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The Overlook
Winter Garden, FL 34787

- Studio–3 Bedrooms
- 679–1,553 Square Feet
About The Overlook
Spring into Deals You Will Love! B2, 2 bedroom receives 50% OFF 4 Months on a 15-month lease. All other floor plans receive 50% Off 3 Months on a 14-month lease. Must apply by 4/15. Now leasing spacious studio, one-, two-, and three-bedroom apartments and townhomes for rent in Winter Garden, FL, near Horizon West and Disney! The Overlook is positioned in the heart of Flamingo Crossings and Horizon West, the best place to live in Florida. As a new resident of Overlook, get ready to experience the perfect blend of comfort, convenience, and elegance coupled with only top-notch amenities. Located just off of the Walt Disney World property, The Overlooks upscale studio, one, two, and three-bedroom apartments and premier town homes are spacious, thoughtfully designed, and embellished with gorgeous modern finishes. The Overlook is a pet-friendly community in Winter Garden, located right off SR-429 and US 192, allowing you to easy access from work to the best that Orlando has to offer.
The Overlook is located in the Four Corners Neighborhood and 34787 Zip code of Winter Garden, FL.
Unique Features and Amenities
- EV Charging
- EV charging stations available
- Full Size Washer and Dryer Included In Every Home
- Garage
- Higher Vaulted Ceilings Available in Select Homes
- Luxury Townhomes Include a Ring Video Doorbell
- Private Balcony or Patio Included in Every Home
- Spanish Speaking Team Members Available
Property Contact Info
Floorplan Pricing and Availability
New! Interactive Property Map
Studio
Hampton S2
Studio, 1 Bath, 679 sq ftAvailable Apr 17Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit April 17, 2026 2428 679 $250 Apartment Model: Hampton S2Studio, 1 Bath, 679 sq ftAvailable April 17, 2026![]()
Hampton S2 - Floorplan Apartment Unit: 2428Apartment Model: Hampton S2Studio, 1 Bath, 679 sq ftAvailable April 17, 20261 Bedroom
Catalina A3
1 Bed, 1 Bath, 798 sq ftAvailable NowLargest 1 BedroomThis is the largest 1 Bedroom at this PropertyModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit Available Now 2125 798 $250 Apartment Model: Catalina A31 Bedroom, 1 Bath, 798 sq ftAvailable Now![]()
Catalina A3 - Floorplan Apartment Unit: 2125Apartment Model: Catalina A31 Bedroom, 1 Bath, 798 sq ftAvailable NowCottonwood A1
1 Bed, 1 Bath, 742 sq ftAvailable Apr 10Cheapest 1 BedroomThis is the cheapest 1 Bedroom at this PropertyModel Gallery
Floorplans
Photos
Availability Details
Availability Date Unit Sq Ft Deposit View Details April 10, 2026 1319 742 $250 April 13, 2026 2403 742 $250 April 24, 2026 2204 742 $250 Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable April 10, 2026FloorplansPhotos![]()
Cottonwood A1 - Image 1 ![]()
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Cottonwood A1 - Floorplan Apartment Unit: 1319Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable April 10, 2026Apartment Unit: 2403Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable April 13, 2026Apartment Unit: 2204Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable April 24, 2026Sapphire A2
1 Bed, 1 Bath, 789 sq ftAvailable Apr 10Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit View Details April 10, 2026 1108 789 $250 April 10, 2026 2408 789 $250 May 23, 2026 2108 789 $250 Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable April 10, 2026![]()
Sapphire A2 - Floorplan Apartment Unit: 1108Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable April 10, 2026Apartment Unit: 2408Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable April 10, 2026Apartment Unit: 2108Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable May 23, 20262 Bedrooms
Show Unavailable FloorplansCypress B2
2 Beds, 2 Baths, 1093 sq ftAvailable NowCheapest 2 BedroomThis is the cheapest 2 Bedroom at this PropertyModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit View Details Available Now 2306 1093 $250 Available Now 2121 1093 $250 April 24, 2026 2221 1093 $250 Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable Now![]()
Cypress B2 - Floorplan Apartment Unit: 2306Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable NowApartment Unit: 2121Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable NowApartment Unit: 2221Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable April 24, 2026Magnolia B5
2 Beds, 2 Baths, 1118 sq ftAvailable Apr 13Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit View Details April 13, 2026 1211 1118 $250 June 10, 2026 1423 1118 $250 June 16, 2026 1111 1118 $250 Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftAvailable April 13, 2026![]()
Magnolia B5 - Floorplan Apartment Unit: 1211Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftAvailable April 13, 2026Apartment Unit: 1423Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftAvailable June 10, 2026Apartment Unit: 1111Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftAvailable June 16, 2026Laurel B3
2 Beds, 2 Baths, 1198 sq ftAvailable Jul 7Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit July 7, 2026 2126 1198 $250 Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable July 7, 2026![]()
Laurel B3 - Floorplan Apartment Unit: 2126Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable July 7, 2026Avalon B4
2 Beds, 2 Baths, 1270 sq ftModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Unavailable Avalon B4 1270 sq ft Apartment Model: Avalon B42 Bedroom, 2 Bath, 1270 sq ftUnavailable![]()
Avalon B4 - Floorplan Newport 2-Car Garage Townhome
2 Beds, 3 Baths, 1553 sq ftLargest 2 BedroomThis is the largest 2 Bedroom at this PropertyModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Unavailable Newport 2-Car Garage Townhome 1553 sq ft Model Amenities and Features
Unique Features
- Luxury Townhomes Include a Ring Video Doorbell
Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftUnavailable![]()
Newport 2-Car Garage Townhome - Floorplan 3 Bedrooms
Sycamore C2
3 Beds, 2 Baths, 1501 sq ftAvailable NowModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit View Details Available Now 1302 1501 $250 April 12, 2026 1202 1501 $250 April 17, 2026 1330 1501 $250 Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable Now![]()
Sycamore C2 - Floorplan Apartment Unit: 1302Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable NowApartment Unit: 1202Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable April 12, 2026Apartment Unit: 1330Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable April 17, 2026
Property Information
- 232 Units
- 4 Stories
- Built in 2023
Lease Terms
- 13 mo
Fees and Policies
The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified.
