Rolling Oaks Homes under $400,000

Rolling Oaks Homes under $400,000

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of sunny Florida! This charming community is perfect for families, retirees, and anyone seeking a tranquil lifestyle without sacrificing convenience. With its lush landscapes and friendly atmosphere, Rolling Oaks offers a slice of paradise where neighbors become friends and memories are made.

One of the standout features of Rolling Oaks is its impressive selection of homes priced under $400,000. This makes it an ideal destination for first-time homebuyers, young families, and those looking to downsize without breaking the bank. The homes in this subdivision boast a variety of architectural styles, ensuring that there’s something for everyone. From cozy single-family homes to spacious townhouses, you’ll find the perfect fit for your lifestyle and budget.

Rolling Oaks is more than just beautiful homes; it’s a community filled with amenities that cater to all ages. Enjoy leisurely strolls along tree-lined streets, take advantage of nearby parks, or relax by the community pool. The subdivision is conveniently located near shopping centers, restaurants, and top-rated schools, making daily life a breeze.

With its affordable housing options and welcoming environment, Rolling Oaks is an excellent choice for those looking to plant their roots in Florida. Come experience the charm and warmth of this delightful community, where your dream home awaits! Whether you’re ready to buy or just exploring your options, Rolling Oaks is a place you’ll be proud to call home.

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
$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
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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