Windsor Landing Homes for Sale

About Windsor Landing Neighborhood

Windsor Landing sits at the southern edge of Ocoee, just south of Thornebrooke Drive off Maguire Road, with primary access at Maguire Road and Sagecrest Drive and a second entrance at Thornebrooke Drive and Kentshire Boulevard. The location places it geographically between the established Gotha hamlet to the south and the Windermere community to the southeast, while remaining inside Ocoee's 34761 ZIP and Orange County tax jurisdiction.

The neighborhood was developed and built out across roughly four years, from 2001 through 2005, producing a community of about 215 single-family residences. Homes range from approximately 2,400 to 4,000 square feet with four to five bedrooms, three to five bathrooms, and two- or three-car garages. The architectural program is consistently Mediterranean-themed — barrel-tile roofs, stucco exteriors, and arched entryways predominate — giving the streetscape a unified appearance that has aged well as the landscaping has matured.

Two gated entrances control access, an unusual feature for a community of this size and one that residents tend to cite as a practical advantage. Within the gates, the streets are well-maintained, lots are landscaped, and the amenity package is intentionally compact rather than expansive: a fishing dock, a children's play area, and a basketball court rather than a clubhouse, pool, or fitness center. That positioning matters when comparing Windsor Landing to neighbors with full amenity decks — the trade-off is reflected in the HOA structure.

Windsor Landing Location & Connections

Windsor Landing is located in southern Ocoee off Maguire Road, less than a mile from the Windermere boundary and within walking distance of Thornebrooke Elementary School. The placement gives residents an unusual combination: an Ocoee address with its lower property values, but day-to-day proximity to Windermere-zoned schools and the Butler Chain corridor to the southeast.

SR 429 (the Western Beltway) is approximately a mile west of the community, providing fast routes north toward Apopka or south toward the Florida Turnpike, Disney World, and I-4. SR 408 access via the Good Homes Road interchange puts downtown Orlando within roughly 25 minutes in non-rush-hour traffic.

Windsor Landing Amenities & Lifestyle

Windsor Landing's character comes more from its location than its on-site amenity package. Residents trade a clubhouse and resort pool for direct access to a Windermere-zoned school feeder pattern, the Butler Chain corridor, and the Maguire Road retail strip — a calculated trade for buyers prioritizing schools and location over communal amenities.

How Windsor Landing Compares

Windsor Landing's pitch isn't amenities — it's positioning. The community trades the resort-style amenity package found in larger nearby developments for a simpler dues structure, gated security, and a school feeder pattern shared with Windermere addresses that typically command higher prices.

Windsor Landing HOA & CDD Information

Windsor Landing operates under a mandatory homeowners association (HOA) responsible for maintaining the gated entrances, common-area landscaping, community amenities (fishing dock, playground, basketball court), and the private community streets. The community does not carry a Community Development District (CDD) assessment, which is a meaningful distinction from many newer developments in West Orange County where CDD fees can add $1,500–$3,000+ annually to property tax bills.

HOA fees and management company information change from time to time, so we don't publish specific dollar amounts here — they go out of date quickly and create more confusion than clarity.

Frequently Asked Questions