Where is Brookshire Heights in Winter Park?

Brookshire Heights is an established residential neighborhood in the Cady Way and Greene Drive area of Winter Park, Florida. Nearby recreation includes public parks and the Cady Way Trail. Use the map above for neighborhood context, then check routes from each property's address to the places you would visit regularly.

What types of homes are for sale in Brookshire Heights?

Brookshire Heights has an established single-family setting, with development beginning in the late 1950s and later construction also represented. Homes vary in age, layout, condition and updates. Compare each listing's details rather than expecting a uniform style or specification across the neighborhood.

How can I compare prices for Brookshire Heights homes for sale?

Start with the current listings and market snapshot above to see available homes and the median asking price. Asking prices alone do not establish a home's value. Compare the individual properties' size, layout, condition, updates and outdoor space. Tell us your budget and priorities, and we can help you narrow your shortlist.

Which schools serve a Brookshire Heights address?

Check elementary, middle and high school assignments through Orange County Public Schools using the property's address and the applicable school year. Brookshire Elementary, at 2500 Cady Way, is a local landmark, but proximity does not establish enrollment eligibility. Confirm assignments for each home rather than relying on a neighborhood-wide assumption.

Does buying a home include access to nearby recreation facilities?

The nearby parks, courts, Cady Way Pool and Winter Park Pines Golf Club are public municipal facilities, not a Brookshire Heights residents-only amenity package. Buying a home does not itself include pool access or golf privileges. Check each facility's current access arrangements and any applicable fees separately.

Do Brookshire Heights homes have private pools or garages?

Private pools, garages and carports are property-specific features, not neighborhood standards. Check the individual listing and confirm details during a viewing. If a pool or covered parking is essential, tell us early so we can focus your shortlist and help you identify questions about condition and maintenance.

Illustrative Central Florida residential street with varied single-family homes, green lawns and mature shade trees in natural daylight.

Winter Park, Florida

Brookshire Heights Homes for Sale

Browse Brookshire Heights homes for sale. Compare renovations, outdoor space and Cady Way recreation to focus your shortlist.

Established Homes with Individual Character

We help you compare Brookshire Heights homes for sale around Cady Way and Greene Drive in Winter Park. The established single-family setting includes different construction periods, original layouts and renovated homes. We weigh condition and completed improvements with outdoor space, pools or garages where present, then compare the route to Cady Way recreation with your routine.

Explore the wider Winter Park neighborhood guide for other settings.

Homes for Sale in Brookshire Heights

4 listings

View Brookshire Heights homes for sale

Top Villas Intelligence

Review available property reports, ownership costs and nearby-sale comparisons. Report availability varies by home.

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Gross rental revenue

$118,400

74% projected occupancy

Breaks even at 27% occupancy

Annual income and costs

Gross rental revenue$118,400
Booking commission (18%)−$21,300
HOA and CDD fees−$9,800
Property tax−$11,200
Insurance−$6,400
Utilities and upkeep−$7,800
Operating income$61,900

Price per sq ft against nearby sales

8% below nearby sales

MedianThis home

$240$340

Operating income

$61,900

Operating yield

7.2%

Operating income

$61,900

per year

This home

$268 /sq ft

High confidence

Fixed ownership costs

$35,200

Nearby median

$292 /sq ft

Browse Brookshire Heights properties by price

Search price ranges within this area while keeping the property criteria for this page.

Recent sales near Brookshire Heights

58 properties sold within half a mile in the last 12 months · median $630,000

See all sold

624 Fitzwalter Drive
3 bed · 2 bath · 1,335 sqft
$545,000
Sold Oct 23, 2026
2332 Sherbrooke Road
4 bed · 3 bath · 1,842 sqft
$540,000
Sold Oct 22, 2026
410 Saint Dunstan Way
3 bed · 2 bath · 1,512 sqft
$525,000
Sold Oct 15, 2026
744 Cornwall Road
4 bed · 2 bath · 1,968 sqft
$610,000
Sold Sep 25, 2026

Brookshire Heights Market Snapshot

See current public sale inventory and median asking price as you begin comparing homes in Brookshire Heights.

For sale now: 4
Median asking price: $850,000

Brookshire Heights Closed Sales: July–September 2026

The mapped Brookshire Heights search area recorded 6 completed sales from July through September 2026. The median closed price was $937,500, and the median time on market was 14 days. These are completed-sale measures, separate from the live asking prices above. Different home sizes, conditions and locations can materially change an individual property's value.

Source: Top Villas Realty area sales snapshots, three months ending September 2026; retrieved 29 October 2026. All property types within this page's mapped search area are included.

Brookshire Heights Location Map

Explore Brookshire Heights in Winter Park, then compare each home's routes to Cady Way recreation, shopping and everyday destinations.

Public Recreation Near Brookshire Heights

These nearby public facilities support everyday recreation, rather than forming a residents-only amenity package included with your home.

Parks, Playgrounds and Sports Fields
Adjoining Ward Park, Cady Way Park and Showalter Field form a municipal recreation complex with playgrounds and sports fields for time outdoors.
Tennis and Pickleball
Nearby public tennis and pickleball facilities give you options for regular exercise and social games beyond your own backyard.
Swimming at Cady Way Pool
Cady Way Pool provides a nearby public swimming option. Consider how its access arrangements would fit the routine you want in your next home.
Winter Park Pines Golf Club
This separate municipal golf facility has an 18-hole course, driving range, putting green and chipping area. Homeownership does not include golf privileges.

Walking and Cycling on the Cady Way Trail

The 6.5-mile Cady Way Trail gives you a local option for making walking and cycling part of an ordinary week. Its mapped route includes Cady Way Park, the pool and Baldwin Park, with a connection toward the Cross Seminole Trail. For a prospective owner, the useful question is how comfortably you could reach and use the trail from a particular home. Compare access points and the route from each address rather than assuming direct frontage or the same walking time throughout Brookshire Heights. If regular rides or walks are important to you, exploring that connection during a neighborhood visit can help you weigh trail access alongside the home's own features.

Shopping and Dining Around Winter Park

Winter Park's shopping and dining districts serve different parts of your weekly routine. Park Avenue is a walkable shopping destination, suited to browsing several stops once you arrive. Hannibal Square has a dining-oriented character, while Aloma Corners provides a more locally focused convenience-shopping option. When comparing homes in Brookshire Heights, consider which of these places you would use regularly and how you would reach them from each address. Walkability within Park Avenue does not mean every neighborhood home is within walking distance of it. Visiting the surrounding areas alongside a property viewing can help you assess the location in practical terms, from routine errands to an evening out, rather than judging the home in isolation.