Homes for Sale with a Pool in Clearwater, FL

4 Beds ⋅ 2 Baths ⋅ Trails Of Countryside SubDv.

Short Sale. SHORT SALE ALERT — $699,000 — SUBMIT YOUR OFFER ASAP! NEW PRICE + SHORT SALE OPPORTUNITY! This vacant, move-in-ready home in the highly desirable Trails of Countryside is now offered at $699,000 and is subject to lender approval. Seller is motivated and looking for offers NOW! Don’t miss the opportunity to secure this beautifully updated 4-bedroom, 2-bath home with a 3-car garage, screened pool, and private outdoor living area. The spacious split-floor-plan residence is designed for comfortable everyday living and entertaining. The remodeled kitchen features granite countertops, wood cabinetry, stainless steel appliances, and a brand-new stove, opening seamlessly to a light-filled family room with a cozy wood-burning fireplace and peaceful backyard views. The primary suite features an updated bath, while the second bathroom has a new bathtub. Luxury vinyl flooring has been installed throughout the bedrooms, living and dining areas, and bathrooms for a modern, cohesive feel. Recent improvements include a new roof (2023), new lights and ceiling fans throughout (2023), digital water softener (2025), updated sprinkler system (2024–2025), completed stucco repairs, and fresh exterior paint. The screened pool and outdoor living area provide the perfect setting for entertaining or relaxing, with pavers, a covered lanai, and an updated koi pond with new fish creating a tranquil backyard retreat. VACANT AND READY FOR ITS NEXT OWNER! Conveniently located in Clearwater’s Countryside area near shopping, dining, beaches, and airports. SHORT SALE — LENDER APPROVAL REQUIRED. Submit your strongest offer ASAP. All offers are subject to lender approval.

3408 Fairfield Trail, Clearwater

$6,749,000

5 Beds ⋅ 8 Baths ⋅ Belleview Island Sub SubDv.

This private, world-class waterfront estate sits within the exclusive double-gated enclave of Belleview Island. Perfectly positioned on a rare double lot, the property offers breathtaking panoramic views of Clearwater Harbor and the historic Donald Ross–designed Belleair Golf and Country Club, Florida’s first golf course. A true boater’s paradise, the protected cove features a custom dock with a jet ski lift, along with 60,000 lb. and 80,000 lb. boat lifts, providing quick and direct access to Clearwater Pass and the Gulf of America. Inside, the custom-built residence showcases refined craftsmanship and elegant living spaces. A grand, custom staircase introduces the home and opens into an expansive great room designed for sophisticated entertaining, complete with a dining area, wet bar, custom built-ins, and sweeping water views. The gourmet kitchen offers a large island, custom cabinetry, granite countertops, a butler’s pantry, and a charming breakfast room overlooking both the bay and golf course. The second floor is a private retreat featuring a luxurious primary suite with its own balcony, vaulted ceilings, fireplace, and dual spa-caliber bathrooms—one with a walk-in shower and the other with a whirlpool tub—plus two walk-in closets. Three additional guest suites each include marble bathrooms and walk-in closets. Outdoor living is exceptional, with a beautifully designed pool house featuring an open wood ceiling, wine refrigerator, and grilling area, all overlooking an elegant paver pool deck. The 1,100 sq ft air-conditioned three-car garage offers high ceilings ideal for car lifts, while the landscaped grounds and custom paver driveway enhance the home’s grand presence. Engineered for long-term resilience, this elevated block construction features custom electric hurricane shutters, a whole-home Generac generator, and a new seawall (2023). The home further benefits from updated AC systems (all under warranty), a new pool and hot tub heater, tankless water heater, water softener, solar panels, LED lighting throughout, and numerous updated appliances. This exceptional residence combines pedigree, privacy, craftsmanship, and unmatched waterfront living. Secure your place in the winner's circle and experience one of Belleview Island’s finest estates.

