Rolling Oaks Homes with Pool Amenities

Rolling Oaks Homes with Pool Amenities

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming community is ideal for those seeking a blend of suburban tranquility and convenient access to the excitement of Central Florida. Rolling Oaks features beautifully designed homes that cater to a variety of lifestyles, making it a perfect choice for families, retirees, and everyone in between.

One of the standout features of many homes in Rolling Oaks is the inclusion of inviting pool amenities. Imagine stepping into your backyard oasis, where you can unwind in your private pool, soak up the Florida sun, and create lasting memories with family and friends. Whether you’re hosting summer barbecues or enjoying a quiet evening under the stars, these poolside retreats enhance the overall appeal of the homes in this delightful subdivision.

Rolling Oaks is not just about beautiful homes; it’s also about community. Residents enjoy well-maintained streets, lush landscaping, and a welcoming atmosphere that fosters neighborly connections. The area is conveniently located near shopping, dining, and recreational opportunities, making it easy to embrace the vibrant lifestyle Kissimmee has to offer.

With its blend of comfort, style, and community spirit, Rolling Oaks is more than just a place to live; it’s a place to thrive. Come explore the homes with pool amenities that await you in this idyllic subdivision, and discover the perfect backdrop for your Florida dream lifestyle!

Newest Rolling Oaks Homes with Pool Amenities

$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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