Rolling Oaks Homes under $400,000

Rolling Oaks Homes under $400,000

Welcome to Rolling Oaks, a delightful subdivision nestled in the heart of Florida, where charm meets affordability! This vibrant community offers a perfect blend of serene living and modern convenience, making it an ideal choice for families, retirees, and everyone in between.

Rolling Oaks boasts a variety of homes priced under $400,000, providing an excellent opportunity for first-time buyers or those looking to downsize without compromising on quality. Each residence in this picturesque neighborhood is designed with comfort and style in mind, featuring spacious layouts, contemporary finishes, and inviting outdoor spaces. Imagine sipping your morning coffee on a sunlit patio or hosting weekend barbecues in your private backyard oasis!

The community is not just about beautiful homes; it’s also about a lifestyle. Residents enjoy easy access to local parks, walking trails, and recreational facilities, perfect for outdoor enthusiasts and families alike. The neighborhood is conveniently located near shopping centers, restaurants, and schools, ensuring that everything you need is just a stone's throw away.

Rolling Oaks is more than a subdivision; it’s a welcoming community where neighbors become friends and memories are made. Whether you’re looking for a cozy starter home or a place to retire, you’ll find that Rolling Oaks offers a warm, inviting atmosphere that truly feels like home. Discover the charm of Rolling Oaks today and take the first step towards your dream home in this enchanting Florida community!

Newest Rolling Oaks Homes under $400,000

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
536 Bison Circle, Apopka
$380,000
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
$398,000
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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