429 St Andrews Drive, Clearwater

$205,000

2 Beds ⋅ 2 Baths ⋅ Oaks Of Northwood Condo SubDv.

Move-In Ready Condo in Clearwater’s Countryside Area — Located in The Oaks of Northwood! Welcome to this beautifully maintained 2-bedroom, 2-bathroom end-unit condo in the highly desirable Countryside area of Clearwater, nestled within the peaceful and tree-lined community of The Oaks of Northwood. This updated condo offers modern comfort, flexible living space, and an unbeatable location close to shopping, beaches, parks, and major conveniences. Step inside and you'll immediately appreciate the upgrades and thoughtful layout. The open-concept main living area connects seamlessly to the kitchen and dining space—ideal for both everyday living and entertaining. The in-unit washer and dryer are tastefully tucked behind double doors in the kitchen, maintaining a clean and functional design. One of the standout features of this home is the fully screened and tiled porch, surrounded by hurricane shutters and screened doors, allowing this space to be enjoyed year-round. This bonus area can serve as a cozy reading nook, hobby space, fitness area, or even a private home office—a rare and valuable feature in condo living. The desirable split-bedroom floor plan provides privacy, with the spacious primary suite offering a large walk-in closet, private en-suite bathroom, and direct access to the enclosed porch. The secondary bedroom and full bathroom are located on the opposite side of the condo, making it perfect for guests, family, or additional workspace. As an end unit, the condo is filled with natural light, enhancing the warm and inviting feel throughout the home. Located in the heart of Clearwater’s Countryside community, this condo offers quick access to: Countryside Mall, Whole Foods & major retailers, Downtown Dunedin, Safety Harbor & Palm Harbor, Clearwater Beach & Honeymoon Island State Park, Enterprise Dog Park (walking distance!), Tampa International Airport & major roadways. Residents of The Oaks of Northwood enjoy beautifully landscaped grounds, a community pool, and assigned covered parking. HOA Fee Includes: Basic Cable TV, Internet, Water, Sewer, Trash, Building Insurance, Exterior & Grounds Maintenance, Escrow Reserves, and Community Pool. Whether you're searching for a low-maintenance primary residence, seasonal getaway, or investment property, this Clearwater condo offers location, lifestyle, value, and flexibility—all in one of the most convenient and established neighborhoods in North Pinellas County. Schedule your private showing today and discover why homes in The Oaks of Northwood don’t stay on the market long.

2737 Enterprise Road E Unit 112, Clearwater

$229,900

2 Beds ⋅ 2 Baths ⋅ Cove Cay 26-20 Village Ii SubDv.

Wake up every day to a wraparound picture-postcard view. This highly desired 2 bedroom, 2 bath corner condo in beautiful Cove Cay offers water, golf course, and lush green scenery from just every window and even as you walk up to your front door – plus a front-row seat to the pond, fairways, bridge, Tampa Bay and even the Tampa skyline from your raised living room sitting area. Inside, you’ll love the light, airy feel. PGT impact windows (including larger kitchen and guest bedroom windows than the interior units) bring in extra natural light and frame the views. Neutral tile runs throughout the condo for a clean, cohesive look, while fresh paint in soft neutrals and pastels adds a serene, coastal vibe. Both bathrooms are completely updated – the hall bath with a newer vanity, decorator mirror, and stylish tile around the tub, and the primary suite bath with a beautiful shower and a vanity offering plenty of storage. The spacious primary bedroom easily accommodates larger furniture and features a generous walk-in closet. The kitchen is a delight to cook and dine in, with warm wood KraftMaid cabinets, a handy pantry, an eating space with a view, and a raised ceiling trimmed with crown moulding for an extra touch of elegance. Storage is no problem here – the rooms are comfortably sized and closets are plentiful. Even better, the HVAC was replaced in 2024, so you can enjoy perfect temperatures year-round without the worry of a big-ticket replacement. Convenience is also part of the package: your private laundry room is just across the hall from the front door and includes a laundry sink, stackable washer and dryer, and room for shelving or additional storage. A covered carport is included as well. With its corner location, upgraded finishes, abundant storage, and truly stunning views in every direction, this Cove Cay condo offers the Florida lifestyle you’ve been hoping to find. And as for the community of Cove Cay… there is no equal. This gated, 24-hour secured waterfront community feels like a private resort tucked along Tampa Bay. The 18-hole Championship golf course winds gracefully through the grounds and along the bay itself, offering sweeping water views and a setting that’s as relaxing as it is scenic. Whether you’re an avid golfer or simply love the view, the course is available by membership or on a flexible pay-as-you-go basis. The on-site bar and grille is open seven days a week and serves up full menus, cold drinks, and an easy social atmosphere—perfect for casual lunches, sunset dinners, or meeting neighbors who quickly become friends. Boating enthusiasts will appreciate the community marina right within the complex, offering docking and storage options, rentals, food and drink, and that unmistakable salty-breeze lifestyle (all available separately, so you can choose your level of fun). Lush grounds, golf, dining and boating possibilities, a prime central location close to beaches, airports, dining and shopping, and the feeling that every day is a mini-vacation, make it easy to see why this is the paradise known as Cove Cay.

