Passing the picturesque shore of Lake Brim, the West Orange Trail entices residents to explore the outdoors—whether walking, jogging, biking or simply meeting friends. This landmark amenity delivers access to 22 miles of walkways, trails and preserved wetlands, while connecting residents to nature, local shopping (including the nationally heralded Farmers Market), dining, culture and entertainment in charming Winter Garden.

or pool, or lake, or trail.

Grassy areas, open spaces, pools, trails, and pristine Lake Brim mark our community’s canvas like a colorful paintbrush. The Meadowmarsh Park and Pool offers a civic space for fields, pathways, and playgrounds, while a linear park connects Lake Apopka to the West Orange Trail and Lake Brim. These natural community landmarks create remarkable spaces for neighbors to meet, connect and enjoy.

kick back at The Clubhouse

Designed to be a gathering place for all, The Clubhouse at Oakland Park is the perfect location for reunions, holiday parties or quiet time to finish up the last chapter of a book, complete with a catering kitchen, a private conference room and comfortable seating for dozens. The Clubhouse is also home to the Oakland Park Lifestyle Director and a backdrop for community activities and events. The nearby pool, playground, fire pit and pavilion complete a seamless blend of nature and architectural charm. Residents will come to think of The Clubhouse as an extension of their own living room.

Countless amenities just outside your door…

The Clubhouse – Centrally located within the community; Certified Green by FGBC; 3330 SF of conditioned space in the main building; Open Community Clubroom; Thoughtfully decorated with furniture selected for multiple uses/configurations;  233 SF conference room; Fully equipped state of the art open kitchen with large island; Gas Fireplace inside; Firepit outside overlooking Eagle Pond

Clubhouse Pool – 3313 SF, Zero entry, center island, shooting fountains

Clubhouse Playground – Kompan designed and manufactured; encourages imagination and creative play; Unique slide on hill

Eagle Pond Walking Trail – Gravel path surrounding the pond with short dock extending over water

Climbing Tree – Behind Clubhouse by Eagle Pond — Fallen tree moved and repurposed as climbing structure

Meadowmarsh Pool – Completed in 2013. Restrooms, covered area, showers, pergolas; 1882 SF

Meadowmarsh Park – Large open areas, infant swings, swings, climbing arch, riding apparatuses

 Quesinberry Oak – Dedicated to Jack Quesinberry, Mayor of COWG from 1991-2008 (WG’s longest serving mayor)

Lake Brim – Walking trail around the lake, connects to WOT; fishing pier extends over water

Community Garden –  Consists of fourteen raised bed planters. Each bed has a drip irrigation system; the garden is fenced and includes a tool storage area. Planter beds are rented to homeowners through the HOA.

Eastshore – Gravel walking path on shore of Lake Apopka

Westshore – Gravel walking path on shore of Lake Apopka

Union Park – Screened pavilion over looking Lake Apopka with picnic tables and ceiling fans

Reciprocity Park – Kompan sliding board structure

Oak Grove Lawn – Open green spaces for impromptu kickball, soccer, etc. games

North Lawn – Open green spaces for impromptu kickball, soccer, etc. games

 South Lawn – Open green spaces for impromptu kickball, soccer, etc. games

North Mews – Open green spaces for impromptu kickball, soccer, etc. games

South Mews – Open green spaces for impromptu kickball, soccer, etc. games

 Allenhurst Park – Open green spaces for impromptu kickball, soccer, etc. games

Kershaw Park – Open green spaces for impromptu kickball, soccer, etc. games

Walkway to Tildenville Elementary School – Provides easy connection to Tildenville School Road and Tildenville Elementary School

Mail Kiosks – Tastefully designed to blend in with architecture and located throughout Oakland Park for convenient mail pickup

West Orange Trail – 22 mile trail through the middle of Oakland Park, connecting to Winter Garden, Town of Oakland and beyond.

Phase 3 Round Park – Large green space between beautiful Live Oaks with tree swing

Gator Bench – Phase 3 – Repurposed tree stump, handcrafted into bench featuring gators, turtles, OP logo

Golf Cart Accessability – Travel by golf cart between Oakland Park and Winter Garden (Map)