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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7783 Basnett Cir, Kissimmee, Florida 34747

Residential For Sale

CHARLES RUTENBERG REALTY ORLANDO
Beautiful – Fun – A True Turnkey Short Term Rental Vacation Home. This home was completely renovated in 2022. During the renovation, the home was professionally decorated with hand-painted décor in the Avengers theme game room and in the Harry Potter and the Star Wars theme bedrooms. Luxury vinyl plank has been installed in all bedrooms and living areas. There is no carpet in the home.
$695,000
6Bedroom(s)
4Bathroom(s)
2,869

7751 Basnett Cir, Kissimmee, Florida 34747

Residential Lease For Rent

GRAND REALTY
Gorgeous fully furnished and turn-key screened pool & Spa home in awesome location!!! Just 1.4 miles from Walmart Super-Center Lake Wilson, 10" drive to Walt Disney World Resort Theme Parks, less than 10" drive to Margaritaville Resort - Water Park & Shopping areas. Plenty of family world-class entertainment options and major retail shopping with national-recognized anchors.
$3,000
6Bedroom(s)
4Bathroom(s)
GuestParking(s)
2,812

2631 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

NEXTHOME LOCATION
Welcome to this pristine 5/5 in Windsor Hills, one of the most preferred locations for Disney visitors. This spacious, fully furnished, two-story villa has beautiful wooden floors throughout the ground floor area. With a spacious living room, open dining area and breakfast nook providing plenty of living space for the entire family.
$639,900
5Bedroom(s)
5Bathroom(s)
2,342

2548 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
This stunning 6-bedroom, 4-bath POOL+SPA home is located in the highly sought-after Windsor Hills Resort. Enjoy ultimate relaxation by the private, south-facing pool and spa, complete with a spacious lanai and a privacy wall for added seclusion.
$670,000
6Bedroom(s)
4Bathroom(s)
2,812

2508 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

CGY REALTY
Don’t miss out on this fantastic 6-bedroom, 4-bathroom single-family home located in the sought after gated Windsor Hills community. Perfectly designed for either a primary residence or investment property this home has it all. With a private screened-in pool and spa, it provides the ideal place to relax after a hard day at either work or the Theme Parks that are located close by.
$685,000
6Bedroom(s)
4Bathroom(s)
2,812

2683 Manesty Ln, Kissimmee, Florida 34747

Residential For Sale

GLOBAL REAL ESTATE SERVICES IN
TURNKEY VACATION HOME & INVESTMENT OPPORTUNITY IN WINDSOR HILLS! This fully furnished 5-bedroom, 5-bathroom home in the highly sought-after Windsor Hills Resort is a prime short-term rental property, just minutes from Orlando’s world-famous theme parks, shopping, and dining.
$640,000
5Bedroom(s)
5Bathroom(s)
2,297

7759 Basnett Cir, Kissimmee, Florida 34747

Residential For Sale

KELLER WILLIAMS REALTY SMART 1
Under contract-accepting backup offers.
$624,999
6Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
2,812

7709 Comrow St, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
Welcome to your ultimate vacation retreat, just 5 miles from the world-famous Walt Disney World! This stunning 5-bedroom POOL and SPA home offers exceptional privacy with no rear neighbors and overlooks the resort’s sports complex—featuring tennis, basketball, and pickleball courts—along with a beautiful recreation area.
$659,000
5Bedroom(s)
5Bathroom(s)
2,342

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.
$530,000
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

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.
$649,999
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
2,494
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