Windermere Crossing Homes for Sale

About Windermere Crossing Neighborhood

Windermere Crossing sits in the east-central section of Winter Garden's 34787 ZIP, on the south side of Stoneybrook West Parkway where it meets Windermere Road. The community's recorded plat is Cambridge Crossing — and that name still appears on county records, MLS listings, and the original phase markers (Cambridge Crossing Ph 01, Ph 02). But because the community signage at the gate reads "Windermere Crossing," that's the name local agents, residents, and search portals use day to day. Both names refer to the same 142-home community.

The neighborhood was developed by Cambridge Homes in two phases between 2000 and 2002, putting it in the small group of established gated communities that pre-date Horizon West's southward expansion. Homes are single-family two-story executive plans on roughly quarter-acre to half-acre lots, with floor plans generally running between approximately 2,100 and 3,700 square feet. Most include two- or three-car garages, formal living and dining rooms, family rooms with fireplaces, and the screened pool decks that have become almost standard for the era's executive product. Many homes have been updated over the past five to ten years with newer roofs, HVAC systems, and kitchens.

The interior layout is built around two long loops: Windermere Crossing Circle (the primary loop, which carries the prettiest pond and its fountain) and Spring Mill Drive (the secondary connector). Twelve homes sit directly on Lake Reaves with private rear lake frontage. Roughly twenty more enjoy waterfront or water-view positions on one of four interior ponds. The remaining homes are interior lots, most backing to landscape buffers or other homes rather than collector streets — a function of the site's pinched, irregular footprint between the lake and the school.

What makes Windermere Crossing distinct in the Winter Garden inventory is the combination of three things that rarely line up together at this price point: a true gated entrance with controlled access, a private lakefront community park on Lake Reaves, and walk-across-the-street access to Lake Whitney Elementary. There is no community pool, but most homes have private pools, and the lakefront park functions as the neighborhood's social anchor.

Windermere Crossing Location & Connections

Windermere Crossing is located on the south side of Stoneybrook West Parkway in the eastern section of Winter Garden's 34787 ZIP, where the city begins to transition into the Town of Windermere. The neighborhood is enclosed on all four sides by natural and physical boundaries rather than other named subdivisions: SR-429 (the Daniel Webster Western Beltway) sits to the north past a buffer of vacant land; Lake Reaves forms the western edge; George Bailey Park and Lake Whitney Elementary sit immediately to the east across Windermere Road; and wetland and private residences buffer the southern boundary.

This isolated footprint is one of the reasons the community stays quiet — there is no through-traffic. Vehicles enter and exit through a single gated entrance off Windermere Road and circulate on Windermere Crossing Circle and Spring Mill Drive. The nearest SR-429 on-ramp is at Stoneybrook West Parkway, putting Walt Disney World, I-4, and the Florida's Turnpike all within a short drive.

Windermere Crossing Amenities & Lifestyle

Windermere Crossing's lifestyle is defined by what's inside the gate and what's a few minutes away — not by community-style mega-amenities. There is no clubhouse, no community pool, and no resort-style fitness center. What residents get instead is genuine privacy behind a controlled-access gate, a quiet park on Lake Reaves, and a layout where children can ride bikes between the loops without worrying about cut-through traffic.

Beyond the gate, the practical advantages are short drives in every direction: Lake Whitney Elementary is across the street, Plantation Grove and its Publix are ~1.5 miles east, Winter Garden Village and its 80-plus stores are ~2 miles west, and historic downtown Winter Garden with Plant Street, the Garden Theatre, and the West Orange Trail is roughly 10 minutes north.

How Windermere Crossing Compares

Windermere Crossing competes in an unusual slice of the Winter Garden / Windermere market: gated, established, lakefront-adjacent, with a recognized elementary school at the curb — but at a price point well below the new-construction luxury communities a few miles south. The closest comparison points within Florida Neighborhood Realty's coverage are Stoneybrook West (the larger pre-Horizon-West gated/golf community just across SR-429) and the newer Horizon West villages south of the beltway.

Windermere Crossing HOA & CDD Information

Windermere Crossing operates under a mandatory homeowners association that manages the gated entrance, the community lakefront park on Lake Reaves, the four community ponds (including the fountain feature), and the common landscaping along Windermere Crossing Circle and Spring Mill Drive. Because the recorded plat is Cambridge Crossing, some older HOA and county documents reference that name; both names refer to the same governing association.

Based on the community's 2000–2002 build era — predating the wave of Community Development District financing that became standard for Horizon West-era construction — Windermere Crossing is believed to have no CDD assessment. Verify against current Orange County records before relying on this for a purchase decision.

Frequently Asked Questions