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Homes for Sale with a Pool in Clearwater, FL

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Welcome to your dedicated resource for homes for sale with a pool in Clearwater, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Clearwater, FL agents, Joseph Sullivan Real Estate specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Clearwater, FL

$230,000
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv.
Welcome to 2295 Americus Blvd E #59, a spacious 2-bedroom, 2-bathroom condominium offering approximately 1,340 square feet of comfortable living space in the highly sought-after On Top of the World community in Clearwater. Designed for easy Florida living, this home offers an open and functional floor plan with generously sized living areas, an inviting kitchen with abundant cabinetry and an eat-in area, two comfortable bedrooms, two full bathrooms, and plenty of closet and storage space. Central heating and air conditioning, ceramic tile and vinyl flooring, and an elevated third-floor location provide both comfort and convenience, while the building offers elevator access. The true highlight, however, is the lifestyle that comes with living in On Top of the World, one of Clearwater’s premier active-adult communities. Residents enjoy an incredible selection of amenities and activities designed to keep life fun, social, and active, including two private golf courses available exclusively to residents, two swimming pools including a heated pool, tennis and pickleball courts, shuffleboard, lawn bowling, a fitness center, hobby studios, billiards, clubs, dancing, entertainment, fitness classes, a dog park, libraries, and multiple activity centers. There is even an on-site café, making it easy to enjoy everything the community has available to you without having to leave home. The gated community also provides sidewalks, maintained grounds, recreational facilities, security, and convenient access to transportation and everyday necessities. The monthly association fee includes a wide range of services and amenities, including water, sewer, trash, internet, cable TV, exterior and grounds maintenance, pest control, recreational facilities, and more, helping make ownership remarkably convenient. Located in Clearwater’s desirable 33763 area, the community places you within easy reach of shopping, restaurants, medical facilities, entertainment, major roadways, and the beautiful Gulf beaches that make the area so desirable. Whether you are looking for a full-time residence, a comfortable Florida retreat, or a low-maintenance home in an amenity-rich community, this property offers an outstanding opportunity to enjoy the best of the Clearwater lifestyle. Come see why On Top of the World continues to be one of the area’s most popular destinations

2295 Americus Boulevard E Unit 59, Clearwater
$209,900
2 Beds ⋅ 2 Baths ⋅ Rustlewood At Countryside SubDv.
Move-in ready in sought after Rustlewood at Countryside! Premium location! Beautiful 2-bedroom, 2 bath home has an updated kitchen and both bathrooms have modern, updated showers featuring designer tile work. The flooring is 2022 new and the A/C was new in 2023! Newer electrical panel and newer windows. Convenient, newer stackable washer and dryer. The great room living space is sizable and extends to the screened balcony boasting a fabulous outside storage closet. Designated parking and plenty of guest parking. Rustlewood is a well-kept community in the heart of Countryside featuring a lovely community pool and near to shopping, restaurants, entertainment and gorgeous Gulf beaches! True move-in condition, desirable third floor unit... better hurry!

2650 Countryside Boulevard Unit C309, Clearwater
$175,000
2 Beds ⋅ 2 Baths ⋅ Rustlewood At Countryside Condo SubDv.
Recently remodeled 2-bedroom, 2-bathroom, 1,110 sq. ft. first-floor condo in Clearwater, Florida. Located in Building B, this move-in-ready unit combines modern updates with comfortable living and a peaceful garden view. The kitchen features elegant granite countertops and like-new appliances, while the home offers laminate flooring throughout for a clean, contemporary look. Both bathrooms have been beautifully updated, and new impact windows provide added peace of mind and energy efficiency. Enjoy your own enclosed patio/porch, perfect for relaxing, enjoying the garden surroundings, or entertaining guests.

2650 Countryside Boulevard Unit B104, Clearwater
$435,000
3 Beds ⋅ 3 Baths ⋅ Bay Isle Landings SubDv.
Experience elevated living in this spacious end-unit townhouse located in the gated Bay Isle community. This 3BR/2.5BA home offers a bright, refined open layout enhanced by extra windows and natural light exclusive to end units. Enjoy a screened patio for effortless indoor-outdoor living and an attached two-car garage providing secure parking and generous storage. The first-floor primary suite adds convenience, while the upstairs loft creates a flexible space for a home office, media lounge, or quiet retreat. Two additional bedrooms and a full bath complete the second level, offering privacy and comfort for guests or family. The larger end-unit floor plan delivers a more expansive, private feel throughout. Residents enjoy an in-ground community pool and the peace of a gated neighborhood, all while being minutes from shopping, dining, airports, and major roadways. A rare blend of comfort, privacy, and thoughtful design in a well-kept Clearwater community

