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The Overlook
Winter Garden, FL 34787

- Studio–3 Bedrooms
- 679–1,553Square Feet
About The Overlook
BLACK FRIDAY DEAL! EXTRA $500 OFF Move-In Costs + 50% OFF Your First 4 Months, PLUS, Ask About Our Look & Lease Specials. Limited Availability. Call For Details. Leasing spacious and upscale studio, one-, two-, and three-bedroom apartments and townhomes for rent in Winter Garden, FL, near Horizon West and Disney! The Overlook is ideally positioned in the heart of Flamingo Crossings and Horizon West, one of the best places 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
From $1,658
Studio, 1 Bath, 679 sq ftAvailable NowModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $1,698 Available Now 2131 679 $250 $1,658 November 25, 2025 2328 679 $250 Model Rent and Fees
Model Price Range
- $1,658 - $1,698
Model Rent and Fees
Model Price Range
- $1,658 - $1,698
Apartment Model: Hampton S2Studio, 1 Bath, 679 sq ftAvailable Now![]()
Hampton S2 - Floorplan 1 Apartment Unit: 2131Apartment Model: Hampton S2Studio, 1 Bath, 679 sq ftAvailable NowApartment Unit: 2328Apartment Model: Hampton S2Studio, 1 Bath, 679 sq ftAvailable November 25, 20251 Bedroom
Show Unavailable FloorplansSapphire A2
$1,810
1 Bed, 1 Bath, 789 sq ftAvailable Nov 24Model Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $1,810 November 24, 2025 2320 789 $250 $1,810 January 30, 2026 1324 789 $250 Model Rent and Fees
Price
- $1,810
Model Rent and Fees
Price
- $1,810
Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable November 24, 2025![]()
Sapphire A2 - Floorplan 1 Apartment Unit: 2320Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable November 24, 2025Apartment Unit: 1324Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable January 30, 2026Cottonwood A1
1 Bed, 1 Bath, 742 sq ftModel Gallery
Floorplans
Photos
Availability Details
Availability Date Unit Sq Ft Unavailable Cottonwood A1 742 sq ft Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftUnavailableFloorplansPhotos![]()
Cottonwood A1 - Image 1 ![]()
Cottonwood A1 - Image 2 ![]()
Cottonwood A1 - Image 3 ![]()
Cottonwood A1 - Image 4 ![]()
Cottonwood A1 - Image 5 ![]()
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Cottonwood A1 - Image 7 ![]()
Cottonwood A1 - Floorplan 8 Catalina A3
1 Bed, 1 Bath, 798 sq ftLargest 1 BedroomThis is the largest 1 Bedroom at this PropertyModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Unavailable Catalina A3 798 sq ft Apartment Model: Catalina A31 Bedroom, 1 Bath, 798 sq ftUnavailable![]()
Catalina A3 - Floorplan 1 2 Bedrooms
Show Unavailable FloorplansCypress B2
From $2,138
2 Beds, 2 Baths, 1093 sq ftAvailable NowCheapest 2 BedroomThis is the cheapest 2 Bedroom at this PropertyModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $2,173 Available Now 1328 1093 $250 $2,183 Available Now 2116 1093 $250 $2,138 Available Now 2219 1093 $250 Model Rent and Fees
Model Price Range
- $2,138 - $2,183
Model Rent and Fees
Model Price Range
- $2,138 - $2,183
Model Rent and Fees
Model Price Range
- $2,138 - $2,183
Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable Now![]()
Cypress B2 - Floorplan 1 Apartment Unit: 1328Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable NowApartment Unit: 2116Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable NowApartment Unit: 2219Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable NowLaurel B3
$2,297
2 Beds, 2 Baths, 1198 sq ftAvailable NowModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $2,297 Available Now 2325 1198 $250 Model Rent and Fees
Price
- $2,297
Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable Now![]()
Laurel B3 - Floorplan 1 Apartment Unit: 2325Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable NowNewport 2-Car Garage Townhome
$3,100
2 Beds, 3 Baths, 1553 sq ftAvailable NowLargest 2 BedroomThis is the largest 2 Bedroom at this PropertyModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $3,100 Available Now 6 1553 $250 Unit 6 Amenities and Features
Unique Features
- Luxury Townhomes Include a Ring Video Doorbell
Model Rent and Fees
Price
- $3,100
Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftAvailable Now![]()
Newport 2-Car Garage Townhome - Floorplan 1 Apartment Unit: 6Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftAvailable NowMagnolia B5
2 Beds, 2 Baths, 1118 sq ftModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Unavailable Magnolia B5 1118 sq ft Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftUnavailable![]()
Magnolia B5 - Floorplan 1 Avalon 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 1 3 Bedrooms
Sycamore C2
3 Beds, 2 Baths, 1501 sq ftModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Unavailable Sycamore C2 1501 sq ft Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftUnavailable![]()
Sycamore C2 - Floorplan 1
Property Information
- 232 Units
- 4 Stories
- Built in 2023
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Lease Terms
- 13 mo
Fees and Policies
The fees below are based on community-supplied data and may exclude additional fees and utilities.
Required Fees
One-Time Move-In Fees
- Due at Move-In
- Administrative Fee$300
- Due at Application
- Application Fee Per Applicant$100
Pet Policy and Fees
Dogs
- Fees Not Specified
| Restrictions: None
Cats
- Fees Not Specified
| Restrictions: None
Parking Info and Fees
- Garage Parking
- Assigned Parking
- $200/Mo
- Other
- Surface Lot
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 |
Getting Around
Walk Score®
1 / 100
Car-Dependent
Almost all errands require a car
Bike Score®
25 / 100
Somewhat Bikeable
Minimal bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
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
Central Florida Behavioral Hospital
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 | $1,601 | $1,099 | $1,755 |
| Winter Garden 1 Bedroom Apartments | $1,856 | $1,210 | $4,116 |
| Winter Garden 2 Bedroom Apartments | $2,244 | $1,310 | $3,525 |
| Winter Garden 3 Bedroom Apartments | $2,701 | $1,827 | $4,432 |
| Winter Garden 4 Bedroom Apartments | $3,020 | $2,875 | $3,100 |
Nearby Apartments
Nearby Homes
Did You Know?
The average Apartment shopper researches 4 properties in detail before signing a lease.










