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.

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2508 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

CGY REALTY
NEW PRICE - 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.
$650,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft
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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.
$629,900
5Bedroom(s)
5Bathroom(s)
2,297Sqft
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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.
$629,900
5Bedroom(s)
5Bathroom(s)
2,342Sqft
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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)
2,812Sqft
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7735 Teascone Blvd, Kissimmee, Florida 34747

Residential For Sale

META ONE REALTY GROUP LLC
**PRICE TO SELL!!! 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.
$520,000
4Bedroom(s)
4Bathroom(s)
1,878Sqft
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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)
2,494Sqft
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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.
$629,999
5Bedroom(s)
5Bathroom(s)
2,342Sqft
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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.
$735,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft
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2609 Archfeld Blvd, Kissimmee, Florida 34747

Residential For Sale

REAL BROKER, LLC
Under contract-accepting backup offers.
$745,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft
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2673 Manesty Lane, Kissimmee, Florida 34747

Residential For Sale

CHAMPION HOMES
If you are looking for resort style living then look no further than this beautiful 6 bedrooms/3.5 bathrooms 2-story Turn-Key home located in the gated community of Windsor Hills Resort, Kissimmee. Although it is currently a very popular short term rental vacation home, it would also make an ideal family home.
$649,999
6Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
2,469Sqft
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