Brookshire Heights
Located near the vibrant Downtown Winter Park, this charming community offers easy access to a variety of dining, shopping, and entertainment options. Positioned off Cady Way and Greene Drive, with entrances from Cady Way North, Whitehall Circle South, Darcey Drive West, and Cady Way Trail East, the neighborhood offers a mix of suburban tranquility and urban convenience. Development began in the late 1950s, with the final phase completed in 2017. Homes in the area feature 3 to 7 bedrooms, 1 to 2-car garages, and living spaces ranging from approximately 1,000 square feet to over 5,000+ square feet. Many residences also boast private pools, providing a perfect backyard retreat.
The community is known for its tree-lined streets, sidewalks, and a variety of amenities, including tennis and basketball courts, a community pool, and a clubhouse, offering residents ample opportunities for recreation and relaxation.
Community Highlights
Location: Cady Way and Greene Drive (Entrances from Cady Way North, Whitehall Circle South, Darcey Drive West, and Cady Way Trail East)
Year Built: 1958–2021
Homesites: 360
Square Footage: 989–5,005 sq. ft.
HOA: None
Community Amenities: Tennis court, basketball court, community pool, clubhouse
Nearby Schools (Seminole County Area)
Brookshire Elementary School-0.5 miles
Glenridge Middle School-0.5 miles
Winter Park High School- 1 mile
Dining & Shopping
Publix at University Plaza – 2 miles
Downtown Winter Park – 3 miles
Aloma Square Shopping Center – 2 miles
The Grove at Winter Park – 4 miles
Walmart Supercenter – 4 miles
Winter Park Village (Dining, Shopping & Entertainment) – 4.5 miles
Shoppes at Aloma Walk with Publix – 5 miles
Downtown Orlando – 6 miles
Parks & Recreation
Lake Baldwin Park – 1.5 miles
Phelps Park – 2 miles
Mead Botanical Garden – 4 miles
Goldenrod Park – 3 miles
Interlachen Country Club – 2.5 miles
Howell Branch Preserve Pavilion – 3.5 miles
Amway Center – 2 miles
Ward Park (Sports fields, Cady Way Pool, Wetlands Trail) – <1 mile
Major Attractions
Walt Disney World Resort – 25 miles
Universal Studios – 17 miles
SeaWorld – 22 miles
Hospitals
AdventHealth Winter Park – 1 mile
Orlando VA Medical Center – 1.5 miles
Additional Features: Conveniently located near Full Sail University for those interested in entertainment and media careers, the neighborhood is also close to the Winter Park/Cady Way Bike Trail. The bustling Downtown Winter Park offers a farmers’ market, festivals, museums, and cultural events, providing a dynamic lifestyle for residents.
