Rolling Oaks Homes under $500,000

Rolling Oaks Homes under $500,000

Welcome to Rolling Oaks, a hidden gem nestled in the heart of Florida, where charm meets modern living! This inviting subdivision offers a serene escape while being conveniently located near bustling city amenities. With its lush landscapes and beautifully designed homes, Rolling Oaks is the perfect community for families, retirees, and everyone in between.

One of the standout features of Rolling Oaks is its diverse selection of homes, all available for under $500,000. Whether you're searching for a cozy starter home, a spacious family residence, or a charming retirement retreat, you'll find a variety of options that cater to different lifestyles and budgets. The homes are thoughtfully designed, often featuring open floor plans, modern kitchens, and ample outdoor spaces perfect for enjoying Florida's sunny weather.

Residents of Rolling Oaks enjoy a tight-knit community atmosphere, complete with lush parks, walking trails, and recreational areas that encourage an active lifestyle. The subdivision is also conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

In Rolling Oaks, you'll experience the perfect blend of tranquility and convenience. Imagine sipping your morning coffee on your patio while the gentle sounds of nature surround you, all while being just minutes away from the vibrant life that Florida has to offer. With homes priced under $500,000, this community is not just a place to live; it’s a place to thrive. Come discover the beauty and charm of Rolling Oaks today!

Newest Rolling Oaks Homes under $500,000

2939 Castaway Lane, Kissimmee
$330,000
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code
Welcome to resort-style living in the heart of Margaritaville Resort Orlando! This bright and spacious 2-bedroom townhome with a bonus room is located in the desirable Rolling Oaks community, just minutes from Walt Disney World. The flexible bonus room is currently set up with a twin bed, making it a great additional sleeping space, guest room, or cozy retreat. Inside, you’ll find stylish wood-look tile, quartz countertops, upgraded appliances, wood stairs, high ceilings, a private owner’s closet, and plenty of space to relax and unwind. Whether you’re looking for a full-time residence, a Florida getaway, or a short-term rental investment, this property offers incredible flexibility. Margaritaville Resort delivers the vacation lifestyle with multiple resort-style pools, restaurants and bars, a fitness center, full-service spa, walking trails, gated security, and convenient access to Sunset Walk, where shopping, dining, entertainment, and Island H2O Water Park are practically at your doorstep. With exterior maintenance, landscaping, and lawn care included, you can spend less time worrying about upkeep and more time enjoying everything Central Florida has to offer!

2939 Castaway Lane, Kissimmee
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
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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