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Homes for Sale with a Pool in Clearwater, FL

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.

All Homes for Sale with a Pool in Clearwater, FL

$829,000
4 Beds 3 Baths Wynwoods Landing SubDv.
Welcome to 3441 Hinsdale Ct privately positioned on a peaceful cul-de-sac in Clearwater’s desirable Countryside area, this exceptional 4-bedroom, 2.5-bath home sits on nearly half an acre of privacy and delivers the space, style, and setting you have been waiting for. From the moment you step inside, the thoughtful split-bedroom design makes an impression. The heart of the home is the beautifully appointed open kitchen, featuring granite countertops, stainless steel appliances, a breakfast bar, and a sunny dinette overlooking the pool. And when entertaining is on the agenda, the dedicated butler’s pantry is ready for everything from cocktail hour to dinner parties keeping beverages, serving pieces, and party essentials conveniently out of sight. The kitchen opens effortlessly to the dining, living, and family rooms, creating the perfect flow for gathering with family and friends. When the evening winds down, cozy up beside the wood-burning fireplace in the family room, or escape with a good book in the living room just off the primary suite. With two bedrooms on each side of the home, everyone enjoys their own space and privacy. Then, step outside and let the fun begin! The sparkling pool, expansive screened lanai, and oversized fenced backyard create your own private outdoor retreat. There’s plenty of room for the grill master with space for both a barbecue grill and smoker, plus ample room for lounging, dining, entertaining or simply soaking up the Florida sunshine. The fully fenced yard is also perfect for your four-legged family members. With southwestern exposure, the outdoor spaces are bathed in beautiful natural light and offer a front-row seat to spectacular evening sunsets. And the location? Hard to beat. Enjoy easy access to the charming downtowns of Safety Harbor and Dunedin, beautiful Honeymoon Island, and Tampa International Airport, all while coming home to the peace and privacy of your own Countryside retreat. Nearly half an acre. Sparkling pool. Incredible outdoor living. Split-bedroom floor plan. Cul-de-sac privacy. $150/year HOA. Wired for portable generator. This is more than a house, it’s the Florida lifestyle you’ve been looking for. Come see why this home deserves to be at the top of your list!

3441 Hinsdale Court, Clearwater

$139,900
2 Beds 2 Baths Marilyn Pines Condo Apts SubDv.
JUST BRING YOUR TOOTHBRUSH! Whether you're searching for a full-time Florida home, seasonal getaway, or investment opportunity, this fully furnished 2-bedroom, 2-bath condo in a desirable 55+ Clearwater community is ready for you to move right in! Located on the second floor, this spacious condo offers a fantastic view overlooking the community pool, sauna, clubhouse, and shuffleboard courts. The open and comfortable floor plan provides plenty of space for everyday living and entertaining, with two generously sized bedrooms and two full bathrooms. Start your morning with coffee overlooking the peaceful pool area, or relax at the end of the day while enjoying the wooded tree views from the front. The kitchen features an updated countertop and sink, adding a fresh touch to the home.One of the biggest perks is the competitive monthly maintenance fee, which includes water, sewer, trash, cable, internet, and more! And when it's time for fun in the sun, you're just a short drive from beautiful Clearwater Beach and all the shopping, dining, entertainment, and attractions that make the Tampa Bay area such a desirable place to live. Fully furnished. Great location. Fantastic amenities. Move-in ready. Come see why this Clearwater condo could be the perfect place to call your Florida home! Maintenance is very competitive an includes Water, Sewer, Trash, Cable , Internet and More! Just a short drive to beautiful Clearwater Beach and everything the Tampa Bay area has to offer.

