Highland Estates Homes with Pool

Welcome to Highland Estates, a hidden gem nestled in the heart of Winter Haven, Florida. This charming subdivision is a perfect blend of serene living and vibrant community life, making it an ideal place for families, retirees, and everyone in between. With its lush landscapes and friendly neighbors, Highland Estates offers a welcoming atmosphere that feels like home from the moment you arrive.

One of the standout features of Highland Estates is the stunning array of homes equipped with private pools. Imagine stepping out into your backyard oasis, where you can soak up the Florida sun or host delightful gatherings by the poolside. These homes are designed for both relaxation and entertainment, ensuring that every day feels like a vacation. Whether you're an avid swimmer or simply enjoy lounging by the water with a good book, the poolside lifestyle here is truly enticing.

The location of Highland Estates is another significant advantage. Situated in Polk County, Winter Haven is renowned for its beautiful lakes, recreational parks, and a variety of shopping and dining options. Residents can easily explore the nearby attractions, including the famous Legoland Florida Resort and the scenic Chain of Lakes, which offers endless opportunities for outdoor adventures.

In Highland Estates, you’ll find not just a home, but a lifestyle that celebrates the joys of Florida living. With homes featuring pools and a community spirit that welcomes all, this subdivision is the perfect place to create lasting memories. Come and discover your dream home in Highland Estates today!

Newest Highland Estates Homes with Pool

$289,000

3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 33598 Zip Code

SELLER IS OFFERING UP TO $10,000 IN SELLER CONCESSIONS! Welcome to 14441 Alistar Manor Dr, a charming 3-bedroom, 2-bathroom home located in the desirable Ayersworth community of Wimauma! This inviting home features a comfortable and functional layout with plenty of space to make your own. Step outside to a large backyard offering plenty of room for entertaining, outdoor activities, gardening, or simply enjoying the Florida sunshine. Ayersworth offers an impressive selection of community amenities, including a resort-style swimming pool, fitness center, basketball courts, tennis court, and playground. Conveniently located near restaurants, shopping, and everyday essentials, the community also offers easy access to I-75 for travel north toward Tampa or south toward Bradenton and Sarasota. Whether you're purchasing your first home, looking for more space, or simply want to enjoy a community filled with amenities, 14441 Alistar Manor Dr is ready to welcome you home. Schedule your private showing today!

14441 Alistar Manor Drive, Wimauma

$425,000

3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 34698 Zip Code

Back on the market! No fault of the sellers. Buyer's financing fell through. All 4-point repairs have been made! Clean house! Bring all offers!! Must see to truly appreciate! Step into this 3-bed, 2-bathroom slice of paradise nestled underneath grand oak trees in delightful Dunedin. This home has old Florida charm without sacrificing modern amenities. Located in the coveted GOLF CART ZONE in one of the most sought-after areas in the Tampa Bay region. Conveniently situated with a short golf cart ride or walk to everything that Dunedin has to offer but far enough away to have the peace and quiet when wanted. Open floor plan with tons of natural light. The cozy kitchen boasts granite countertops with stainless steel appliances, under-cabinet recessed lighting and a tavern-height breakfast bar. Through one of the two living areas, you’ll pass through double French doors to your roughly 19x35 enormous patio with a metal gazebo already included. That’s over 650 square feet of endless options. Plenty of space to put in an outdoor kitchen, hot tub, or both. You will also be able to cool off in the sparkling pool! The backyard is completely fenced in with 6ft vinyl privacy fence that keeps you totally secluded from neighbors and passersby. This home has been meticulously maintained and is turnkey ready! Major updates include a new roof and PGT hurricane-impact-resistant windows and doors in 2019. A new Carrier Infinity HVAC system in 2021, and a new Rheem hot water heater in 2023. The garbage disposal and dishwasher were also replaced in 2026. This gem also sits high and dry in an X non-evacuation flood zone. Located just .08 miles to TD Ballpark, where the Toronto Blue Jays play spring training games, 1 mile to downtown, where you can enjoy breweries, multiple restaurants and bars, shopping, and the beautiful Dunedin Marina. Along with multiple parks and the Pinellas Trail, you’ll never run out of things to do. Just a 15-minute drive to both Clearwater Beach and Honeymoon Island and everything else that Pinellas County has to offer. Don’t miss out on this one!

961 Lexington Drive, Dunedin

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