Courtleigh Park Homes for Sale

About Courtleigh Park Neighborhood

Courtleigh Park sits in the eastern half of Windermere, accessed off Apopka-Vineland Road less than a mile south of the Florida Turnpike interchange. The community was developed over a six-year period from 1990 through 1996, which gives it the architectural variety of a build-out era spanning multiple builders rather than a single production-builder feel — homes range across traditional, Mediterranean-influenced, and contemporary Florida styles.

The 114 single-family homes in Courtleigh Park typically run 2,300 to 3,900+ square feet with 4 to 5 bedrooms and 2.5 to 3+ bathrooms. Lots are notably generous compared to newer Windermere subdivisions, and approximately 24 homes back to one of several interior ponds — these properties trade at a premium when they come available. The community park near the entrance includes a tennis court, basketball court, playground, and is monitored by video surveillance. There is no community pool, though many individual homes have private pools.

The neighborhood's mature oak canopy is its most defining visual feature. Streets that were planted with young oaks in the early 1990s have grown into a continuous tree canopy that distinguishes Courtleigh Park from newer Windermere developments where mature trees won't exist for another decade or more. Combined with the absence of CDD fees — a meaningful annual cost present in most newer Windermere-area communities — the neighborhood offers an established-home value proposition that's harder to replicate at the same price point in the 34786 ZIP code.

Courtleigh Park Location & Connections

Courtleigh Park is positioned in eastern Windermere off Apopka-Vineland Road, near the boundary with Dr. Phillips. The location balances established residential character with practical commuter access — the Florida Turnpike is less than a mile north, Conroy-Windermere Road provides a direct east-west route to I-4, and downtown Windermere is a short drive west via Conroy-Windermere Road.

The neighborhood is roughly 7.8 miles west-southwest of downtown Orlando and within reasonable reach of Sand Lake Road's Restaurant Row, the Mall at Millenia, and the medical campus at Dr. Phillips Hospital. Disney property sits to the south and southwest; Universal and SeaWorld are east via Conroy-Windermere Road.

Courtleigh Park Amenities & Lifestyle

Courtleigh Park residents trade resort-style master-plan amenities for the kind of established-neighborhood character that takes decades to develop — mature trees, settled landscaping, and a small private park used primarily by families who actually live in the community. The lifestyle is quieter than the active-amenity master plans south of Windermere, which is the appeal for buyers who want established Windermere character rather than a clubhouse calendar.

Day-to-day amenities sit just outside the neighborhood: shopping and dining cluster at Sand Lake Road and the Dr. Phillips area to the southeast, with downtown Windermere and the Grove at Isleworth a short drive west. The Butler Chain of Lakes public access points are within 10 minutes for boating, fishing, and lakeside recreation.

How Courtleigh Park Compares

Courtleigh Park's value proposition is straightforward: established 1990s construction with mature landscaping, no CDD fees, and larger lots than most newer Windermere subdivisions can offer at the same price. Buyers comparing it against newer master-planned options in southern Windermere or Horizon West should weigh the trade-offs honestly.

Courtleigh Park HOA & CDD Information

Courtleigh Park is governed by a homeowners association that maintains the entrance landscaping, the community park (tennis court, basketball court, playground), surveillance equipment, and shared common areas. The neighborhood does not carry a CDD (Community Development District) fee — a meaningful annual cost difference compared to most newer 34786 communities, where CDD assessments commonly run $1,500 to $3,500+ per year on top of the HOA.

HOA fees and management contacts change periodically. We confirm current figures directly with the management company before any purchase discussion.

Frequently Asked Questions