
$179,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Welcome to On Top of the World Golf Course Community in Clearwater! This fully furnished 2-bedroom, 2-bath, 1,400 sq. ft. end unit offers extra windows for added natural light and an exceptional location directly across from the East Activity Center (Building 11). Thoughtful upgrades include PGT hurricane rated windows installed in 2025, luxury vinyl plank flooring, updated kitchen cabinets and counter tops with newer appliances, and a convenient coffee bar. The spacious primary suite features an updated ensuite bathroom, while generous storage throughout provides plenty of room to stay organized. The Florida Room is perfect for Relaxing and enjoy a beautiful, peaceful view of mature trees and a quiet stream, creating a lovely backdrop to everyday living. Live in the Florida lifestyle at On Top of the World Clearwater, where there’s always something to enjoy! This active 55+ community offers golf, swimming pools, fitness facilities, tennis, pickleball, shuffleboard, lawn bowling, fishing and kayaking, a dog park, and a wonderful variety of clubs and social activities. With so many ways to stay active, socialize, and enjoy your surroundings, OTOW offers much more than a home, it offers a lifestyle. Financing requires a minimum 35% down payment.

2040 World Parkway Boulevard Unit 22, Clearwater
2459 Franciscan Drive Unit 35, Clearwater
$115,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
MOTIVATED OWNERS, PRICED TO SELL!!! WASHER & DRYER IN THE UNIT! Come and GRAB this MOVE IN READY condo in a HIGHLY DESIRABLE 55+ On Top of the World active gated community! Enjoy amenities galore, clubs and social activities, situated at a PERFECT LOCATION close to restaurants, shopping, entertainment, medical clinics, major hospitals, beaches, golf courses and more! This BEAUTIFUL home features: open concept living and dining area, spacious bedrooms, and additional Florida room for relaxing and entertaining! It’s updated with a NEW Water Heater (2024), Updated kitchen with NEW built in oven, refrigerator, dishwasher, microwave, storage cabinet and more! It comes fully furnished and beautifully decorated! HOA includes: water, sewer, garbage, basic cable, internet, maintenance of the building, insurance of common areas, maintenance of all amenities including 2 golf courses which you can enjoy every day with no additional costs! Enjoy 2 Activity Centers, 2 Heated Swimming Pools, Fitness Center, Library, Billiard Room, Tennis Courts, Shuffleboard Courts, Horseshoes, and more! HOA application with $150 fee and approval is required! If financing, 35% down is required! Come see it today!!!

2459 Franciscan Drive Unit 35, Clearwater
8569 Sw 92nd Lane Unit E, Ocala
$159,500
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
ROOF 2021 | PAINTED 2024 | EXTENDED ENCLOSED LANAI Enjoy flexible living spaces in this Montgomery model featuring 2 bedrooms, 2 bathrooms, a 2-car garage, and a separate family room. New flooring in the common areas provides a fresh look, while the extended enclosed lanai offers additional space for relaxing or entertaining. An additional screened porch is the perfect spot to enjoy fresh air and your morning coffee. The primary suite features an ensuite bathroom with a walk-in shower and a walk-in closet, along with convenient access to the family room. With multiple gathering areas, a roof replaced in 2021, and the home painted in 2024, this Montgomery offers comfort, versatility, and room to make it your own. Newer Windows

