Windsor Hills Condos for Sale

Windsor Hills Resort Condos: Your Perfect Orlando Investment Property

Experience the best of Orlando vacation rental investing with Windsor Hills Resort’s luxurious condos, located just 2.5 miles from Walt Disney World. These well-appointed 2-bedroom, 2-bathroom units offer investors an excellent entry point into the lucrative Orlando vacation rental market, combining prime location with strong rental potential.

Windsor Hills condos typically range from 1,000 to 1,200 square feet and feature open-concept floor plans that maximize space and comfort. Each unit comes complete with a fully equipped kitchen, washer/dryer, and screened balcony or patio. Modern furnishing packages are available, making it easy to get your investment property ready for immediate rental.

These condos are particularly attractive to budget-conscious families and couples who want luxury accommodation near Disney without the premium price tag. The units’ efficient layouts and resort amenities, including the spectacular lagoon-style pool, tennis courts, and fitness center, make them highly competitive in the rental market.

Investors appreciate Windsor Hills condos for their lower initial investment compared to single-family homes and minimal maintenance requirements. The professional on-site management options ensure hassle-free ownership, while the resort’s guard-gated security helps maintain premium nightly rates.

With Orlando’s year-round tourist demand, condo owners often enjoy high occupancy rates averaging over 70%. The resort’s prime location near major attractions, combined with comprehensive amenities, helps maintain strong rental income throughout the year. Recent sales data shows these units have demonstrated solid appreciation potential, making them an excellent choice for both first-time investors and experienced property owners looking to expand their portfolio in the Orlando vacation rental market.

For those seeking a proven investment in Central Florida’s vacation rental market, Windsor Hills condos offer an attractive combination of location, amenities, and rental potential, all wrapped in an easier-to-manage package compared to larger vacation homes. Contact WindsorHillsProperty.com and Holiday Realty LLC today for investment opportunities.

Search all Condos Currently for Sale in Windsor Hills

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2778 Almaton Loop #302, Kissimmee, Florida 34747

Residential For Sale

LPT REALTY, LLC
Vacation, Invest, Repeat — Your Orlando Getaway That Pays You Back! Welcome to Unit 302 at Windsor Hills, a beautifully updated 2-bedroom, 2-bath condo just minutes from the gates of Walt Disney World.
$349,900
2Bedroom(s)
2Bathroom(s)
1,081Sqft

2784 Almaton Loop #204, Kissimmee, Florida 34747

Residential For Sale

LPT REALTY, LLC
Own the Vacation Lifestyle—And Let It Pay You Back. Welcome to Resort 204A, a smart investment and a relaxing escape all in one. Perfectly situated in the sought-after Windsor Hills community just minutes from Disney, this fully furnished 3-bedroom, 2-bath condo offers everything you want in a Central Florida getaway—plus the potential to generate rental income when you're not using it.
$349,900
3Bedroom(s)
2Bathroom(s)
1,450Sqft

2788 Almaton Loop #202, Kissimmee, Florida 34747

Residential For Sale

ZIRO REALTY
Beautiful resort community of Windsor Hills just minutes to Disney!! This spacious 2 bedroom condo comes fully furnished and is currently being used for short term rental. BRAND NEW AC AND WATER HEATER! Turn-key condo is a perfect blend of comfort, convenience, and investment potential makes is a great choice for vacationers, snow birds, or savy investors.
$315,000
2Bedroom(s)
2Bathroom(s)
1,081Sqft

7650 Comrow St #403, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
In all of Windsor Hills, there is only one corner, penthouse condominium that overlooks the pool and clubhouse... This is the one! This crown jewel delivers the kind of views and lifestyle most people only dream about. Perched on the top floor, this rare 3-bed, 2-bath gives you front-row seats to the best sights in the resort.
$389,900
3Bedroom(s)
2Bathroom(s)
OpenParking(s)
1,246Sqft

2778 Almaton Loop #403, Kissimmee, Florida 34747

Residential For Sale

IMAGINATION REALTY, INC
Welcome to this charming fully furnished 3 bedrooms, 2 bath condo that could be yours! The condo is located on the 4th floor of an elevator building. It has a screened in lanai that has new patio lights and new padded chairs and a coffee table that overlooks a peaceful landscaped view. Beyond the green space is mini golf/tennis and basketball courts.
$349,000
3Bedroom(s)
2Bathroom(s)
1,246Sqft

2785 Almaton Loop #202, Kissimmee, Florida 34747

Residential For Sale

ALL REAL ESTATE & INVESTMENTS
Great opportunity to get in to the Windsor Hills community! This 2-bedroom 2-bathroom condo is fully furnished and ready to rent out or move in! It has convenient elevator access, and it is located less than 2.8 miles from Walt Disney World Resort.
$279,900
2Bedroom(s)
2Bathroom(s)
1,081Sqft

2781 Almaton Loop #105, Kissimmee, Florida 34747

Residential For Sale

ZIRO REALTY
Under contract-accepting backup offers.
$340,000
3Bedroom(s)
2Bathroom(s)
1,410Sqft

2781 Almaton Loop #404, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
Don’t miss your chance to own a turnkey condo in Windsor Hills Resort—one of the most sought-after vacation home communities just minutes from Disney World! This is the largest floor plan available in the resort, offering a more spacious hall bathroom and two primary suites for maximum comfort and flexibility.
$349,000
3Bedroom(s)
2Bathroom(s)
1,450Sqft

7654 Comrow St #104, Kissimmee, Florida 34747

Residential For Sale

LA ROSA REALTY LLC
Under contract-accepting backup offers. Live Your Disney Dream in This Windsor Hills Resort Condo! Picture yourself steps away from a resort-style pool right next to the clubhouse of the prestigious Windsor Hills Resort. This perfectly positioned 3-bedroom, 2-bath condo isn't just a home – it's your ticket to the Florida lifestyle you've always wanted.
$335,000
3Bedroom(s)
2Bathroom(s)
1,410Sqft

2781 Almaton Loop #203, Kissimmee, Florida 34747

Residential For Sale

MARTIN PROPERTY INVESTMENTS REALTY LLC
Cleverly renovated 3-bedroom, 2-bathroom condo with 1,246 square feet of living space located in the highly sought-after Windsor Hills community. This unit is positioned on the second floor at the corner of the building, offering extra windows and light. The condo's Marvel and Disney decorations will definitely attract guests planning to visit Orlando, FL.
$359,000
3Bedroom(s)
2Bathroom(s)
1,246Sqft

2781 Almaton Loop #304, Kissimmee, Florida 34747

Residential Lease For Rent

LOKATION
This is a beautifully 3/2 condo in the popular resort community of Windsor Hills. This highly popular.
$2,400
3Bedroom(s)
2Bathroom(s)
1,450Sqft

7675 Comrow St #204, Kissimmee, Florida 34747

Residential For Sale

HOPKEY REALTY
Step into your fully renovated dream home in the heart of the coveted Windsor Hills community. This Santa Anna floor plan, the largest in the neighborhood, offers 3 bedrooms and 2 bathrooms, combining modern design with spacious comfort. Freshly painted throughout, the condo features spa-like bathrooms with ceramic tile, floating Italian cabinets, and quartz countertops.
$394,000
3Bedroom(s)
2Bathroom(s)
1,450Sqft
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