Oakland Real Estate

Oakland Real Estate

Welcome to Oakland, Florida – a hidden gem nestled in the heart of Orange County that perfectly blends small-town charm with modern conveniences. This picturesque subdivision is known for its lush landscapes, friendly community, and a serene lifestyle that appeals to families, retirees, and everyone in between.

Oakland boasts a rich history, with roots dating back to the late 1800s. Today, it has evolved into a vibrant community that retains its historical charm while embracing contemporary living. The town is characterized by beautiful oak trees, scenic parks, and delightful walking trails that encourage outdoor activities and foster a sense of community. The popular West Orange Trail runs through Oakland, offering residents an excellent opportunity for biking, walking, and jogging amidst nature.

One of the standout features of Oakland is its strong sense of community. Residents enjoy engaging in local events, farmers' markets, and seasonal festivals that bring neighbors together. The town's commitment to preserving its heritage is evident in its well-maintained historic district, where you can find charming architecture and quaint shops that tell the story of Oakland's past.

Families will appreciate the highly-rated schools in the area, as well as the proximity to major attractions like Walt Disney World, Universal Studios, and the beautiful lakes and parks that Florida is known for. With easy access to major highways, commuting to nearby cities like Orlando is a breeze.

Whether you’re looking for a peaceful retreat or an active lifestyle, Oakland, Florida, offers a welcoming environment that makes it a perfect place to call home. Discover the magic of Oakland and become part of this thriving community today!

Newest Listings in Oakland

$499,999
3 Beds ⋅ 2 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code
Virtually Staged. Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and timeless appeal. Surrounded by mature landscaping and stately oak trees, this property offers a serene escape with no HOA to limit your creativity. Quiet dirt roads wind through the neighborhood, adding a touch of rural nostalgia, while the vibrant shops and cafes of Oakland’s quaint downtown are just a short stroll away. Inside, the home welcomes you with a warm and inviting layout. The living room, filled with natural light, provides a cozy space for relaxing or entertaining. It connects seamlessly to a well-appointed kitchen, featuring stainless steel appliances, granite countertops, and plenty of cabinetry for storage—ideal for home-cooked meals. The primary bedroom offers a peaceful retreat with a standard closet and an en-suite bathroom boasting dual vanities and a luxurious soaking tub. Two additional bedrooms, each with standard closets, provide versatile space for family, guests, or a home office, with a second full bathroom conveniently nearby. The exterior is a true highlight, with mature landscaping creating a private, tranquil setting. Towering oak trees provide shade and beauty, complemented by colorful, well-kept gardens. The spacious backyard is perfect for barbecues, gardening, or simply soaking in the calm of your own oasis. A charming front porch invites you to enjoy morning coffee while greeting neighbors on the peaceful dirt road. Located in the heart of Oakland, this home blends small-town charm with modern convenience. Enjoy local events, dining, and community spirit just steps away, with easy access to highways for commuting. With no HOA, you have the freedom to make this property your own.

409 E Gulley Avenue, Oakland
$449,000
7 Beds ⋅ 4 Baths ⋅ Oakland SubDv. ⋅ 32206 Zip Code
Fully renovated duplex in Jacksonville featuring a total of 7 bedrooms and 4 bathrooms. This property has been completely updated with modern finishes throughout, offering excellent quality and move-in-ready condition. All systems, interiors, and finishes are new, making it a great opportunity for investors or end-users. The seller is highly motivated and the price is negotiable. Don’t miss this exceptional opportunity!

1150 Pippin Street, Jacksonville
$1,250,000
6 Beds ⋅ 8 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code
PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!

620 N Tubb Street, Oakland
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