Required Fees
One-Time Basics
- Due at Application
- Application Fee Per ApplicantiCharged per applicant.$100.00
- Due at Move-In
- Administrative FeeiCharged per unit.$300.00
Pet Policy and Fees
CatsNone
Comments: | Restrictions: None
DogsNone
Comments: | Restrictions: None
Parking Info and Fees
- Surface Lot
- 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
- EV Charging
- EV charging stations available
- Full Size Washer and Dryer Included In Every Home
- Garage
- Higher Vaulted Ceilings Available in Select Homes
- Luxury Townhomes Include a Ring Video Doorbell
- Private Balcony or Patio Included in Every Home
- Spanish Speaking Team Members Available
Living Area Features
- Walk In Closets
Unique Amenities
- Garage Available
Map
- Shopping
- Grocery
- Medical
- Parks
- Nearby Properties

Map
Hours and Contact Info
| Monday | 9:00 am–6:00 pm |
| Tuesday | 9:00 am–6:00 pm |
| Wednesday | 9:00 am–6:00 pm |
| Thursday | 9:00 am–6:00 pm |
| Friday | 9:00 am–6:00 pm |
| Saturday | 10:00 am–5:00 pm |
| Sunday | 10:00 am–5:00 pm |
Renters Reviews and Ratings
Where to even begin?
November 27, 2024I would give The Overlook zero stars if I could. I’ve lived in FL for 5 years now and have always rented apartments. I thought I had lived in some pretty awful places until I moved here. Where to even begin? First off, something is always broken here, whether it be a lock to a door, or a gate. Next, the noise. This is NOT a quiet community, even though they try to market it as one. Not only the people, but their broken equipment is always beeping loudly, and we have tried to put in several noise ...complaints or maintenance requests for it, none of which are ever fixed. Oh, and if you try to go to the office, they’re either all magically on lunch or have zero idea how to fix anything. The biggest zero for me though is their absolute lack of communication. At the beginning of the lease, I wasn’t sure if I’d be staying the whole time, so I made sure to check and see if subleasing was an option, and it supposedly was. So at the end of October, I called ( several times, until someone finally answered ), and asked about the process, once again. I was told yes, the person in question just needs to email them over some information. Okay great, that person did so. It’s now November 27th, we have been trying to call, leave voicemails, send emails, and even gone into the office, to, once again, find them all somehow on lunch, no matter what time of day, or be told “ we’ll talk to the property manager. “ Not one call back, no emails in response, nothing. Today I called and was hung up on after saying my name. I just don’t understand why not ONE person can get back to us, including their property manager. So, before being drawn in by the outwards beauty of the community, be aware that you will not matter one little bit after you move in, and you will be trying for weeks to get in contact with them, even for the smallest thing.Read MoreReview from Apartments.com
Spider infestation
December 30, 2023If you want to share your “luxury” apartment with spiders move here ! No wonder it’s 6 weeks free , they make you suffer with spider infestations and a dirty apartment upon move in and a staff who never reply and a corporate office who doesn’t either . Great property !!!Property Manager Responded
January 3, 2024Hi Falestean, We're sorry to hear about your experience. We take your concerns seriously and will address them with our team. We strive to provide a clean and comfortable living environment for all residents. Thank you for bringing this to our attention. The Overlook Team
Review from Apartments.com
Nearby Schools
Bridgewater Middle
Keenes Crossing Elementary
About GreatSchools Data on ApartmentHomeLiving.com.
Points of Interest
Time and distance from The Overlook.
Big Box and Retail
Walgreens
Aldi
Walmart
Groceries
Aldi
Publix
Hospitals
Parks and Recreation
The Overlook has 2 parks within 11.5 miles, including Tibet-Butler Reserve, and Universal Studios Florida.
Restaurants and Dining
Shopping Centers
The Overlook has 5 shopping centers within 1.8 miles.
Nearby Neighborhoods
Rental Price Ranges in the Area
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Garden Studio Apartments | $1,557 | $1,099 | $1,695 |
| Winter Garden 1 Bedroom Apartments | $1,873 | $1,295 | $3,223 |
| Winter Garden 2 Bedroom Apartments | $2,275 | $1,444 | $4,979 |
| Winter Garden 3 Bedroom Apartments | $2,898 | $1,884 | $7,841 |
| Winter Garden 4 Bedroom Apartments | $2,782 | $2,734 | $2,840 |
Nearby Apartments
Nearby Homes
Did You Know?
The average Apartment shopper researches 4 properties in detail before signing a lease.










