Discover Windsor Hills Resort: Your Premier Investment Opportunity
Windsor Hills Resort stands as one of the most sought-after communities for vacation rental properties, located just 2.5 miles from Walt Disney World. This guard-gated resort community offers investors a range of properties designed to maximize rental potential while providing guests with an exceptional Orlando vacation experience. Learn more about what's nearby.
Single-family homes at Windsor Hills are the crown jewels of the community. These spacious residences feature private pools, covered lanais, and generous living areas that appeal to large families and groups visiting Orlando's world-famous theme parks. With floor plans ranging from 4 to 6 bedrooms, these homes command premium nightly rental rates. See our income and expense report for detailed projections.
All homes were built by Pulte Homes with quality construction and Florida-friendly design. Most properties are sold fully furnished and turnkey-ready, making them ideal for investors looking to generate rental income immediately upon purchase. Read our guide to investing in Windsor Hills for more insights.
Free Income & Expense Report
See exactly how much Windsor Hills vacation homes earn. Get real rental income data, expense breakdowns, and ROI projections — delivered straight to your inbox.
Windsor Hills Single-Family Home Market
Live active and sold data for Windsor Hills Resort homes.
Figures are calculated live from current Windsor Hills Resort MLS data for this property type. Sold metrics cover closings in the last 180 days.
Windsor Hills Homes for Sale
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16 properties for sale in Windsor Hills Resort
For Sale$629,900
7795 Basnett Circle
Kissimmee, FL 34747
MLS# O6434446
Courtesy of The Agency Fl
For Sale$698,000
2536 Holtrock Street
Kissimmee, FL 34747
MLS# O6432734
Courtesy of Ratio Real Estate, Llc
For Sale$679,000
7777 Teascone Boulevard
Kissimmee, FL 34747
MLS# S5154949
Courtesy of Frontline Florida Realty, Inc.
For Sale$569,900
2568 Archfeld Boulevard
Kissimmee, FL 34747
MLS# O6428649
Courtesy of Global Florida Realty
For Sale$639,000
2689 Manesty Lane
Kissimmee, FL 34747
MLS# S5153919
Courtesy of Top Villas Realty Llc
For Sale$699,000
7765 Tosteth Street
Kissimmee, FL 34747
MLS# O6423586
Courtesy of Florida 360 Realty Llc
For Sale$690,000
2623 Pawnall Street
Kissimmee, FL 34747
MLS# O6419768
Courtesy of Exp Realty Llc
For Sale$610,000
Kissimmee, FL 34747
MLS# O6413930
Courtesy of In Touch Real Estate Llc
For Sale$615,000
7743 Comrow Street
Kissimmee, FL 34747
MLS# S5151580
Courtesy of Real Broker, Llc
For Sale$665,000
7805 Beechfield Street
Kissimmee, FL 34747
MLS# O6412454
Courtesy of Charles Rutenberg Realty Orlando
For Sale$585,000
7755 Grassendale Street
Kissimmee, FL 34747
MLS# O6396993
Courtesy of Florida Realty Results Llc
For Sale$630,000
7759 Tosteth Street
Kissimmee, FL 34747
MLS# O6398878
Courtesy of Re/max Prime Properties
For Sale$625,000
2648 Dinville Street
Kissimmee, FL 34747
MLS# O6394288
Courtesy of Beycome Of Florida Llc
For Sale$649,000
7788 Basnett Circle
Kissimmee, FL 34747
MLS# O6371195
Courtesy of La Rosa Realty Llc
For Sale$540,000
7739 Teascone Boulevard
Kissimmee, FL 34747
MLS# O6350201
Courtesy of Keller Williams Classic
For Sale$589,999
2615 Pawnall Street
Kissimmee, FL 34747
MLS# S5118985
Courtesy of The Property Firm
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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. Data is deemed reliable but is not guaranteed by MLS GRID. Sold properties may have been listed or sold by various participants in the MLS.
Property Highlights
Spacious Living
Single-family homes ranging from 2,500 to over 4,000 square feet with 4-6 bedrooms and private pools.
Strong Returns
High rental demand near Disney World generates excellent short-term rental income year-round.
Fully Furnished
Most homes are sold fully furnished and rental-ready, making it easy to start earning immediately.
Family-Friendly
Private pools, game rooms, and spacious layouts — perfect for families and large groups.
Available Floor Plans
Built by Pulte Homes — quality construction throughout
Model: Sheldon
Model: Seville
Model: Spencer
Model: Brentwood
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Ready to Find Your Dream Vacation Home?
Contact Holiday Realty LLC today for a free consultation. We'll help you buy or sell your Windsor Hills Resort property.