Longleaf/Oakland Homes for Sale

Longleaf/Oakland Homes for Sale

Welcome to Longleaf/Oakland, a charming subdivision nestled in the heart of Winter Garden, Florida. This picturesque community offers a perfect blend of suburban tranquility and vibrant city life, making it an ideal place for families, retirees, and everyone in between. With its lush landscapes and friendly atmosphere, Longleaf/Oakland stands out as a hidden gem within Orange County.

The homes for sale in Longleaf/Oakland boast a variety of architectural styles, ensuring that there’s something to suit every taste and lifestyle. From cozy single-family homes to spacious modern residences, each property is designed with comfort and functionality in mind. Many of these homes feature open floor plans, gourmet kitchens, and beautifully landscaped yards, perfect for entertaining guests or enjoying peaceful evenings at home.

Residents of Longleaf/Oakland enjoy access to a wealth of amenities, including scenic parks, walking trails, and community playgrounds. The neighborhood is also conveniently located near top-rated schools, shopping centers, and dining options, making daily errands a breeze. Additionally, its proximity to major highways allows for easy commutes to downtown Orlando and other nearby attractions.

Whether you’re looking to invest in your first home or seeking a peaceful retreat, Longleaf/Oakland offers a welcoming community and a variety of homes for sale that cater to your needs. Come experience the charm of this enchanting subdivision and discover why so many are proud to call Longleaf/Oakland home. Your dream home awaits!

Newest Longleaf/Oakland Homes for Sale

$499,900
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland SubDv. ⋅ 34787 Zip Code
A rare opportunity to own a beautifully maintained home in the heart of Oakland, offered at an exceptional value under $500,000. Located in the sought-after Longleaf at Oakland community, this 3-bedroom, 2.5-bath home offers a thoughtful layout, beautiful outdoor space, and a prime location—all at a price point that is increasingly hard to find in this desirable area. Set on a quiet cul-de-sac, the home welcomes you with a modern and functional layout designed for both everyday living and entertaining. Inside, luxury vinyl plank flooring, recessed lighting throughout, and a bright, comfortable feel create a welcoming atmosphere. The kitchen features granite countertops and custom shelving, while additional custom shelving in the laundry room adds both style and practical storage. Spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room provide flexibility for everyday living. A water softener system adds another thoughtful touch to the home. Step outside to a fully fenced backyard offering privacy and flexibility for pets, play, gardening, or simply enjoying your own outdoor space. The peaceful setting and cul-de-sac location create an inviting sense of privacy while still keeping you close to everything Oakland and Winter Garden have to offer. The location is hard to beat. Take a quick walk to the West Orange Trail or enjoy easy access to the Oakland Nature Preserve. Downtown Winter Garden's shops, restaurants, farmers market, and charming atmosphere are just minutes away, while the Florida Turnpike provides convenient access throughout Central Florida. Orlando's world-class theme parks are approximately 20 minutes away. Beautifully cared for, ideally located, and thoughtfully priced, 1184 Bobcat Chase Blvd offers an exceptional opportunity to enjoy the best of Oakland living with comfort, convenience, and a price point that makes this home stand out.

1184 Bobcat Chase Boulevard, Oakland
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