Winter Haven Homes with Pool

Winter Haven Homes with Pool

Welcome to Winter Haven, a charming city located in Polk County, Florida. Known for its beautiful lakes, Winter Haven offers a perfect blend of natural beauty and urban convenience.

If you're looking for homes with pools in Winter Haven, you're in luck! With the warm Florida climate, having a pool is a great way to relax and enjoy the sunshine right in your own backyard. Whether you're looking for a cozy bungalow or a spacious family home, there are plenty of options available in Winter Haven.

Imagine spending your weekends lounging by the pool, hosting barbecues, and creating lasting memories with family and friends. Homes with pools in Winter Haven offer not just a place to live, but a lifestyle of leisure and luxury.

Whether you're a first-time homebuyer or looking to upgrade to your dream home, Winter Haven has something for everyone. With its friendly community, top-rated schools, and abundance of recreational activities, Winter Haven is a great place to call home.

Newest Winter Haven Homes with Pool

395 San Jose Dr, Winter Haven
$170,000
2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Patio Homes SubDv. ⋅ 33884 Zip Code
Charming 2 bedroom, 2 bath home with a 1 car garage in Orchid Springs! The expansive main living space flows effortlessly into a dedicated dining area, creating a bright and airy atmosphere perfect for effortless entertaining. Slightly tucked away, the kitchen boasts ample counter space, tons of cabinets, and even a closet pantry for extra storage. The primary bedroom is located at the rear of the home, complete with its own bathroom and large closet. The laundry area can be found in the garage for added convenience. The rear screened porch, great for relaxation. Don't delay; make your appointment today.

395 San Jose Dr, Winter Haven
3944 Giorgio Drive, Winter Haven
$275,000
4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Aug 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3944 Giorgio Drive, Winter Haven
306 Eagle Pond Drive Unit 306, Winter Haven
$211,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Beautiful completely updated condo in the highly desirable gated community of Cypresswood Golf and Country Club. It features tile flooring throughout the whole condo, marble kitchen countertops with an extended breakfast island, new water heater, matching marble on both bathroom vanities, upgraded lighting fixtures/ceiling fans, interior laundry with washer and dryer, pond view, and so much more. The master bedroom features an en suite bathroom while both bedrooms have a walk-in-closet. Additional linen storage exists in the main bedroom and hallway, plus an additional outside storage closet with shelves. The Cypresswood community features an 18-hole championship golf course designed by Ron Garl, junior Olympic sized community pool, lighted tennis courts, clubhouse with a restaurant, event space and more. Minutes from Hwy 27 and the I-4 corridor, Winter Haven's chain-of-lakes for the water enthusiast, Legoland Fl Park and Resort, Bok Tower gardens, and a brand new Publix shopping center within 2 miles and much more. Centrally located between Orlando and Tampa. Schedule your private showing today.

306 Eagle Pond Drive Unit 306, Winter Haven
4043 Bedford Avenue, Winter Haven
$359,900
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
UPGRADED HOME IN THE GATED RESORT-STYLE COMMUNITY OF TRADITIONS: Meticulously maintained and thoughtfully upgraded 2 bedroom, 2 bath home with a versatile den that can easily serve as a 3rd bedroom, located in the desirable Traditions at Lake Ruby community. Enjoy comfortable living and an active lifestyle in this gated 55+ community in Winter Haven. This beautifully maintained home features extensive improvements, generous outdoor living space and transferable home warranty until April of 2030. The open floor plan brings the great room and kitchen together for easy everyday living and entertaining. New laminate flooring adds warmth, while the kitchen features quartz countertops, an island with seating and pendant lighting, stainless steel appliances including a double oven with air-frying and microwave capabilities and a closet pantry. An adjoining dinette provides a casual dining spot, while the formal dining room offers an inviting setting for intimate dinners and holiday gatherings. The spacious primary suite features a tray ceiling, a walk-in closet with custom built-ins and an ensuite bath with a quartz countertop, dual sinks, a handicap accessible walk-in shower and a private water closet. The comfortably sized secondary bedroom is conveniently situated near the guest bathroom, which features a new walk-in shower. An interior laundry room with storage cabinets adds everyday convenience. Three sets of sliding doors create a natural connection to the expansive covered and screened lanai. Finished with paver flooring, this generous outdoor space offers room for relaxing, dining and hosting larger gatherings. A separate paver patio just outside the enclosure provides a convenient grilling area, while refreshed tropical landscaping enhances the setting. Enjoy added peace of mind in Florida with a new roof installed in 2024 and a 2024 Generac 24kW whole-house generator with a transferable warranty and powered by a 500-gallon buried propane tank capable of providing up to three weeks of backup power eliminating much of the stress and uncertainty associated with unexpected power outages, whether short-term or extended. Additional significant improvements made in 2023/2024 include new interior and exterior paint, new laminate flooring and a Puragain water purification system with reverse osmosis in the kitchen. The two-car garage features screen doors, epoxy flooring, a 240-volt connection for electric vehicle charging and attic stairs. Additional features include surround sound, an ADT security system, an irrigation system with a separate irrigation meter, rain gutters, a paver driveway and walkway and more. The monthly maintenance fee of $485 includes lawn care, bush and hedge trimming, exterior home painting, cable TV, internet, trash removal and access to the clubhouse and community amenities. Just a short walk from the home, the lakefront clubhouse offers a heated pool and spa, fitness center, ballroom, library, dance studio, arts and crafts studio and a computer room. Outdoor amenities include shuffleboard, basketball, tennis and bocce ball, along with a community boat ramp, dock and dog park. A new Publix located just outside the community gate makes everyday errands especially convenient, with dining and medical facilities only minutes away. Centrally located between Tampa and Orlando, this thoughtfully improved home offers an inviting opportunity to enjoy the maintenance-free lifestyle of Traditions at Lake Ruby.

