Winter Haven Homes with Pool

Winter Haven Homes with Pool

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, known for its stunning lakes and vibrant community spirit. With its picturesque landscapes and a warm, inviting climate, Winter Haven offers a delightful blend of small-town charm and modern amenities. The city is renowned for its beautiful chain of lakes, making it a haven for water enthusiasts and outdoor lovers alike. Whether you enjoy boating, fishing, or simply basking in the sun, Winter Haven provides endless opportunities for recreation and relaxation.

For those considering a move to this enchanting city, you'll find a variety of homes that cater to diverse lifestyles. Among the most sought-after features are homes with pools, perfect for those warm Florida days when you want to unwind and enjoy the sunshine in your own private oasis. Imagine stepping out into your backyard to dive into a refreshing pool, surrounded by lush landscaping and the sound of gentle splashes—it's a lifestyle that many dream of!

Winter Haven boasts a rich array of amenities, including charming shops, delicious dining options, and a strong sense of community. The local schools are highly regarded, making it an ideal location for families. With its strategic position between Orlando and Tampa, residents enjoy easy access to big-city attractions while savoring the tranquility of suburban living.

Explore the possibilities of calling Winter Haven home, where every day can feel like a vacation, especially with your very own pool to enjoy! Dive into the opportunity and discover the perfect home that fits your lifestyle in this delightful city.

Newest Winter Haven Homes with Pool

3 Beds ⋅ 2 Baths ⋅ P4939647 MLS

CUSTOM BUILT HOME WITH HEATED POOL IN LAKE MARIAM HILLS!!! This 3BR/2BA residence is situated on a quiet cul-de-sac in established and gated Lake Mariam Hills. Custom features are found throughout the split floorplan with its open and spacious feel. Large archways, columns, towering vaulted ceilings, custom accent windows, French doors and more are examples of the home's craftmanship and attention to detail. The kitchen is spacious, with a breakfast bar, an eat-in area, custom cabinetry, ample counter space and a great pool view. There are also formal living and dining areas, a comfortable living space with French doors opening onto the covered lanai, pool and screen enclosed patio!!! The pool is salt water, has a lovely water feature and feels secluded behind the mature landscaping and privacy fence. The Master Suite is a great place to relax and offers a custom tile shower and a separate garden tub, dual sinks, large walk-in closet, linen closet and French doors opening to the pool area. Many more features include a whole house generator, an oversize two car garage, extended driveway for additional parking, lush, mature landscaping, architectural shingle roof, in-wall pest defense, some tinted windows for efficiency, upgraded insulation and more. A gorgeous custom pool home in one of Winter Haven's most established gated communities, call today to see this exceptional home!

102 Hillside Court, Winter Haven

5 Beds ⋅ 4 Baths ⋅ O6435502 MLS

Welcome to a truly special waterfront property in Winter Haven, set on 1.28 private acres with water on both sides. Located on Lake Link with Lake Otis directly across the street, the two lakes form a connected two-lake chain offering boating, fishing and plenty of opportunities to enjoy life on the water. Enjoy beautiful lake views from both sides of the home and spectacular sunsets over Lake Otis from the front. A circular driveway welcomes you to this spacious 5-bedroom, 3.5-bath home with over 4,100 square feet of living space. The thoughtfully designed floor plan is filled with natural light and features the primary suite and one additional bedroom on the main level, along with a great room, kitchen and dining area, and a flexible room that could be used as an office or den. Upstairs, three additional bedrooms and a full bath provide plenty of space for family and guests, and the upstairs has been freshly painted. The oversized kitchen is perfect for everyday living and entertaining, offering tons of cabinetry, abundant countertop space and built-in double ovens. The home also offers exceptional storage throughout, providing plenty of room for everything. The outdoor living area features a screened enclosure with an oversized pool overlooking Lake Link, along with a convenient half bath for poolside guests. The backyard is exceptionally private, surrounded by tall bamboo, mature landscaping and fruit trees that create a beautiful natural setting while preserving the gorgeous waterfront views. An oversized dock, replaced in 2020, and a private boat ramp provide convenient access to Lake Link. Recent updates include a new roof in 2024 and one of the two AC systems replaced in 2024. An attached workshop off the laundry room provides additional functional space with direct access to the side yard. The oversized 3-car garage offers plenty of room for vehicles, watercraft and storage. Opportunities like this are truly rare. With 1.26 acres, waterfront on both sides, direct access to Lake Link and Lake Otis, and a spacious home with so much to offer, this property provides an incredible foundation for its next owner. Move in, make it your own, and bring your vision to life in a setting that is truly one of a kind.

