Rolling Oaks Homes with Deed Restrictions Community Features

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Tarpon Springs, Florida, within beautiful Pinellas County. This charming community is known for its serene atmosphere, lush landscapes, and friendly neighbors, making it an ideal place for families and individuals seeking a peaceful retreat from the hustle and bustle of everyday life.

Rolling Oaks features a collection of beautifully designed homes, each reflecting a commitment to quality and aesthetic appeal. The community is governed by deed restrictions, ensuring that the neighborhood remains visually appealing and well-maintained. These guidelines help to preserve the integrity of the area, fostering a sense of pride among residents and promoting a harmonious living environment.

One of the standout features of Rolling Oaks is its commitment to community well-being. Residents enjoy access to various amenities, including well-maintained parks, walking trails, and recreational areas, perfect for family outings or leisurely strolls. The subdivision is conveniently located near local schools, shopping centers, and dining options, providing everything you need just a stone's throw away.

Nature enthusiasts will appreciate the proximity to the stunning Gulf Coast, where you can indulge in sun-soaked beaches, fishing, and water sports. Rolling Oaks is more than just a neighborhood; it's a lifestyle choice that offers a unique blend of tranquility, community spirit, and convenient access to the best that Tarpon Springs has to offer.

Come discover the charm of Rolling Oaks, where your dream home awaits in this vibrant, deed-restricted community!

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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