Winter Haven Homes with Private Pool type

Winter Haven Homes with Private Pool type

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County that perfectly blends small-town warmth with vibrant community spirit. Known as the “Chain of Lakes” city, Winter Haven boasts over 50 sparkling lakes, making it a haven for water enthusiasts and nature lovers alike. With its picturesque landscapes, lush parks, and welcoming neighborhoods, Winter Haven offers an idyllic setting for families, retirees, and everyone in between.

One of the most enticing features of homes in Winter Haven is the availability of properties with private pools. Imagine stepping into your own backyard oasis, where you can soak up the Florida sunshine while enjoying a refreshing dip in your private pool. These homes not only provide a perfect retreat for relaxation and entertainment but also enhance your lifestyle with the luxury of having a personal space to unwind after a long day.

Whether you’re hosting summer barbecues, enjoying a quiet evening under the stars, or simply taking a leisurely swim, a home with a private pool adds a unique touch to your living experience. The real estate market in Winter Haven is diverse, offering a range of styles and sizes to suit your needs. From cozy family homes to sprawling estates, you’ll find the perfect property that meets your desires.

With its friendly community, excellent schools, and a plethora of recreational activities, Winter Haven is not just a place to live – it’s a place to thrive. Come discover the charm of Winter Haven and find your dream home with a private pool today!

Newest Winter Haven Homes with Private Pool type

1007 Mockingbird Circle, Winter Haven
$300,000
3 Beds ⋅ 2 Baths ⋅ Garden Grove South Ph 01 & 02 SubDv. ⋅ 33884 Zip Code
Virtually Staged. Opportunity meets potential in this Winter Haven pool home! Featuring 3 spacious bedrooms, 2 bathrooms, and 1,685 square feet, this property offers TWO living rooms with flexible space for gathering, entertaining, or creating a separate retreat. An appealing option for investors or buyers ready to bring their own vision, this property offers a solid starting point with a newer A/C, attached Generac generator, fireplace, and one renovated bathroom. Enjoy Florida outdoor living with a pool, spacious deck, screened outdoor area, and a large backyard with additional space for recreation, gardening, or entertaining. A great added value: Everything currently in the property conveys with the sale, including furniture, appliances, the washer and dryer, and the attached Generac generator—everything must go! Offering buyers the convenience of purchasing the property with its existing furnishings and equipment. The existing features offer everyday comfort while leaving room to personalize and refresh to your taste. Whether you’re considering your next investment or a home to make your own, this property deserves a look. Sold strictly AS IS; seller will make no repairs.

1007 Mockingbird Circle, Winter Haven
1400 Lake Elbert Drive Se, Winter Haven
$427,000
5 Beds ⋅ 6 Baths ⋅ Elbert Hills SubDv. ⋅ 33884 Zip Code
Welcome to this spacious 2-story home in Winter Haven, offering 5 bedrooms, 5.5 bathrooms, and a private pool. With room for everyone and a layout that works for multigenerational living, this property is ready for its next owner. Inside, the main-floor primary suite offers convenience and privacy, with a walk-in closet to match. A fireplace anchors the living area, adding warmth and a natural gathering spot. Upstairs, the additional bedrooms give family and guests plenty of space, and walk-in closets and extra storage throughout keep everything organized. A dedicated laundry room makes everyday chores easy. Outside, the private pool is ready for year-round Florida enjoyment, and the garage provides parking and additional storage. Don’t miss your chance to own this spacious Winter Haven home.

