Condos
An easy base for park days and pool afternoons. Choose a balcony or patio, and find a view and location that feel right for your visits. Explore Condos.
Windsor Hills Resort · Kissimmee
Windsor Hills Vacation Homes for Sale
Pool mornings, Disney days and space for everyone. Your place to get away in Kissimmee.
Start with your style of home
Choose your Windsor Hills home style
Explore Windsor Hills homes for sale
Windsor Hills Resort
The Windsor Hills experience
Make room for more vacation
At Windsor Hills, the resort can be part of the day: swim, enjoy the clubhouse, then head out to the parks when you are ready. The Kissimmee setting puts Walt Disney World close to home.
Choose an easy-to-own condo, a townhome with a splash pool, or a larger single-family villa for everyone to spread out. Each gives you a different way to enjoy the resort.
Team Donovan helps you compare the resort’s buildings and streets, from condos close to the clubhouse to private-pool homes with space for the whole group.
Property choices
Three ways to make Windsor Hills yours
Townhomes
Room for everyone to gather, with many townhomes offering their own screened splash pool. Explore Townhomes.
Single-Family Homes (Villas)
More bedrooms, space to spread out and, in many homes, a private pool for the days you stay in. Explore Single-Family Homes.
Resort amenities
Designed for family vacations
Water and pool complex
Lagoon-style pool, children’s splash facilities, water slides, hot tub and pool-deck areas form the centerpiece of the resort experience.
Clubhouse entertainment
Movie theater, games and arcade areas, fitness facilities and a marketplace or sundry option support both owners and guests.
Outdoor recreation
Sports courts, playgrounds, putting and recreation areas provide alternatives beyond the theme parks.
Some homes are closer to the clubhouse and pool; others offer more privacy. We can help you explore both.
Buying at Windsor Hills
Find the home you will love coming back to
Tell us who will use the home and how you picture your trips. We will help you compare the streets, views, pools and furnishings that matter to you, then talk through the costs of your favorite homes.
Selling a Windsor Hills home? Explore our seller guide.
Kissimmee, close to Disney
Make the most of every day
Head out for a day at Walt Disney World, then come back to your own space at Windsor Hills. When the parks can wait, spend the day at the resort pool and clubhouse instead.
Ownership costs
Understand the costs of each home style
Windsor Hills has a master association and separate associations for its property types. These 2026 assessments help you compare the three choices.
| Home style | Combined quarterly assessments | What's included in the total |
|---|---|---|
| Ventura Condo | $2,264.83 | $1,202.99 master + $1,061.84 Ventura |
| Vistas Townhome | $1,726.99 | $1,202.99 master + $524.00 Vistas |
| Enclave Single-Family Home | $1,715.48 | $1,202.99 master + $512.49 Enclave |
Ask us for the current fee schedule for the home you like.
Bringing a pet?
Ventura condos do not permit pets. Vistas townhomes permit up to two pets, each under 25 pounds. Enclave single-family homes permit up to two pets; breeding is prohibited.
The practical side
What to compare before you choose
The right home should work as well for your budget and plans as it does for your vacation.
Location and outlook
Consider the walk to amenities, privacy, view and pool orientation. Small differences can change how a home feels and how guests use it.
Condition and furnishings
Look closely at renovations, furniture, appliances and pool equipment so you understand what comes with the property.
Ownership and rentals
Compare association costs and any rental or owner-use arrangements for the specific homes on your shortlist.
Frequently asked questions
Windsor Hills, explained simply
How close is Windsor Hills to Walt Disney World?
Windsor Hills is in Kissimmee, just a short drive from Walt Disney World. Travel time depends on your destination and traffic.
What property types are available?
The resort includes two- and three-bedroom condominiums, three-bedroom townhomes and larger single-family homes, often called villas, commonly ranging from four to six bedrooms.
Do all properties have private pools?
No. Many townhomes have splash pools and many single-family homes have larger pools, while condominiums generally rely on community facilities.
Can Windsor Hills homes be used for short-term rental?
The community is well established for vacation use. Rental use remains subject to applicable zoning, licensing, association and property-specific requirements.
Which details matter most for resale?
Property type, location, amenity distance, outlook, pool orientation, condition, furnishings, floor plan and competition from similar active listings all matter.
Ready to find your Windsor Hills getaway?
Tell us how you plan to enjoy the home. We will help you compare the right condos, townhomes and villas, then guide you from your first tour to closing.
Talk with Team Donovan