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
Live inventory
On the market in Windsor Hills

$384,900
3 bd2 ba1,247 sqft
7660 Comrow Street #403
Ventura Windsor Hls P7 · Kissimmee, FL 34747

$345,000
3 bd2 ba1,246 sqft
2821 E Almaton Loop #401
Ventura At Windsor Hills Condo Ph 6 · Kissimmee, FL 34747

$615,000
6 bd3.5 ba2,469 sqft
2648 Daulby Street
Windsor Hills · Kissimmee, FL 34747

$399,000
3 bd3 ba1,440 sqft
7683 Fitzclarence Street
Windsor Hills Ph 02 · Kissimmee, FL 34747

$420,000
3 bd3 ba1,440 sqft
7677 Fitzclarence Street
Windsor Hills Ph 2 · Kissimmee, FL 34747

$319,000
3 bd2 ba1,246 sqft
7664 Comrow Street #101
Ventura At Windsor Hills Condo Ph 7 · Kissimmee, FL 34747

$700,000
6 bd4 ba2,812 sqft
2623 Pawnall Street
Windsor Hills Ph 6 · Kissimmee, FL 34747

$325,000
3 bd2 ba1,450 sqft
2788 Almaton Loop #404
Ventura At Windsor Hills Condo Ph 1 · Kissimmee, FL 34747

$415,000
3 bd2 ba2,314 sqft
10296 Windsor Court
Seven Hills · Spring Hill, FL 34608

$420,000
3 bd3 ba1,440 sqft
7654 Otterspool Street
Windsor Hills Ph 2 · Kissimmee, FL 34747

$240,000
2 bd2 ba1,081 sqft
2785 Almaton Loop #202
Ventura At Windsor Hills Condo Ph 2 · Kissimmee, FL 34747

$615,000
4 bd4 ba1,824 sqft
7743 Comrow Street
Windsor Hills Ph 1 · Kissimmee, FL 34747