Longleaf/Oakland Homes with Craftsman Architectural style

Welcome to Longleaf/Oakland, a picturesque subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This charming community is a hidden gem that perfectly blends natural beauty with modern living, making it an ideal choice for families, retirees, and everyone in between.

Longleaf/Oakland is renowned for its enchanting Craftsman architectural style homes, which exude warmth and character. These residences showcase exquisite craftsmanship, featuring inviting front porches, exposed beams, and intricate woodwork that harkens back to a simpler time. The spacious interiors are designed with comfort in mind, offering open floor plans that seamlessly connect living spaces, perfect for both entertaining and everyday living.

The community itself is surrounded by lush greenery and beautifully landscaped parks, providing residents with ample opportunities for outdoor activities. Enjoy leisurely strolls along tree-lined streets, or take advantage of the nearby walking and biking trails that wind through the scenic landscapes of Winter Garden. Families will appreciate the top-rated schools in the area, ensuring that children receive a quality education just moments from home.

Longleaf/Oakland is also conveniently located near the vibrant downtown Winter Garden, where you can explore charming shops, delightful restaurants, and a lively farmers market. With easy access to major highways, commuting to nearby Orlando is a breeze, allowing you to enjoy the excitement of city life while returning to the tranquility of your Craftsman-style haven.

Discover the perfect blend of community, comfort, and charm in Longleaf/Oakland—your dream home awaits!

$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

Longleaf/Oakland Homes with Craftsman Architectural style

Newest Longleaf/Oakland Homes with Craftsman Architectural style