5166 Bay Isle Circle, Clearwater
$131,000
1 Beds ⋅ 1 Baths ⋅ Fountain Square Condo SubDv.
Furnished First-Floor Condo Near Beaches, Shopping & More. Enjoy convenient Florida living in this furnished 1-bedroom, 1-bathroom first-floor condominium, offering an easy-to-maintain space in a location close to many of the area’s everyday conveniences and attractions. A private fenced patio entrance creates a welcoming outdoor space and adds a touch of privacy before stepping inside. The condominium is being offered furnished, making it an appealing option for buyers looking for a primary residence, seasonal getaway, or low-maintenance Florida property. Recent mechanical updates provide added value, including a new water heater installed in 2026 and HVAC system replaced in 2024. Community amenities are conveniently located nearby, with the community swimming pool just steps from the unit—perfect for enjoying Florida’s sunny days. A community laundry room is also available for residents as well as a clubhouse and exercise room. Parking is convenient with an assigned parking space, plus visitor parking for guests. The location puts you within easy reach of Florida’s Gulf Coast beaches, shopping, dining, entertainment, and everyday services, while area airports and major roadways are also accessible for travel throughout the Tampa Bay area and beyond. Whether you’re searching for a furnished Florida condo, seasonal residence, or low-maintenance first-floor condominium near the beaches, this property offers a combination of convenience, recent updates, community amenities, and location. Schedule your showing and discover the possibilities of easy Florida condo living!

1799 N Highland Avenue Unit 75, Clearwater
$263,000
2 Beds ⋅ 1 Baths ⋅ Lakes Unit I The SubDv.
Virtually Staged. This tastefully updated single family home, situated on a large lot with no rear neighbors, is located in “The Lakes” - a popular 55+ Resort Style living community. This home has an open floor plan with an abundance of natural light and feels larger than the square footage and includes a 15’ X 9’ screened-in lanai with new epoxy flooring! Many features & upgrades include brand new "wood look" porcelain tile and fresh paint throughout, new ceiling fans and light fixtures, hot water heater (2025), newer windows, new hurricane impact sliding doors (2026), roof (2020) and air conditioner (2020). The owner has also added Cellulose blown-in insulation (Rating R-38) and driveway extension. The kitchen boasts quartz countertops, wood cabinetry, stainless steel appliances, and lovely hardware, backsplash & faucet! The bath is also beautifully renovated from top to bottom! The primary bedroom is a good size and boasts a large walk-in closet. The second bedroom is also a good space and both bedrooms feature new plantation style closet doors! The garage is oversized and includes a designated area for your new washer and dryer which convey with the sale! The Lakes community features a heated pool and picnic area, shuffleboard and a clubhouse that can be reserved for social community or personal events. The amenities also include a game room to enjoy a game of pool and a library! A low $305 monthly HOA fee includes everything except the electric! Truly a maintenance free community! Location is perfect close to the Beaches, Tampa Airport, great restaurants and shopping. This home is equipped with hurricane shutters and is NOT in a flood zone. Note: Some pictures are virtually staged with endless possibilities and also included are the original pictures.

4318 Great Lakes Drive N, Clearwater
$339,000
2 Beds ⋅ 2 Baths ⋅ Seville Condo 12 SubDv.
Experience a stunning million dollar Waterfront view from this unique eighth floor condo the spacious two bedroom two bathroom unit offers the potential to convert into a three bedroom layout. Enjoy the breathtaking views without the hassle or cost of flood insurance as this property is located outside any evacuation zone among the 386 units in this desirable community only two units share this generous 1540 square-foot heated layout and spectacular view The condo features top-notch laminate flooring, a brand, new kitchen and beautifully updated bathrooms plus there are no age restrictions flexible pet policies up to 28 pounds and no lease restrictions conveniently located near everything you need. This is truly a rare find, stylish brand-new granite kitchen with beautiful brand-new cabinet kitchen and two lovely bathrooms tile floor, with brand-new washer & Drayer Machine. all the floor brand new laminate, with fresh paint, It could be easy to restore the unit to 3 bedrooms by adding the partition back, It is located in a hot area. It’s ideally situated behind Clearwater Mall, with easy access to shops like Costco, Target, and various restaurants. It’s also conveniently close to Tampa International Airport, St. Pete-Clearwater Airport, downtown St. Petersburg, and Clearwater Beach, one of the best beaches in the USA, with quick access to US-19. This prime condo won’t last long! It is a beautiful swimming pool with a nice health spa

