Clearwater Homes with Trail(s) Amenities

Clearwater Homes with Trail(s) Amenities

Welcome to Clearwater, Florida – a sun-kissed gem nestled along the Gulf Coast, renowned for its stunning beaches, vibrant culture, and inviting community spirit. Clearwater boasts a perfect blend of relaxation and adventure, making it an ideal destination for families, retirees, and everyone in between. With its crystal-clear waters and soft, sandy shores, the city is home to the famous Clearwater Beach, consistently ranked among the best beaches in the United States.

But Clearwater is more than just its picturesque coastline. The city is rich in history, featuring charming downtown areas filled with unique shops, delightful eateries, and lively entertainment options. From the Clearwater Marine Aquarium, where you can meet Winter the dolphin, to the vibrant festivals that celebrate the local arts, there’s always something exciting happening in this coastal paradise.

For those seeking a home in Clearwater, you’ll find a variety of properties that cater to diverse lifestyles. Many homes in the area come with exceptional trail amenities, perfect for outdoor enthusiasts. Imagine stepping outside your door to find scenic walking and biking trails that wind through lush landscapes, providing a serene escape for leisurely strolls or invigorating rides. These trails not only enhance your living experience but also promote an active lifestyle, connecting you with nature and your community.

Whether you're looking to relax by the beach, explore local attractions, or enjoy outdoor adventures, Clearwater offers the perfect backdrop for your next home. Discover the charm of Clearwater today, and let the beauty of this coastal city inspire your new beginning!

Newest Clearwater Homes with Trail(s) Amenities

2705 Via Murano Unit 123, Clearwater
$222,500
2 Beds ⋅ 2 Baths ⋅ Grand Venezia At Baywatch Condo SubDv. ⋅ 33764 Zip Code
Experience the charm of resort-style living in this inviting 2-bedroom, 2-bathroom second-floor condominium, nestled within the beautiful, 24-hour guard-gated waterfront community of Grand Venezia at Baywatch in Clearwater. Designed for comfortable, easy living, this condo features 2 Primary Bedroom Suites, granite countertops, impact resistant (hurricane) windows, generous walk-in closets, and the convenience of an in-unit laundry. Whether you're looking for a year-round residence or the perfect seasonal escape, you'll appreciate having everything you need to feel right at home. What truly sets Grand Venezia apart is the lifestyle that comes with it! Imagine starting your day with a peaceful walk along the 1.5-mile lighted waterfront promenade, taking in the beautiful scenery of Old Tampa Bay. Spend a relaxing afternoon by the geothermal-heated resort-style pool, unwind in the spa or sauna, or enjoy a friendly game of tennis, pickleball, or volleyball. At the heart of the community, the impressive Villa Rialto clubhouse offers nearly 9,000 square feet of amenities, including a 24-hour fitness center, business center, billiards room, and welcoming gathering spaces. You'll also enjoy a waterfront gazebo, picnic areas, playground, and convenient on-site car care center. Ideally located in Clearwater, you're just a short drive from shopping, dining, entertainment, and the award-winning Gulf beaches. Here, it's not just about where you live, but how you live. Discover the relaxed Florida lifestyle waiting for you at Grand Venezia at Baywatch!

2705 Via Murano Unit 123, Clearwater
19029 Us Highway 19 N Unit 6-3, Clearwater
$130,000
1 Beds ⋅ 1 Baths ⋅ Imperial Cove 6 SubDv. ⋅ 33764 Zip Code
Come enjoy this well-maintained condo at Imperial Cove and enjoy everything this beautiful waterfront community has to offer. With a walking path around the community, waterfront swimming pool, beautiful clubhouse with a ballroom upstairs, fitness center, and billiards room, this community offers everything to live that Florida lifestyle. Conveniently located right off of US 19 and located near plenty of shopping and dining, this location is hard to beat. Schedule your showing and come take a look today!

