Winter Haven Homes with Private Pool type

Winter Haven Homes with Private Pool type

Welcome to Winter Haven, Florida – a hidden gem nestled in the heart of Polk County, where sunshine, serenity, and stunning lakes converge to create an idyllic lifestyle. Known as the "Chain of Lakes," Winter Haven boasts over 50 sparkling lakes, offering endless opportunities for water sports, fishing, and leisurely boat rides. With a charming downtown area featuring boutique shops, delightful cafes, and vibrant community events, this city seamlessly blends small-town warmth with the conveniences of modern living.

For those dreaming of a home with a private pool, Winter Haven is the perfect place to dive into your dream lifestyle. Imagine stepping out into your backyard oasis, where you can bask in the Florida sun or unwind in your sparkling pool after a long day. Homes with private pools in Winter Haven cater to a variety of tastes and budgets, from charming single-family homes to luxurious estates. Whether you're hosting summer barbecues or enjoying peaceful evenings under the stars, having your own pool transforms your home into a personal retreat.

The real estate market in Winter Haven is thriving, making it an ideal time to invest in your piece of paradise. With its friendly community, excellent schools, and proximity to major attractions like Legoland Florida Resort and the beautiful beaches of the Gulf Coast, Winter Haven offers a lifestyle that is both relaxing and exciting. Discover your dream home with a private pool in this enchanting city, where every day feels like a vacation!

Newest Winter Haven Homes with Private Pool type

9457 Waterford Oaks Drive, Winter Haven
$710,000
3 Beds ⋅ 3 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to this beautiful 3-bedroom, 3-bath pool home located in the gated community of Waterford Oaks! Offering over 3,200 square feet of living space, this well-maintained home has so much to offer, including a new roof installed in October 2022, solar panels for energy efficiency, and a spacious 3-car garage. As you enter through the double front doors, you’ll immediately appreciate the high ceilings, open floor plan, and beautiful architectural details throughout. The home features a formal dining area, a separate office, and a spacious living room that opens to the kitchen, making it perfect for everyday living and entertaining. The kitchen offers granite countertops, stainless steel KitchenAid appliances, a gas range, center island with prep sink, breakfast bar, walk-in pantry, and plenty of cabinet space. The spacious primary suite features French doors leading to the pool area, two walk-in closets, and a private bath complete with dual vanities, a jetted tub, and a separate walk-in shower. Two additional bedrooms are located on the opposite side of the home, offering privacy for family and guests, along with a Jack-and-Jill bathroom. Step outside and enjoy your own private backyard retreat! The screened pool area features a beautiful waterfall, heated spa, two covered lanais, an outdoor grilling area, and a convenient pool bath. Whether you’re entertaining friends or simply relaxing at home, this outdoor space is sure to be a favorite. Additional features include a tankless water heater, plantation shutters, app-controlled irrigation, exterior lighting, a central vacuum system, and beautifully maintained landscaping. Waterford Oaks is a gated community offering residents access to a private boat ramp on Lake Winterset, part of the Winter Haven Chain of Lakes. Enjoy boating, fishing, and all that lakefront living has to offer without the maintenance of owning waterfront property. This home offers a wonderful combination of space, comfort, and Florida living. Schedule your private showing today

