Buyers Guide to Windsor Hills Resort Homes for Sale

Windsor Hills Resort view from above showing the townhouses, Reedy lake, the water park, clubhouse and the condos.

What is Windsor Hills Resort?

Windsor Hills Resort is a gated vacation home resort built by Pulte Homes in the Kissimmee area, Osceola County, Florida. Windsor Hills Resort is a little over 2 miles south of Disney’s Animal Kingdom, less than 10 minutes drive.

The Resort offers a fantastic location for buyers looking for a mature, secure location that has proven to be very consistent with annual revenue for owners who set the homes up specifically for short term rental. It is one of the closest major resorts to Disney World theme parks and has good facilities in both the clubhouse, resort pool and water park.

Windsor Hills Resort Overview

 Location

Windsor Hills is located in Osceola county, FL. Property is listed under the city of Kissimmee, which is 18 miles drive to the south east of Windsor Hills.
It is positioned only 4 miles south of Disney’s Magic Kingdom and is regarded as one of the closest major resorts to Walt Disney World.
Its location just off of W Irlo Bronson Memorial Hwy (US Route 192), makes it ideally located for the many popular shops and restaurants, providing important facilities for owners and guests. Irlo Bronson Memorial Hwy south of Disney is regarded as one of the most popular tourist destinations in central Florida.
To understand more on location, follow this link.

Address

2600 N Old Lake Wilson Rd, Kissimmee, FL 34747

Distance to Popular Locations

Windsor Hills is approx. 1 mile south of Walt Disney World. It takes about a 6 minute drive to the entrance of Disney.
Drive time to Orlando International Airport is approx. 35 minutes.
Drive time to Universal Studios – approx. 30 minutes
Drive time to LEGOLAND – approx. 1 hour
Drive time to the Cruise ship terminal at Port Canaveral – approx. 65 minutes
Drive time to the Cocoa Beach – approx. 80 minutes
Drive time to Clearwater Beach approx. 2 hours

Resort Amenities

The resort amenities provide a large resort pool, hot tub and clubhouse with fitness center and amusements and games for the kids. It also has a small dedicated movie theater, and a well stocked sundry shop that provides drinks and snacks.
Outside of the clubhouse it has a good children’s playground, a miniature golf course, tennis courts and a basketball court.
A water park was added in 2018 to the delight of owners and guests alike to help make the resort more competitive with the newer more complex resorts.
The clubhouse is open from 8am to 10pm but the fitness center is open at 6.30am. Seasonal hours may change.

Windsor Hills Design and Timeline

Windsor Hills was the follow up to the successful Windsor Palms Resort, closing its first home in phase one in February of 2005.
Sales were extremely brisk and Windsor Hills fast became the most popular place to buy and stay in the Orlando short term rental market.
The 2007 Florida property market crash saw a decline in sales across the board but such was the popularity of the resort, it continued to sell until finally closing out its final home in 2009.
The following decade saw Windsor Hills as one of the most popular locations for short term rental guests. No new resorts were being built so it remained the top resort until the new resorts such as ChampionsGate The Retreat, Encore Resort and several others were created. So popular Windsor Hills has been, it still retains many of its annual guests to this day making it one of the most stable investments in the STR market.

Size

Total Property 999 Units.
469 Single-Family Houses – 4 to 6 bedrooms
320 Condominiums – 2 to 3 bedrooms
210 Townhouses – 3 bedrooms

Phases

A little known fact about Windsor Hills was it was divided into two phases. The east phase was built first. When the second phase was built, the market had started to decline so the developer improved the upgrades for phase two – adding tile roof and upgraded finishes inside such as natural stone.

Insider Tip

If you look at Windsor Hills Resort from above on a map program, you can see the divide run down the middle of the resort as the gray shingle roofs transition into the terracotta tile roofs.

The Windsors

Builder Pulte homes created the first “Windsor”, Windsor Palms in 2001 and went on to build four more Windsor resorts; Windsor Hills, Windsor at Westside, Windsor Island and the latest Windsor Cay Resort (the first major resort in Lake County).

Property Prices

Prices range from:
The mid $500’s to the high $600’s for houses.
The high $300’s to the mid $400’s for townhouses.
The mid $200’s to the high $300’s for condos.
As Of October 2026

Zoning and Length of Stay

Windsor Hills is zoned for short term rental, does not have any deed restrictions on length of stay and does have an HOA association.
Owners can rent short term, rent long term or live full time.

