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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7745 Comrow St, Kissimmee, Florida 34747

Residential For Sale

BRIDGE REALTY GROUP
Beautiful 4-bedroom, 4-bath Pool Home in Premier Windsor Hills Resort – Income-Producing and Fully Furnished. Don't miss this exceptional opportunity to own a high-performing vacation rental in the highly sought-after Windsor Hills Resort, just minutes from Walt Disney World.
$580,000
4Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
1,824Sqft

2648 Daulby St, Kissimmee, Florida 34747

Residential For Sale

EXP REALTY LLC
*MINUTES TO DISNEY!* WINDSOR HILLS RESORT Welcome to one of the rarest floor plans- a beautifully maintained 6-bedroom, 3.
$665,000
6Bedroom(s)
4Bathroom(s)
2,469Sqft

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.
$785,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
2,342Sqft

2605 Daulby St, Kissimmee, Florida 34747

Residential For Sale

GLOBAL FLORIDA REALTY
Lakefront Executive Home Overlooking Lake Reedy ! This Well Maintained Vacation Home Is Offered Fully Furnished, Offers Two Master Suites With 4 Other Bedrooms, With One Of The Bedrooms And Adjacent Bathroom Located On The First Floor.
$739,900
6Bedroom(s)
4Bathroom(s)
2,812Sqft

2609 Dinville St, Kissimmee, Florida 34747

Residential For Sale

EXP REALTY LLC
Under contract-accepting backup offers. Windsor Hills- just minutes to Disney! Check out the entertainment in this busy short term rental! Large home perfect for large families or rental guests. Windsor Hills amenities: lagoon-style pool, waterpark with slides, movie theater, fitness center, clubhouse, playgrounds, RV parking.
$668,000
6Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
2,812Sqft

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

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.
$709,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft

7719 Comrow St, Kissimmee, Florida 34747

Residential For Sale

TEAM DONOVAN
Your Windsor Hills Dream Home Awaits! Fully Furnished 4-Bedroom Oasis Steps from Resort Amenities. Envision your family enjoying the magic of Central Florida from this exceptional, fully furnished 4-bedroom, 4-bathroom residence at 7719 Comrow Street, nestled within the highly sought-after, guard-gated Windsor Hills Resort.
$549,950
4Bedroom(s)
4Bathroom(s)
1,824Sqft

2543 Holtrock St, Kissimmee, Florida 34747

Residential For Sale

HOUSE PROUD REALTY
In a prime location for all Central Florida has to offer, this extremely spacious 6-bedroom, 4 bath home is spread across two levels and features a multitude of relaxation and dining spaces! As you enter the home you are welcomed into a formal living and dining area where you can entertain guests or use as a secondary dining space for large families or multiple families on vacation.
$695,000
6Bedroom(s)
4Bathroom(s)
2,812Sqft

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)
2,812Sqft

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

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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