Located close to exciting Downtown Winter Park, with its sidewalk cafes, unique shops, and entertainment options, Brookshire Heights is a community in Winter Park with single-family homes for sale. The community is located off Cady Way and Greene Drive, with entrances off Cady Way to the north, Whitehall Circle to the south, Darcey Drive to the west, and Cady Way Trail to the east.

Brookshire Heights Homes for Sale

New

2498 Whitehall Circle

$775,000

WINTER PARK

MLS® # O6196765

4 Beds, 2 Baths, 2,241 Sf

Pending

2358 Whitehall Drive

$650,000

WINTER PARK

MLS® # O6196213

4 Beds, 3 Baths, 2,407 Sf

Pending

2260 Coldstream Drive

$525,000

WINTER PARK

MLS® # O6177655

4 Beds, 2 Baths, 1,509 Sf

The first phase of this large and lovely community was built back in the late-1950s with the last phase built in 2017. Homes here feature 3 to 7 bedrooms with 1 to 2-car garages and carports and between approximately 1,000 square feet to over 5,000+ square feet of living space. Towering, mature trees, and sidewalks line the streets, making it a perfect setting for a leisurely neighborhood stroll. Many homes have added private outdoor pools, making backyards a great escape.

There are several community parks within a short distance of Brookshire Heights. Ward Park, which features public sports fields, Cady Way Pool, and a wetlands trail, is under 1 mile away. The Winter Park/Cady Way Bike Trail is also within a few miles drive. Residents can also explore the many activities in Downtown Winter Park, from a farmers’ market to festivals and concerts, to museums and cultural experiences.

In addition, Brookshire Heights is conveniently located close to shopping and dining. For those who have students wanting to pursue a career in media and entertainment, Full Sail University is nearby.

Call us today to find out more about Brookshire Heights.

Brookshire Heights Community Information

• Location: Cady Way and Greene Drive, with entrances off of Cady Way North, Whitehall Circle South, Darcey Drive West, and Cady Way Trail to the East.
• Number of Homesites: 360
• Year Built: 1958 to 2021
• Square Footage: 989 to 5,005 square feet
• HOA: No
• Community Amenities: tennis court, basketball court, community pool and clubhouse

Seminole County Area Schools

• Brookshire Elementary School: Grades K – 5th – Distance: 0.5 mile
• Glenridge Middle School: Grades 6th – 8th – Distance: 0.5 mile
• Winter Park High School – Grades 9th – 12th – Distance: 1 mile

Dining and Shopping

• University Plaza with Publix Grocery Store – Distance: 2 miles
• Downtown Winter Park - Distance: 3 miles
• Aloma Square Shopping Center – Distance: 2 miles
• The Grove at Winter Park – Distance: 4 miles
• Walmart Supercenter – Distance: 4 miles
• Shoppes at Aloma Walk with Publix Grocery Store – Distance: 5 miles
• Kohls – Distance: 5 miles
• Downtown Orlando – Distance: 6 miles
• Winter Park Village with Dining, Shopping & Entertainment - Distance: 4.5 miles

Parks and Recreation

• Lake Baldwin Park – Distance: 1.5 miles
• Phelps Park – Distance: 2 miles
• Branch Tree Park – Distance: 2 miles
• Amway Center – Distance: 2 miles
• Mead Botanical Garden - Distance: 4 miles
• Goldenrod Park – Distance: 3 miles
• Interlachen Country Club - Distance: 2.5 miles
• Howell Branch Preserve Pavilion – Distance: 3.5 miles
• Walt Disney World Resort: Distance: 25 miles
• Universal Studios – Distance: 17 miles
• SeaWorld – Distance: 22 miles

Hospitals

• AdventHealth Winter Park – Distance: 1 mile
• Orlando VA Medical Center - Distance: 1.5 miles

*Distances are approximately measured from the main entrance to the Brookshire Heights subdivision.