25 Lakewood Causeway, Winter Haven

4 Beds ⋅ 3 Baths ⋅ L4964316 MLS

Welcome to your own private lakefront retreat on 1.23 acres along Lake Hamilton with NO HOA! This stunning 4-bedroom, 3-bath home offers an exceptional combination of luxury, entertaining space, and the ultimate Florida waterfront lifestyle. Bring your boat and jet skis and enjoy the convenience of a private dock featuring an electric covered boat lift and built-in fishing bench. The outdoor living space is truly spectacular! Step through the French doors to a sparkling saltwater PebbleTec pool featuring iridescent tile, fiber-optic lighting, a swim-up bar, fountains, and a roof-line waterfall. The propane-heated pool is surrounded by an expansive travertine deck, while the nearby gas fire pit with custom-cushioned seating creates the perfect setting for evening gatherings. Propane-connected tiki torches add a tropical ambiance, and a hidden sump pump provides worry-free drainage after storms. Entertaining is effortless with the outdoor kitchen, complete with a new grill and refrigerated drawers. The fenced backyard extends halfway to the lake, providing plenty of room for pets to play. Professional Florida-native landscaping, enhances the lush, resort-like setting. Inside, the beautifully designed chef's kitchen features quartz countertops, a copper farmhouse sink, paneled refrigerator, trash compactor, and spacious butler's pantry with a full-size refrigerator and abundant storage. The open floor plan includes a dedicated buffet area with dual wine refrigerators adjacent to the dining space—perfect for hosting family and friends. Nine-foot ceilings, crown molding, porcelain tile, shiplap accents, custom lighting, and a central vacuum system add comfort and sophistication throughout. The luxurious primary suite offers direct access to the pool deck, with a convenient open-air shower just outside. The ensuite features dual vanities and a walk-in shower with dual shower heads. The expansive walk-in closet includes a center island, custom shelving, heated towel rack, and an extra-large Liberty Safe. The home underwent a complete rebuild in 2017, so all features are 2017 or newer. Recent improvements include a new roof (2025), new pool pump (2025), a new 12x24 storage shed (2025) and new irrigation system (2025). The irrigation water comes from the lake so it doesn’t affect your water bill. Additional features include a split-bedroom floor plan, with two guest bedrooms sharing a Jack-and-Jill bath; hurricane shutters; a whole-home Generac generator; and TVs in every room, including the back porch. The spacious 3-car garage features tiled flooring, storage, a workshop, and an industrial ice maker. A pavered circular driveway provides ample parking, plus an additional parking pad with room for an RV. From the custom interior and exterior lighting to the custom painting, bamboo chair rail, and travertine exterior accents, every detail has been thoughtfully designed. The home is also pre-wired for ADT security at the front and rear doors and garage service door. Boating, fishing, entertaining, relaxing, and resort-style living—all in one exceptional Lake Hamilton property with no HOA!

3640 Crump Road, Winter Haven

4 Beds ⋅ 2 Baths ⋅ O6435475 MLS

Virtually Staged. This Winter Haven one-story home offers a two-car garage. Included 100-Day Home Warranty with buyer activation

313 Terranova Boulevard, Winter Haven

4 Beds ⋅ 3 Baths ⋅ TB8540975 MLS

Welcome to 9469 Waterford Oaks Drive, a beautifully maintained and spacious custom built home offering an exceptional combination of comfort, privacy, upgrades, and Florida living in the highly desirable, gated community of Waterford Oaks! A pavered, circular driveway provides an impressive approach to the home with plenty of space for vehicles and guests. Inside, the home features soaring ceilings, elegant archways, crown molding, custom built-ins, a beautiful fireplace, and generous living spaces throughout. The grand primary suite is a true private retreat, featuring two walk-in closets and an expansive primary bath with dual vanity areas, extensive cabinetry, and a large walk-in shower. A dedicated home office with custom built-in cabinetry and bookshelves provides an ideal work-from-home space. Upstairs offers even more flexibility with a large second living room/loft, spacious bedroom, and full bathroom—perfect for guests, family, or a private secondary living area. Outside, enjoy a private screened pool and hot tub/spa with a new spa heater, surrounded by an expansive pool deck with plenty of room for multiple outdoor seating and dining areas. The covered lanai features a high-end built-in outdoor grilling system with a direct gas connection, creating an exceptional space for entertaining year-round. Recent improvements include a new roof, new exterior paint, new hot tub/spa heater, full app-controlled pool automation system, Tesla charger installed in the garage, and multiple filtered-water systems throughout the home. A community boat ramp and dock on Lake Winterset on the Winter Haven Chain of Lakes is just a short distance away. With its spacious floor plan, grand primary suite, private upstairs living area, home office, fireplace, pool and spa, expansive outdoor entertaining space, and extensive recent upgrades, 9469 Waterford Oaks Drive is move-in ready and designed to enjoy the Florida lifestyle.

