Orlando & Kissimmee · 28.33° N
Windsor Hills
The classic Disney-corridor rental resort
Living in Windsor Hills
Windsor Hills is one of the corridor’s proven performers — a gated resort barely 2.5 miles from the Walt Disney World entrance, with a lagoon-style pool, water slides, movie theater, and sports courts. Its two-decade rental track record makes it a favorite for first-time vacation-home investors.
Why buyers choose it
- About 2.5 miles from Walt Disney World
- Lagoon pool with water slides & splash zone
- Established rental history buyers can underwrite
- Condos, townhomes & pool villas
Buying a home in Windsor Hills
Buyers comparing Windsor Hills often begin with the home's intended use, the day-to-day fit of the amenities, and the ownership rules that apply to the community. Live inventory changes quickly, so a current MLS search is only the starting point for a useful comparison.
Our Kissimmee specialists can narrow the options by floor plan, condition, rental suitability where applicable, and the details that affect a Florida purchase after closing. Use the live listings below, then ask us for a practical read on the homes that match your plans.
Comparing nearby areas? Explore Orlando and Kissimmee homes for sale or compare homes for sale near Disney World across the resort corridor.
Live inventory
On the market in Windsor Hills

$379,000
3 bd2 ba1,410 sqft
7654 Comrow Street #205
Ventura At Windsor Hills Condo Ph 8 · Kissimmee, FL 34747

$610,000
5 bd5 ba2,342 sqft
7769 Teascone Boulevard
Windsor Hills · Kissimmee, FL 34747

$419,000
3 bd3 ba1,440 sqft
2592 Maneshaw Lane
Windsor Hills Ph 2 · Kissimmee, FL 34747

$389,999
3 bd2 ba1,410 sqft
7650 Comrow Street #105
Windsor Hills, Ventura At Windsor Hills · Kissimmee, FL 34747

$275,000
2 bd2 ba1,081 sqft
7664 Comrow Street #202
Ventura At Windsor Hills Condo Ph 7 · Kissimmee, FL 34747

$640,000
6 bd4 ba2,812 sqft
2671 Manesty Lane
Windsor Hills Ph 03 · Kissimmee, FL 34747

$585,000
4 bd4 ba1,824 sqft
7747 Teascone Boulevard
Windsor Hills Resort · Kissimmee, FL 34747

$699,900
5 bd5 ba2,494 sqft
7742 Comrow St
Windsor Hills · Kissimmee, FL 34747

$350,000
3 bd2 ba1,450 sqft
2778 Almaton Loop #204
Ventura At Windsor Hills Condo Ph 3 · Kissimmee, FL 34747

$259,999
2 bd2 ba1,081 sqft
2778 Almaton Loop #202
Ventura At Windsor Hills Condo Ph 3 · Kissimmee, FL 34747

$599,900
5 bd5 ba2,494 sqft
7795 Basnett Circle
Windsor Hills Ph 3 · Kissimmee, FL 34747

$338,500
3 bd2 ba1,410 sqft
2784 Almaton Loop #205
Ventura At Windsor Hills Condo Ph 1 · Kissimmee, FL 34747