744 Westcliffe Dr

Winter Garden, FL 34787
(321) 496-6398
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744 Westcliffe Dr

744 Westcliffe Dr
Winter Garden, FL 34787
(321) 496-6398
744 Westcliffe Dr in Winter Garden, FL - Building Photo
4 Bedroom - Home for Rent
  • 4BR, 2BAHome
  • $2,825Price
  • 2,543Square Feet
  • 12-01-2025Availability

About 744 Westcliffe Dr

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. 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 This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist today. 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.

744 Westcliffe Dr is located in the West Orlando Neighborhood and 34787 Zip code of Winter Garden, FL.

Property Contact Info

Fees and Policies

The fees below are based on community-supplied data and may exclude additional fees and utilities.

Required Fees

Utilities & Essentials

utilitiesAdminFee$9.99/mo
smartHomeFee$19.99/mo

Pet Policy and Fees

Cats

  • Fees Not Specified

Dogs

  • Fees Not Specified

Parking Info and Fees

Garage Parking

Property Fee Disclaimer: Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.

Features and Amenities

Unique Amenities

  • smartHomeFee
  • utilitiesAdminFee

On-Site Services

  • Garden Style

Outdoor Features

  • Fenced Lot
  • Yard
  • Patio

Interior Features

  • Double Vanities

Kitchen Amenities

  • Pantry
  • Stainless Steel Appliances
  • Granite Countertops

Living Area Features

  • Window Coverings
  • Tile Floors
  • Sunroom
  • Hardwood Floors

Unique Amenities

  • Garage Available
Google Map

Map

744 Westcliffe Dr, Winter Garden, FL 34787

Frequently Asked Questions about 744 Westcliffe Dr

What type of rentals are available at 744 Westcliffe Dr?

There is currently a 4 Bed 2 Bath Home for rent with 2,543 listed at 744 Westcliffe Dr. It is Available December 1, 2025.

How much is the rent at 744 Westcliffe Dr?

744 Westcliffe Dr is currently listed at $2,825.

What area of town is 744 Westcliffe Dr located in?

Located in the West Orlando Neighborhood, 744 Westcliffe Dr is in the 34787 Zip Code of Winter Garden, FL.

Lifestyle Ratings

  • Cost Per Sq.Ft. 3.6

    The Cost Per Square Foot rating shows you the average cost per square foot for floorplans at this community in relation to the local average.

  • Luxury 3.4

    The Luxury rating shows you how this community's high end floorplan pricing relates to the local average.

    Rating Factors

    This 3.4-star Luxury rating is based on the following features:

    • Granite Countertops
    • Hardwood Floors
    • Stainless Steel Appliances
    • Garden Style
    • Fenced Lot(s)
    • Tile Floors
    • Sunroom(s)
    • Double Vanities
    • Pantries
    • Window Coverings
    • Yards
    • Patios
    See more
    See less
  • Pet Friendly 3.6

    Top Pet Friendly apartments have specified that they accept pets and feature a number pet friendly amenities for renters with furry friends.

    Rating Factors

    This 3.6-star Pet Friendly rating is based on the following features:

    • Fenced Lot(s)
    • Hardwood Floors
    • Tile Floors
    • Patios
Learn more about Lifestyle Search

Nearby Schools

Dillard Street Elementary

Orange County Public Schools
311 North Dillard Street
Public School - Grades PK-5 (498 Students)
4/10

Lakeview Middle

Orange County Public Schools
1200 West Bay Street
Public School - Grades 6-8 (843 Students)
3/10

Ocoee High

Orange County Public Schools
1925 Ocoee Crown Point Parkway
Public School - Grades 9-12 (2536 Students)
6/10
School data provided by GreatSchools.
details
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on scale of 1 (below average) and to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider needs as part of the school selection process.

About GreatSchools Data on ApartmentHomeLiving.com.

Points of Interest

Time and distance from 744 Westcliffe Dr.

Big Box and Retail

Autozone

13855 W Colonial Dr
6 minute drive / 2.92 miles away

Goodwill

14190 W Colonial Dr
6 minute drive / 3.21 miles away

Jcpenney

9409 W Colonial Dr
8 minute drive / 3.92 miles away

Colleges and Universities

Valencia Community College - West Campus

1800 South Kirkman Road
17 minute drive / 8.01 miles away

Seminole State College of Florida - Altamonte Springs Campus

850 South SR 434
21 minute drive / 10.13 miles away

Valencia Community College - Sand Lake Campus

2411 Sand Lake Road
28 minute drive / 13.44 miles away

Groceries

Iga

23 W Silver Star Rd
5 minute drive / 1.91 miles away

Winn-Dixie

611 E Main St
15 minute drive / 7.27 miles away

Publix

5400 Hamlin Groves Trl
19 minute drive / 8.9 miles away

Hospitals

Health Central Hospital

10000 W Colonial Dr
8 minute drive / 3.77 miles away

Aspire Health Partners

1800 Mercy Dr
18 minute drive / 8.61 miles away

Orlando Health South Lake Hospital

1900 Don Wickham Dr
20 minute drive / 9.69 miles away

Parks and Recreation

Universal Studios Florida

1000 Universal Studios Plaza
20 minute drive / 9.68 miles away

744 Westcliffe Dr has 1 park within 9.7 miles, including Universal Studios Florida.

Restaurants and Dining

Lee & Ricks Oyster Bar

5621 Old Winter Garden Rd
16 minute drive / 7.72 miles away

P.F. Chang's

4200 Conroy Road
23 minute drive / 11.0 miles away

Shopping Centers

Starlite Commerce Center

1165 E Plant St
4 minute drive / 1.36 miles away

Fountains West

West Rd
4 minute drive / 1.5 miles away

Ocoee Shopping Center

501 W Silver Star Rd
4 minute drive / 1.52 miles away

744 Westcliffe Dr has 5 shopping centers within 1.9 miles.

Nearby Neighborhoods

Studio to 3 Bedroom Apartments from $1,344
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Studio to 4 Bedroom Apartments from $750
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Studio to 4 Bedroom Apartments from $1,041
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Nearby Apartments

Rental Price Ranges in the Area

BedroomAverage RentCheapest RentHighest Rent
Winter Garden Studio Apartments $1,625$1,150$1,950
Winter Garden 1 Bedroom Apartments $1,861$1,210$4,112
Winter Garden 2 Bedroom Apartments $2,240$1,310$3,525
Winter Garden 3 Bedroom Apartments $2,721$1,841$4,432
Winter Garden 4 Bedroom Apartments $3,020$2,875$3,100

Browse Top Apartments in Winter Garden

Viewing: 744 Westcliffe Dr | Desktop Version | Listing Updated: 11/15/2025