
Windsor Hills homes for sale
Discover a super range of homes for sale in this well-placed Kissimmee Resort

Invest in Windsor Hills Resort - the closest vacation rental community to Disney
Located under 2 miles from Disney World, Windsor Hills Resort in Kissimmee offers an unbeatable location for classic Orlando vacations and effortless resort living.
Designed for fun multigenerational stays, Windsor Hills Resort is home to an incredible new waterpark, sports facilities and much more!
Within the secure-gated community, a selection of property types offers a feasible way to buy into this classic Florida resort. In fact, the range of Windsor Hills homes for sale appeals to all stages of property ownership. From modest 2 to 3-bed condos to larger 5-bed family homes and contemporary 7-bed deluxe homes, this short-term rental community is a sound investment choice.
What's more, Windsor Hills is strategically placed for reaching the best of Orlando and the wider Florida state. Just take the surrounding golf courses for example. Located in the heart of Florida golf country, the resort enjoys proximity to a plethora of first-class courses. Its closest is Mystic Dunes, just 6 minutes' drive away.
Aside from the easy-to-reach world-class theme parks and Orlando attractions, the Space Kennedy Center is 70 minute's drive away, whilst the pristine Gulf Coast beaches are 1.5-hrs drive away.
Our Realtors will be happy to answer any inquiries, as well as show you around available Windsor Hills Resort homes for sale.
Windsor Hills Homes for sale




Take a look at our Windsor Hills Resort Homes for sale
Modestly priced compared to further-away neighbors, Windsor Hills Resort offers a feasible way to buy into the world-class Orlando lifestyle.
Explore a world of choice here. From a fully optimized 7-bedroom resort home with private pool cage to a 2-bed resort condo in need of refurbishment - Windsor Hills offers a wealth of options for the savvy Orlando investor.
Within the resort you will find condo apartments, flexible townhomes and larger single-family detached homes.
Both townhomes and larger detached homes are equipped with private pools, whilst the condo apartments benefitting from shared access to the on-site resort pool and amenities.

Windsor Hills Resort amenities
Within the 24-hr secure gated community, Windsor Hills Resort is a pure vacation oasis. For many, the timeless resort appeal centers around the main attraction here; the double-sized Olympic pool. Heated in the winter months, this lagoon-style pool with beach entry and 10-person hot tub invites all ages to enjoy some classic Florida fun in the sun.
Next door, the new waterpark makes for a fantastic addition to Windsor Hills Resort. Complete with a double spiral waterslide, 2 tot-friendly slides and splash pad, this family-friendly amenity promises endless entertainment.
Sports fans can re-energize at the on-site fitness center and on the sports courts, or practice their precision on the golf putting green. Families looking to let-off steam can take on the imaginatively-designed castle playground and custom-designed tot lot. An indoor arcade, free home theater and billiards room are also on hand to guarantee some all-weather amusement.
Residents and guests with pets are catered for too - thanks to a purpose-built dog park.
An on-site Marketplace and Grill provides a convenient spot for picking up some sundries, tucking into a hamburger or ordering a home-delivery.
Away from Windsor Hills Resort, a host of shopping malls and dining options can be reached under 1 mile away, whilst Disney World is under 2 miles away.
Discover the Windsor Hills Resort amenities
Lagoon-style Pool with beach entry
New Waterpark with Spiral Flumes
Interactive Splash pad
2 kids' playgrounds + tot lot
Volleyball, tennis, basketball + golf putting
Fitness Center & Game Room
Free On-site Theater
Marketplace + Grill
Dog Park

Source your dream Windsor Hills Resort home today
For Investors and those looking to live an effortless Floridian lifestyle, Top Villas Realty offer the best selection of resort listings currently on the market.
Whether you are searching for a carefree condo, a modernized townhome or a large luxury home with pool, our Realtors have the perfect resort investment for you.
Our experienced Orlando Realtors have first-hand knowledge of Windsor Hills Resort and are on hand for open days and 1-2-1 viewings to help secure your dream property.
Their personal approach throughout the entire buying process and strong negotiating experience ensures you the best outcome. Take the first step on your Realty journey and contact our Realtors today.
Looking for another Orlando Resort with homes for sale?
Check out our other Orlando short-term rental communities with luxury vacation homes for sale:
- Reunion Resort
- Encore Resort at Reunion
- Storey Lake Resort
- Windsor Island Resort
- Solara Resort
- Margaritaville Resort
- Champions Gate Resort
- Windsor Cay Resort
Learn more about what makes Orlando an incredible destination for investors and explore the #1 Orlando Resort communities here!
FAQs
As the closest Resort community to the Walt Disney World theme park entrance gates (less than 2 miles away), Windsor Resort offers unrivaled proximity to world-class fun.
Aside from reaching Disney World by car in 10 minutes, the resort enjoys close proximity to Orlando's other major theme parks, including Universal Studios and Sea World (18-20 minutes' drive away).
Windsor Hills is one of the safest communities to stay in when visiting Disney World and the Orlando area.
This is due to the resort operating a gated entrance, which is guarded 24/7 by security officers.
Guests arriving into the resort must present valid forms of ID and valid vacation information. Number plates are also logged and there are security cameras throughout the community. Community security officers also undertake daily drives around the resort, to ensure everyone is safe and abiding by the neighborhood rules.
This proactive stance on security and guest/owner well-being makes Windsor Hills Resort one of the safest vacation home communities in the Disney area of Orlando.
All Windsor Hills property owners are responsible for paying homeowner association fees (HOA). This fee is aside from the property taxes and utility costs.
The basic 2023 HOA fees are approximately $980.86 per quarter. This includes the following:
- Basic cable/internet
- Landscaping
- Clubhouse amenities
- 24-hr guard gated security
- Sports courts
- Roadways + sidewalks
- Common areas + insurance for common facilities
An additional Association fee is also payable, which differs depending on the type of property you own:
Villas/ Single family homes (The Enclave) - approx. $466.72 per quarter. This covers lawn care, irrigation, lawn spray, plant replacement, mulch and daily garbage removal.
Town homes (The Vistas) - approx. $472.00 per quarter. This covers the roof, exterior paint (excluding front door), the lawn and exterior pest control.
Condos/ Apartments (The Ventura) - approx. $616.35 per quarter. This covers water utility, building maintenance and insurance.
For further information please contact our licensed Realtors, or reach out to the Windsor Hills Master Association on 407-787-4255.
Our global vacation rental partner, Top Villas is home to the world's leading villa collection. With their expertise and extensive Orlando portfolio, they are perfectly placed to market and rent your Windsor Hills vacation home.
Top Villas currently list 100+ vacation homes in Windsor Hills resort, so they have first-hand experience of this Orlando resort and are best-placed to attract the best clientele and bookings.
What's more, their Travel Planners are on hand to maximize your guest's vacation, with a plethora of payable extras. From private chef hire, baby equipment and character visits to grocery deliveries, theme park tickets, car hire and more - they offer all the concierge facilities of a 5-star hotel, for a truly world-class stay.
Contact them today!
Yes, indeed. Our licensed Orlando Realtors will be happy to assist you all the way, from listing to closing. They provide a dedicated and personal service, ensuring you only sell to the right buyer, at the right price.
Contact us today to speak with the #1 Realty experts.