1400 Lake Elbert Drive Se, Winter Haven
100 Alachua Drive, Winter Haven
$495,000
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Mariam Unit SubDv. ⋅ 33884 Zip Code
MAIN HOME PLUS TWO INCOME-PRODUCING STUDIO APARTMENTS – $1,800 IN MONTHLY RENTAL INCOME! Looking for a property that offers more than just a place to call home? This unique property features a main residence plus two studio apartments. Situated on an oversized, fully fenced double corner lot, this property offers incredible flexibility and income potential. With its convenient location near LEGOLAND Florida and Winter Haven’s famous Chain of Lakes, there is also exciting potential for short-term rentals or Airbnb opportunities. Enjoy the Florida sunshine in your private 15’ x 30’ screened-in pool or unwind in the hot tub. Inside the main home, you’ll find a beautifully updated kitchen and bathrooms, luxury vinyl plank flooring throughout, newer windows, and a versatile bonus room that could easily serve as a fourth bedroom. There’s plenty of room for vehicles with a triple-wide concrete driveway and paved parking for approximately 10 cars. Additional features include an RV hookup, fully paid-off solar panels to help reduce electric costs, a large storage shed, portable generator hookup, and the possibility of adding a detached garage. Best of all, NO HOA! Whether you’re looking for additional rental income, multigenerational living, or a property with room to grow, this move-in-ready home offers flexibility, convenience, and plenty of possibilities. Live in one, rent the others, and let your property work for you! Don’t miss this unique Florida lifestyle opportunity!

100 Alachua Drive, Winter Haven
2097 Whispering Trails Boulevard, Winter Haven
$410,000
4 Beds ⋅ 3 Baths ⋅ Whispering Trails Ph 01 SubDv. ⋅ 33884 Zip Code
Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 10 minutes from the exciting attractions of Legoland, and less than an hour from the Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and amenities. This charming home comes move-in ready, including all essential appliances such as a range, refrigerator, microwave, garbage disposal. The secure, gated community offers peace of mind and added privacy, making it an ideal place to call home. Whether you're looking for a primary residence, vacation home, or investment property, this residence offers comfort, convenience, and easy access to some of Florida’s top attractions. Don’t miss your chance to own this fantastic 4 bed 3 full bath pool home in the fast-growing City of Winter Haven!

2097 Whispering Trails Boulevard, Winter Haven
4157 Rolling Oaks Drive, Winter Haven
$118,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood. The roof is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

4157 Rolling Oaks Drive, Winter Haven
2019 Kapree Court, Winter Haven
$330,000
3 Beds ⋅ 2 Baths ⋅ Winterset North SubDv. ⋅ 33884 Zip Code
Your Florida poolside retreat awaits! Welcome to this inviting 3-BEDROOM, 2-BATH POOL HOME with approximately 1,718 square feet, located on the north side of Lake Winterset in Winter Haven. Thoughtful updates, generous storage, and comfortable indoor and outdoor spaces make this home a standout—including RE-PLUMBING and a NEW GENERATOR that will convey with the sale! Step inside to a spacious living room where VOLUME CEILINGS and a NATURAL STONE WOOD-BURNING FIREPLACE create a welcoming setting for relaxing or gathering with guests. The UPDATED KITCHEN features MAPLE CABINETRY, newer appliances, an island with BREAKFAST BAR seating, and a large WALK-IN PANTRY. The adjoining dining area opens to the pool and patio, making entertaining flow easily outdoors. Enjoy your own backyard getaway with a SWIMMING POOL and a large COVERED, SCREENED PATIO with convenient bathroom access. The FULLY FENCED BACKYARD provides room to enjoy the landscaped setting, while a STORAGE BUILDING keeps outdoor essentials organized. Interlocking STONE PAVERS along the driveway and walkway add curb appeal, complemented by landscape lighting. The primary bathroom features CUSTOM CABINETRY, a solid-surface countertop, and a shower. An approximately 9-BY-13-FOOT INDOOR LAUNDRY ROOM offers a utility sink, built-in cabinets, and ample storage. The TWO-CAR GARAGE adds even more functionality with a workbench, tool storage, and a side exterior door. Additional highlights include DUAL-PANE INSULATED WINDOWS AND DOORS, HURRICANE SHUTTERS, and RADIANT BARRIER INSULATION. Conveniently located near shopping, restaurants, schools, and LEGOLAND, this home brings together practical upgrades and the outdoor lifestyle you love. Schedule your private showing today!

