Oakland Homes for Sale

Welcome to Oakland, Florida – a hidden gem nestled in the heart of Orange County. This charming subdivision offers a delightful blend of small-town warmth and modern conveniences, making it an ideal place for families, professionals, and retirees alike. With its picturesque tree-lined streets, Oakland boasts a rich history and a vibrant community spirit that welcomes newcomers with open arms.

The homes for sale in Oakland reflect a variety of architectural styles, from cozy bungalows to spacious family residences, all designed to cater to diverse lifestyles and preferences. Many of these homes are situated on generous lots, providing ample outdoor space for gardening, play, or simply enjoying the beautiful Florida sunshine. Inside, you’ll find modern amenities combined with classic charm, ensuring comfort and functionality in every corner.

Residents of Oakland enjoy easy access to a range of recreational activities, including nearby parks, lakes, and nature trails. The community is also conveniently located near major highways, making commutes to Orlando and surrounding areas a breeze. Local shops, restaurants, and schools are just a stone’s throw away, ensuring that everything you need is within reach.

Living in Oakland means being part of a close-knit community that values connection and collaboration. Whether you’re exploring the local farmers market, participating in community events, or simply enjoying a leisurely stroll through the neighborhood, you’ll quickly discover that Oakland is more than just a place to live – it’s a place to call home. Explore the homes for sale in this enchanting subdivision today, and take the first step towards your dream lifestyle in Oakland, Florida!

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

Start Your Search