4043 Bedford Avenue, Winter Haven
997 Harold Pass, Winter Haven
$299,999
4 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to 997 Harold Pass, a nearly new home built in 2024 in the Peace Creek Reserve community of Winter Haven. This 4 bedroom, 2.5 bath home offers 1,933 square feet of bright, open living space. Tile flooring runs throughout the main level. The open concept kitchen features white cabinetry, stainless steel appliances, a large center island with breakfast bar seating, and a generous pantry. It flows straight into the living and dining areas, a layout that works as well for busy weeknights as for hosting friends. Upstairs, a flexible loft makes a great second living area, playroom or home office. The private primary suite has an ensuite bath and a spacious walk in closet, and three more bedrooms all have ample closet space. A dedicated laundry room adds everyday convenience. Out back, a covered patio overlooks a fully fenced backyard with plenty of room to play, garden or entertain, and the owners added an irrigation system to keep the lawn and landscaping looking great with less effort. A 2 car garage completes the package- the home is also within walking distance of South Pointe Elementary School. Schedule your private showing today!

997 Harold Pass, Winter Haven
114 Belmont Drive, Winter Haven
$459,000
4 Beds ⋅ 2 Baths ⋅ Montego Place SubDv. ⋅ 33884 Zip Code
New roof. Newer A/C. New pool resurface. New paint inside and out. The big-ticket items are done, and this home is ready for years to come. Step inside and the split floor plan does its job. To the left, the kitchen and the living room flow together with three bedrooms and a full bath. The kitchen is all new, with new cabinets, new quartz countertops and new stainless appliances. The living room has warm LED cove lighting and a fluted fireplace wall framed by built-ins. To the right is a quiet retreat: a cozy sitting area that leads to the pool and the primary suite, with French doors that open right onto the pool deck. The primary bath is the showstopper, with a new marble-look tiled shower behind glass, a rain head, a wall head and a handheld wand, plus a separate tub. The second bath has new tile on the shower walls and a new tub, and both baths have new quartz tops and new hardware. New flooring runs throughout. Out back is a large screened pool on an oversized deck, then a big fully fenced lawn with a detached workshop for your weekend projects. With a 2-car garage and a low HOA on a quiet street near LEGOLAND and the Chain of Lakes, it's ready to move in. Come see it in person!