2019 Kapree Court, Winter Haven
9457 Waterford Oaks Drive, Winter Haven
$710,000
3 Beds ⋅ 3 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to the exceptionally beautiful guard gated community of Waterford Oaks! This stunning 3 bed, 3 bath pool home offers over 3,200 square feet of thoughtfully designed living space, showcasing custom craftsmanship, elegant architectural details, and an abundance of desirable features both inside and out. Meticulously maintained and beautifully appointed, this home offers a spacious, side entry three car garage with custom built ins. A few of the recent improvements include a new roof installed in October 2022, a new pool screen, and a tankless water heater. From the moment you step through the front door, you are welcomed by soaring ceilings, an inviting open floor plan, and beautiful architectural details that create an immediate sense of space and elegance. Builder Lori Waters thoughtfully included distinctive custom touches throughout the home. The formal dining room is beautifully complemented by decorative ceiling details and a decorative niche. A separate private office provides the ideal setting for working from home.  The spacious family room serves as the heart of the home, featuring a custom built-in entertainment center with a gas fireplace, and an impressively designed tray ceiling with surround-sound speakers. Open to the expansive gourmet kitchen, this thoughtfully designed living space makes the flow of everyday living effortless. The expansive gourmet kitchen is both beautiful and functional, offering granite countertops, stainless steel appliances, a gas range, and a center island with a convenient prep sink, and a separate wine/coffee bar, complete with a wine refrigerator. The cleverly hidden, oversized walk-in pantry provides additional storage in this well-appointed kitchen. The spacious primary suite with its magnificent tray ceiling, offers a peaceful retreat with a private door providing direct access to the lanai and pool area. The suite features two walk-in California closets, offering exceptional organization and storage. The private primary bath creates a spa-inspired experience with two vanities, a jetted soaking tub, and a separate walk-through shower featuring dual shower heads and a built-in sitting bench. On the opposite side of the home, are 2 additional generously sized bedrooms. Both feature large closets and share a convenient Jack-and-Jill bathroom. The screened pool and lanai area provide an extension of the home's living and entertaining space. Enjoy the beautiful pool featuring a waterfall, a sun ledge, and a heated spa. The outdoor kitchen and grilling area, complete with its own prep sink, make entertaining effortless. A conveniently located third full bathroom provides easy access for poolside guests without having to enter the main living areas. Additional features include an irrigation system, exterior lighting, central vacuum, and beautifully maintained landscaping that enhances the home's overall curb appeal. Waterford Oaks offers an exceptional lifestyle in a desirable guard-gated community. Residents enjoy access to a private community boat ramp on Lake Winterset, part of the renowned Winter Haven Chain of Lakes, where one can enjoy boating, fishing, or spending time on the water. Beautifully designed, thoughtfully maintained, and filled with custom details. It offers the complete Florida lifestyle. Don't miss the opportunity to experience all that this exceptional Waterford Oaks home has to offer. Schedule your private showing today! **Professional photos coming soon**

9457 Waterford Oaks Drive, Winter Haven
1151 Carefree Cove Drive, Winter Haven
$399,000
3 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
Looking for a peaceful lakefront pool home or well appointed Airbnb property? This beautiful 3-bedroom, 2-bath home sits on Lake Conine in Winter Haven’s northern Chain of Lakes, with easy access to the Chain of Lakes Trail. The home has been completely renovated to include a brand new roof, A/C, luxury vinyl plank flooring, interior / exterior paint, water heater, and much more! The kitchen features tons of solid wood cabinets, all new stainless steel appliances, and granite countertops. It includes both a breakfast area and a picturesque cutout with a view of the pool area and lakefront! The laundry room is also built into the kitchen area and includes a unique custom built porthole window that provides both natural light and views to the Florida room and beyond. The kitchen flows into a large enclosed porch (Florida room) with tons of potential! It could be used as a second living room space, dining room, and even space for a game room or office area! The Florida room includes additional cabinets and a bar area with a granite countertop. From the Florida room you can access the screened open porch where you can enjoy a stunning lake view. The primary bedroom features an en suite bathroom with jetted tub/shower, new vanity & fixtures, as well as a large closet. The 2nd bedroom also includes a large closet. The garage has been converted into a 3rd oversized bedroom with a very large closet and shiplap feature wall. Both bathrooms have been fully renovated with gorgeous subway tile in the showers, new ceramic tile floors and vanities with solid surfaces. Outside the house has been completely repainted including newly painted concrete from the front to the back of the property. The home features a newly screened pool cage, a brand new pool liner, with a multi-colored LED pool light. There is a carport and large outdoor storage closet out front, and also a second driveway to park an extra vehicle or boat. The newly painted boathouse, which includes a roll-up door, is wired with electricity and could also function as a workshop. It features new lights, a new side door, and new wood stairs. The boathouse / workshop is approximately 10x20 feet and has tons of room for all your toys! There is no HOA to hassle with! The property includes its own large dock and a concrete slab along the beach area for launching your own boat. Most furnishings in listing are available for separate purchase. As a potential Airbnb, the unit currently sleeps 8, but could be configured to sleep more. Come see this beautiful renovated home today!

