WINDSOR HILLS RESORT
If you are thinking of buying a property in Windsor Hills Resort it is important to understand all the benefits and costs involved with owning a short-term rental property. Will you book the property rentals yourself or will you want a property manager to book it in addition to looking after the property?
As an owner of a short-term rental property at Windsor Hills Resort you have the advantage of owning a property within a few miles of Disney World that you can use as much as you would like every year. When you are not using it you can rent it out and receive income to cover some or all of your running costs.
The property market at Windsor Hills can change daily so be sure to check out the most up-to-date listings below. Contact Holiday Realty LLC today to discuss purchase opportunities.
Windsor Hills properties generate excellent short-term rental revenue due to their proximity to Disney World and resort-style amenities.
The community is guard-gated 24/7, giving owners and guests peace of mind and adding long-term property value.
Most properties are sold fully furnished and rental-ready, allowing you to begin earning income from day one.
We specialize in helping international and out-of-state buyers purchase properties remotely with full transparency.
Windsor Hills property owners are responsible for paying homeowner association dues (HOA) as well as property taxes and utilities costs. The 2025 HOA dues are as follows:
Basic cable/internet, landscaping, clubhouse amenities, 24-hour guard-gated security, sports courts, roadways, sidewalks, common areas, insurance for common facilities.
Lawn care, irrigation, lawn spray, plant replacement, mulch, daily garbage removal.
Periodic roof replacement (not storm repairs), exterior paint excluding front door, lawn, exterior pest control.
Water utility, building maintenance and insurance.
*You can reach the Windsor Hills Master Association at 407-787-4255
If you are purchasing a Windsor Hills property as a vacation/holiday rental property you will have the additional costs of a local property manager. This property manager will charge at least $120/month in addition to any possible cleaning fees and maintenance costs. Utility costs will also be higher with a rental property.
We'll discuss your investment goals, budget, and preferred property type — whether it's a single-family home, townhome, or condo at Windsor Hills.
We'll curate a selection of available properties that match your criteria and arrange virtual or in-person tours at your convenience.
Our team will prepare a competitive offer and negotiate on your behalf to secure the best price and terms for your investment.
We coordinate inspections, appraisals, and closing logistics — guiding you smoothly to the finish line, even if you're purchasing remotely.
Let's Talk
Contact Holiday Realty LLC today for a free consultation. We'll help you buy or sell your Windsor Hills Resort property.