Rolling Oaks Homes with Pool

Welcome to Rolling Oaks, a serene and picturesque subdivision nestled in the heart of Tarpon Springs, Florida. This charming community is located in Pinellas County, where the sun shines brightly, and the lush landscapes invite you to explore the beauty of the Sunshine State. Rolling Oaks is a haven for families and individuals seeking a tranquil lifestyle, surrounded by nature yet conveniently close to all the amenities you desire.

One of the standout features of homes in Rolling Oaks is the availability of private pools, perfect for those warm Florida days. Imagine stepping out into your backyard oasis, where you can take a refreshing dip or lounge by the poolside with a good book. These homes are designed for relaxation and entertainment, offering spacious layouts that seamlessly blend indoor and outdoor living. Whether you're hosting a summer barbecue or enjoying a quiet evening under the stars, your pool area will be the heart of your home.

The community of Rolling Oaks is not just about beautiful homes; it’s also about a vibrant lifestyle. Enjoy nearby parks, walking trails, and the stunning beaches of the Gulf Coast, all just a short drive away. With excellent schools, shopping, and dining options nearby, Rolling Oaks is the perfect place to call home.

Discover the charm and allure of Rolling Oaks in Tarpon Springs, where your dream home with a pool awaits. Embrace the Florida lifestyle and make this wonderful community your own!

Newest Rolling Oaks Homes with Pool

$499,000

4 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv.

POOL HOME in Apopka – Move-In Ready! Enjoy your own private oasis with a screened-in pool, ideal for Florida living! This beautifully remodeled 4BR/2BA home features a NEW ROOF & AC (2026), new luxury vinyl flooring, and a gorgeous kitchen with quartz countertops. Spacious master suite, updated bathrooms, and fresh paint throughout. Prime location minutes from Kelly Park, Wekiva Springs, shopping & dining. Some pictures have been virtually staged to give the buyer an idea of how the home could look. Don't miss this one – schedule your showing today!

436 Bison Circle, Apopka

$615,000

3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv.

**Rare waterfront cottage in Margaritaville Resort Orlando!** One of the few cottages in the community with a premium direct waterfront location, this beautiful 3-bedroom, 2-bath home offers breathtaking water views from both private balconies and a lifestyle unlike any other. **Unlike heavily rented vacation homes, this residence has been privately enjoyed and carefully maintained**, giving it a like-new feel without the wear and tear often associated with short-term rental properties. Whether you're looking for a primary residence, vacation home, or investment property, this home is eligible for short-term rentals and can easily be placed into the resort's rental program if desired. Inside, you'll find numerous upgrades, including tile flooring throughout, an open-concept floor plan, a durable metal roof, quartz countertops, stainless steel appliances, and beautifully designed living spaces that are both stylish and functional. The thoughtfully selected coastal décor perfectly complements the home's character and inviting atmosphere. The spacious kitchen opens seamlessly to the living and dining areas, creating the perfect space for entertaining family and friends. One of the home's most desirable features is its two private waterfront balconies—one on each level—where you can enjoy peaceful water views, your morning coffee, or spectacular Florida sunsets. Margaritaville Resort Orlando offers an exceptional resort lifestyle with multiple resort pools, a fitness center, live entertainment, shopping, dining, Island H2O Water Park, and the vibrant Promenade at Sunset Walk featuring restaurants, bars, boutiques, and year-round entertainment. Located just minutes from Walt Disney World and Orlando's other world-famous attractions, this rare waterfront property offers an outstanding opportunity as a primary residence, second home, or income-producing investment.

8117 Surf Street, Kissimmee

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