2620 Cove Cay Drive Unit 601, Clearwater

$123,000

1 Beds ⋅ 1 Baths ⋅ Residence At Renaissance SubDv.

Welcome to your Florida Gulf Coast getaway in Clearwater, ideally located approximately 5 minutes from the beautiful Clearwater beaches. This well-maintained 1-bedroom, 1-bathroom condo in the desirable Residence at Renaissance offers comfort, convenience, and a host of recent updates. The open floor plan features high ceilings and natural hardwood flooring throughout the main living areas. The spacious bedroom offers a peaceful retreat with a generous walk-in closet. Sliding through a newer glass door, the living area opens to a private, covered balcony overlooking lush tropical landscaping and mature trees. The kitchen is thoughtfully appointed and includes a brand-new full-size washer and dryer conveniently located just off the kitchen. Recent improvements include a new water heater, hurricane windows in the main living area, a newer balcony door, and an HVAC system approximately 5 years old. Residence at Renaissance is a gated, pet-friendly community offering a resort-style pool, fitness center, business center, two elevators, and a dedicated dog run. The community roof was replaced in 2022, and the milestone inspection has been completed. The HOA provides added convenience by including cable, high-speed internet, water, sewer, and trash. Additional features include a private 6x8 storage unit (#202S) located on the same floor just steps from the condo and one assigned covered garage parking space (#87). With shopping, dining, and everyday conveniences located directly across the street, this condo offers an ideal combination of location and low-maintenance living. Whether you're looking for a full-time residence, vacation retreat, or investment opportunity, this Clearwater condo is ready to enjoy.

1216 S Missouri Avenue Unit 202, Clearwater

$619,900

4 Beds ⋅ 3 Baths ⋅ Glenwood SubDv.

PRICE IMPROVEMENT NOW $619900!! BEAUTIFUL 4BR 2 & 1/2 BATH POOL HOME IN CLEARWATER!! THIS IS A GREAT FAMILY HOME WITH HUGE ROOMS AND LARGE LIVING SPACES!! THE GIGANTIC PRIMARY BEDROOM HAS A BIG WALK IN CLOSET THAT IS CURRENTLY CONVERTED TO A 5TH BEDROOM!! LIVING ROOM IS LARGE WITH COZY FIREPLACE AND OPENS WITH 12FT SLIDERS TO FANTASTIC RECREATION OASIS!! HEATED POOL, OUTDOOR KITCHEN AND TABLE THAT SEATS 12!! THE GARAGE HAS BEEN CONVERTED TO A MEDIA AND GAME ROOM WITH LOTS OF GAMES, AND CUSTOM LIGHTING!! THERE IS A LARGE CIRCULAR DRIVE THAT WILL ACCOMMODATE SEVERAL VEHICLES!! MAKE YOUR APPOINTMENT TO SEE THIS HOME SOON!! HOME HAS BEEN OPERATED AS A VACATION RENTAL, REPORTS AVAILABLE. ASKING PRICE $619900

