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$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
$500,000
Oakland Park SubDv. ⋅ 34760 Zip Code
Lot 262

1264 Ridge Lake Way, Oakland
$450,000
Town/Oakland SubDv. ⋅ 34760 Zip Code
Discover this rare 0.31-acre residential lot in the heart of Oakland, one of the most charming and fastest-growing towns in Central Florida. Tucked just a few blocks from downtown Oakland, you’ll find yourself surrounded by the area’s signature tree-lined unpaved and stone roads, giving the neighborhood a warm, small-town character that’s hard to find today. Oakland continues to grow with new, luxurious communities, yet opportunities like this, a vacant lot with no HOA in the downtown core, are truly uncommon. From here, you’re just minutes to Plant Street in downtown Winter Garden, with its award-winning restaurants, local shops, and vibrant events, while still enjoying the peaceful lakeside setting Oakland is known for along the shores of Lake Apopka, one of Florida’s largest lakes. This property blends charm, convenience, and location, an ideal setting to build your dream home in a community that feels both timeless and connected.

N Daniels Street, Oakland
$375,000
The Grove SubDv. ⋅ 34760 Zip Code
Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home. Set in the illustrious community of The Grove, Lot 41 is a generously sized corner lot ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal location. Access to modern amenities, including walking trails, parks, and recreational areas. Close proximity to top-rated schools, shopping, dining, and entertainment. Easy access to major highways, ensuring seamless connectivity to Orlando and surrounding areas. This homesite is your chance to become part of a vibrant and growing community while enjoying the privacy and comfort of a custom-built home tailored to your lifestyle. Don’t miss this opportunity to secure your spot in one of Oakland’s most desirable locations.

1225 Water Maple Drive, Oakland
$480,000
4 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Discover the wonderful blend of functionality, efficiency, and flexibility in this beautifully maintained two-story home nestled in the heart of Oakland, FL. Built in 2006, this 4-bedroom, 2-bathroom residence offers a rare opportunity to enjoy modern amenities, income potential, and eco-conscious living—all just minutes from the West Orange Trail and charming downtown Winter Garden. Property Highlights: - 1,680 sq ft of well-designed living space - Fully fenced in backyard - No HOA – enjoy the freedom to use your property your way - Solar-powered with a robust 15kWh system, keeping energy costs low - Dual HVAC systems for optimal comfort on both floors - Full kitchen downstairs + half kitchen upstairs — possibilities of in-law suite, rental potential, or multi-generational living - 14' x 12' elevated deck / covered patio — outdoor entertaining or private oasis - Optional furnished sale for a move-in ready experience - 10' gate to access backyard— boat, RV, or trailer storage - 18' x 22' carport as well as 12' x 30' gravel lot offers ample parking - Roof estimates available—opportunity for buyers to personalize or negotiate Outdoor Appeal: A spacious backyard offers room to expand patios, garden, or build additional outdoor amenities. The elevated deck and gated access make it both functional and private—perfect for Florida living. Location: Enjoy small-town charm with easy access to major highways, schools, parks, and the community of Oakland. Zoned for top-rated schools and close to everything Central Florida has to. Don't miss your chance to own this energy-efficient, flexible-use property in a sought-after location.

312 W Hull Avenue, Oakland
$450,000
3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code
Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space. Inside, enjoy a warm and functional layout with 1,419 sq ft of living space and central heating and cooling. The living room is perfect for relaxing evenings by the fire, while the outdoor area is built for Florida living—splash in the pool or unwind under the shade of the trees. Located just minutes from downtown Winter Garden and the West Orange Trail, you’ll love the peaceful setting with quick access to local shops, restaurants, and parks.

310 E Gulley Avenue, Oakland
$410,000
Town/Oakland SubDv. ⋅ 34760 Zip Code
Discover this RARE 0.31-acre residential lot located in the charming town of Oakland, one of the most desirable and rapidly appreciating areas in West Central Florida. Just a few blocks from Oakland’s historic downtown, this property is set on picturesque unpaved and stone roads, adding a unique character and peaceful atmosphere to the neighborhood. Oakland is known for its warm community feel, seasonal events, and its privileged location along the shores of Lake Apopka, one of Florida’s largest lakes. Additionally, it borders the sought-after area of Winter Garden, renowned for its vibrant historic downtown, local restaurants, excellent infrastructure, and appeal as a top destination for Central Florida residents. This lot offers the perfect blend of serenity and convenience, ideal for building your dream home in a location that combines nature, culture, and close access to everything you need. Bonus: The seller already has a custom home project available, featuring 4 bedroom suites, 6 bathrooms, 2 offices, a den, and a bonus room. The planned layout includes 3,850 sqft of air-conditioned space and a total construction area of 5,024 sqft, offering a spacious and well-designed floor plan ready to be brought to life.

N Daniels Street, Oakland
$410,000
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Beautiful oversized corner lot in charming Oakland. Nice open floor plan. Workshop is in the Garage and offers tons of storage. There is no HOA, so bring your boats and RV's to this property that has plenty of room to park/store them. This house has been under renovation, so requires work including a new roof. However, the property offers many possibilities to suit your vision of a dream home.

202 W Oakland Avenue, Oakland