City of Winter Garden, FL

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A charming little city with a juicy past

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Shop Local September Sidewalk Sale

Event Date: Thursday, September 27 – Saturday, September 29
Event Time: 11:00 am – 5:00 pm

The Shop Local September Sidewalk Sale is the first of several events scheduled for the fall to promote supporting local businesses as part of the Shop Small national campaign. Shoppers can reap the benefits of special sales while enjoying the sights of historic downtown and sounds of outdoor live musical performances.

For list of participating merchants and special discounts, plus live music schedule, please visit the event’s Facebook page.


Important Road Construction Announcements

Roundabout at Stoneybrook West Parkway / Windermere Road / Roberson Road
NOTE: Starting Sept. 9 there will be traffic pattern change at this intersection
A roundabout is being constructed at this intersection, along with the installation of drainage improvements, utility relocations, and signing and pavement marking improvements. The project is scheduled to be completed in the spring of 2019. Normal working hours will be 7:00 am to 5:00 pm, Monday through Friday, although some operations (i.e. paving, etc.) may need to occur at night when there is less traffic.


Entrance Ramp Widening Project (from CR 535 / Winter Garden Vineland Road to the northbound SR 429) – This project, which runs from CR 535 to the Stoneybrook West Parkway overpass, is expected to improve traffic flow with the additional entrance ramp lane. Work began in late March 2018 and is expected to be completed in Fall 2018. Click HERE for more details.

UPDATE: The entrance ramp to northbound SR 429 at CR 535 and Stoneybrook West Parkway, as well as a single lane on northbound SR 429 near the ramp, are scheduled to be closed from 10 p.m. Thursday, September 20 to 6 a.m. Friday, September 21 for paving. Click HERE for the detour map. Minor delays are possible. Bad weather and other unforeseen circumstances could delay or prolong work. Motorists are urged to use caution in the construction area for their safety and that of the work crews.



Click Here for Road Construction and Closure Announcements

Roundabout at Stoneybrook West Parkway / Windermere Road / Roberson Road – NOTE: Starting Sept. 9 there will be traffic pattern change at this intersection - A roundabout is being constructed at this intersection, along with the installation of drainage improvements, utility relocations, and signing and pavement marking improvements. The project is scheduled to be completed in the spring of 2019. Normal working hours will be 7:00 am to 5:00 pm, Monday through Friday, although some operations (i.e. paving, etc.) may need to occur at night when there is less traffic.


Entrance Ramp Widening Project (from CR 535 / Winter Garden Vineland Road to the northbound SR 429) – This project, which runs from CR 535 to the Stoneybrook West Parkway overpass, is expected to improve traffic flow with the additional entrance ramp lane. Work began in late March 2018 and is expected to be completed in Fall 2018. Click HERE for more details.

UPDATE: The entrance ramp to northbound SR 429 at CR 535 and Stoneybrook West Parkway, as well as a single lane on northbound SR 429 near the ramp, are scheduled to be closed from 10 p.m. Thursday, September 20 to 6 a.m. Friday, September 21 for paving. Click HERE for the detour map. Minor delays are possible. Bad weather and other unforeseen circumstances could delay or prolong work. Motorists are urged to use caution in the construction area for their safety and that of the work crews.


Weekly Street Closure for the Farmers Market - Lakeview Avenue from Plant Street to the northern entrance of the Parking Garage and Tremaine Street from Highland Avenue to Boyd Street is closed every Saturday from 6:30 am until 3:30 pm. The Pavilion area is also reserved every Saturday from 6:30 am until 3:30 pm.


Quarterly Street Closure for the Cruz N Car Show - Plant Street from Woodland Avenue to Central Avenue is closed for the Car Show from 3:30 pm until 9:00 pm on the following dates – January 20, April 21, June 16 and September 15.




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