Similar Locations to Windsor Hills

Windsor Palms Resort
Windsor at Westside Resort
Paradise Palms Resort
Encore Resort

NEW Listings at WINDSOR HILLS

Buyer questions

What types of homes are available at Windsor Hills Resort?

Windsor Hills has four house floor plans:
The 4-bedroom “Sheldon”.
The 5-bedroom “Seville” and the 5-bedroom “Spencer II”
The 6-bedroom “Brentwood”

Windsor Hills has one townhouse floor plan:
The 3-bedroom “Saddlebrook”.

Windsor Hills has five condo floor plans:
The 2-bedroom “Napa”
The 3-bedroom “Sonoma”
The 3-bedroom “Santa Ana”
The 3-bedroom “Santa Cruz”
The 3-bedroom “Santa Rosa”

See all Windsor Hills Floor Plans HERE

Who built Windsor Hills Resort, and when?

Pulte Homes built Windsor Hills Resort. Construction of the 999 properties started in 2004 and the resort was completed by 2009. It was the second fully amenitized short term rental resort completed by Pulte, following on from Windsor Palms (2001).

Can I rent my Windsor Hills home short-term?

Yes. Windsor Hills Resort is zoned for short-term rental.
There are no deed restrictions on length of stay, so owners can rent short term, rent long term or live full time.

Is Windsor Hills gated and secure?

Yes. Windsor Hills Resort has excellent manned and gated 24 hour security. It also has one electronic exit only gate on the north side.

What are the HOA and CDD fees?

The master community fee is $1,202.99 per quarter. All homeowners pay this.
In addition:
House owners pay an additional  $512.49 per quarter
Townhome owners pay an additional $524.00 per quarter
Condo owners pay an additional $920.81 per quarter
Combined quarterly HOA totals: houses $1,715.48, townhomes $1,726.99, condos $2,123.80.
Fees may change, you can call the master association to check at 407-787-4255

There is no CDD fee at Windsor Hills

How does Windsor Hills compare to similar resorts?

Windsor Hills was the last of the first generation of fully amenitized vacation home resorts, built between 2000 and 2009. No new resorts followed until around 2015, so between 2005 and 2015 it was the main location for upscale short term rental guests, with no direct comparison among the earlier resorts. Since 2015, nine new resorts have opened, and Windsor Hills has moved back in overall popularity but still retains much of the goodwill and loyalty of guests who visited during the peak years.
Its fantastic location has not changed, although the floor plans are dated and the clubhouse is not comparable to most of the newer resorts, Windsor Hills still retains a significant level of popularity.
It is important to note that generally, Windsor Hills tends to have less inventory ratio than any of the other newer resorts per the consistent data from the MLS.  This speaks volumes to level of comfort buyers and owners feel towards the consistent revenue it is able to generate annually for its owners.

Comparable communities include Paradise Palms, Encore Resort and Windsor Island

Is Windsor Hills a good investment for vacation rentals?

Yes. Owners and managers we work with often describe Windsor Hills as one of the more stable resorts for short-term rentals, helped by repeat guests, its location near Disney, and the shops and restaurants of US 192. Results still vary by property, ownership, management and season, so see the next question for how to estimate your own numbers.

Should I consider historical returns in my investment strategy?

Because rental results may vary by property, ownership, management, and time of year,  one home’s or owner’s history is not a reliable guide to another. A better approach is to gather potential nightly rates and occupancy from comparable listings on Airbnb and VRBO, or use a rental revenue and occupancy program like AirDNA. Then enter them along with your expected costs into our Short Term Rental Property Calculator to estimate cash flow and return. Results are estimates that depend on accurate input, so confirm them with a qualified accountant.

For help running the numbers on a specific home, contact The Jerry Barker Group at 407.286.8170.

Does Windsor Hills have a golf course?

No, but directly to the south is Mystic Dunes Golf Club which is a very popular public golf course and only a few minutes drive from Windsor Hills.

Can I park an RV at Windsor Hills?

Yes. It’s the only resort we know of that has a dedicated RV parking area (next to the condos)

Author Jerry Barker

Realtor & Vacation Home Specialist
Last verified October 9, 2026

For more information on buying and rental potential at Windsor Hills Resort, or an introduction to property management companies we trust, please contact us directly online via our support page or call us directly at 407.286.8170