505 N Highland Avenue, Clearwater

$223,700

2 Beds ⋅ 2 Baths ⋅ Bryn Mawr At Countryside SubDv.

Virtually Staged. PRICED TO SELL!! Welcome home to this beautifully maintained 2-bedroom, 2-bath condo located in a NO flood zone and just minutes from shopping, dining, entertainment, and Clearwater’s world-famous beaches. Recent updates include fresh interior paint and a NEW AC system (2026). A charming courtyard entry leads to a bright, open living and dining area, with a kitchen that overlooks the space—ideal for everyday living and entertaining. Sliding doors open to an enclosed screened patio, perfect for morning coffee or year-round relaxation. The split-bedroom floor plan provides added privacy, while the spacious primary suite features a double-sink vanity and ample closet space. Community amenities include a pool, clubhouse, covered parking, laundry inside unit, and additional storage. Offering a low-maintenance lifestyle, this condo is ideal as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today.

2701 Countryside Boulevard Unit 102, Clearwater

$250,000

2 Beds ⋅ 2 Baths ⋅ Residence At Renaissance SubDv.

Gated community just a short drive to Clearwater Beach! 3rd floor 2 bedroom, 2 bath condo with very spacious split bedroom plan. Both bedrooms have large windows and walk-in closets. Master has bath en suite. Kitchen open to living room & dining room with eating bar/island. Washer & dryer conveniently located in pantry. West-facing side building with balcony to watch sunsets! Two storage closets next to unit right down the hall. Two assigned parking spaces (one under building & one inside main gate). Amenities include fitness & business center, club room, pool, bike storage. Office manager and maintenace staff also included in monthly fees. Walking distance to grocery, restaurants, shopping. Short drive to downtown Clearwater, Tampa, St Pete and 2 international airports.

1216 S Missouri Avenue Unit 311, Clearwater

$255,000

2 Beds ⋅ 3 Baths ⋅ Sunset Pointe Twnhms SubDv.

Welcome to Florida living at its finest! This charming two-story townhome offers a bright and functional layout featuring 2 bedrooms, 2.5 bathrooms, and a desirable split-bedroom floor plan for comfort and privacy. Both bedrooms also have private ensuite bathrooms and are conveniently located upstairs near the inside laundry room, making daily living effortless. On the main level, you’ll find a spacious living room and a flexible family room that can also serve as a dining area—perfect for entertaining or customizing the space to fit your lifestyle. Sliding glass doors fill the home with natural light and open to a serene wooded view, giving you both privacy and a peaceful connection to nature. Located near the end unit, this townhome also offers easy access to a large open grassy area—ideal for relaxation, play, or pets. The beautifully maintained community features a gorgeous gated pool and impressive HOA-covered perks including trash, cable (currently includes HBO Max, Fox Sports 1, Paramount Plus, and Disney Plus), internet, amenities, exterior paint, roof, and landscaping—all included for truly worry-free living. Just moments from shopping and dining—you can even walk to Aldi—this home combines ultimate convenience with tranquil surroundings. Florida living at its best. Come live the Florida dream! Recent Updates: • Vinyl flooring throughout (2022) • Kitchen appliances (2022) • ROOF (2023, HOA paid) • Exterior painting (2023, HOA paid) • AC system (2025) • All new doorknobs and hinges (2025) •New fans (2022)

