Rolling Oaks Homes with Deed Restrictions Community Features

Welcome to Rolling Oaks, a hidden gem nestled in the picturesque city of Tarpon Springs, Florida. This charming subdivision, located in the heart of Pinellas County, offers a serene lifestyle surrounded by natural beauty and a strong sense of community. With its lush landscapes and well-maintained properties, Rolling Oaks is the perfect place for families, retirees, and anyone seeking a tranquil retreat.

The homes in Rolling Oaks are part of a deed-restricted community, ensuring that the neighborhood maintains its aesthetic appeal and quality of life for all residents. These restrictions promote harmonious living, with guidelines that help preserve the beauty of the area while fostering a welcoming atmosphere. You can expect to find a variety of architectural styles, each home reflecting the care and pride of its owners.

Residents of Rolling Oaks enjoy a wealth of community features that enhance their living experience. The subdivision is conveniently located near top-rated schools, shopping centers, and recreational facilities, making daily errands a breeze. Outdoor enthusiasts will appreciate the nearby parks and nature trails, perfect for hiking, biking, or simply enjoying the Florida sunshine.

Moreover, the community spirit in Rolling Oaks is palpable, with regular neighborhood gatherings and events that encourage connections among residents. Whether you’re looking to socialize with neighbors or simply enjoy the peaceful surroundings, Rolling Oaks offers a lifestyle that balances relaxation and community engagement.

Discover the charm of Rolling Oaks, where your dream home awaits in a vibrant community that feels like family. Welcome home!

Newest Rolling Oaks Homes with Deed Restrictions Community Features

$330,000

2 Beds ⋅ 3 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code

Welcome to resort-style living in the heart of Margaritaville Resort Orlando! This bright and spacious 2-bedroom townhome with a bonus room is located in the desirable Rolling Oaks community, just minutes from Walt Disney World. The flexible bonus room is currently set up with a twin bed, making it a great additional sleeping space, guest room, or cozy retreat. Inside, you’ll find stylish wood-look tile, quartz countertops, upgraded appliances, wood stairs, high ceilings, a private owner’s closet, and plenty of space to relax and unwind. Whether you’re looking for a full-time residence, a Florida getaway, or a short-term rental investment, this property offers incredible flexibility. Margaritaville Resort delivers the vacation lifestyle with multiple resort-style pools, restaurants and bars, a fitness center, full-service spa, walking trails, gated security, and convenient access to Sunset Walk, where shopping, dining, entertainment, and Island H2O Water Park are practically at your doorstep. With exterior maintenance, landscaping, and lawn care included, you can spend less time worrying about upkeep and more time enjoying everything Central Florida has to offer!

2939 Castaway Lane, Kissimmee

$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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