Rolling Oaks Homes with Pool

Welcome to Rolling Oaks, a picturesque subdivision located in Kissimmee, FL. This charming community is nestled in Osceola County, offering a peaceful retreat while still being close to all the amenities and attractions that Kissimmee has to offer.

One of the standout features of Rolling Oaks is the abundance of homes with pools. Whether you enjoy a morning swim to start your day or a relaxing dip in the evening, having a pool right in your backyard adds a touch of luxury to everyday living. Imagine hosting pool parties with friends and family or simply lounging by the water on a lazy Sunday afternoon.

The homes in Rolling Oaks are not only beautiful but also offer a true sense of Florida living. With spacious layouts, modern amenities, and lush landscaping, these properties are perfect for those seeking a blend of comfort and style.

Living in Rolling Oaks means being part of a welcoming community where neighbors become friends, and every day feels like a vacation. Enjoy the tranquility of suburban living while still being just a short drive away from shopping, dining, entertainment, and the world-famous theme parks that make Kissimmee a sought-after destination.

Come and discover the beauty of Rolling Oaks, where homes with pools and a relaxed lifestyle await you. Experience the best of Florida living in this charming subdivision in Kissimmee.

Newest Rolling Oaks Homes with Pool

$499,000

4 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 32712 Zip Code

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. ⋅ 34747 Zip Code

**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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