Oakland Park: New Homes in Winter Garden FL by David Weekley & RockWell Homes (2026 Guide)

If you have been hunting for new homes in Winter Garden FL that feel less like a subdivision and more like a small town, Oakland Park deserves a look. This 258-acre traditional neighborhood development sits on the border of Winter Garden and the Town of Oakland, wrapped around Lake Brim and stretching toward the shoreline of Lake Apopka. Front porches sit close to the street, live oaks were preserved rather than cleared, and the West Orange Trail runs straight through the middle of it.

Oakland Park Quick Facts (September 2026)

Pricing and availability move quickly. Figures above reflect publicly posted information as of September 2026 and should be verified with each builder before you write an offer.

About the Builders at Oakland Park

Oakland Park is unusual among new build communities near Winter Garden in that it uses a curated team of builders rather than one production giant. David Weekley Homes anchors the community with its Village Series and Park Series and has one of the strongest reputations in Central Florida for design flexibility and post-closing service. RockWell Homes, headquartered in nearby Ocoee, is building luxury single-family homes in the final phase, including rear-entry garage plans with optional above-garage living space. RCB Homes and J&J Building round out the roster on the higher-end and semi-custom side, where pre-construction homes have listed above $2 million.

The developer, Landeavor, has kept a tight architectural review process across all four builders, which is why the streetscapes read as one cohesive neighborhood instead of four competing product lines.

Floor Plans & Pricing

Homes at Oakland Park span a genuinely wide range. Cottage and village plans start near 1,600 square feet with three bedrooms, while estate and lakefront plans push past 5,700 square feet with six bedrooms, bonus rooms and detached casitas. Common features across builders include main-floor owner's suites, upper-level lofts, courtyards, lanais, and detached or rear-loaded garages served by alleys.

Because this is the final phase, the mix of new construction homes in Winter Garden FL 2026 here skews toward move-in-ready inventory and a shrinking number of buildable homesites rather than a full menu of plans. If a specific lot or lake view matters to you, this is a community where waiting costs you options.

Amenities at Oakland Park

The clubhouse is the social center — catering kitchen, private conference room, and seating for dozens, with a fire pit and pavilion just outside. Two pools serve the community: a zero-entry clubhouse pool of roughly 3,300 square feet with a center island and fountains, and the smaller Meadowmarsh pool near the park of the same name.

Beyond that, the amenity package is deliberately outdoor-first: a Kompan playground, open lawns, a community garden, a linear park connecting Lake Apopka to Lake Brim, and direct access to the West Orange Trail — 22-plus miles of paved trail that functions as Oakland Park's real main street.

Location: How Close Is Oakland Park to Downtown Winter Garden?

Oakland Park sits about 1.5 miles from historic downtown Winter Garden, close enough that many residents bike the trail to the Saturday Farmers Market rather than drive. Downtown Orlando is roughly 14 miles east. State Road 429 is minutes away and connects north to the Turnpike and south to I-4 and the Disney corridor. Winter Garden Village, Hamlin Town Center, and AdventHealth Winter Garden are all within a short drive, and the Oakland Nature Preserve on Lake Apopka is essentially next door.

What Makes Oakland Park Stand Out?

Three things separate it from most homes for sale in Winter Garden FL. First, it is a certified green community, with energy-efficient specifications such as high-performance low-E windows, zoned high-SEER HVAC, Energy Star insulation and LED lighting built in rather than sold as upgrades. Second, the site design preserved mature oaks, wetlands and lake frontage instead of flattening them — something you cannot retrofit into a newer community. Third, the trail-and-front-porch layout produces a walkability that Horizon West's larger masterplans, for all their amenities, rarely match.

The honest tradeoff: Oakland Park is in its final phase and priced accordingly. Buyers looking for entry-level pricing will find better value elsewhere in West Orange County. Buyers who want character, mature landscaping, and a genuine downtown Winter Garden lifestyle will find very little that competes.

Want to walk the remaining homesites, compare builders side by side, or see how Oakland Park stacks up against Ovation, Waterleigh or Briley Farm? I represent buyers throughout West Orange and Lake County and can register you with the builder so you have representation at no cost to you.

Rebecca Hamaoui, REALTOR® | Bella Trae Realty | 📞 407-922-8986 | ✉ rebecca@bellatraerealty.com