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

6052 Kaley Drive, Winter Haven
$375,000
4 Beds ⋅ 3 Baths ⋅ Sunridge Village East SubDv. ⋅ 33880 Zip Code
Welcome to 6052 Kaley Dr in Sunridge Village! This spacious 4-BEDROOM, 3-FULL-BATH POOL HOME PLUS a dedicated HOME OFFICE/BONUS ROOM offers 2,200 square feet of living space, an impressive outdoor entertaining area, and numerous valuable upgrades! THE SELLERS WILL OFFER $10,000 TOWARDS A RATE BUY DOWN WITH A FULL PRICE OFFER! Located in a desirable NO CDD community with an exceptionally LOW HOA OF JUST $165 PER YEAR, this home offers both space and affordability! THE ROOF, A/C SYSTEM, REMODELED KITCHEN, and INTERIOR PAINTING ALL DONE IN 2019, while additional recent updates provide even more value and appeal. This inviting two-story home features an OPEN FLOOR PLAN with TALL CEILINGS, attractive CROWN MOLDING, and generous living spaces designed for both everyday comfort and entertaining. The beautifully UPDATED ISLAND KITCHEN boasts GRANITE COUNTERTOPS, DOUBLE CLOSET PANTRIES, and STAINLESS STEEL APPLIANCES. The spacious living room features a distinctive SPECIALTY CEILING and FRENCH DOORS opening directly to the covered lanai, creating a wonderful connection between indoor and outdoor living. A separate dining room provides additional space for gatherings, while the convenient inside laundry room includes a washer and dryer. The spacious PRIMARY SUITE features a private EN SUITE BATHROOM with a WALK-IN SHOWER and relaxing GARDEN TUB. Three additional bedrooms provide comfortable accommodations, while the DOWNSTAIRS BONUS ROOM, currently used as a HOME OFFICE, offers incredible flexibility and POTENTIAL TO CONVERT INTO A FULL 5TH BEDROOM! With one of the THREE FULL BATHROOMS conveniently located downstairs, this layout provides excellent options for guests, multigenerational living, or anyone looking for additional living space. SPACIOUS 3 CAR GARAGE! Get the full FLORIDA EXPERIENCE by stepping outside to your own PRIVATE BACKYARD OASIS! The spacious COVERED LANAI features TILE FLOORING and OUTDOOR CEILING FANS, providing the perfect setting for relaxing or entertaining. Beyond the lanai, you'll discover a SCREEN-ENCLOSED IN-GROUND SWIMMING POOL & SPA, complete with an OUTDOOR BAR, BUILT-IN PLANTERS, and a charming TIKI-STYLE COVER OVER THE SPA! The pool area has also benefited from several improvements, including a NEW POOL PUMP in 2023, EPOXY-COATED POOL DECK PAVERS in 2023, and a POOL HEAT EXCHANGER replaced approximately 4.5 years ago. The current owners have also installed VINYL PRIVACY FENCING, creating a FULLY FENCED BACKYARD for additional privacy and enjoyment. Other improvements include a BEAUTIFUL NEW DOUBLE FRONT ENTRY DOOR installed in 2025, adding to the home's curb appeal. Situated on a generous .25-ACRE LOT in Sunridge Village, this property offers an EXCELLENT CENTRAL FLORIDA LOCATION! Enjoy convenient access to the POLK PARKWAY, providing easy connections toward TAMPA and ORLANDO, as well as nearby HIGHWAY 60, offering a direct route west toward TAMPA and east toward VERO BEACH and Florida's Atlantic Coast. Shopping, restaurants, and everything Winter Haven has to offer are also conveniently located nearby. With ALL THE UPDATES, 4 BEDROOMS PLUS A FLEXIBLE DOWNSTAIRS BONUS ROOM, 3 FULL BATHROOMS, FULLY FENCED BACKYARD, and spectacular SCREENED POOL & SPA AREA, this home offers an outstanding combination of space, improvements, and Florida living! Add in the NO CDD and incredibly LOW ANNUAL HOA of just $165, and this is an opportunity you won't want to miss. Schedule your private showing today!

