Winter Garden/Oakland Homes with Lake Privileges Frontage

Winter Garden/Oakland Homes with Lake Privileges Frontage

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Central Florida, where the picturesque landscapes and vibrant lifestyle converge to create a truly enchanting living experience. Known for its rich history, Winter Garden boasts a quaint downtown area filled with boutique shops, delightful eateries, and a lively farmers market that draws locals and visitors alike. Just a stone's throw away, the serene town of Oakland offers a tranquil atmosphere, with lush greenery and stunning lake views that beckon nature enthusiasts and families seeking a peaceful retreat.

One of the most appealing features of homes in this region is the availability of properties with lake privileges. Imagine waking up to the soothing sounds of water lapping against the shore, with breathtaking lake frontage right at your doorstep. These homes provide not just a residence, but a lifestyle filled with recreational opportunities. Whether it’s fishing, kayaking, or simply enjoying a sunset stroll along the water’s edge, living by the lake adds a unique charm to everyday life.

The real estate market in Winter Garden and Oakland is thriving, with a variety of options ranging from cozy single-family homes to luxurious lakefront estates. The sense of community is palpable, with friendly neighbors and a calendar full of local events that foster connections. With excellent schools, beautiful parks, and easy access to major highways and Orlando's attractions, this region is perfect for families, retirees, and anyone looking for a vibrant yet peaceful place to call home. Discover the magic of Winter Garden and Oakland, where every day feels like a vacation by the lake!

Newest Winter Garden/Oakland Homes with Lake Privileges Frontage

$1,400,000
4 Beds ⋅ 4 Baths ⋅ Hull Island At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to this extraordinary custom lakefront estate offering breathtaking views of Lake Apopka and the ultimate Florida waterfront lifestyle. Designed with luxury and functionality in mind, this one-of-a-kind home showcases premium upgrades, exceptional craftsmanship, and direct lake access. The heart of the home is a chef-inspired kitchen featuring a natural gas cooktop, double ovens, expansive center island, abundant counter space, separate breakfast dinette, and a custom walk-in pantry with floor-to-ceiling shelving. The kitchen opens seamlessly to the spacious family room with soaring 12-foot ceilings and triple sliding glass doors that frame spectacular lake views and fill the home with natural light. Step outside to your private waterfront oasis where a covered, screened lanai overlooks professionally landscaped grounds and unforgettable sunsets. The impressive 20' x 60' brick paver patio leads to a private dock with an electric covered boat lift, providing direct access to Lake Apopka. Enjoy fishing from your dock, boating the scenic Harris Chain of Lakes via the Apopka-Beauclair Canal, or spending the day exploring the waterfront restaurants, shops, and attractions of historic downtown Mount Dora and Tavares. The thoughtfully designed floor plan includes a formal dining room with soaring ceilings and a private office with double doors, ideal for working from home. The luxurious primary suite is a true retreat with panoramic lake views, spa-inspired bath featuring a frameless floor-to-ceiling tiled double shower with dual shower heads and built-in bench, soaking tub, dual vanities, and custom walk-in closets. A hidden Murphy door provides private access to two secondary bedrooms and a full bath, creating the perfect guest or family wing. The oversized fourth bedroom offers an ensuite bath and walk-in closet, ideal for guests or multigenerational living. Additional premium features include a 24kW natural gas whole-house generator, electric vehicle charging station, water softener, security system, surround sound, insulated garage doors and ceiling, garage utility sink, overhead storage, and a spacious laundry room with built-in cabinetry, extensive counter space, and utility sink. The oversized three-car garage and expansive six-car brick paver driveway provide ample parking and storage. Located in the sought-after gated community of Hull Island, residents enjoy resort-style amenities including a community pool, gazebo, playground, bark park, and exclusive private access to the 150-acre Oakland Nature Preserve with miles of scenic trails. Nestled in the charming Town of Oakland, this exceptional home is just minutes from Winter Garden Village, historic Downtown Winter Garden, the award-winning Winter Garden Farmers Market, the West Orange Trail, Downtown Clermont, shopping, dining, major hospitals, Orlando's world-famous attractions, Orlando International Airport, and major highways. Florida's beautiful east and west coast beaches are approximately one hour away.

1112 Hull Island Drive, Oakland
$1,195,000
Briley Farm Ph 1b SubDv. ⋅ 34787 Zip Code
Discover an exceptional opportunity to build a custom lakefront residence on Lot 45 in Briley Farm Phase 1B. Located at 552 Walker Street in Oakland, this approximately 0.82-acre homesite offers beautiful Lake Apopka views, direct lake frontage and generous space to create a personalized retreat exclusively with Element Home Builders. With no predetermined floor plan, buyers can collaborate with Element to create a custom design subject to applicable approvals. Briley Farm offers a peaceful setting near downtown Winter Garden, the West Orange Trail, shopping, dining and major roadways. Public water, public sewer, electricity and natural gas are available within the community. The list price is for the homesite only and does not include home construction. The purchaser must build with Element Home Builders; outside builders are not permitted.

552 Walker Street, Oakland
$2,099,000
5 Beds ⋅ 5 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code
Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

16038 Johns Lake Overlook Drive, Winter Garden
$2,550,000
5 Beds ⋅ 6 Baths ⋅ Johns Cove 43/104 SubDv. ⋅ 34787 Zip Code
Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout. Designed for effortless entertaining, the open-concept layout showcases a chef’s kitchen with a waterfall quartz island, custom cabinetry, premium stainless steel appliances, and a full-slab backsplash, all flowing into an expansive living area with designer lighting and seamless indoor-outdoor access. The primary suite offers a private retreat with abundant natural light, custom closets, and a spa-inspired bath featuring a freestanding soaking tub and luxury walk-in shower. Step outside to a screened pool, upgraded travertine deck, and private pier, creating an unparalleled waterfront lifestyle ideal for relaxation and entertaining. Additional highlights include a concrete tile roof (maintained), smart home features, updated HVAC, epoxy garage, modern laundry room, and high-end upgrades throughout. Ideally located minutes from Downtown Winter Garden, premier dining, shopping, and top-rated schools, this is a rare opportunity to own an unparalleled lakefront property.

812 Johns Point Drive, Oakland
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