Windsor Hills Resort
Vacation resort living 2.5 miles from Disney World with world-class amenities and strong rental potential.
Live the MaxLife.
$265K
Median Price
$180K – $425K
999
Homes
$1585–$1734
Monthly HOA
2005
Established
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Background
A brief history
Windsor Hills Resort was developed beginning in 2005 and built over a 5-year period by Pulte Homes, becoming fully operational around 2010. The community was designed as a vacation resort destination for families and investors seeking homes near central Florida's theme parks. Today it stands as one of the largest individually-owned vacation rental communities in the region, with 999 properties consisting of condominiums, townhomes, and single-family villas. The master-planned approach emphasized amenities and security from its inception, appealing to both vacation guests and investment-focused homeowners.
The feel
What it's like to live here
Windsor Hills Resort is a gated, amenity-rich community with the feel of a resort destination rather than a traditional residential neighborhood. Tree-lined streets lead to clusters of properties surrounding the spectacular 10,000-square-foot clubhouse, lagoon-style pool with waterslide, waterpark, and recreational facilities. The atmosphere is vibrant and family-oriented, with activities available year-round from the fitness center to the game arcade. Properties are individually owned but managed professionally for vacation rentals, creating a dynamic mix of vacationing families and owners capitalizing on strong tourism demand. The community maintains resort-quality grounds, landscapes, and common areas that appeal to international visitors and domestic tourists.
The details
What to expect
Architecture & Homes
Windsor Hills offers three main property types. Condominiums include 2-bedroom (1,081 sq ft) and 3-bedroom (1,440 sq ft) units with shared amenities. Townhomes feature 3–4 bedrooms with individual entrances and private small yards. Single-family villas come in 4–6 bedroom floor plans (up to 2,812 sq ft) with private pools and spas. Most units feature modern finishes, open-concept living, and vacation-ready furnishings. Many properties include full kitchens, washer/dryer, and furnished bedrooms—standard for the vacation rental market. Architecture is contemporary Florida style with pitched roofs, stucco, and tile accents.
Amenities & Lifestyle
The resort centerpiece is the 10,000-square-foot clubhouse featuring a lagoon-style pool with twisty waterslide, hot tub, and kids' splash zone. A separate waterpark offers double spiral waterslides, tot-friendly slides, and splash pad. Additional amenities include a fitness center, game arcade, billiards room, surround-sound movie theater, lighted tennis and basketball courts, sand volleyball, putting green, and meeting spaces. The community offers 24-hour gated security, basic cable and internet included in master HOA fees, and professional property management services. Restaurants, shopping, and entertainment venues are within minutes, including Disney Springs, Universal Studios, SeaWorld, and Gatorland.
Schools
Windsor Hills is served by Westside K–8 School for elementary and middle grades, and Celebration High School for high school students. These are Osceola County public schools. However, most Windsor Hills residents purchase for vacation rental investment rather than as primary residences, so school assignments are rarely a primary concern in buyer decisions. Families vacationing or staying short-term don't typically enroll in public schools.
Location & Access
Windsor Hills Resort is located at 2600 Old Lake Wilson Road, Kissimmee, FL 34747—just 2.5 miles south of Walt Disney World. The strategic location puts the community minutes from all major Central Florida attractions: Disney World (2.5 mi), Disney Springs (3 mi), Universal Studios (13 mi), SeaWorld (15 mi), the ESPN Sports Complex (5 mi), and Gatorland (8 mi). I-4 access is quick via US-192 and Poinciana Boulevard, making the community accessible to international airport (MCO is 25 miles). This proximity to theme parks and tourism infrastructure is the primary draw for investors and vacation renters.
Community
Amenities
- 10,000 sq ft clubhouse with lagoon pool and waterslide
- Waterpark with double spiral waterslide and splash pad
- Fitness center and gym
- Game arcade and billiards room
- Movie theater with surround sound
- Lighted tennis courts
- Lighted basketball courts
- Sand volleyball
- Putting green
- 24-hour gated security
- Professional property management available
- Basic cable and internet (included in master HOA)
- Meeting and event rooms
- Children's playground
- Sundry shop on premises
Know Before You Buy
HOA rules worth knowing
- Master association fee (~$1,118/quarter) covers basic cable/internet, landscaping, clubhouse amenities, 24-hour security, sports courts, roadways, sidewalks, and common area insurance
- Property-type fees in addition to master: villas/single-family homes (~$467/quarter for lawn care, irrigation, and maintenance); townhomes (~$472/quarter for roof, exterior, and pest control); condos (~$616/quarter for water, building maintenance, and insurance)
- Vacation rental operations permitted and encouraged; many residents rent through professional management companies
- Property management services available through community-approved vendors
- Rental income typically not subject to additional HOA restrictions beyond standard maintenance requirements
- 24-hour security includes gated entrance with controlled access
- Common area maintenance standards enforced to preserve resort appearance and rental appeal
- Pets allowed subject to community guidelines (typical for vacation rental properties)
Market Commentary
What the market is doing
I see Windsor Hills Resort attracting vacation rental investors who understand the Central Florida market. 2-bedroom condos run $180K, 3-bedrooms $265K, and larger villas $300K–$425K depending on the floor plan and amenities. Price per square foot typically ranges $151–$184. The numbers work because of the location—2.5 miles from Disney—and the established rental infrastructure. If you're selling, focus on your property's rental history, condition, and any upkeep you've invested in. Buyers here are sophisticated investors who compare cap rates and occupancy, so transparency about your costs and performance matters.
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Homes available in Windsor Hills Resort
12 homes currently listed in Windsor Hills Resort.
$1,600 /mo
5283 Images Cir #304
Kissimmee, FL 34746
2 bd · 2 ba · 969 sqft
Images Condo
MLS ID #O6414122
Listing provided by Stellar MLS
$150,000
1433 Swan Ct
Kissimmee, FL 34759
3 bd · 2 ba · 1,650 sqft
Poinciana Sub Nbrhd 6 South Vil 3
MLS ID #O6412432
Listing provided by Stellar MLS
$259,000
4560 E Yellowgold Rd #Apt 105
Kissimmee, FL 34746
3 bd · 2 ba · 1,296 sqft
Villas At 07 Dwarfs Lane
MLS ID #S5142963
Listing provided by Stellar MLS
$610,000
Kissimmee, FL 34747
5 bd · 5 ba · 2,297 sqft
Windsor Hills Ph 3
MLS ID #O6413930
Listing provided by Stellar MLS
$340,000
1147 Normandy Dr
Kissimmee, FL 34759
3 bd · 2 ba · 1,485 sqft
Poinciana Village 5 Nbhd 1
MLS ID #O6413648
Listing provided by Stellar MLS
$434,997
1350 Greenfield Loop
Kissimmee, FL 34747
3 bd · 2 ba · 1,497 sqft
Reunion Village Ph 4 & 5
MLS ID #A4683415
Listing provided by Stellar MLS
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 13, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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