114 Belmont Drive, Winter Haven
6733 Kensington Drive Ne, Winter Haven
$165,500
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates SubDv. ⋅ 33881 Zip Code
Charming 2-Bedroom, 2-Bath Home on a Corner Lot Near Lake Henry! Welcome to this beautifully maintained 2-bedroom, 2-bathroom home, where pride of ownership shines from the moment you arrive! From the unique guitar-themed driveway artwork to the immaculate interior, this inviting home is ready for you to move in and enjoy. A new HVAC system installed in 2026 adds to the home's appeal. Situated on a desirable corner lot, the home is located on a street leading directly to the community boat dock overlooking scenic Lake Henry. Whether you enjoy spending time on the water, participating in community activities, or simply relaxing and socializing with neighbors, this location offers plenty of opportunities to enjoy the Florida lifestyle. Inside, the thoughtfully designed floor plan features a bright kitchen with white cabinetry, white appliances, and a convenient center island with seating—perfect for casual meals or morning coffee. Just off the kitchen, the indoor laundry area offers upper cabinets for added storage and organization. The formal dining room features a built-in china cabinet, providing a lovely setting for entertaining family and friends. Adjacent to the dining area, the family room flows seamlessly into the home's entertaining spaces, with sliding glass doors leading to an oversized lanai that spans nearly the entire width of the home. This generous outdoor living area offers plenty of room to relax, entertain, and enjoy Florida's beautiful weather. Both bedrooms offer convenient access to their own bathrooms, providing added privacy and comfort for residents and overnight guests alike. Residents enjoy an active community lifestyle with a variety of amenities and social events offered throughout the month. Conveniently located near shopping, medical facilities, restaurants, and live entertainment, this home also provides easy access to the recreational opportunities and social activities available within the community. Come discover the charm, comfort, and lifestyle this inviting home has to offer!

6733 Kensington Drive Ne, Winter Haven
668 Reggie Road, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code
Virtually Staged. WELCOME TO PEACE CREEK RESERVE! Discover modern Florida living in this beautifully designed 2024-built, single-story home offering 3 bedrooms, 2 bathrooms, approximately 1,444 square feet of living space, and a 2-car garage. The inviting open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating a comfortable setting for everyday living and entertaining. The contemporary kitchen features attractive cabinetry, solid-surface countertops, a center island, and an open view of the main living area. The spacious primary suite offers a private bathroom with dual sinks and a walk-in closet, while two additional bedrooms provide flexibility for guests or a home office. Enjoy the benefits of newer construction and community amenities including a resort-style swimming pool, playground, and recreational spaces. CONVENIENTLY LOCATED near everyday essentials, including Publix, ALDI, Walmart Supercenter, shopping centers, restaurants, and retail destinations along Cypress Gardens Boulevard and US Highway 27. Outdoor enthusiasts will appreciate Winter Haven's renowned Chain of Lakes, scenic parks, boating opportunities, and nearby LEGOLAND Florida Resort. With convenient access to Winter Haven, Lake Wales, Lakeland, and surrounding Central Florida communities, this property offers an appealing combination of modern comfort, recreation, and everyday convenience. Whether you're looking for a primary residence, seasonal getaway, or investment property, this home is worth exploring. SCHEDULE YOUR PRIVATE SHOWING TODAY!

668 Reggie Road, Winter Haven
1921 Manor Circle Se, Winter Haven
$1,295,000
3 Beds ⋅ 3 Baths ⋅ Laha-Wa Manor SubDv. ⋅ 33880 Zip Code
Imagine waking each day to breath-taking lake views, swaying palms, spectacular sunsets, and the tranquil beauty of Lake Lulu. Quietly positioned on one of the most desirable lakes within Winter Haven's renowned Chain of Lakes, this beautifully maintained and thoughtfully updated single-story residence enjoys a private setting on 0.45-acre lot, surrounded by mature landscaping and established tropical gardens. Designed for both comfortable everyday living and exceptional entertaining, the home offers spacious, versatile accommodation with stunning lake views from the moment you enter through the front door. The flowing floor plan seamlessly connects the formal living and dining areas, with 50-inch SAMSUNG TV & rich wood flooring to the family room, kitchen, breakfast nook, and outdoor living spaces, creating an inviting atmosphere throughout. At the heart of the home is a well-appointed gourmet kitchen featuring a large center island, breakfast bar, premium stainless-steel appliances, updated Kitchen-aid double ovens with air fryer, microwave, French-door refrigerator, and dishwasher. Custom cabinetry includes soft-close drawers, pull-out shelving, glass display cabinets, wine storage, pantry space, and appliance garage. Beautiful non-slip tile flooring extends throughout the main living areas. Adjacent to the kitchen, the breakfast nook offers direct access to the pool area through sliding glass doors, while the spacious family room features a stunning Travertine fireplace, built-in SAMSUNG 50-inch television, neutral finishes, and expansive 12-foot sliding glass doors that open directly to the screened resort-style swimming pool & paved Lanai (1485sq,ft ) The laundry room is equipped with custom cabinetry, generous storage, a large linen closet, and includes a front load washer and dryer. A conveniently located half bath provides direct access to the pool and outdoor entertainment area. The fourth bedroom is currently configured as a home office. NEW (AUGUST 2026) ARCHITECTURAL SHINGLE ROOF on home, boathouse and storage shed. Owned security system. Phone, internet, and Wi-Fi connectivity throughout the home. Extensive custom cabinetry and storage solutions. Walk-in closet system in the primary suite. Landscaped with irrigation and lighting. Circular paved driveway with courtyard entrance and carriage lighting. Attached 2 car garage has staircase to large, walk-up attic for extra storage. 106ft frontage on Lake Lulu with a private dock, boathouse with lift. Direct access to Winter Haven's Chain of Lakes for boating, fishing, and water recreation. Convenient location with easy access to downtown Winter Haven, shopping, dining, LEGOLAND, Highway 27, Interstate 4. Tampa and Orlando Airports.

