Cobblestone

Cobblestone is just south of Deerfield Place, on Black Springs Lane and Cobblestone Pointe Drive. It is inside City of Winter Garden limits.

Cobblestone has 84 single-family homes built in 2006 and 2007, according to Orange County Property Appraiser records. Homes range from about 1,900 to 3,920 square feet; 44 are one-story and 40 are two-story. There are no townhomes.

Over the past two years (MLS data, October 2026), homes in Cobblestone sold seven times for a median of about $539,000, ranging from about $485,000 to $545,000. For today's listings, see the top of this page.

Recent MLS listings show HOA dues of about $83 to $115 per month as of October 2026. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Cobblestone, but check the property tax bill for any special assessments. Florida's list does include a Cobblestone CDD, but it is in Pasco County and is not related to this neighborhood.

Orange County Public Schools' 2026-27 school zones place Cobblestone in Maxey Elementary, SunRidge Middle and West Orange High School.

Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.

Realtor sites describe Cobblestone as a gated community. Confirm gate access and any related rules with the association.

No Cobblestone-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.