Oakland Homes with Pool

Welcome to Oakland, Florida – a hidden gem nestled in the heart of Orange County! This charming town, known for its picturesque landscapes and friendly community, offers a unique blend of suburban tranquility and vibrant local culture. With its rich history and stunning natural surroundings, Oakland is the perfect place for families, retirees, and anyone looking to escape the hustle and bustle of city life while still enjoying convenient access to nearby amenities.

One of the standout features of Oakland is its stunning homes, many of which come complete with private pools. Imagine spending sunny Florida afternoons lounging by your poolside oasis, surrounded by lush greenery and the soothing sounds of nature. Homes with pools in Oakland not only provide a refreshing escape during the warmer months but also create an inviting space for entertaining friends and family. Whether you’re hosting a summer barbecue or enjoying a peaceful evening under the stars, a pool is the perfect addition to your dream home.

In addition to its beautiful residences, Oakland boasts a range of recreational opportunities, including scenic parks, walking trails, and lake access for those who enjoy outdoor activities. The town's strong sense of community is evident in its local events and festivals, where neighbors come together to celebrate and connect.

With its idyllic setting, charming homes with pools, and a welcoming atmosphere, Oakland, Florida, is not just a place to live – it’s a place to thrive. Discover your perfect home in this enchanting town and start making memories that will last a lifetime!

Newest Oakland Homes with Pool

$3,295,000

6 Beds ⋅ 7 Baths ⋅ O6429415 MLS

Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thoughtfully designed living space on a private 0.5-acre homesite. Featuring 6 bedrooms, 6 full bathrooms, and 1 half bath, this home showcases one of Element's most sought-after floor plans, blending timeless architecture with modern luxury. Designed for both everyday living and elegant entertaining, the open-concept layout features a gourmet chef's kitchen, expansive great room, private office, loft, and spacious covered lanai. Enjoy true Florida living with an extended outdoor entertaining area complete with a resort-style pool, spa, and fully equipped summer kitchen for seamless indoor-outdoor living. Every detail reflects the exceptional craftsmanship, premium finishes, and attention to detail that define Element Home Builders. With construction just beginning, buyers have the rare opportunity to personalize select finishes and own a brand-new custom luxury home in one of Oakland's most desirable communities. Briley Farm is an exclusive enclave just minutes from historic Downtown Winter Garden, the West Orange Trail, top-rated schools, boutique shopping, dining, and major highways, offering convenient access to Downtown Orlando, Walt Disney World, and Orlando International Airport. Experience the perfect blend of luxury, privacy, and convenience in one of Central Florida's premier custom home communities.ning, and major roadways, while maintaining the privacy and charm of luxury estate living. Renderings are for illustration purposes only. Features, specifications, and finishes are subject to change without notice.

312 Briley Avenue, Oakland

$999,000

4 Beds ⋅ 3 Baths ⋅ G5110973 MLS

Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

250 N Walker Street, Oakland

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