744 Westcliffe Dr Winter Garden, FL 34787
About This Home
Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.
This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at
Want to tour on your own? Click the “Self Tour” button on this home’s listing or call to register for a self-guided showing at a time that works best for you.
Interested in this home? You clearly have exceptional taste. This charming 4-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and connected. Homes like this don’t stay on the market for long—don’t miss your chance to make it yours. Apply today!
The Homeowners Association (HOA) for this home has a separate application process that applicants will need to complete in addition to Progress Residential's application. This includes self-registering with the HOA, completing the HOA's approval process, and paying any fees required by the HOA.
Some images have been virtually staged to help showcase the potential of spaces in the home. The furnishings shown are for illustrative purposes only and are not included in the home.
Map
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 01/03/2026 01/03/26 | Price Changed | $2,755 | -2.3% | $1 / Sq Ft |
| 12/30/2025 12/30/25 | Price Changed | $2,820 | -2.1% | $1 / Sq Ft |
| 12/28/2025 12/28/25 | Price Changed | $2,880 | -2.5% | $1 / Sq Ft |
| 12/24/2025 12/24/25 | Price Changed | $2,955 | +0.2% | $1 / Sq Ft |
| 12/23/2025 12/23/25 | Price Changed | $2,950 | +0.2% | $1 / Sq Ft |
| 12/22/2025 12/22/25 | Price Changed | $2,945 | +0.3% | $1 / Sq Ft |
| 12/21/2025 12/21/25 | Price Changed | $2,935 | -1.2% | $1 / Sq Ft |
| 12/16/2025 12/16/25 | Price Changed | $2,970 | -2.1% | $1 / Sq Ft |
| 12/12/2025 12/12/25 | Price Changed | $3,035 | +11.8% | $1 / Sq Ft |
| 12/11/2025 12/11/25 | Price Changed | $2,715 | -0.5% | $1 / Sq Ft |
| 12/08/2025 12/08/25 | Price Changed | $2,730 | +0.2% | $1 / Sq Ft |
| 12/07/2025 12/07/25 | Price Changed | $2,725 | +0.2% | $1 / Sq Ft |
| 12/06/2025 12/06/25 | Price Changed | $2,720 | -1.8% | $1 / Sq Ft |
| 12/05/2025 12/05/25 | Price Changed | $2,770 | -0.2% | $1 / Sq Ft |
| 12/04/2025 12/04/25 | Price Changed | $2,775 | +0.2% | $1 / Sq Ft |
| 11/30/2025 11/30/25 | Price Changed | $2,770 | -0.2% | $1 / Sq Ft |
| 11/26/2025 11/26/25 | Price Changed | $2,775 | +0.2% | $1 / Sq Ft |
| 11/18/2025 11/18/25 | Price Changed | $2,770 | -1.9% | $1 / Sq Ft |
| 11/12/2025 11/12/25 | Price Changed | $2,825 | -2.1% | $1 / Sq Ft |
| 11/07/2025 11/07/25 | Price Changed | $2,885 | -2.0% | $1 / Sq Ft |
| 09/24/2025 09/24/25 | For Rent | $2,945 | 0.0% | -- |
| 08/11/2025 08/11/25 | Off Market | $2,945 | -- | -- |
| 08/01/2025 08/01/25 | Price Changed | $2,945 | -1.0% | $1 / Sq Ft |
| 07/24/2025 07/24/25 | Price Changed | $2,975 | -1.0% | $1 / Sq Ft |
| 06/30/2025 06/30/25 | For Rent | $3,005 | -- | -- |
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