Rolling Oaks Homes with Deed Restrictions Community Features

Welcome to Rolling Oaks, a serene subdivision nestled in the heart of Tarpon Springs, Florida, within the picturesque Pinellas County. This charming community offers a perfect blend of tranquility and modern living, making it an ideal place for families, retirees, and everyone in between.

Rolling Oaks is known for its beautifully maintained homes, each thoughtfully designed to enhance the overall aesthetic of the neighborhood. With deed restrictions in place, residents can enjoy a cohesive environment that promotes pride of ownership and enhances property values. These guidelines ensure that the community remains visually appealing and well-kept, allowing homeowners to enjoy a sense of stability and security.

The subdivision boasts a variety of amenities that cater to an active lifestyle. Residents can take advantage of lush green spaces, walking trails, and nearby parks perfect for leisurely strolls or family picnics. The community spirit is palpable, with friendly neighbors who often gather for social events, fostering a sense of belonging that is hard to find elsewhere.

Rolling Oaks is conveniently located near shopping, dining, and entertainment options, making it easy for residents to enjoy all that Tarpon Springs has to offer. From the stunning beaches of the Gulf Coast to the vibrant downtown area filled with unique boutiques and restaurants, there’s always something to explore.

If you’re looking for a welcoming community with a strong sense of pride and beautiful homes in Tarpon Springs, Rolling Oaks is the perfect place to call home. Experience the charm of this delightful subdivision and discover the lifestyle you’ve always dreamed of!

Newest Rolling Oaks Homes with Deed Restrictions Community Features

$615,000

3 Beds ⋅ 2 Baths ⋅ O6421843 MLS

**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

$415,000

4 Beds ⋅ 2 Baths ⋅ TB8488914 MLS

Welcome to this beautifully maintained 4-bedroom, 2-bathroom, 2-Car Garage home located in a sought-after neighborhood in Tarpon Springs—where homes rarely become available! Offering a spacious and inviting open floor plan, this residence is enhanced by soaring vaulted ceilings that create a bright, airy atmosphere perfect for both everyday living and entertaining. Step inside this lovely home and you’ll find beautiful wood-look tile flooring throughout the main living areas, combining style and durability, while the bedrooms offer easy-care laminate flooring for comfort and convenience. The kitchen is spacious with light cabinetry, stainless steel appliances, modern backsplash and breakfast bar. The Primary bedroom is located at the back of the home with ensuite bath, and access to the large screened rear porch. The primary bathroom has been tastefully updated with new faucets, toilet, shower fixtures, and a vent fan. The home features a split-floor plan which offers a hedge of privacy between the primary suite and the 3 additional guest bedrooms. The guest bathroom is beautiful with a large custom vanity with granite countertop, large decorative mirror and features newer shower fixtures with modern white tile in the shower/bath combo. Thoughtful updates throughout provide both comfort and peace of mind, including a 2018 roof, new Stainless-Steel appliances (2021), modern backsplash in kitchen (2025), a new hot water heater installed in 2023, updated smoke alarms throughout the home for added safety, while the living room and primary bedroom showcase newer ceiling fans for added comfort. Enjoy added confidence knowing this neighborhood experienced no flooding during the 2024 storms, and the home is located outside of the flood zone—meaning no flood insurance is required. With low HOA fees of just $150 per year, this property offers both value and peace of mind. Conveniently located near the iconic Tarpon Springs Sponge Docks, you’ll enjoy easy access to waterfront dining, shopping, and local culture. Love the beach? Sunset Beach and Fred Howard Park are just a short drive away! Plus, the home is zoned for excellent schools, making it an ideal choice for families and those looking to continue their education at nearby St. Pete College. This move-in ready home perfectly blends desirable updates, a rarely available location, and an exceptional layout—schedule your private showing today!

1640 Countrywood Street, Tarpon Springs

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