9469 Waterford Oaks Drive, Winter Haven

4 Beds ⋅ 3 Baths ⋅ TB8535328 MLS

Spacious 4BR/2.5BA home with 2,836 SF in desirable Windridge! Enjoy a screened saltwater pool, spacious fenced backyard, flexible living areas, and parking for up to 8 vehicles (2-car garage + oversized driveway). Major updates include a 2023 roof and 2022 A/C. Low HOA, no CDD, and convenient access to shopping, dining, schools, and major roads. Quick closing available and priced to sell. Act fast; schedule your private showing today!

5888 Windridge Drive, Winter Haven

3 Beds ⋅ 2 Baths ⋅ S5155806 MLS

Welcome home to this 3-bedroom, 2-bath pool home in Winter Haven! Featuring a spacious and comfortable layout with plenty of room for everyday living and entertaining. Step outside to your private backyard pool, perfect for enjoying Florida’s year-round sunshine, relaxing after a long day, or simply unwinding in your own outdoor space. The backyard provides plenty of room to create your own private retreat. Conveniently located near shopping, dining, schools, and major roadways with easy access to everything Winter Haven and Central Florida has to enjoy. Come make this house your home and enjoy the Florida lifestyle!

153 Browning Cir, Winter Haven

3 Beds ⋅ 2 Baths ⋅ L4964412 MLS ⋅ N/A BLDG.

3 bedroom, 2 bath ground-floor end-unit condo home with gorgeous views of Lake Winterset and a private 1 car garage—the perfect combination in one of Winter Haven’s most desirable gated communities. Welcome to 701 Magnolia Place, a spacious lakeview residence designed for easy single-level living with approximately 1,180 square feet, durable luxury vinyl plank flooring, and a comfortable, open layout. The living room is anchored by a fireplace and flows naturally into the dining area, creating an inviting space for everyday living and entertaining. The kitchen features white cabinetry, soft close drawers, newer stainless steel appliances, generous counter space, and an adjoining breakfast nook. The primary suite is spacious, measuring approximately 11x16, with lake views, a private bath with walk-in shower, generous closet space and direct access to the back patio. Two additional bedrooms provide flexibility for guests, a home office, hobby room, or den—a combination that makes this 3-bedroom floor plan especially hard to find in Winterset. A second full bath with tub and shower combo completes the interior. Step outside to the private screened porch, where wide-open green space and beautiful Lake Winterset views create the perfect place to enjoy your morning coffee, unwind at the end of the day, and watch sunsets you truly have to see to believe. As an end unit, the home enjoys an added sense of openness and privacy, while the attached one-car garage provides valuable parking and storage. Beyond the residence, the community of Winterset delivers on the Florida lifestyle. Residents have access to a heated lakefront swimming pool and spa, clubhouse, tennis and pickleball courts, shuffleboard, and a private boat ramp with direct access to the Winter Haven Chain of Lakes—opening the door to boating, fishing, water skiing, sunset cruises, and waterfront dining. Shopping, restaurants, medical facilities, LEGOLAND Florida Resort, and downtown Winter Haven are all just minutes away, while convenient routes toward Tampa and Orlando make the location equally appealing for everyday living and weekend adventures. Ground-floor living, an end-unit location, three bedrooms, private garage, screened porch, Chain of Lakes access, resort-style amenities, and gorgeous Lake Winterset views—701 Magnolia Place offers a combination that is difficult to find.