1151 Carefree Cove Drive, Winter Haven
1010 Edgewater Drive, Winter Haven
$795,000
4 Beds ⋅ 3 Baths ⋅ Lake Eloise Estates SubDv. ⋅ 33884 Zip Code
FULLY REMODELED WATERFRONT HOME,PRIVATE POOL and BOAT DOCK WITH LIFT and NO HOA! Enjoy the best of Florida living in this beautifully remodeled 4-bedroom, 3-bathroom waterfront home in Winter Haven, offering modern finishes, a desirable split floor plan, and exceptional indoor-outdoor living. The inviting interior features stylish tile flooring, recessed lighting, and a stunning living room highlighted by a custom stacked-stone electric fireplace with a rustic wood mantle. The beautifully updated kitchen is a standout, featuring sleek solid-surface countertops, contemporary white shaker cabinetry, stainless steel appliances, and a HUGE STACKED-STONE CENTER ISLAND with breakfast bar, providing abundant workspace, seating, and the perfect gathering spot for family and guests. The split floorplan offers added privacy, while the spacious primary suite features sliding glass door access to the patio and an updated ensuite bathroom with a double-sink vanity and frameless glass walk-in shower. Additional highlights include NEW ROOF INSTALLED IN 2023, REMODELED KITCHEN AND BATHROOMS, french door, and TWO LAUNDRY AREAS—one conveniently located in the interior laundry room and another in the garage for added flexibility. The home also features NEW PLUMBING AND ELECTRICAL IN 2023, city water, and irrigation. Step outside to your private backyard oasis featuring a sparkling in-ground pool with a NEW POOL SURFACE AND NEW SCREEN ENCLOSURE, BOTH UPDATED IN 2023, an expansive paver patio, and a HUGE COVERED LANAI with a pine-paneled ceiling, outdoor TV, and stone accents, creating an ideal space for entertaining, relaxing, and enjoying the Florida sunshine. Waterfront enthusiasts will love the PRIVATE COVERED BOAT DOCK WITH BOAT LIFT on the canal leading to LAKE ELOISE, offering access to Winter Haven's renowned Chain of Lakes for boating, fishing, and watersports. With NO HOA, enjoy greater freedom and flexibility to accommodate your boat, trailer, and recreational equipment. Conveniently located near shopping, dining, parks, and everyday essentials, with access to Winter Haven's attractions and major Central Florida destinations, this move-in-ready property combines extensive updates, versatile living spaces, and an exceptional waterfront lifestyle. Enjoy your own private pool, spacious covered lanai, and boating access to Lake Eloise—all with NO HOA!

1010 Edgewater Drive, Winter Haven
138 Saint Kitts Circle, Winter Haven
$259,000
3 Beds ⋅ 2 Baths ⋅ Planters Walk SubDv. ⋅ 33884 Zip Code
Beautiful 3-bedroom, 2-bath POOL home in the Planters Walk community! This home features granite countertops, stone backsplash, and updated flooring. The layout offers a nice, open and spacious feel. Pool area needs a touch of love, but otherwise ... this home is move-in ready! Just a few miles from major road access for ease of commute, and within minutes of dining and shopping options. Come see this home today!