2060 Marilyn Street Unit 209, Clearwater

$1,495,000
2 Beds 2 Baths Serena By The Sea Condo SubDv.
Welcome to the pinnacle of waterfront luxury living at Serena by the Sea, Clearwater's premier boutique waterfront condominium community. This spectacular penthouse residence offers an extraordinary blend of sophisticated design, modern construction, and resort-inspired amenities, all perfectly positioned between vibrant Downtown Dunedin and Downtown Clearwater. Built to the latest luxury construction standards, Serena by the Sea was thoughtfully designed with a focus on wellness, sustainability, energy efficiency, and resident comfort, featuring solar-powered common-area systems, advanced air-quality technology, enhanced sound insulation, and high-performance building systems that elevate everyday living. Inside, you'll discover an elegant coastal retreat with expansive living spaces, designer finishes, and breathtaking water views that create the perfect backdrop for both entertaining and relaxation. Floor-to-ceiling glass invites abundant natural light while showcasing stunning sunsets and panoramic waterfront scenery. Residents enjoy over 23,000 square feet of world-class amenities, including a spectacular saltwater infinity pool, spa and wellness facilities, state-of-the-art fitness center and yoga studio, billiards room, poker and gaming lounge, stylish social gathering spaces, private party areas, outdoor entertaining venues with summer kitchens and fire pits, and dedicated concierge service designed to deliver a true lock-and-leave luxury lifestyle. The location is second to none—just minutes from Downtown Dunedin, Downtown Clearwater, Clearwater Beach, and Belleair, with convenient access to waterfront dining, private and public golf courses, marinas, boating, shopping, entertainment, and outdoor recreation. Tampa International Airport and Downtown Tampa are easily accessible, making travel effortless while keeping you connected to everything Tampa Bay has to offer. Experience the luxury, convenience, and coastal elegance that only Serena by the Sea can offer. Schedule your private showing today and discover why this exceptional penthouse is one of Clearwater's most coveted waterfront opportunities.

1020 Sunset Point Road Unit 601, Clearwater

$185,900
2 Beds 2 Baths On Top Of The World SubDv.
Virtually Staged. Welcome home to carefree Florida living in On Top of the World Clearwater, one of Florida’s most desirable 55+ golf communities. Located at 2285 Israeli Drive, #57, this spacious 2-bedroom, 2-bath third-floor condo offers approximately 1,400 sq ft of comfortable living designed for easy enjoyment and relaxation. The kitchen features upgraded cabinetry, countertops, and backsplash, creating a stylish and functional space for everyday living or entertaining. The generous primary suite includes a spacious closet and private bath with shower, along with the convenience of an in-unit stackable washer and dryer. The guest bedroom sits adjacent to a full hall bath with tub — perfect for visitors or an ideal home office setup. Start your day with coffee or unwind in the enclosed Florida room overlooking peaceful, landscaped grounds — a perfect extension of your living space. Recent updates provide peace of mind and modern appeal, including a refrigerator, dishwasher, HVAC system, double-pane windows, updated lighting, new toilets, refreshed bathroom cabinetry and countertops, recessed lighting in the kitchen and Florida room, and attractive vinyl flooring throughout (no carpet). Residents enjoy an exceptional resort-style lifestyle with world-class amenities, including two activity centers, two private golf courses (9-hole and 18-hole) free exclusively to owners, two heated pools, a remodeled cardio gym, hobby studios, wood-working shop, and a fenced dog park with covered seating. Social opportunities abound with fitness classes, clubs, dancing, cards, billiards, entertainment, and more. The on-site Good Karma Café offers convenient take-and-bake meals and snacks. Your monthly condo fee (approximately $565) covers water, sewer, trash, cable, internet, exterior maintenance, and full access to recreational facilities — delivering truly maintenance-free living. Ideally located just minutes from Clearwater Beach, the Dunedin Causeway, shopping, dining, medical centers, and transportation, this home offers the perfect blend of convenience, community, and coastal lifestyle. Whether you’re downsizing, searching for a seasonal getaway, or planning for long-term living, this move-in-ready residence is a wonderful opportunity to enjoy the best of Florida living. Note: Property is conveyed by leasehold estate deed. Association approval required. If financing, a minimum 35% down payment is required.

2285 Israeli Drive Unit 57, Clearwater

$225,000
2 Beds 2 Baths Azalea Woods Condo SubDv.
This beautifully updated 2-bedroom, 2-bathroom first-floor condo at Azalea Woods in the heart of Clearwater's coveted Countryside area offers the perfect blend of comfort, style, and unbeatable location. Step inside and you'll immediately notice the clean, bright tile flooring throughout, giving the home a fresh and modern feel that's easy to maintain in Florida's climate. The kitchen has been fully renovated- truly move-in ready. Both bathrooms have been thoughtfully updated, offering a polished, refreshed look. A new electrical panel (2020), 2016 A/C unit, tankless hot water heater, and a water softener mean you can move in with confidence and peace of mind. The hurricane window tint adds an extra layer of protection and energy efficiency, keeping your home cooler and your insurance costs in check. One of this unit's most unique features is the enclosed patio space- a true bonus room ideal for relaxing, extra storage, or a laundry area complete with washer and dryer hookups. And the location of this unit within the community is simply unbeatable. You step right off your patio and you're directly poolside. No stairs, no elevator, no long walks, just instant resort-style living steps from your door. The Azalea Woods community is well-maintained and offers a community pool and cabana, covered carport parking, car wash area, and meticulously kept landscaping throughout. Small pets are welcome for owners. The community is conveniently located minutes from Westfield Countryside Mall, top-rated dining, excellent medical facilities, downtown Dunedin, Safety Harbor, and the world-famous Gulf beaches including Honeymoon Island and Clearwater Beach.