19029 Us Highway 19 N Unit 6-3, Clearwater
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
2401 Franciscan Drive Unit 41, 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
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
2333 Feather Sound Drive Unit A401, Clearwater
$269,000
2 Beds ⋅ 2 Baths ⋅ Crystal Bay Condo SubDv. ⋅ 33762 Zip Code
BEAUTIFULLY REMODELED CORNER UNIT FACING THE GOLF COURSE AND RESORT STYLE AMENITIES! This move in ready condo features a freshly remodeled kitchen with granite countertops and under cabinet lighting, two beautifully updated bathrooms, one with a bathtub and the other with a walk in shower, and gorgeous polished porcelain flooring throughout. Decorative granite stone accent walls frame the patio doors, adding a distinctive touch. Additional upgrades include new hurricane rated windows, excluding the bathrooms and sliding patio door, plus an A/C system and water heater that are both approximately two years old. Enjoy the privacy of a desirable corner unit and a screened in back porch overlooking the private golf course, with mature trees providing a peaceful natural buffer between the building and the green. Experience resort style living with a heated pool, jacuzzi, fully equipped fitness center, saunas, clubhouse, game room, pool table, ping pong, four commercial grills, and a spacious poolside patio. The clubhouse features a kitchen and can be reserved at no additional charge for private gatherings. Additional amenities include a dog park, playground, walking trails, assigned parking, guest parking, and storage. The HOA includes water, sewer, trash, internet, cable, grounds maintenance, and storage, providing exceptional convenience and value. Conveniently located near St. Pete Clearwater International Airport and Tampa International Airport, just minutes from I275 with easy access to downtown Tampa, downtown St. Petersburg, shopping, dining, and Gulf Coast beaches. Beautiful upgrades, peaceful golf course views, and outstanding amenities make this condo an exceptional opportunity to enjoy the Florida lifestyle. Schedule your private showing today!

2333 Feather Sound Drive Unit A401, Clearwater
420 N Bayshore Boulevard Unit 104, Clearwater
$89,000
1 Beds ⋅ 1 Baths ⋅ Harbour Towne Condo SubDv. ⋅ 33759 Zip Code
LOCATION, LIFESTYLE & FLORIDA CHARM — ALL IN ONE! Welcome to Harbour Towne Condominiums, where convenience meets the relaxed Florida lifestyle! Ideally situated along the Clearwater side of the Courtney Campbell Causeway, just minutes from charming downtown Safety Harbor, this cozy studio condo offers the perfect opportunity to enjoy everything the Tampa Bay area has to offer. LOVE THE OUTDOORS? YOU’RE IN THE RIGHT PLACE! With the scenic Ream Wilson Trail and Bayshore Boulevard nearby, walking, biking, and enjoying Florida’s beautiful weather can become part of your everyday routine. Harbour Towne offers beautifully maintained green spaces and an impressive selection of community amenities, including a sparkling swimming pool, tennis and pickleball courts, a clubhouse with kitchen, fitness center, and on-site management. LOCATION IS EVERYTHING! Enjoy easy access to Tampa, St. Petersburg, two international airports, the delightful shops and restaurants of downtown Safety Harbor, and the world-famous sugar-white sands of Clearwater Beach. Whether you’re searching for a full-time residence, seasonal Florida escape, or an investment opportunity with leasing subject to association approval, this studio offers flexibility in a fantastic location. YOUR PIECE OF FLORIDA PARADISE IS WAITING — COME EXPERIENCE THE HARBOUR TOWNE LIFESTYLE!

420 N Bayshore Boulevard Unit 104, 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
2320 Brisbane Street Unit 44, Clearwater
$148,000
2 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 33763 Zip Code
Looking for the perfect move-in ready condo? This is it. This beautifully updated home features new windows, modernized bathrooms, a refreshed kitchen, and a updated air conditioning system. Enjoy easy-maintenance flooring throughout the kitchen, dining area, and hallways, along with comfortable, plush carpeting in the bedrooms and living room. Nestled in the highly desirable 55+ community of On Top of the World, you’ll enjoy an active, worry-free lifestyle with unlimited amenities. Residents have access to two golf courses, two recreation centers, tennis courts, lawn bowling, a lapidary studio, social clubs for every interest, hosted dances, and live shows. Centrally located, you are just a short drive to world-famous Clearwater Beach, major shopping centers, convenient transportation options, and two international airports. Between the pristine condo, the active association, and the prime location, this property has everything you need to live your ideal lifestyle!

2320 Brisbane Street Unit 44, Clearwater
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