Oakland Homes for Sale

Oakland Homes for Sale

Welcome to Oakland, Florida – a hidden gem nestled in the heart of Orange County that beautifully marries small-town charm with modern conveniences. This picturesque community is characterized by its lush landscapes, historic architecture, and a welcoming atmosphere that makes it a perfect place to call home. With its rich history dating back to the late 1800s, Oakland boasts a unique character that resonates through its tree-lined streets and friendly neighborhoods.

The subdivision of Oakland offers a diverse range of homes for sale, catering to various lifestyles and preferences. Whether you’re searching for a quaint bungalow, a spacious family home, or a contemporary retreat, Oakland has something to suit everyone’s needs. Many properties feature stunning outdoor spaces, ideal for enjoying Florida’s year-round sunshine, and are often situated near local parks and recreational areas, perfect for families and outdoor enthusiasts alike.

In addition to its beautiful homes, Oakland is conveniently located just a short drive from the bustling city of Orlando, providing residents with easy access to world-class dining, shopping, and entertainment. The community also prides itself on its strong sense of togetherness, with regular events and gatherings that foster connections among neighbors.

If you’re looking for a serene yet vibrant community that offers the best of both worlds, consider making Oakland, Florida, your next home. With a variety of homes for sale, now is the perfect time to discover the charm and allure of this enchanting subdivision. Come and experience the warmth of Oakland – where your dream home awaits!

Newest Oakland Homes for Sale

$375,000
3 Beds 2 Baths L4964982 MLS
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

Listing courtesy of COLDWELL BANKER REALTY. 863-294-7541

$1,250,000
6 Beds 8 Baths O6362142 MLS
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

Listing courtesy of OAKSTRAND REALTY. 888-912-5258

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© 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved. This data is up-to-date as of . For the most current information, contact William Raveis Real Estate.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.