Rolling Oaks Homes with Block Exterior Construction

Welcome to Rolling Oaks, a charming subdivision nestled in the heart of Kissimmee, FL. This picturesque neighborhood is located in Osceola County, offering residents a peaceful retreat while still being conveniently close to all the amenities of city life.

One of the standout features of the homes in Rolling Oaks is their sturdy block exterior construction. This not only provides durability and low maintenance for homeowners but also adds a timeless appeal to the properties. With true block exterior construction, residents can enjoy peace of mind knowing that their homes are built to last.

Living in Rolling Oaks means enjoying a tranquil environment surrounded by lush greenery and beautiful landscaping. The community is perfect for those seeking a serene escape from the hustle and bustle of the city, while still being just a short drive away from shopping, dining, entertainment, and major roadways for easy commuting.

Whether you're looking to settle down in a cozy single-family home or a spacious property with room to grow, Rolling Oaks offers a variety of housing options to suit your needs. Come and discover the beauty and tranquility of Rolling Oaks – where you can find the perfect blend of comfort, convenience, and charm in the heart of Kissimmee, FL.

Newest Rolling Oaks Homes with Block Exterior Construction

$499,000

4 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 32712 Zip Code ⋅ O6428546 MLS ⋅ Active Status

POOL HOME in Apopka – Move-In Ready! Enjoy your own private oasis with a screened-in pool, ideal for Florida living! This beautifully remodeled 4BR/2BA home features a NEW ROOF & AC (2026), new luxury vinyl flooring, and a gorgeous kitchen with quartz countertops. Spacious master suite, updated bathrooms, and fresh paint throughout. Prime location minutes from Kelly Park, Wekiva Springs, shopping & dining. Some pictures have been virtually staged to give the buyer an idea of how the home could look. Don't miss this one – schedule your showing today!

436 Bison Circle, Apopka

$615,000

3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code ⋅ O6421843 MLS ⋅ Active Status

**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

Start Your Search

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,