2699 Seville Boulevard Unit 802, Clearwater
$250,000
2 Beds ⋅ 3 Baths ⋅ Raintree Village Condo SubDv.
55+ COMMUNITY. THIS GORGEOUS CONDO IS LOCATED CLOSE TO THE SHOPPING CENTERS, MEDICAL CARE, RESTAURANTS, AND AWARD WIINNING BEACHES! THE CONDO IS WELL UPDATED FEAURING A BEUTUFUL KITCHEN WITH STONE COUNTERTOPS AND GORGEOUS CABINTRY, 2 VERY LARGE BEDROOMS WITH WALK-IN CLOSETS AND ATTACHED UPDATED BATHROOMS. ONE BEDROOM IS ON THE FIRST FLOOR AND ONE BEDROOM IS ON THE SECOND FLOOR, LUXURY VINYL PLANK FLOORING THROUGHOUT THE DOWNSTAIRS, FORMAL DINING ROOM, FIREPLACE, CATHEDRAL CEILINGS, AND A BONUS ROOM. CONDO IS AN END UNIT WITH GREAT VIEWS OF THE POOL AND GROUNDS. RAINTREE VILLAGE IS LOCATED IN A NON-EVACUATION ZONE AND NOT IN A FLOOD ZONE. THE MONTHLY FEE COVERS CABLE, INTERNET, WATER, SEWER, TRASH, ROOF, LAWN CARE, BUILDING MAINTANANCE, POOL, CLUBHOUSE AND EXTERIOR INSURANCE. A MUST SEE!

2101 Sunset Point Road Unit 2105, Clearwater
$120,000
1 Beds ⋅ 1 Baths ⋅ Winding Creek SubDv.
Short Sale. Welcome to 2400 Winding Creek Blvd #17-203, a well-maintained condo in the Winding Creek community of Clearwater. This 2nd floor unit offers a comfortable layout, practical updates, and a convenient location close to shopping, dining, beaches, and everyday essentials. Inside, the living area feels open and bright, with plenty of natural light. The kitchen features granite countertops, 2 tone cabinets, and modern appliances, making it functional for both everyday meals and entertaining. The washer and dryer are located inside the unit and will convey with the sale, adding extra convenience. The bedroom offers good storage with 2 large closets, and the large updated bathroom gives the home a clean, refreshed feel with plenty of space to get ready. Residents of Winding Creek can enjoy the community pool and spa, tennis courts, and shuffleboard court while still being close to everything Clearwater has to offer. Clearwater Beach, local parks, restaurants, shopping, and entertainment are all within easy reach, with the Gulf beaches less than 20 minutes away. Whether you're looking for a full-time home, seasonal Florida getaway, or low-maintenance Clearwater condo, this property offers a practical combination of location, updates, and convenience.

2400 Winding Creek Boulevard Unit 17-203, Clearwater
$1,429,000
3 Beds ⋅ 2 Baths ⋅ Belleair Estates SubDv.
FULLY RENOVATED BELLEAIR POOL HOME-DESIGNER KITCHEN AND BATHS, TRULY MOVE-IN READY!!! DISCOVER TIMELESS ELEGANCE, QUALITY CRAFTSMANSHIP, AND INTELLIGENT DESIGN AT 802 OSCEOLA ROAD, where classic Belleair charm has been reimagined for today's lifestyle. FOLLOWING A COMPREHENSIVE RENOVATION completed between 2024 and 2025, this 3 BEDROOM, 2 BATH home showcases quality craftsmanship and carefully selected finishes that create a residence as functional as it is beautiful. The CUSTOM KITCHEN showcases handcrafted Olde World cabinetry, NATURAL QUARTZITE countertops, a PREMIUM JENNAIR APPLIANCE PACKAGE featuring an INDUCTION RANGE, INTEGRATED BUILT-IN REFRIGERATOR, MICROWAVE DRAWER, BUILT-IN WINE REFRIGERATOR, and exceptional storage designed for everyday living. ENGINEERED HARDWOOD FLOORING extends throughout the main living areas and bedrooms, while TILE FLOORING enhances the bathrooms. Beautifully remodeled SPA-INSPIRED BATHROOMS include a guest/pool bath with DUAL VANITIES and a CUSTOM WALK-IN SHOWER. Additional interior features include CALIFORNIA CLOSETS throughout, a GAS FIREPLACE, and an OPEN FLOOR PLAN designed to accommodate both elegant entertaining and comfortable everyday living. BEYOND ITS BEAUTIFUL FINISHES, THE HOME OFFERS EXCEPTIONAL FUNCTIONAL IMPROVEMENTS, including a HIGH-EFFICIENCY HVAC SYSTEM (2024), TANKLESS GAS WATER HEATER, TWO-STAGE WHOLE-HOUSE WATER SOFTENER (2024), ELECTROLUX WASHTOWER (2025), a RELOCATED AIR HANDLER for improved accessibility and serviceability, and HIGH-END CUSTOM GARAGE CABINETRY with a UTILITY SINK. These upgrades enhance efficiency, functionality, and long-term value. Step outside to enjoy the COVERED LANAI overlooking the RESURFACED SALTWATER FIBERGLASS POOL, PROFESSIONALLY UPDATED LANDSCAPING, and the CIRCULAR PAVER DRIVEWAY and POOL DECK, professionally RESET AND SEALED (2026). Additional features include a WHOLE-HOUSE GAS GENERATOR, HURRICANE-RATED WINDOWS, and HURRICANE SHUTTERS, combining convenience with exceptional storm protection. Ideally located within walking distance of the BELLEAIR RECREATION CENTER, community parks, and year-round town events, including the popular SUNDAYS IN BELLEAIR outdoor concert series, this home is also just a short golf-cart ride to BELLEAIR COUNTRY CLUB, featuring TWO DONALD ROSS-DESIGNED CHAMPIONSHIP GOLF COURSES, and the prestigious PELICAN GOLF CLUB. Boutique shopping, fine dining, waterfront parks, and the WORLD-FAMOUS GULF BEACHES are all just minutes away, completing the exceptional Belleair lifestyle.

