Rolling Oaks Homes for Sale

Rolling Oaks Homes for Sale

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Florida, where charm meets modern living. This serene community is designed for those who appreciate the beauty of nature while enjoying the conveniences of contemporary life. With its lush landscapes, tree-lined streets, and a friendly atmosphere, Rolling Oaks is the perfect place to call home.

Homes for sale in Rolling Oaks offer a variety of architectural styles, ensuring there’s something for everyone. From cozy single-family homes to spacious residences with stunning outdoor spaces, the options are plentiful. Many of these homes feature open floor plans, updated kitchens, and inviting backyards—ideal for entertaining or simply unwinding after a long day. The community is known for its well-maintained properties and a sense of pride among homeowners, making it a desirable location for families, retirees, and first-time buyers alike.

Rolling Oaks is conveniently located near top-rated schools, shopping centers, and recreational facilities, providing residents with everything they need just a stone's throw away. Enjoy weekend outings at nearby parks, take leisurely strolls through the neighborhood, or indulge in the vibrant local dining scene. With easy access to major highways, exploring all that Florida has to offer is a breeze.

If you’re searching for a place that combines tranquility with a vibrant community spirit, look no further than Rolling Oaks. Discover your dream home in this enchanting subdivision and embrace a lifestyle of comfort and convenience. Your new chapter awaits!

Newest Rolling Oaks Homes for Sale

1484 Aladdin Road, Spring Hill
$249,950
3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34609 Zip Code
Country Living at its best. This 3 bedroom 2 bath manufactured home on 1.3 acres is nestled in the heart of Spring Hill in the Beautiful Rolling Oaks Neighborhood with no HOA. Large corner acreage provides so much privacy. Open floor plan featuring eat in kitchen with new stainless steel appliances, A primary bedroom with walk in closet and large private bath, split plan guest rooms all with new flooring. New Roof in 2019. New ac system 2026, new water heater 2026, freshly painted. Fenced yard and 2 car carport along with a large shed. Close to Anderson Snow Park equipped with baseball, soccer and football fields, walking trails, a playground and pavilions. Conveniently located to the Veterans Expressway making it an easy commute to Tampa for work or play. Minutes to the Bravera Hospital, Churches, Grocery stores, and restaurants. Schedule your private showing today and prepare to be awed!

1484 Aladdin Road, Spring Hill
536 Bison Circle, Apopka
$384,000
3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 32712 Zip Code
Welcome to 536 Bison Circle - this is an ideal home or rental property for those seeking an updated living space. This renovated home has 3 bedrooms with 2 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated luxurious bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2026, AC and Water Heater in 2025! This home also has a newly painted interior/exterior. Quiet Neighborhood, Close to all Major Highways, and Shopping Centers. Also an excellent rental investment opportunity.

536 Bison Circle, Apopka
436 Bison Circle, Apopka
$425,000
4 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 32712 Zip Code
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
8117 Surf Street, 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
1672 Countrywood Street, Tarpon Springs
$365,000
3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34689 Zip Code
Virtually Staged. Check out this Tarpon Springs stunner located on a gorgeous tree-lined street in the highly desirable Rolling Oaks community. This beautiful home features gorgeous tile flooring, soaring cathedral ceilings, and an inviting eat-in kitchen complete with a breakfast bar. The thoughtfully designed split-bedroom floor plan offers privacy and comfort, while the spacious primary suite boasts attractive laminate flooring and a walk-in closet. An inside utility room with additional storage adds convenience, and the tranquil screened porch overlooks a shady, fenced backyard, creating the perfect setting for relaxing or entertaining. Nestled in a quiet and established section of Tarpon Springs, Rolling Oaks offers a peaceful setting while remaining close to everything that makes the area so special. Enjoy easy access to the world-famous Tarpon Springs Sponge Docks, charming downtown Palm Harbor, Fred Howard Park, and the award-winning beaches of Honeymoon Island and Caladesi Island. This is Florida living at its finest—don't miss your opportunity to call this exceptional property home.

1672 Countrywood Street, Tarpon Springs
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