Rolling Oaks Homes with Deed Restrictions Community Extras

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of sunny Florida! This charming community is designed for those who appreciate both the tranquility of nature and the conveniences of modern living. With its lush landscapes and carefully curated homes, Rolling Oaks offers a serene retreat for families, retirees, and everyone in between.

One of the standout features of Rolling Oaks is its commitment to maintaining the beauty and integrity of the neighborhood through well-enforced deed restrictions. These guidelines ensure that the community retains its aesthetic appeal, fostering a sense of pride among residents. Each home is thoughtfully designed, blending seamlessly into the natural surroundings, while still providing the comfort and functionality that today’s homeowners desire.

Residents of Rolling Oaks enjoy a range of community extras that enhance the quality of life. Take leisurely strolls along the tree-lined streets, or gather with friends and neighbors at the community park, which features playgrounds, picnic areas, and walking trails. The subdivision is also conveniently located near shopping centers, dining options, and recreational facilities, making it easy to access everything you need.

Moreover, Rolling Oaks is situated within a friendly, welcoming atmosphere that encourages community involvement and camaraderie. Whether you’re hosting a backyard barbecue or enjoying a quiet evening under the stars, this neighborhood is the perfect place to call home.

Discover the charm and elegance of Rolling Oaks, where your dream home awaits amidst the natural beauty of Florida!

Newest Rolling Oaks Homes with Deed Restrictions Community Extras

$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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