Rolling Oaks Homes with Deed Restrictions Community Features

Welcome to Rolling Oaks, a charming community nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This delightful subdivision is characterized by its serene environment, making it an ideal haven for families and individuals alike.

Rolling Oaks is a deed-restricted community, which ensures that the neighborhood maintains its aesthetic appeal and high standards. This commitment to quality is evident in the well-kept homes and beautifully landscaped yards that grace the streets of Rolling Oaks. Here, you'll find a harmonious blend of modern living and natural beauty, with homes that reflect a variety of architectural styles to suit diverse tastes.

Residents of Rolling Oaks enjoy a wealth of community features designed to enhance their lifestyle. The neighborhood is dotted with lush green spaces and parks, perfect for leisurely strolls, picnics, or simply soaking up the Florida sunshine. Families will appreciate the proximity to top-rated schools, ensuring that education is just a stone's throw away.

Convenience is key in Rolling Oaks, with easy access to major highways, shopping centers, dining options, and recreational activities. Whether you're looking to explore the vibrant attractions of nearby Orlando or enjoy a quiet day at one of the local lakes, this community offers the best of both worlds.

Discover the charm and allure of Rolling Oaks, where a welcoming community spirit and a commitment to quality living come together to create the perfect place to call home. Your dream home awaits in this idyllic Kissimmee neighborhood!

Newest Rolling Oaks Homes with Deed Restrictions Community Features

$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

$429,900

4 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34689 Zip Code

BUYERS-take advantage of a rare and valuable opportunity as this home has an ASSUMABLE LOAN at an incredibly low 3.25% interest rate! In today’s higher-rate environment, qualified buyers can potentially step into significant monthly savings and long-term financial benefits by assuming the seller’s existing mortgage. Opportunities like this are few and far between—don’t miss your chance! 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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