6052 Kaley 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

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

888 Twin Oaks Lane, Winter Haven
$2,000,000
5 Beds ⋅ 5 Baths ⋅ Twelve Oaks Estates SubDv. ⋅ 33880 Zip Code
Welcome to 888 Twin Oaks Lane, where striking custom architecture, luxury features, four acres of privacy, and resort-style outdoor living come together in prestigious, gated Twelve Oaks Estates. Built by respected custom builder Alan Ulch on a quiet cul-de-sac, this distinctive residence offers 4,565 square feet of heated living space with five bedrooms, four full bathrooms, one half bathroom, and a versatile bonus room. A dramatic two-story foyer and living room showcase soaring 22-foot ceilings, an architectural catwalk, and custom shiplap detailing. Abundant windows fill the home with natural light and frame peaceful property views, complemented by engineered wood flooring, oversized doorways, plantation shutters, and custom window treatments with motorized shades. The chef-inspired kitchen pairs premium Bosch and Thermador appliances with Misterio quartz countertops, floor-to-ceiling cabinetry, a custom range hood, and floating shelves. A built-in coffee maker, Ice-O-Matic nugget ice machine, and separate wine and beverage refrigeration elevate everyday living and entertaining. Two oversized sinks, concealed small-appliance closets, deep island drawers, and an expansive walk-in pantry provide exceptional storage and functionality. The main-level primary suite offers direct pool access and a spa-like bathroom with an oversized soaking tub, floor-to-ceiling tiled shower, dual vanities, dedicated makeup area, and two expansive walk-in closets with custom shelving. A separate main-level mother-in-law suite welcomes extended family or guests. Oversized secondary bedrooms with walk-in closets, an office nook, and a spacious bonus room offer flexibility for work and recreation. The oversized laundry and mudroom feature abundant counter space, a utility sink, laundry chute, barn door, and dedicated pet-washing station. Expansive covered porches with elegant pavers and wood-planked ceilings invite you to enjoy the peaceful setting. Relax on the twin-size bed swing and enjoy the nature. Expansive sliding glass doors connect the interior to an oversized custom heated saltwater pool with a sun shelf, integrated spa, wraparound seating bench, and beautiful lighting. An outdoor shower and plumbing provisions for a future outdoor kitchen enhance this private retreat. Beautiful acreage framed by horse fencing provides room to gather, play, and explore. Quality construction and modern conveniences include Hardie board siding, metal roofing over the porches, whole-home spray foam insulation, a Generac whole-house generator, Culligan water treatment system, three tankless water heaters, two central air-conditioning systems plus a mini-split, and an integrated residential fire sprinkler system. An oversized driveway provides ample parking. With controlled gated access and paved community roads, Twelve Oaks Estates offers a peaceful home base convenient to Winter Haven, Lakeland, Auburndale, and Bartow, with shopping, dining, downtown entertainment, parks, lakes, and boating nearby. Polk Parkway connections to I-4 put Tampa, Orlando, both international airports, and attractions including LEGOLAND Florida, Walt Disney World, Universal Orlando, and Busch Gardens Tampa Bay within reach. Grand spaces for gathering. Quiet places to retreat. Four private acres to call your own. 888 Twin Oaks Lane brings together custom craftsmanship, luxury finishes, resort-style outdoor living, and everyday comfort for an exceptional expression of private estate living.

888 Twin Oaks Lane, Winter Haven

251 Lake Link, Winter Haven
$579,900
3 Beds ⋅ 2 Baths ⋅ Lake Link Estates SubDv. ⋅ 33884 Zip Code
Welcome to your own slice of Florida WATERFRONT LIVING! Situated on an oversized .41-acre lot in the desirable GATED COMMUNITY of Lakewood, this 3-bedroom, 2-bath POOL HOME offers a wonderful combination of indoor comfort, outdoor entertaining, and lakefront lifestyle. Accessed by crossing a private bridge, this unique community offers a distinctive setting, and the home is POSITIONED ON LAKE LINK, WHICH HAS A CANAL CONNECTING DIRECTLY TO LAKE OTIS. Enjoy skiing, fishing, or just hanging out on the lake! Inside, the thoughtfully designed split floorplan provides privacy and functionality, with the primary suite separated from the secondary bedrooms. The pool has recent updates including a new variable speed pool pump, new skimmer, new piping, new jets, and a new pool light. The pool also includes a robotic surface cleaner and robotic skimmer skimmer. Beautiful new luxury vinyl plank flooring flows throughout the home, creating a fresh, updated feel. The updated kitchen offers a modern touch and the window to the pool deck is perfect for cooking, entertaining, or an indoor-outdoor BBQ. The primary suite is spacious, and features an updated master bath, dual walk-in closets, and an oversized sliding glass door out to the pool deck. The additional bedrooms offer flexibility for guests, family, or a home office, and the guest bathroom offers a door straight to the pool deck so your guests can use the bathroom without tracking water in the main house. Step outside to discover one of the home's standout features: an oversized swimming pool surrounded by an expansive paver pool deck, offering plenty of room for lounging, entertaining, and enjoying the Florida sunshine. The large lot provides additional space to enjoy the outdoors and is a perfect place to host a party! Big-ticket improvements offer added peace of mind, including a NEW ROOF IN 2024, A NEW ELECTRICAL PANEL IN 2024, AND A NEW HVAC SYSTEM IN 2025. New insulation has also been added in the attic to improve efficiency. Desirable location, updated major appliances, lakefront living, what’s not to love! Schedule your private showing today!

251 Lake Link, Winter Haven

260 Greenfield Road, Winter Haven
$349,900
3 Beds ⋅ 2 Baths ⋅ Cypresswood Greenfield Village SubDv. ⋅ 33884 Zip Code
Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed private POOL deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle.Tucked away on the golf course with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando International Airport, and the gulf-side beaches of Tampa/St. Pete! Schedule your private showing today, and don't miss the opportunity to make this incredible home yours.

260 Greenfield Road, Winter Haven

Start Your Search

How much is your home worth?

Get instant property value now!