2460 Northside Drive Unit 1202, Clearwater

$290,000
2 Beds 2 Baths Grand Bellagio At Baywatch Condo The SubDv.
Resort living in Clearwater! Luxury living at the Grand Bellagio as soon as you enter the 24 hour live guard gate you're greeted with a beautiful Italian fountain..The clubhouse boasts beautiful marble and Italian style decor.. An impressive array of amenities, including a resort-style pool and spa, with cabanas. Outdoor kitchen. Movie room, fitness center, community docks, tennis courts, sand volleyball, playground, sauna, walking trails, car wash, business center, billiards.. The community is also pet friendly and welcomes residents of all ages. Located in building 6.. The unit is newly renovated , new paint, laminate floors, and baseboards.. Both bathrooms have new tile and the walk in shower has a new custom glass door.. The unit is a spacious 2-bedroom, 2-bathroom condominium offering an inviting open floor plan designed for both everyday living and entertaining. The kitchen features granite countertops, maple cabinetry with crown molding, stainless-steel appliances, a gas range, and a generous breakfast bar that opens to the dining and family room areas. The spacious layout creates an easy flow throughout the home and plenty of room to entertain family and friends. This unit comes with an extra storage unit on the 1st floor..This luxury community also has gazebos, grills and benches out back for watching dolphins and manatees.. Conveniently located just off US-19 and Belleair Road, Grand Bellagio offers easy access to Tampa, St. Petersburg, Clearwater Beach, and two international airports-all within approximately 25 minutes. Costco, Target, Sams Club are minutes away.

2717 Via Cipriani Unit 621B, Clearwater

$468,900
3 Beds 2 Baths Woodgate Of Countryside SubDv.
Welcome to 2376 Millwood Lane, a well-presented 3-bedroom, 2-bath pool home offering an open interior, a two-car garage, and inviting outdoor spaces designed for enjoying the Florida lifestyle. Mature palms, established landscaping, and a covered entry create an attractive first impression, while the fenced backyard provides privacy around the home’s outdoor amenities. Inside, the spacious living and dining area features wood-look flooring, crown molding, recessed lighting, a tray-ceiling detail, and a neutral color palette. Sliding glass doors provide natural light and create an easy connection between the main living space and the screened porch. The kitchen features decorative raised-panel cabinetry, stone countertops, stainless-steel appliances, abundant storage, and a breakfast bar that adds casual seating and additional workspace. The primary bedroom includes an ensuite bathroom with a vanity and tiled walk-in shower. Two additional bedrooms and a second full bathroom with a tub-and-shower combination provide space for guests, a home office, hobbies, or other needs. The attached two-car garage includes the laundry area, a utility sink, and room for parking and storage. Outdoor living is a central feature of the property. The large screened porch offers plenty of room for dining, seating, and entertaining while overlooking the inground pool. The pool is surrounded by a paved deck and has separate safety fencing, while tropical landscaping creates an appealing backdrop. The fully fenced yard also includes additional open space beyond the pool area for gardening, recreation, or pets. The central Clearwater location provides convenient access to shopping, grocery stores, restaurants, medical services, and major roadways. Countryside Mall, Countryside Recreation Center and Library, Moccasin Lake Nature Park, and the trails and waterfront activities of nearby Dunedin are all within convenient reach. Clearwater Beach and Honeymoon Island State Park are approximately 10 to 12 miles away, while Downtown Clearwater and Coachman Park are about 7 miles from the property. St. Pete-Clearwater International Airport is approximately 10 miles away, Tampa International Airport is about 19 miles away, and Downtown Tampa is approximately 25 miles away, depending on the route. With its open living area, primary ensuite, updated interior finishes, substantial screened porch, private pool, fenced yard, and two-car garage, this Clearwater home offers an appealing combination of indoor comfort, outdoor enjoyment, and access to the many amenities of the Tampa Bay area. All distances are approximate and may vary by route. All information is believed to be accurate but is not guaranteed. Buyers and agents should verify all facts and information pertinent to their purchase decision.

2376 Millwood Lane, Clearwater

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