Oakland Homes for Sale

Welcome to Oakland, Florida – where charm meets community in the heart of Orange County! Nestled just a stone's throw from the vibrant city of Orlando, Oakland offers a serene escape from the hustle and bustle while still keeping you connected to all the excitement. Known for its picturesque landscapes and rich history, this quaint town is perfect for those seeking a blend of tranquility and convenience.

Oakland’s unique subdivision features a variety of homes for sale that cater to diverse lifestyles and preferences. From charming single-family homes with spacious backyards to modern townhouses with contemporary designs, there’s something here for everyone. Many properties boast stunning views of the surrounding lakes and lush greenery, creating a peaceful haven for families and individuals alike.

Residents of Oakland enjoy a close-knit community atmosphere, with local parks, walking trails, and recreational facilities that encourage an active lifestyle. The town’s commitment to preserving its natural beauty is evident in its many outdoor spaces, making it easy to enjoy Florida’s year-round sunshine. Plus, the proximity to major highways ensures that shopping, dining, and entertainment options are just a short drive away.

Whether you’re a first-time homebuyer, looking to downsize, or seeking an investment opportunity, Oakland’s real estate market is thriving. Explore the homes for sale in this charming town and discover the perfect place to call home. Embrace the Oakland lifestyle – where community spirit and beautiful surroundings come together in perfect harmony!

Newest Oakland Homes for Sale

$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

$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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