Cobblestone Homes for Sale

About Cobblestone Neighborhood

Cobblestone sits on a quiet stretch of Roper Road in Winter Garden's 34787 ZIP code, tucked between Daniels Road to the west and the woodland buffer that separates the neighborhood from the Florida's Turnpike corridor to the north. The community is gated with a single controlled entrance off Roper Road, which keeps through-traffic out of the interior streets and helps maintain the established, residential feel that has defined Cobblestone since its build-out.

Construction took place primarily during 2006 and 2007, which puts Cobblestone in the established-suburban category rather than the new-construction wave currently reshaping nearby Horizon West. Homes are single-family, two-story (with some single-story plans) on conventional lots, typically ranging from about 1,900 to 3,600 square feet of interior living space. Mature landscaping, established lawns, and sidewalks throughout the loop give the streets a settled look that newer 34787 builds won't have for another decade or more.

The interior layout is straightforward: a single road in from Roper Road branches into a residential loop, with a small retention pond anchoring the northeastern corner. There is no community pool, clubhouse, or playground inside Cobblestone — by design, this is a low-amenity gated neighborhood, which keeps HOA dues modest compared to amenity-heavy alternatives like nearby Bronson's Landing or Stoneybrook West. Buyers who prioritize gated privacy and a low HOA over resort-style amenities are Cobblestone's natural fit.

Cobblestone's location matters as much as its physical layout. Daniels Road runs north-south just to the west, feeding directly to Winter Garden Village at Fowler Groves in about three minutes and to SR 50 / West Colonial Drive in about five. The 34787 ZIP gives buyers the Winter Garden mailing address along with the Plant Street downtown, the West Orange Trail, and the school options that come with West Orange County's most active small city.

Cobblestone Location & Connections

Cobblestone is located in the northeastern part of Winter Garden's 34787 ZIP, in the wedge between Florida's Turnpike to the north and SR 50 to the south. The single gated entrance opens onto Roper Road, with Daniels Road providing the primary north-south connection to Winter Garden Village, the SR 50 retail corridor, and the SR-429 interchange.

This is a location-by-corridor neighborhood: Cobblestone trades direct lake or trail frontage for a central position on the road network that makes virtually everywhere in metro Orlando reachable within a reasonable drive. The Turnpike on-ramp at SR 50 is about three minutes away, and the SR-429 interchange at Daniels Road is roughly five minutes south.

Cobblestone Amenities & Lifestyle

Cobblestone's lifestyle proposition is simple: gated privacy and an established, low-key residential setting, with the city's full amenity menu reachable in a short drive. Inside the gates there is no pool, clubhouse, or playground — that absence is part of why HOA dues stay manageable. The trade-off is that residents lean on city and county parks, Winter Garden Village's recreation tenants, and the broader West Orange amenity network for active recreation.

Roper Road's central position in 34787 makes Cobblestone particularly well-suited to buyers who want a Winter Garden address without paying for resort amenities they may not use. Day-to-day errands, weekend dining downtown, school commutes to West Orange High School, and weekend Theme Park trips are all reasonable from a single base.

How Cobblestone Compares

Cobblestone's clearest value proposition is gated privacy without resort-amenity HOA dues, in an established neighborhood with mature trees and a build vintage that's already settled. The trade-off is no community pool, clubhouse, or playground inside the gates — and a price-per-square-foot that typically reflects the older housing stock rather than current new-construction pricing.

Cobblestone HOA & CDD Information

Cobblestone is a mandatory-HOA community. Because there is no community pool, clubhouse, or fitness center inside the gates, the HOA's responsibilities focus on entry-gate maintenance, common-area landscaping along the entry, the community pond, and standard architectural review. That scope generally results in modest dues compared with amenity-heavy alternatives in 34787.

Cobblestone is not currently believed to fall within a Community Development District (CDD), which is typical for single-family neighborhoods built in 2006–2007. Verify CDD status with the title company at contract — Florida CDDs occasionally cover adjacent corridors, and a one-call confirmation through the title is the safest path.

Frequently Asked Questions