8569 Sw 92nd Lane Unit E, Ocala
2451 Canadian Way Unit 51, Clearwater
$139,900
2 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
YOU FOUND IT!! Welcome to one of the most highly coveted 55+ communities in Clearwater, Florida. You will enjoy being just minutes away from Downtown Dunedin, Pinellas County Beaches, and Countryside Mall. This completely remodeled 2-bedroom, 1-bathroom condo offering 1,100 square feet of living space is thoughtfully updated throughout, this home offers a fresh, modern feel with earth tones, quality finishes and attention to detail. The beautifully redesigned kitchen features custom solid maple cabinetry, Corian countertops, a stainless steel sink, stone tile backsplash, and a matching refrigerator enclosure. Enjoy brand-new LG appliances, including a spacious 28-cubic-foot refrigerator and glass-top range with air-fryer functionality, along with a Bosch dishwasher. Additional improvements include custom manufactured hardwood flooring, tiled kitchen flooring, an updated bathroom with new tile and vanity, fresh Behr paint throughout, modern light fixtures, solid basswood living room shutters, Bali blinds in the Florida room and second bedroom, impact/wind-mitigation windows, and elegant French doors. Enjoy the wonderful lifestyle On Top of the World has to offer, with two private golf courses, swimming pools, fitness centers, tennis courts, hobby studios, a dog park, and numerous social activities. Conveniently located near Downtown Dunedin, beautiful Gulf beaches, shopping, and dining.This move-in-ready condo offers a wonderful opportunity to enjoy comfortable Florida living in a vibrant and established community. Schedule your private showing today! (Pictures are true to life and are not AI enhanced).

2451 Canadian Way Unit 51, Clearwater
2341 Haitian Drive Unit 41, Clearwater
$245,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Virtually Staged. Stunning turnkey end-unit condo in Clearwater’s premier 55+ community, On Top of the World! Step inside this beautifully renovated, move-in-ready home featuring new impact windows, new A/C, an open-concept floor plan filled with natural light, luxury vinyl plank flooring, and a newer water heater. The spacious kitchen showcases custom solid-wood soft-close cabinets with crown molding, gorgeous countertops, stainless steel appliances, ceramic tile backsplash, and a beautiful oversized island perfect for entertaining. The generous primary suite offers ample closet space and a fully remodeled en-suite bathroom with a stunning tiled shower. The updated guest bathroom features new flooring, a modern vanity, and stylish lighting. Additional convenience includes in-unit washer and dryer hookups. Enjoy resort-style living with two private golf courses (9 and 18 holes, free for resident owners), two heated pools, tennis, pickleball, fitness center, dog park, and over 100 clubs and activities. The community also features a grand ballroom, live entertainment, and an on-site café.

2341 Haitian Drive Unit 41, Clearwater
2459 Franciscan Drive Unit 3, Clearwater
$209,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Beautifully updated first-floor condo in the sought-after 55+ community of On Top of the World! This move-in-ready home features an open floor plan, a stunning remodeled kitchen with modern finishes, and durable hard-surface flooring throughout. Enjoy the convenience of ground-floor living with no stairs and easy access to parking and amenities. OTOW offers golf, pools, fitness center, numerous social activities, and maintenance-free living. A perfect blend of comfort, style, and convenience!

2459 Franciscan Drive Unit 3, Clearwater
2331 Finlandia Lane Unit 21, Clearwater
$127,000
1 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Enjoy comfortable Florida living in this clean, first-floor, one-bedroom, one-bathroom condo located in the desirable 55+ community of On Top of the World. The unit features luxury vinyl tile flooring throughout, two private patios, one in the front and one in the back, and the convenience of a dedicated parking space directly in front of your door. Its location near the community entrance and exit provides easy access. On Top of the World offers an abundance of amenities and activities for an active lifestyle, including private lake access for fishing and kayaking, activity centers, golf courses, swimming pools, organized clubs and activities, a dog park, tennis courts, shuffleboard, and so much more. Whether you're looking for relaxation, recreation, or an active social lifestyle, this condo offers a wonderful opportunity to enjoy all that On Top of the World has to offer! The 55+ community has two activity centers, and two private golf courses with 9 and 18 holes, free exclusively for residents & owners. There are two heated swimming pools. The remodeled Cardio Gym has the latest exercise equipment. A very pet-friendly community, there is a fenced dog park with covered seating. There are hobby studios, and a wood shop for the exclusive use of the residents. Activities include fitness classes, dancing, clubs, cards, billiards, entertainment, classes, and much more. The on-site Good Karma Café has take & bake meals and snacks. Close to beaches, transportation, shopping, entertainment, and fine dining. All room sizes, floor plans and square footage are approximate. This property is being transferred by a leasehold estate deed. Association approval is required. If financing, a 35% down payment is required.

