Preston Square Homes for Sale

About Preston Square Neighborhood

Preston Square is one of the smaller and more architecturally distinctive subdivisions in Windermere's southern corridor. Where most of the 34786 ZIP code is dominated by guard-gated estate communities or sprawling master plans, Preston Square went a different direction: a tight Charleston-inspired plan with homes oriented around a central square, a community pond, and a network of rear-loaded alleyways that hide garages behind the streetscape. The result is a walkable feel that's rare west of Orlando.

Homes in Preston Square include both single-family residences and attached townhome-style configurations, most built in the 2010s era. Architecture leans toward Coastal/Lowcountry — front porches, dormers, side-entry walks, and modest setbacks that put life on the front of the house instead of the back. Lots are smaller than the Windermere norm, but the trade-off is the streetscape: trees, sidewalks, and a courtyard-style green at the heart of the community.

The neighborhood sits inside the southern Windermere school corridor and on the east side of CR 535, which gives families the same Disney-side commute geometry as larger neighbors like Summerport, Lakeside Village, and Lake Burden, but at a different price point and lifestyle pace. Buyers who want a Windermere address but don't need a half-acre lot tend to find the value here.

Preston Square Location & Connections

Preston Square sits in the southern half of Windermere, just east of Winter Garden Vineland Road (CR 535). CR 535 is the spine route through southern Windermere — north to downtown Windermere and Town Square, south to Disney property, and the primary connector to the SR 429 Western Beltway. From the neighborhood, it's a short drive to the Cornerstone at Summerport center, Lakeside Village, and the Orlando Health Medical Pavilion on CR 535.

Adjacency-wise, Preston Square shares its southern edge with Ashlin Park, sits west of the Lake Burden corridor, east of Wickham Park, and north of the school corridor. Inside the gates, the central square and pond function as the geographic anchor for the community.

Preston Square Amenities & Lifestyle

Preston Square's lifestyle is defined more by its layout than by big-ticket amenities. There's no resort pool or 24-hour gatehouse — instead, the community sells walkability, the central green, and proximity to the CR 535 corridor's everyday services. For households that want the Windermere school zone and Disney-adjacent geometry without paying for a full estate-community amenity package, that's an intentional fit.

Just outside the neighborhood, Lakeside Village and the Cornerstone at Summerport center handle most everyday shopping and dining. Winter Garden Village is a short drive north for the larger outdoor shopping experience, and the Butler Chain of Lakes is reachable for boating and watersports through the public ramps at Fernwood Park and R.D. Keene Park.

How Preston Square Compares

Preston Square's value proposition isn't square footage or lot size — it's the layout, the price-of-entry, and the address. Buyers evaluating it almost always compare it to two alternatives in the same area: a townhome in Lakeside Village (similar walkability, lower price), or a single-family home in Ashlin Park or Summerport (more lot, more amenity, higher price). The table below frames the typical trade-offs.

Preston Square HOA & CDD Information

Preston Square is governed by a homeowners association that handles common-area maintenance, the central square and pond, and the rear-alley/garage corridors. Because the streetscape and shared green are the defining design feature of the community, HOA-controlled standards on landscaping, paint, and exterior modifications carry more weight here than in a typical Windermere subdivision — buyers should review CC&Rs carefully before committing.

For an explanation of how Florida HOAs work in general, see What's an HOA?. For CDD basics, see What's a CDD?.

Frequently Asked Questions