Oakland Waterfront Homes

Small-Town Charm Meets Peaceful Lakefront Living in Central Florida

Tucked between Winter Garden and Clermont, the town of Oakland offers a rare blend of quiet charm, scenic lakes, and easy access to Orlando’s best amenities. With direct frontage along Johns Lake—a popular spot for boating, fishing, and wakeboarding—Oakland waterfront homes deliver an unmatched lakeside lifestyle in one of Central Florida’s most tranquil communities.

Whether you’re looking for a custom-built lakefront estate or a new construction home with water views, explore the best Oakland waterfront homes for sale today.

Why Buy a Waterfront Home in Oakland, FL?

• Access to Johns Lake, a 2,400-acre lake ideal for boating, fishing, and water sports

• Peaceful, nature-filled setting with a small-town feel

• Minutes to Winter Garden Village, Downtown Winter Garden, and SR-429

• Close to the West Orange Trail and outdoor recreation

• Lower density and more space compared to nearby suburbs

Popular Waterfront Communities in Oakland

Johns Landing

Gated community offering luxury lakefront homes with private docks and lake access. Community boat ramp and tennis courts included.

Johns Cove

Exclusive gated community featuring custom homes on large lots with panoramic lake views. Quiet and private, ideal for long-term residents.

Oakland Trails (nearby water features)

While not directly on the lake, this community offers water-view homes, nature trails, and green space near Johns Lake.

Oakland Park

Straddling Winter Garden and Oakland, this charming, walkable neighborhood features lake—and conservation-view homes with classic Craftsman architecture and access to trails.

What You’ll Find in Oakland Waterfront Homes

• Spacious lots with private docks, boat lifts, and lakefrontage

• Newer construction and custom homes with high-end finishes

• Scenic porches, outdoor kitchens, and screened lanais

• Peaceful streets, mature landscaping, and gated privacy

• HOA communities with low traffic and family-friendly amenities

Things to Do Near Oakland ,Waterfront Homes

Life in Oakland is about slowing down, connecting with nature, and enjoying the water—all while being close to shopping, dining, and recreation.

Outdoor Activities

• Boating and fishing on Johns Lake – One of the region’s most popular lakes for wakeboarding and bass fishing

• West Orange Trail – Over 20 miles of scenic trails for walking, biking, and running

• Speer Park – Local green space with shaded playgrounds, basketball courts, and tennis

• Oakland Nature Preserve – Boardwalk trails, birdwatching, and environmental education

• Hiking and kayaking at Lake Apopka Wildlife Drive – A short drive away for birders and nature lovers

Dining & Shopping

• Downtown Winter Garden – Just minutes away, offering restaurants, cafés, breweries, and weekly farmers markets

• Winter Garden Village – Major retail center with shopping, salons, and grocery stores

• The Tasting Room, Rosallie Le French Café, and Urban on Plant – Local favorites in the historic Winter Garden

• Clermont Waterfront Park and dining options only 15 minutes west

• Easy access to SR-429, Florida’s Turnpike, and Downtown Orlando

Work With a Local Waterfront Real Estate Expert

I’m Mike Chen, a licensed Realtor specializing in lakefront and new construction homes across Central Florida. Oakland is a hidden gem, and I’m here to help you find the perfect waterfront home—whether it’s a primary residence, second home, or investment property.

• Expert guidance on Johns Lake properties and gated communities

• Local knowledge of dock permits, HOA rules, and lake regulations

• Access to private, off-market, and coming-soon listings

• Full-service support with 5-star results and trusted referrals

Ready to Find Your Waterfront Home in Oakland?

Whether you’re looking for peaceful mornings on the water or a home base close to both nature and Orlando’s best suburbs, Oakland is an excellent place to call home.

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Frequently Asked Questions (FAQs)

What lake is in Oakland, FL?

Oakland sits on the western edge of Johns Lake, a large and well-known body of water popular for boating, water skiing, and fishing.

Can I build a dock or boat lift?

Yes—many lakefront homes include docks, and most neighborhoods around Johns Lake allow for private boat access with the right permits.

Is Oakland good for commuting to Orlando?

Absolutely. With quick access to SR-429 and the Turnpike, you can be in Downtown Orlando, Disney, or the airport within 30–40 minutes.

Are there new construction homes on the water in Oakland?

Yes—select communities like Johns Landing and Oakland Park offer newer homes with lake or water views, as well as build-to-suit options.