$639,000Price reduced by $20,000 on May 19, 2026
2621 Archfeld BoulevardKissimmee, FL, 34747
- 5 beds
- 5 baths
- 2,297 sqft
Kissimmee, Florida
Windsor Hills Resort Homes for Sale
Explore condos, townhomes and detached homes in this gated Kissimmee community. Start your search for a personal retreat, second home or property to consider for rental ownership.
Explore Properties for Sale in Windsor Hills
41 listings
Get to Know Windsor Hills Resort
Windsor Hills Resort is an individually owned, gated community at 2600 N Old Lake Wilson Road in Kissimmee, Florida. A 24-hour staffed entrance serves a neighborhood that combines condominiums, townhomes and detached houses with shared recreation. For prospective owners, that combination makes both the individual property and the wider community important parts of the decision. You can compare the space and features you want at home while considering how often you would use the pool, sports courts or indoor facilities. The result is a property search shaped by more than bedroom count alone.
Condos, Townhomes and Detached Homes
Use these community-described property types as a starting point, then confirm the layout, pool and included features in each sale listing.
| Aspect | Condominiums | Townhomes | Detached Homes |
|---|---|---|---|
| Community-described layouts | Two- and three-bedroom configurations. | Three-bedroom configurations. | Four-, five- and six-bedroom configurations. |
| Pool arrangements | Review the listing for outdoor features; consider the shared pool separately. | Described with private splash pools; confirm the chosen home's pool details. | Described with full-size private pools; examine each home's specific setup. |
| What to examine | Compare the floor plan, bedroom arrangement and features included in the sale. | Examine living spaces, bedroom placement and the splash-pool area. | Compare interior gathering spaces, bedroom layouts and private pool areas. |
| Ownership review | Review the applicable association documents and maintenance responsibilities. | Check exterior maintenance coverage alongside private-pool responsibilities. | Clarify which home, pool and grounds responsibilities remain with the owner. |
Shared Amenities for Time at Home
These shared facilities complement individual homes, giving owners more ways to enjoy personal visits and second-home time.
Heated Pool and Hot Tub
The heated, zero-entry community pool and hot tub offer places to swim and unwind beyond your own home's outdoor space.
Water Park and Splash Pad
Two large slides, smaller slides and a splash pad add water play to family afternoons spent within the community.
Fitness Center
A shared fitness center gives owners an on-site option for keeping exercise part of their routine during time at their property.
Movies and Games
The movie theater and games room provide indoor recreation, adding alternatives to pool time and outings beyond the community.
Courts and Putting Green
Tennis, basketball and volleyball courts, plus a putting green, create opportunities to spend active time together without leaving Windsor Hills.
Playgrounds, Picnics and Dining
Playgrounds, a tot lot and picnic facilities support outdoor family time, while Marketplace & Grill adds an on-site food option.
Local Shopping and Orlando-Area Leisure
The Old Lake Wilson Road location brings practical errands into the ownership picture alongside Orlando-area recreation. Walmart Supercenter at 2855 N Old Lake Wilson Road, on the same road as the community entrance, offers grocery shopping and pharmacy services. Those everyday facilities matter when stocking the kitchen or settling in for time at your second home. Walt Disney World and Disney Springs are among the surrounding leisure destinations, giving owners options beyond Windsor Hills' shared amenities. When comparing properties, think about the balance you want between time at home, recreation within the gates and outings in the wider area.
Windsor Hills Property Market at a Glance
View community property totals, the number of homes currently for sale and the median asking price of current listings.
- Homes in community
- 2,008
- For sale now
- 47
- Median list price
- $409,000
Rental figures are modelled from comparable nightly rates and are not a guarantee of income.
Understanding Associations and Maintenance
Windsor Hills has a Master Association and separate Enclave, Vistas and Ventura associations, so maintenance responsibilities depend on the property. Master responsibilities include the staffed entrance, shared amenities, roads, sidewalks, common-area maintenance, and basic cable and internet. Enclave and Vistas responsibilities include specified landscaping, irrigation and garbage-removal services. Exterior painting is identified specifically for Vistas townhomes, excluding front doors. When comparing homes, review the applicable association documents, current assessments and division of maintenance duties rather than assuming every property carries the same fees or services. Architectural changes also follow an approval process, making those requirements worth reviewing before planning exterior alterations. This helps you understand both the home you would own and the services surrounding it.
Match Your Property to Your Plans
Start with how you intend to use the property: personal visits, a second home, rental ownership or a combination. Windsor Hills includes individually owned properties used for short-term rentals, making rental use a relevant consideration alongside personal enjoyment. For a specific purchase, check the property's permissions, required registrations, restrictions and occupancy rules against your plans. Consider how its bedroom arrangement and private outdoor features would work for your household, too. A home that looks appealing in photographs still needs to fit your intended use, whether that centers on family time or includes letting the property.
Find Your Windsor Hills Property
Explore Windsor Hills Resort homes for sale with your priorities in mind. Compare property type, layout and private outdoor features, then look closely at the applicable association responsibilities. Whether you want a place for personal enjoyment, a second home or a property to evaluate for rental use, focus on the details that support your plans. Use the listings to build a shortlist of homes worth a closer look.