701 Magnolia Place, Winter Haven

4 Beds ⋅ 2 Baths ⋅ L4964379 MLS

Virtually Staged. Newer home with NO CDD and large yard!!! Welcome home to this beautifully maintained 4 bedroom, 2 bath home offering 1,983 square feet of comfortable living space and modern finishes throughout. Built in 2023, this home features a desirable open split-floor plan designed for both everyday living and entertaining. The spacious kitchen boasts granite countertops, large island, stainless steel appliances, and plenty of room to gather with family and friends. The split-bedroom layout provides privacy for the primary suite while keeping the additional bedrooms conveniently accessible. Step outside to enjoy the large yard and relaxing covered lanai—perfect for morning coffee, outdoor dining, or entertaining. Additional highlights include a 2-car garage, new carpet, and no CDD. With its modern construction, spacious layout, and move-in-ready appeal, this home is a must-see!

1425 Engelberg Street, Winter Haven

4 Beds ⋅ 2 Baths ⋅ O6434394 MLS

3D tour available! Welcome to this spacious 4-bedroom, 2-bath single-family home in the Lake Smart Estates community of Winter Haven. With an open-concept layout and 1,842 square feet of living space, the home offers plenty of room for everyday living and entertaining. Major updates provide added peace of mind, including a new roof in 2026, new A/C in 2024, and brand-new appliances in 2026. The kitchen offers generous cabinet and counter space and opens directly to the main living and dining areas. The primary suite features a walk-in closet and private bathroom with dual sinks and a spacious shower. An interior laundry room and attached two-car garage add everyday convenience. One of the property's biggest highlights is the oversized lot, one of the largest in the community. The expansive backyard provides exceptional outdoor space with plenty of possibilities for entertaining, play areas, gardening, or creating your own Florida outdoor retreat. Lake Smart Estates offers community amenities including a swimming pool, dock, gazebo, and water access. Golf enthusiasts will appreciate having Willowbrook Golf Course just minutes away, a public 18-hole course offering a driving range, putting green, chipping areas, and practice facilities. Conveniently located near US-17, the home provides easy access to Downtown Winter Haven, shopping, restaurants, schools, Polk State College, and everyday services. With four bedrooms, significant recent upgrades, an oversized yard, community amenities, and golf nearby, this move-in-ready home offers an excellent combination of indoor and outdoor space in a convenient Winter Haven location.

3695 Julius Estates Boulevard, Winter Haven

2 Beds ⋅ 2 Baths ⋅ P4939620 MLS ⋅ Winter Ridge Condo BLDG.

MUST SEE! Discover the perfect blend of comfort, convenience, and Florida lifestyle in this beautifully maintained 2-bedroom, 2-bathroom unit in the desirable Winter Ridge Condominium Community. Featuring new laminate flooring throughout the living areas and bedrooms, fresh paint, updated baseboards, and A/C, this move-in-ready home offers a clean, modern feel with no carpet. The open-concept layout is thoughtfully designed to maximize every square foot, creating a spacious and inviting atmosphere for everyday living or entertaining. The property also includes two dedicated parking spaces, providing added convenience for residents and guests. Enjoy resort-style community amenities including a heated pool, clubhouse, chain-of-lakes access, boat dock, and boat slips, making it easy to embrace the best of Central Florida living. The HOA includes exterior and grounds maintenance as well as trash service, helping simplify ownership and enhance the property's appeal for both homeowners and investors. Conveniently located just minutes from downtown amenities, Legoland, shopping, dining, and entertainment, this property offers an excellent opportunity for a primary residence, second home, or income-producing investment. Seller or private financing available with an easy and fast approval process and just 20% down! Don't miss this exceptional opportunity schedule your showing today before it's gone!

244 Winter Ridge Boulevard Unit 244, Winter Haven

4 Beds ⋅ 3 Baths ⋅ L4964361 MLS

Welcome home to this spacious 4-bedroom, 3-bathroom home offering over 2,000 square feet of comfortable living space on a large corner lot. Designed with both everyday living and entertaining in mind, this home features two bedrooms with private en-suite bathrooms, providing flexibility and privacy for family members or guests. Step outside to the screened lanai, where you can relax and enjoy views of the expansive backyard and in-ground pool—perfect for Florida living and entertaining year-round. The large fenced backyard provides plenty of room for outdoor activities, pets, gardening, or simply enjoying your own private outdoor retreat. With its generous living space, desirable split-bedroom potential, pool, and oversized corner lot, this home offers plenty of room to make it your own. Don’t miss the opportunity to make this spacious pool home your next address!

506 Clayton Circle, Winter Haven

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