Rolling Oaks Homes with Deed Restrictions Community Extras

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming community is designed for those who appreciate a blend of tranquility and convenience, making it the perfect place to call home.

Rolling Oaks is characterized by its beautifully landscaped streets, adorned with mature oak trees that provide a serene backdrop for everyday life. The homes in this community are thoughtfully designed, featuring a variety of architectural styles that cater to diverse tastes. Each residence reflects a commitment to quality and craftsmanship, ensuring that you’ll find a space that resonates with your vision of home.

One of the standout features of Rolling Oaks is its deed restrictions, which help maintain the integrity and aesthetic appeal of the neighborhood. These guidelines ensure that the community remains pristine and inviting, fostering a sense of pride among residents. You'll appreciate the well-maintained common areas and the overall ambiance that comes from living in a community where everyone shares a commitment to excellence.

Beyond the beautiful homes, Rolling Oaks offers a wealth of community extras. Enjoy leisurely walks along the scenic pathways, or take advantage of nearby parks and recreational facilities that cater to families and outdoor enthusiasts alike. With shopping, dining, and entertainment options just a stone's throw away, you’ll find that convenience is at your fingertips.

Discover the charm and comfort of Rolling Oaks, where every day feels like a retreat in this idyllic Kissimmee community. Your dream home awaits!

Newest Rolling Oaks Homes with Deed Restrictions Community Extras

$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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