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The Overlook
Winter Garden, FL 34787

- 1–3 Bedrooms
- 742–1,553Square Feet
About The Overlook
Spring into Savings with Reduced pricing and ONE MONTH FREE! Now 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 Overlook's 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
1 Bedroom
From $1,760
Sapphire A2
1 Bed, 1 Bath, 789 sq ftAvailable NowModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $1,775 Available Now 2112 789 $250 $1,775 Available Now 2120 789 $250 $1,805 Available Now 1308 789 $250 Model Rent and Fees
Price
- $1,760 - $1,805
Model Rent and Fees
Price
- $1,760 - $1,805
Model Rent and Fees
Price
- $1,760 - $1,805
Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable NowSapphire A2 - Floorplan 1 Apartment Unit: 2112Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable NowApartment Unit: 2120Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable NowApartment Unit: 1308Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable NowFrom $1,703
Cottonwood A1
1 Bed, 1 Bath, 742 sq ftAvailable May 7Model Gallery
Floorplans
Photos
Availability Details
Price Availability Date Unit Sq Ft Deposit $1,703 May 7, 2025 1307 742 $250 $1,728 May 9, 2025 2209 742 $250 $1,703 May 9, 2025 2329 742 $250 Model Rent and Fees
Price
- $1,703 - $1,733
Model Rent and Fees
Price
- $1,703 - $1,733
Model Rent and Fees
Price
- $1,703 - $1,733
Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable May 7, 2025FloorplansPhotosCottonwood A1 - Image 1 Cottonwood A1 - Image 2 Cottonwood A1 - Image 3 Cottonwood A1 - Image 4 Cottonwood A1 - Image 5 Cottonwood A1 - Image 6 Cottonwood A1 - Image 7 Cottonwood A1 - Floorplan 8 Apartment Unit: 1307Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable May 7, 2025Apartment Unit: 2209Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable May 9, 2025Apartment Unit: 2329Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable May 9, 20252 Bedrooms
From $2,003
Cypress B2
2 Beds, 2 Baths, 1093 sq ftCheapest 2 BedroomThis is the cheapest 2 Bedroom at this PropertyAvailable NowModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $2,003 Available Now 2221 1093 $250 $2,248 Available Now 1304 1093 $250 Model Rent and Fees
Price
- $2,003 - $2,248
Model Rent and Fees
Price
- $2,003 - $2,248
Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable NowCypress B2 - Floorplan 1 Apartment Unit: 2221Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable NowApartment Unit: 1304Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable NowFrom $2,262
Laurel B3
2 Beds, 2 Baths, 1198 sq ftAvailable NowModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $2,287 Available Now 1325 1198 $250 $2,262 Available Now 2225 1198 $250 $2,282 May 16, 2025 1226 1198 $250 Model Rent and Fees
Price
- $2,262 - $2,302
Model Rent and Fees
Price
- $2,262 - $2,302
Model Rent and Fees
Price
- $2,262 - $2,302
Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable NowLaurel B3 - Floorplan 1 Apartment Unit: 1325Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable NowApartment Unit: 2225Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable NowApartment Unit: 1226Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable May 16, 2025From $2,375
Avalon B4
2 Beds, 2 Baths, 1270 sq ftAvailable NowModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $2,390 Available Now 2130 1270 $250 $2,375 Available Now 1233 1270 $250 $2,410 Available Now 1333 1270 $250 Model Rent and Fees
Price
- $2,375 - $2,410
Model Rent and Fees
Price
- $2,375 - $2,410
Model Rent and Fees
Price
- $2,375 - $2,410
Apartment Model: Avalon B42 Bedroom, 2 Bath, 1270 sq ftAvailable NowAvalon B4 - Floorplan 1 Apartment Unit: 2130Apartment Model: Avalon B42 Bedroom, 2 Bath, 1270 sq ftAvailable NowApartment Unit: 1233Apartment Model: Avalon B42 Bedroom, 2 Bath, 1270 sq ftAvailable NowApartment Unit: 1333Apartment Model: Avalon B42 Bedroom, 2 Bath, 1270 sq ftAvailable NowFrom $3,095
Newport 2-Car Garage Townhome
2 Beds, 3 Baths, 1553 sq ftLargest 2 BedroomThis is the largest 2 Bedroom at this PropertyAvailable NowModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit View Details $3,100 Available Now 2 1553 $250 $3,095 Available Now 1 1553 $250 $3,100 Available Now 4 1553 $250 Model Amenities and Features
Unique Features
- Luxury Townhomes Include a Ring Video Doorbell
Unit 2 Amenities and Features
Unique Features
- EV Charging Stations Available
- Luxury Townhomes Include a Ring Video Doorbell
Model Rent and Fees
Price
- $3,095 - $3,100
Unit 1 Amenities and Features
Unique Features
- Luxury Townhomes Include a Ring Video Doorbell
Model Rent and Fees
Price
- $3,095 - $3,100
Unit 4 Amenities and Features
Unique Features
- EV Charging Stations Available
- Luxury Townhomes Include a Ring Video Doorbell
Model Rent and Fees
Price
- $3,095 - $3,100
Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftAvailable NowNewport 2-Car Garage Townhome - Floorplan 1 Apartment Unit: 2Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftAvailable NowApartment Unit: 1Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftAvailable NowApartment Unit: 4Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftAvailable Now$2,336
Magnolia B5
2 Beds, 2 Baths, 1118 sq ftAvailable May 21Model Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $2,336 May 21, 2025 2311 1118 $250 Model Rent and Fees
Price
- $2,336
Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftAvailable May 21, 2025Magnolia B5 - Floorplan 1 Apartment Unit: 2311Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftAvailable May 21, 20253 Bedrooms
From $2,852
Sycamore C2
3 Beds, 2 Baths, 1501 sq ftAvailable NowModel Gallery
Floorplans
Availability Details
Price Availability Date Unit Sq Ft Deposit $2,902 Available Now 1302 1501 $250 $2,867 Available Now 1230 1501 $250 $2,892 Available Now 1330 1501 $250 Model Rent and Fees
Price
- $2,852 - $2,902
Model Rent and Fees
Price
- $2,852 - $2,902
Model Rent and Fees
Price
- $2,852 - $2,902
Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable NowSycamore C2 - Floorplan 1 Apartment Unit: 1302Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable NowApartment Unit: 1230Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable NowApartment Unit: 1330Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable Now
Property Information
- 232 Units
- 4 Stories
- Built in 2023
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Lease Terms
- 13
Parking Fees & Info
Parking Surface
- Surface Lot
Parking Garage
- Garage Fee: $180 To $200 /Mo
Parking Other
- Other
Fee & Deposit Info
Recurring Fees
- $180 Garage Fee
One-Time Fees
- $300 Admin Fee
- $100 Application Fee
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
Groceries
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 | $1,686 | $1,099 | $3,341 |
Winter Garden 1 Bedroom Apartments | $1,841 | $1,210 | $3,185 |
Winter Garden 2 Bedroom Apartments | $2,314 | $1,260 | $3,670 |
Winter Garden 3 Bedroom Apartments | $2,800 | $1,450 | $4,685 |
Winter Garden 4 Bedroom Apartments | $3,028 | $2,430 | $4,499 |
Nearby Apartments
Nearby Homes
Did You Know?
The average 3 Bedroom Apartment in Winter Garden is $2,800.