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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7763 Tosteth St, Kissimmee, Florida 34747

Residential For Sale

CINDEE T LAVY
Stunning 6-Bedroom Home Just 5 Minutes from Walt Disney World! Welcome to this beautiful and spacious residence located in the highly sought-after Windsor Hills Resort, a premier 24-hour guard-gated community just minutes from the magic of Walt Disney World.
$629,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft
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2669 Manesty Ln, Kissimmee, Florida 34747

Residential For Sale

RATIO REAL ESTATE, LLC
Welcome to your ultimate vacation retreat—ideally situated just 5 miles from the world-renowned Walt Disney World®! This stunning 6-bedroom, 4-bathroom home sits on an elevated premium corner lot in the highly sought-after Windsor Hills Resort, offering exceptional privacy and unobstructed backyard views.
$729,900
6Bedroom(s)
4Bathroom(s)
2,812Sqft
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2616 Bowring St, Kissimmee, Florida 34747

Residential For Sale

ORLANDO REGIONAL REALTY
Book your Appointment now! Welcome to this well maintained pool home, perfectly situated on one of the most private streets in the highly desirable Windsor Hills Community. With a strong history as a short-term rental and future bookings already in place, this property is both a charming retreat and a smart investment.
$625,000
5Bedroom(s)
5Bathroom(s)
2,342Sqft
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7751 Tosteth St, Kissimmee, Florida 34747

Residential For Sale

TEAM DONOVAN
Welcome to 7751 Tosteth Street, a beautifully maintained and updated 6-bedroom, 4-bathroom pool home in Windsor Hills Resort's highly sought-after guard-gated community. This fully furnished property represents a perfect turnkey opportunity for investors or short-term rental owners, ideally just minutes from Walt Disney World and Central Florida’s world-class attractions, dining, and shopping.
$659,999
6Bedroom(s)
4Bathroom(s)
2,812Sqft
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2648 Daulby St, Kissimmee, Florida 34747

Residential For Sale

EXP REALTY LLC
BEST PRICED 6 BED - WINDSOR HILLS RESORT *MINUTES TO DISNEY!* Roof- 2023 HVAC-2017 Water Heater-2024 Pool Pump-2017 Updates kitchen, bathroom, flooring-2022 Welcome to one of the rarest floor plans- a beautifully maintained 6-bedroom, 3.
$649,999
6Bedroom(s)
4Bathroom(s)
2,469Sqft
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2624 Daulby St, Kissimmee, Florida 34747

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
Sunshine Villa, unrivaled short-term rental opportunity in Windsor Hills Resort. Sunshine Villa is a unique opportunity in Windsor Hills, the sought-after resort community in the Disney corridor.
$680,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
2,342Sqft
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7790 Teascone Blvd, Kissimmee, Florida 34747

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
Welcome to 7790 Teascone Blvd!Discover the charm of this beautifully maintained home in the desirable Windsor Hills community. With 5 spacious bedrooms and 5 bathrooms, this residence offers ample space for relaxation and entertainment.
$740,000
5Bedroom(s)
5Bathroom(s)
2,297Sqft
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2530 Holtrock St, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
Welcome to this stunning, fully renovated 6-bedroom, 4-bathroom pool home in the highly sought-after Windsor Hills community. This turnkey property sits on a rare, oversized corner lot just over ¼ acre and offers exceptional upgrades throughout. As you step inside, you're greeted by updated flooring that flows seamlessly through the open-concept layout.
$699,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft
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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)
2,342Sqft
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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)
2,812Sqft
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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
More Details

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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