Windsor Hills Homes for Sale

Discover Windsor Hills Resort: Your Premier Investment Opportunity in Kissimmee, Florida

Windsor Hills Resort stands as one of the most sought-after communities for vacation rental properties, located just 2.5 miles from Walt Disney World. This guard-gated resort community offers investors a range of properties designed to maximize rental potential while providing guests with an exceptional Orlando vacation experience.

Property Options:

From cozy 2-bedroom condos to spacious 6-bedroom homes, Windsor Hills caters to various guest group sizes and investment budgets. The condos, typically ranging from 1,000 to 1,200 square feet, offer excellent entry points for investors, appealing to smaller families and couples seeking affordable luxury near Disney. Townhomes feature 3 bedrooms across 1,500 square feet, providing a perfect middle ground with private garage parking and multiple bathrooms.

The resort’s crown jewels are its single-family homes, available in 4, 5, and 6-bedroom configurations. These properties, ranging from 2,000 to 3,500 square feet, feature private pools, game rooms, and themed children’s bedrooms – amenities that command premium nightly rates and maintain high occupancy levels throughout the year.

Investment Appeal:

Windsor Hills properties consistently rank among the top-performing vacation rentals in Central Florida for several reasons:
– Prime location minutes from Disney World, Universal Studios, and other major attractions
– Resort-style amenities including a lagoon-style pool with water slide, movie theater, fitness center, and sports facilities
– Guard-gated security providing peace of mind for both owners and guests
– Professional on-site management options
– Strong year-round rental demand due to Orlando’s constant tourist flow
– Potential for significant rental income with occupancy rates often exceeding 70%

Guest Experience:

Vacation rentals in Windsor Hills offer visitors substantial savings compared to Disney resort hotels while providing more space and home-like amenities. Families particularly appreciate the fully equipped kitchens, private pools, and multiple bedrooms that allow everyone to spread out comfortably. The resort’s location enables guests to quickly return for mid-day breaks from the parks, making it especially attractive for families with young children.

For investors, Windsor Hills represents a proven vacation rental market with established rental histories and strong appreciation potential. The variety of property sizes allows investors to match their investment goals with the right property type, while the resort’s reputation and amenities help maintain consistent bookings throughout the year. Contact Holiday Realty LLC for purchase opportunities and detailed property analysis.

Search all Windsor Hills Homes Currently for Sale

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7716 Teascone Blvd, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
South-facing pool home ideally located just a short walk from the Windsor Hills Clubhouse and directly across from a playground. A new roof was installed in 2020. This well-maintained Spencer Model offers 5 bedrooms and 5 bathrooms, a dedicated game room, and a private swimming pool with spa, making it perfect as a personal vacation retreat or a high-performing short-term rental property.
$649,000
5Bedroom(s)
5Bathroom(s)
2,297Sqft

7772 Basnett Cir, Kissimmee, Florida 34747

Residential For Sale

FLORIDA CONNEXION PROPERTIES
Great opportunity to own a Renovated Stunning 6-bedroom (2 Master Suites), 4-bathroom vacation home located in Windsor Hills Resort! With its spacious, open layout and luxurious amenities, this home provides the ideal setting for a relaxing and exciting vacation.
$750,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft

2619 Daulby St, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
LAKEFRONT HOME! New Roof 2023. Welcome to your ultimate vacation retreat just 5 miles from world-famous Walt Disney World. This stunning 5-bedroom, 5-bath pool and spa home offers exceptional privacy and breathtaking views overlooking Reedy Lake.
$700,000
5Bedroom(s)
5Bathroom(s)
2,342Sqft

2607 Daulby St, Kissimmee, Florida 34747

Residential For Sale

FATHOM REALTY FL LLC
Can you say CASH COW?? Unbelievable investment opportunity in the highly sought after WINDSOR HILLS COMMUNITY!! This property has proven rental history with a Superhost well over $100,000 annually with reservations on the books for 2026!! Why not supplement your income with this PROVEN income producing slice of heaven situated just 5 minutes from Disney? Windsor Hills amenities are hard to beat wi
$849,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft

7768 Basnett Cir, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
This beautifully updated, turnkey single-level pool home stands out as one of the finest offerings in Windsor Hills.
$610,000
4Bedroom(s)
4Bathroom(s)
1,824Sqft

2619 Pawnall St, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
This beautifully updated, turnkey vacation single-level POOL home —enhanced by over $75K in recent upgrades—stands out as one of the finest in Windsor Hills. Just two miles from Walt Disney World’s main gates, this meticulously renovated four-bed, four-bath villa features four true en-suite bedrooms, including two primary king suites with private baths.
$610,000
4Bedroom(s)
4Bathroom(s)
1,824Sqft

7757 Basnett Cir, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
This beautifully updated 6-bedroom, 3.5-bath vacation home stands out with more than $150,000 in recent renovations and upgrades, offering an exceptional turnkey opportunity in the popular gated Windsor Hills Resort—just minutes from Disney.
$695,000
6Bedroom(s)
4Bathroom(s)
2,469Sqft

2708 Manesty Ln, Kissimmee, Florida 34747

Residential For Sale

LPT REALTY, LLC
Discover the ideal blend of comfort, space, and resort-style living in this beautifully designed 5-bedroom, 3.5-bath pool home located in one of Kissimmee’s most desirable gated resort communities.
$610,000
5Bedroom(s)
4Bathroom(s)
2,469Sqft

7730 Teascone Blvd, Kissimmee, Florida 34747

Residential For Sale

REAL BROKER, LLC
***TOP PRODUCING RENTAL HOME IN WINDSOR HILLS RESORT*** Come see this TASTEFULLY FURNISHED & THEMED home in beautiful WINDSOR HILLS RESORT! This home has been optimized to stand out in the short-term rental market and is ready to hit the ground running for the new owner!! This home did just over $110,000 in bookings in 2023-2024! This home has a proven track record of successful rentals and future
$649,800
6Bedroom(s)
4Bathroom(s)
2,469Sqft

2693 Manesty Ln, Kissimmee, Florida 34747

Residential For Sale

ORLANDO REGIONAL PROPERTY MANAGEMENT
This Stunning, fully renovated, turnkey 6-bedroom, 4-bathroom pool home is located in the highly sought-after resort community of Windsor Hills. From the moment you enter, you're greeted by updated flooring that complements the open-concept layout and spacious interior. The bright and modern formal dining room flows seamlessly into a family room filled with natural light.
$689,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft

2703 Manesty Ln, Kissimmee, Florida 34747

Residential For Sale

IN TOUCH REAL ESTATE LLC
Explore this beautifully furnished, updated and Disney themed home in the sought-after Windsor Hills Resort by clicking on the virtual tour! Thoughtfully renovated to excel in the short-term rental market, this fully furnished, 4-bedroom, 4-bathroom retreat is rent ready, and booking will transfer at settlement. This home features a wall of windows to bring the outdoors in.
$590,000
4Bedroom(s)
4Bathroom(s)
1,824Sqft

7763 Tosteth St, Kissimmee, Florida 34747

Residential For Sale

CINDEE T LAVY
Beautiful 6-Bedroom Home Just 5 Minutes from Walt Disney World! Discover this spacious, beautifully maintained home in the sought-after Windsor Hills Resort, a premier 24-hour guard-gated community just minutes from Disney. Perfect as a vacation retreat, rental investment, or full-time residence, this property offers exceptional value and an unbeatable location.
$629,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft
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