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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7761 Tosteth St, Kissimmee, Florida 34747

Residential For Sale

EMPIRE NETWORK REALTY
Discover this Stunning Vacation Home or Rental Investment in Windsor Hills Resort, near Disney, just two miles from the entrance! This 6-bedroom, 4-bathroom Brentwood model is the largest floor plan available, offering 2,812 sq. ft. of spacious living.
$710,000
6Bedroom(s)
4Bathroom(s)
2,812

7735 Teascone Blvd, Kissimmee, Florida 34747

Residential For Sale

META ONE REALTY GROUP LLC
STUNNING FULLY FURNISHED 4-BEDROOM, 4-BATH TURNKEY HOME WITH PRIVATE POOL. Located in the highly sought-after gated resort community of Windsor Hills, this exceptional home is just minutes from Disney and offers an incredible opportunity for short-term or long-term rentals, a vacation getaway, or a full-time residence.
$545,000
4Bedroom(s)
4Bathroom(s)
1,878

2621 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

RATIO REAL ESTATE, LLC
Welcome to your ultimate vacation retreat, ideally located just 5 miles from the world-renowned Walt Disney World®! This gorgeous 5-bedroom home sits on a premium corner lot, offering a west-facing front with an unobstructed conservation view. Nestled in the highly sought-after Windsor Hills Resort, this property presents the perfect escape for families or an exceptional investment opportunity.
$639,000
5Bedroom(s)
5Bathroom(s)
2,297

2641 Daulby St, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
Under contract-accepting backup offers. Absolutely amazing!—don’t miss out! Explore this beautifully furnished, renovated and uniquely themed home with Lake View in the sought-after Windsor Hills Resort! Thoughtfully renovated by the current owners to excel in the short-term rental market, this fully furnished, one-level 4-bedroom, 4-bathroom retreat is move-in ready and primed for success.
$589,000
4Bedroom(s)
4Bathroom(s)
1,824

7733 Teascone Blvd, Kissimmee, Florida 34747

Residential For Sale

PREFERRED REAL ESTATE
Under contract-accepting backup offers. VACATION DREAM HOME ... THIS BEAUTIFUL TURNKEY 5 BEDROOM, 5 BATHROOM HOME is located in the very popular guard-gated Windsor Hills Resort. This incredible retreat offers ample space for family & friends to gather and relax. Be blown away as you enter the home with the open floor plan & spacious living area that has just been updated.
$635,000
5Bedroom(s)
5Bathroom(s)
2,297

2615 Pawnall St, Kissimmee, Florida 34747

Residential For Sale

THE PROPERTY FIRM
Highly Desirable Windsor Hills Subdivision – Just 4.5 Miles from Disney! Welcome to Windsor Hills, a premier guard-gated community built by Pulte, known for its luxury and convenience. This fully furnished, turnkey home features one of the best floor plans in the neighborhood with 5 bedrooms and 5 bathrooms.
$650,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
2,494

2549 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

ALLIANCE REAL ESTATE GROUP
Welcome to a completely furnished 5bedroom and 5 bathrooms pool home in the Windsor Hills community resort. This well-decorated home with luxury vinyl planking and tile throughout the house, features a spacious and beautifully furnished living room, where you can relax and unwind with your family and friends.
$640,000
5Bedroom(s)
5Bathroom(s)
2,342

2715 Manesty Ln, Kissimmee, Florida 34747

Residential For Sale

TOP NATION REALTY ADVISORS
High Grossing Rental Opportunity in Windsor Hills! This home in Windsor Hills, which is one of Orlando’s five-star communities close to Walt Disney world which is only 5 minutes away. It sleeps 12-14 people, and it comes fully furnished.
$750,000
6Bedroom(s)
4Bathroom(s)
2,812

2659 Dinville St, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
Under contract-accepting backup offers. Welcome to this breathtaking, fully renovated, turnkey 6-bedroom, 4-bathroom pool home in Windsor Hills. Upon entering, you're greeted by newer flooring that seamlessly enhances the open-concept design and expansive interior. The bright and modern formal dining area flows into a family room bathed in natural light.
$705,000
6Bedroom(s)
4Bathroom(s)
2,812

7731 Comrow St, Kissimmee, Florida 34747

Residential For Sale

CINO INTERNATIONAL INC
This high quality attractive home is situated in exclusive gated community of private resort vacation homes on one of the best lots in the sought after community of Windsor Hills. It's located on the doorstep of Walt Disney World with Universal Orlando, Sea World parks. Shopping and amultitude of restaurants are nearby. This well designed home have major upgrades and improvements.
$645,000
5Bedroom(s)
4Bathroom(s)
2,342

2619 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

TEAM DONOVAN
Escape to your private paradise with this stunning, fully furnished 5-bedroom, 5-bathroom pool home in the highly sought-after guard-gated Windsor Hills Resort community. Perfectly positioned in the community and just minutes from Disney World and all the magic of Orlando, this exceptional property offers an incredible opportunity for vacation home buyers and savvy investors.
$599,950
5Bedroom(s)
5Bathroom(s)
2,297

2615 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

EXP REALTY LLC
Fresh Exterior Paint! This stunning two-story, fully furnished home, located at 2615 Archfeld Blvd in Kissimmee, FL 34747, welcomes you with an impressive Mediterranean-style exterior, featuring a tile roof and elegant architectural details. Inside, the spacious kitchen boasts rich wood cabinetry, granite countertops, and stainless steel appliances, perfect for culinary enthusiasts.
$655,000
6Bedroom(s)
4Bathroom(s)
2,812
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