2331 Finlandia Lane Unit 21, Clearwater
9156 Sw 91st Circle, Ocala
$224,900
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
Welcome to this beautifully maintained Madison model courtyard home in the premier, gated 55+ community of On Top of the World! Offering an inviting blend of comfort, style, privacy, and convenience, this home is designed for enjoying the best years of life with less maintenance and more time for the things you love. From the moment you enter the foyer, you'll appreciate the vaulted ceilings, spacious feel, and thoughtfully designed split-bedroom floor plan. Meticulously cared for and loaded with desirable updates, this home offers peace of mind along with plenty of room to relax and entertain. The spacious living and dining areas provide an open, welcoming atmosphere, while the large eat-in kitchen is sure to impress. Beautiful wood cabinetry with crown molding, soft-close doors and drawers, granite countertops, under-cabinet task lighting, convenient pull-out pantry storage, and abundant drawers make this kitchen as functional as it is attractive. An additional pantry in the laundry room provides even more storage. The generously sized primary bedroom suite is a wonderful private retreat, featuring a walk-in closet, additional closet, linen closet, and a spacious ensuite bath with a large vanity, comfort-height features, roomy step-in shower with frameless glass door, and separate potty room. Guests will appreciate their own private bedroom with walk-in closet and a conveniently designed guest bath featuring a separate shower and comfort height toilet. Love the outdoors? You'll especially enjoy the beautiful, fenced private courtyard, completely remodeled with attractive pavers, seating areas, outdoor lighting, and a fire pit. It's the perfect place for morning coffee, entertaining friends, or relaxing under the Florida sunshine. The insulated, enclosed lanai features dual-pane argon gas windows and offers peaceful views of the backyard, with extra distance from neighboring homes. Furnishings are available. You'll appreciate the many valuable updates and features, including: Roof replaced in 2013. HVAC replaced in 2015. Energy-efficient Pella double-pane windows installed in 2018. Insulated garage door installed in 2018. Water heater replaced in 2018. Newer flooring throughout, including tile, carpeting, and attractive wood-look flooring. Custom plantation shutters. Granite countertops in kitchen and bathrooms. Wood cabinetry with crown molding and soft-close doors and drawers. Comfort-height bathroom vanities and commode. Private courtyard and enclosed lanai. Oversized garage with additional insulation. And there's even more to love! Enjoy the On Top of the World lifestyle! Your monthly HOA fee includes an impressive array of amenities and services, helping make everyday living easier and more enjoyable. Take advantage of lawn care, access to the fitness center, multiple swimming pools, exercise classes, 24-hour gated security, exterior painting, and more! Whether you're looking forward to staying active, enjoying social activities, entertaining friends and family, or simply relaxing and enjoying a beautiful Florida home, this community offers wonderful opportunities to make the most of every day. Come discover the comfort, privacy, convenience, and lifestyle you've been looking for. This special Madison courtyard home is ready to welcome you home!

9156 Sw 91st Circle, Ocala
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
9028 Sw 91st Circle, Ocala
$249,000
3 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 34481 Zip Code
Welcome Home! This 3/2/2 home is move in ready with many upgrades. So much to do in OTOW and Williamsburg has their own get-togethers. 1. Gutters w/ Leaf filter installed{lifetime warranty} 2Appliances are 2 years or less 3.contiguous LVP 4. custom built cabinets is dining room 5.UV Ray film on windows in Bonus rm and Master 6. Granite counter tops and reverse osmosis in Kitchen 7.Upgraded bathrooms 8.New lighting and fans 9. new paint inside and out 10. New air conditioning system. There is mor, see list in the home. Take a look and get closed before the end of year to take advantage of homestead and other discounts from the county

9028 Sw 91st Circle, Ocala
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
Start Your Search

How much is your home worth?

Get instant property value now!