Winter Garden offers historic and new neighborhoods, residential housing choices and price points.

Some of our newest housing opportunities include:

• Oakland Park is a Castle & Cooke community. Castle & Cooke is an award-winning development company that was founded in 1851 by Samuel Northrup Castle & Amos Starr Cooke. Castle & Cooke is known for creating places where belonging, gathering and connecting with neighborhoods is an everyday event.

Their newest community encompasses approximately 258 acres of land stretching from the shores of Lake Apopka to Oakland Avenue. Oakland Park includes 750 dwelling units that make up a beautiful community designed to foster walkability, giving residents natural opportunities to build relationships that give the sense of belonging to a small town.

Full service marina and union club
Connecting Lake Apopka, West Orange Trail and Oakland Avenue
Five distinctive neighborhoods surrounded by nature, parks and unique places

• Hickory Hammock is being developed by SouthStar Development Partners and the project will have an overall architectural style of Southern Plantation and Old Florida homes. Hickory Hammock encompasses 848 acres of 391 single-family homes, 109 townhomes and acres of marshes, lakes and uplands.
  
  
• 30 new downtown residential lofts and flat units are currently being developed by Downtown Winter Garden LLC. This newest development is in the heart of Winter Garden’s downtown historic district.

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