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

$375,000
3 Beds ⋅ 2 Baths ⋅ Oakland SubDv. ⋅ 33801 Zip Code
COMPLETELY REMODELED HOME WITH A COUNTRY SETTING...Come see this spacious 3 Bedroom/2 Bath is ready for new owners! Your main living room features a vaulted ceiling and a prop fan to help keep the giant space cool all year long. The kitchen is completely remodeled with granite countertops, beautiful tiled backsplash, brand new Stainless Steel Appliances, and a detached buffet-style counter with plenty of cabinet and counter space! Your kitchen also flows into an attached dining room area, perfect for family meals. The primary bedroom features an en-suite bathroom, dual sinks, tiled walk-in shower and large walk-in closet. The remaining bedrooms are perfect for extra living space or even an office area. The hall bathroom is complete with tile flooring, dual sinks, and a tiled shower/bathtub combination. You’ll find all laminate waterproof flooring throughout the home, making clean ups extremely easy and convenient. In addition to the main living area, you will also find a large bonus room with its own mini-split A/C unit, perfect for an extra living room, man cave or even a movie room! Other updates include: NEWER ROOF (2021), HVAC (2018), Hot Water Heater (2021) The home also features an detached oversized 20x36, 2 car garage which offers room for a shop & workspace. Your fully-fenced backyard has plenty of space for all your furry friends to run, or to test out your green thumb with a garden space. Only minutes away from convenient shopping and local restaurants, this home is perfect for first time home buyers. Don’t miss out on this beautifully remodeled home and schedule your own private showing today!!

3225 Oakland Road N, Lakeland
$499,000
4 Beds ⋅ 2 Baths ⋅ Oakland SubDv. ⋅ 33801 Zip Code
NO HOA. 7,86 acres. RANCH PROPERTY. Unique opportunity for those looking for space, privacy, and country living! Situated on an expansive property surrounded by mature trees, this home offers abundant open space, fenced areas, a large storage structure, garden and growing areas, and plenty of room for horses, poultry, and other animals. The property also features established edible landscaping, including cassava, sugarcane, banana, okra, passion fruit, jabuticaba, cajá-manga, and papaya. The land extends to a natural preserve with a lake/park area, creating a peaceful and private setting. The home is livable and functional, with excellent potential for updating and personalization. A standout feature is the additional adjacent portion of the property, previously used for a mobile home and already equipped with its own driveway, septic system, and connections. This area provides valuable flexibility for potential future construction, residential use, or possible lot separation, subject to county approval, zoning, and permitting. A rare opportunity to own a large property with usable land, existing infrastructure, and exceptional future potential.

1735 Oakland Road E, Lakeland
$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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