138 Saint Kitts Circle, Winter Haven
4462 Emerald Palms Lane, Winter Haven
$975,000
4 Beds ⋅ 3 Baths ⋅ Emerald Palms SubDv. ⋅ 33884 Zip Code
Luxury Living in Emerald Palms – Southeast Winter Haven Welcome to an exceptional custom-built residence in Emerald Palms, one of Southeast Winter Haven’s desirable gated communities. Situated on an expansive 0.41-acre homesite, this beautiful four-bedroom, three-bath home has been used primarily as a private vacation retreat and occupied sparingly. This Arthur Rutenberg designed home is an exceptionally well-maintained property that offers the look and feel of a nearly new home, with quality craftsmanship, elegant finishes, and outstanding indoor-outdoor living. The home’s impressive exterior features a concrete tile roof, attractive modern architecture, and beautifully maintained landscaping that creates an inviting first impression. Step inside to a spacious entry foyer highlighted by designer lighting and decorative inlay tile, leading into an open-concept living area designed for both comfortable everyday living and entertaining. Soaring ceilings with double tray details, oversized porcelain tile flooring, and an expansive wall of sliding glass doors fill the great room with natural light while providing picturesque views of the pool and lanai. At the heart of the home, the gourmet kitchen combines style and functionality with a large center island, granite countertops, upgraded cabinetry, premium stainless-steel appliances, and a walk-in pantry. The adjoining dining and living areas create a natural gathering space for family, friends, and special occasions. The generously sized primary suite offers a peaceful escape, featuring tray ceilings, abundant natural light, and an oversized walk-in closet. Its luxurious en-suite bathroom includes dual granite vanities, a jetted soaking tub, a separate walk-in shower, and a private water closet. The additional bedrooms are thoughtfully arranged in a split-bedroom floor plan to provide privacy and flexibility. Each offers comfortable living space and ample closet storage, while one guest bedroom features its own private en-suite bathroom. The fourth bedroom provides exceptional versatility and can easily serve as a game room, media room, hobby space, or secondary living area. An extraordinary outdoor living experience awaits. The custom heated pool and spa, representing an investment of more than $120,000, serves as the centerpiece of the expansive screened lanai. Features include integrated self-cleaning systems, decorative tile accents, deck jets, therapeutic spa jets, and a full-length sitting shelf with jets. Upgraded pavers and linear drainage contribute to the attractive, finished appearance of the outdoor entertaining space. The fully equipped outdoor kitchen is designed for serious entertaining, featuring a premium Lynx gas grill, side burner, beverage cooler, granite countertops, and stainless-steel range hood. Prepare meals, entertain guests, or enjoy game day while relaxing beside the pool. Under the covered lanai, a contemporary outdoor gas fireplace with a striking black-stone surround and TV mount creates an inviting setting for relaxing evenings throughout the year. Additional premium features and upgrades include: • Whole house 22KW Generac Guardian standby generator • Irrigation well for cost-effective landscape watering • Tankless Rinnai water heater • Multiple zoned air-conditioning systems • Salt-filtered pool system • Oversized side-entry three-car garage with durable epoxy flooring Oversized side-entry three car garage with durable stained concrete.

4462 Emerald Palms Lane, Winter Haven
725 Heritage Drive Ne, Winter Haven
$560,000
4 Beds ⋅ 3 Baths ⋅ Hamilton Pointe SubDv. ⋅ 33881 Zip Code
BEAUTIFUL HAMILTON POINTE POOL HOME! Welcome to this 4-bedroom, 2.5-bath pool home sits on a half-acre lot with no rear neighbors, offering 3,114 square feet of living space and peaceful conservation views. Inside, you’ll find a spacious kitchen with an eat-in area, a large living room with 13-foot ceilings, crown molding, a coral tile fireplace, and French doors opening to the screened pool and lanai. The split-bedroom layout features a primary suite with lanai access, dual vanities, a garden tub, separate walk-in shower, and ample closet space. Three additional bedrooms and a flexible office provide room for a variety of needs. The formal dining room also offers access to the pool area, creating an easy flow for entertaining. Outside, the oversized screened lanai and pool offer plenty of space to relax and enjoy Florida living. Notable improvements include a 2019 roof and exterior paint, 2020 gutters and screens, a 2021 hybrid water heater and whole-house repipe, plus a resurfaced pool, new sand filter, and refreshed pool screening. Conveniently located near downtown Winter Haven, Highway 27, LEGOLAND, golf courses, shopping, dining, and area airports.

725 Heritage Drive Ne, Winter Haven
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