Wesmere Homes for Sale

About Wesmere Neighborhood

Wesmere sits in south Ocoee just north of the Windermere line, with primary entrances off Maguire Road and Roberson Road and Wesmere Parkway running through the heart of the community to the amenity center. The original development was built largely between 1991 and the late 1990s by Calton Homes of Florida, with additional construction by Beazer Homes and Arvida extending into the early 2000s. Homes range from approximately 1,331 to just under 4,000 square feet of living area, with three to five bedrooms and two- or three-car garages.

Architectural styles vary across the community's 16 cul-de-sacs, with screened lanais a common feature for enjoying Central Florida evenings. The street layout — with its twists, turns, and dead-end streets — keeps through-traffic minimal and produces larger, more irregular lots in many sections. Several large stocked ponds with fountains anchor the community's interior, and roughly 100 of the homes back directly to water, providing pond views and casual fishing access.

Wesmere is a fully gated community with mandatory HOA membership covering access to the resort-style amenity center. The community garden, walkable sidewalk network, and mature landscaping give the neighborhood the feel of an established place that has settled into itself rather than a recent build. A separate but related sub-community — Villages at Wesmere — was developed later (2008–2014) by K. Hovnanian Homes and Taylor Morrison along Wesmere's northern edge, offering newer townhomes and smaller single-family homes; Wesmere proper remains the original 1990s–early 2000s gated community.

Wesmere Location & Connections

Wesmere is located in Ocoee's southern edge, in the 34761 ZIP code, sitting just north of the Windermere community line and just east of SR 429 (the Western Beltway). The community is bracketed by Maguire Road on the east, Roberson Road on the south, and Tomyn Boulevard along its northern edge — a road grid that gives residents multiple ways onto the expressway system without ever needing to use West Colonial Drive.

Position-wise, Wesmere sits roughly between downtown Winter Garden to the north and downtown Windermere to the south, with quick connections to Florida's Turnpike, SR 408, and SR 429. Plantation Grove Shopping Center with its Publix anchor is roughly half a mile from the community, and the Maguire Road corridor offers everyday convenience without the chain-retail volume of SR 50.

Wesmere Amenities & Lifestyle

Life inside Wesmere centers on the resort-style amenity complex along Wesmere Parkway and the network of stocked ponds woven through the cul-de-sacs. Residents walk or bike between homes and amenities on the community's sidewalk system, and the gated entrances on Maguire and Roberson Roads keep traffic to residents and guests only. The community's mix of waterfront homes, mature trees, and 16 cul-de-sacs creates a settled, residential feel that newer Ocoee neighborhoods are still decades away from matching.

Outside the gates, Wesmere's southern Ocoee position puts residents close to the daily-needs retail at Plantation Grove and West Colonial Drive, while keeping a relatively short drive to downtown Winter Garden's restaurant and brewery scene and the West Orange Trail.

How Wesmere Compares

Wesmere occupies a fairly specific niche in the West Orange County market: an established, gated, amenity-rich community with mature landscaping, but at price points and lot configurations that newer construction in Horizon West and Villages at Wesmere can't match. The table below compares Wesmere to two of its closest direct alternatives — Villages at Wesmere (the newer K. Hovnanian/Taylor Morrison sub-community) and Belmere Village (the comparable gated community on the Windermere side of the line).

Wesmere HOA & CDD Information

Wesmere has a mandatory homeowners association covering access to the gated entrances, the resort-style amenity center (pool, clubhouse, fitness center, tennis, basketball, playground), the community garden, common-area landscaping, and the maintenance of the community's stocked ponds and fountains. The HOA also handles the architectural review process that has helped Wesmere maintain its established character over more than three decades.

Wesmere is not in a Community Development District, so there is no CDD fee in addition to the HOA assessment — a meaningful distinction from many newer master-planned communities in West Orange County and Horizon West.

Frequently Asked Questions