802 Osceola Road, Clearwater
$165,000
2 Beds ⋅ 2 Baths ⋅ Penthouse Groves SubDv.
Beautifully updated 2-bedroom, 2-bath condominium featuring a thoughtfully remodeled interior, granite countertops, updated cabinetry, and a spacious spa-style shower in the second bathroom. This move-in-ready home offers a bright, functional layout with durable tile and vinyl flooring throughout, stone countertops, ceiling fans, and a walk-in closet in the primary suite. The kitchen is equipped with a breakfast bar and a full appliance package, including a range, refrigerator, dishwasher, microwave, washer, and dryer. Major mechanical updates provide added peace of mind, with all rooftop A/C components replaced, appliances approximately four years old, and a garbage disposal replaced just two months ago. Penthouse Groves amenities include a Clubhouse with kitchen, billiards, card room, library, fitness center, sauna, and more. Outside amenities include a pool, shuffleboard, grilling area, and community dock. Enjoy covered parking and a convenient Clearwater location close to shopping, dining, parks, beaches, and major roadways.

1655 S Highland Avenue Unit F129, Clearwater
$282,000
2 Beds ⋅ 2 Baths ⋅ Club At Feather Sound The Condo SubDv.
Welcome to 1945 Pelican Landing, Unit 614, a beautifully maintained and inviting home that is well cared for, move-in ready, and waiting for its new owners! From the moment you step inside, you’ll appreciate the warm and welcoming atmosphere along with the open-concept layout, creating a spacious flow that is perfect for everyday living and entertaining. The home features beautiful porcelain tile flooring, adding a clean, modern touch while also providing durability and easy maintenance. The open living and dining areas provide plenty of space to relax, gather with family and friends, or make the space your own. Pride of ownership is evident throughout this well-kept home, allowing the new owners to move right in and start enjoying everything it has. Located within a gated community with security, residents can enjoy added privacy along with an impressive selection of resort-style amenities. Spend sunny Florida days relaxing at the resort-style community swimming pool, unwind in the spa/hot tub, or stay active in the fully equipped fitness center and workout room. For those who enjoy recreation, the community also features tennis and pickleball courts, an indoor basketball court, and a clubhouse perfect for social gatherings and community activities. With so many amenities available, there is something for everyone to enjoy without having to travel far from home. The location adds even more appeal! Enjoy convenient access to Tampa, major interstates and freeways, making commuting and traveling throughout the Tampa Bay area easy. Shopping, dining, entertainment, and everyday conveniences are also within easy reach. With its open-concept design, beautiful porcelain tile, welcoming atmosphere, well-maintained condition, gated entry with security, and outstanding community amenities, 1945 Pelican Landing, Unit 614 offers the perfect combination of comfort, convenience, and Florida living. This home has been lovingly cared for and is ready to welcome its new owners — all that’s missing is you!

1945 Pelican Landing Boulevard Unit 614, Clearwater
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