1921 Manor Circle Se, Winter Haven
219 Terranova Boulevard, Winter Haven
$428,000
5 Beds ⋅ 3 Baths ⋅ Terranova Ph 02 SubDv. ⋅ 33884 Zip Code
Don't miss your opportunity to own this 5 bedroom 3 bath pool home in the gated community of Terranova in SE Winter Haven. Minutes from Hwy 27, Hwy 60 and the Polk Parkway. This is a Fannie Mae Homepath property.

219 Terranova Boulevard, Winter Haven
2022 Kapree Court, Winter Haven
$515,000
5 Beds ⋅ 3 Baths ⋅ Winterset North SubDv. ⋅ 33884 Zip Code
3D Virtual Tour available. Welcome to your dream pool home! This beautifully 5-bedroom, 3-bathroom residence offers the perfect blend of comfort, style, and versatility. Ideally located outside the gates to LEGOLAND, this home is perfect for families, vacation-home buyers, or investors seeking a prime location. No HOA. Step inside to discover a lovely interior featuring a spacious, functional layout. The home also includes a private in-law suite/law suite with its own separate entrance, providing an ideal space for extended family, guests, or additional flexibility. The 1/1 suite currently operates as an income generating Airbnb. Step outside to your backyard oasis and enjoy your private pool, perfect for relaxing, entertaining, and making lasting memories. With generous living space, 5 bedrooms, 3 full baths, a separate-entry suite, and an unbeatable location, this home truly has it all.

2022 Kapree Court, Winter Haven
7380 Bent Grass Drive, Winter Haven
$559,900
4 Beds ⋅ 3 Baths ⋅ Millers Landing SubDv. ⋅ 33884 Zip Code
Welcome to PARADISE! Enjoy a HEATED, SALTWATER POOL, located on almost half an acre (0.42) in the desired gated community of Miller’s Landing! This expansive 4-bedroom, 2.5-bathroom home offers 2,775 sq. ft. of thoughtfully designed living space featuring tile flooring throughout the main living areas and cozy carpet in the bedrooms. The open-concept floor plan includes formal living and dining rooms, a spacious family room, and interior laundry. The fourth bedroom, complete with double doors, is versatile and can easily serve as a home office. The gourmet kitchen features granite countertops, a breakfast bar, a walk-in pantry, and a large breakfast nook overlooking the pool area. The private primary suite boasts a direct patio door exit, two walk-in closets, and an en-suite bathroom equipped with dual vanities, a garden tub, and a separate shower. Upgraded & Modernized for Peace of Mind: Major Capital Enhancements: Brand-new roof (2026), new exterior paint (2026), new gutters, and a brand-new HVAC system. Outdoor Oasis: A sparkling saltwater pool (converted in 2020) paired with a complete 2024 pool renovation and deck resurfacing, overlooking a massive, fully fenced-feel backyard complete with motion-detection floodlights. A convenient cabana half-bath is directly accessible from the pool deck. Everyday Conveniences: New comfort-height toilets throughout, an installed pulley-winch system for easy attic storage access, and a practical utility sink in the laundry room. Advanced Security: A brand-new in-home security system conveying with the property, featuring 6 perimeter cameras with microphones and speakers. Perfectly combining luxury, security, and exceptional space, this home is ready for you to make it yours!

7380 Bent Grass Drive, Winter Haven
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