2096 Sun Down Drive, Clearwater

$157,500

2 Beds ⋅ 2 Baths ⋅ Chateau Belleair Condo SubDv.

ALL AGE COMPLEX, NO FLOOD ZONE! Spacious and clean, move-in ready, ONE STORY VILLA. Large open Floor plan with full size living room, dining room, eat in kitchen, large bedrooms, Florida room (Sun Room), outside patio, Covered Parking #B22 and storage closet! Great for year-round living, rental or vacation home. Master Bath remodeled in 2022, Replaced HVAC system in 2019, updated windows, and Electrical Panel has been replaced! Corner location opening to a lushly tropical landscaped greenbelt, close to the luxurious heated pool and SPA for your year-round swimming enjoyment! Inside stackable washer & dryer. The spacious living room and primary bedroom feature a vaulted ceiling to add to the spaciousness of your unit. Enjoy cooking out on your conveniently located patio. Well Maintained, nice size Complex, convenient to airports, US Hwy19 to Clearwater, St. Petersburg and the exquisite beaches of the Gulf of Mexico. This is a great place to come to relax or retire to Florida and enjoy a new lifestyle! Enough room for guests or extended family to visit! This is NOT a 55+ Community, but sorry, NO PETS allowed. Land lease fee is included in the monthly fee of $832.-

2207 Belleair Road Unit B22, Clearwater

$190,000

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv.

Welcome home to highly sought after location in On Top Of The World with NO LAND LEASE allowing pets large and small tucked away behind the community center, pool, and pickleball / tennis courts. This charming and coastal inspired second-floor 2-bedroom, 2-bath condo located in the vibrant 55+ community. As you step through the front door, you’re greeted by a light and bright living and dining area, enhanced by neutral-tone laminate wood flooring that creates an open, inviting feel. The space features a ceiling fan with a light fixture and an elegant chandelier over the dining area. Around the corner, you’ll find your updated kitchen, complete with wood-block style countertops, rich dark-wood cabinetry, and stainless steel appliances—including a range, microwave, side-by-side refrigerator with bottom freezer, and dishwasher. Just off the kitchen is a spacious bonus room, ideal for an office, den, or hobby area. This room includes a large storage closet and two expansive windows offering serene views of the greenery, the Duke Energy Trail, and the pond beyond. Your primary suite features two large wall closets and an updated en-suite bath with a convenient step-in shower. The second bedroom sits at the front of the home and includes its own generous wall closet. An additional updated hall bath offers a tub/shower combination for added convenience. Furnishings are negotiable. HOA includes basic cable and internet, water, sewer, garbage, ground and building maintenance, building insurance, free bus service to major malls and grocery stores, and building maintenance. The community features 2 pools (1 heated), sauna, spa, 2 golf courses (9 and 18 hole) for owners, fitness center and fitness classes, dog park, a lake with kayak storage, 2 fishing piers, walking trails, a library, auditorium, postal services, outdoor pavilion with bbq's, library, multi-purpose rooms, billiard room, lawn bowling courts, and a variety of clubs, seminars, socials events, special interest and hobby clubs and SOOOO MUCH MORE!

2461 Canadian Way Unit 27, Clearwater

$164,900

2 Beds ⋅ 2 Baths ⋅ Chateau Belleair Condo SubDv.

Tucked away like a secret, to the back of this ALL-AGE Community, is this 2/2/1 FIRST FLR. condo filled with charm. Many sleek improvements including a Kitchen that almost winks at you with its KraftMaid Kitchen Cabinets, QUARTZ Countertops, and GE Stinless Steel Appliances. It's an EASY LIFE complete with IN-Unit Laundry, no grass to cut, and a Pool/Hot Tub to enjoy anytime without having to do the maintenance & work! Did I mention your green thumb will do a victory lap as you watch the plants growing in your personal courtyard? It's already FURNISHED, so just bring your clothes. Your vehicle will always shine as it's parked in your CARPORT and you'll agree the PRIVATE Storage Closet is a help. Close to Eagle Lake County Park, Clearwater Beach, Airports, and plenty of shopping...don't just sit there, see it and BUY IT TODAY!

2209 Belleair Road Unit C21, Clearwater

Homes for Sale with a Pool in Clearwater, FL

All Homes for Sale with a Pool in Clearwater, FL

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