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The Overlook
Winter Garden, FL 34787

- Studio–3 Bedrooms
- 679–1,553 Square Feet
About The Overlook
Memorial Day Deals Are Live! Get 6 Weeks Free plus 4 Months Free Cable & Internet! Apply by MMD to lock in your savings—leasing fast, don't wait.Now leasing spacious studio, one-, two-, and three-bedroom apartments and townhomes in Winter Garden, FL, near Horizon West and Disney. The Overlook sits in the heart of Flamingo Crossings and Horizon West—one of the most desirable places to live in Florida.As a new resident, you'll enjoy a perfect blend of comfort, convenience, and modern elegance, paired with top-tier amenities. Located just off Walt Disney World property, The Overlook offers upscale, thoughtfully designed homes with gorgeous contemporary finishes.Our pet-friendly community provides effortless access to SR-429 and US-192, placing you minutes from work, entertainment, dining, and everything 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 Jul 3Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit July 3, 2026 2131 679 $250 Apartment Model: Hampton S2Studio, 1 Bath, 679 sq ftAvailable July 3, 2026![]()
Hampton S2 - Floorplan Apartment Unit: 2131Apartment Model: Hampton S2Studio, 1 Bath, 679 sq ftAvailable July 3, 20261 Bedroom
Show Unavailable FloorplansCottonwood A1
1 Bed, 1 Bath, 742 sq ftAvailable NowCheapest 1 BedroomThis is the cheapest 1 Bedroom at this PropertyModel Gallery
Floorplans
Photos
Availability Details
Availability Date Unit Sq Ft Deposit View Details Available Now 2127 742 $250 June 12, 2026 2315 742 $250 June 18, 2026 2107 742 $250 Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable NowFloorplansPhotos![]()
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 - Floorplan Apartment Unit: 2127Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable NowApartment Unit: 2315Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable June 12, 2026Apartment Unit: 2107Apartment Model: Cottonwood A11 Bedroom, 1 Bath, 742 sq ftAvailable June 18, 2026Sapphire A2
1 Bed, 1 Bath, 789 sq ftAvailable May 29Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit View Details May 29, 2026 2108 789 $250 June 10, 2026 2412 789 $250 June 13, 2026 1212 789 $250 Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable May 29, 2026![]()
Sapphire A2 - Floorplan Apartment Unit: 2108Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable May 29, 2026Apartment Unit: 2412Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable June 10, 2026Apartment Unit: 1212Apartment Model: Sapphire A21 Bedroom, 1 Bath, 789 sq ftAvailable June 13, 2026Catalina 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 2 Bedrooms
Cypress B2
2 Beds, 2 Baths, 1093 sq ftAvailable Jun 3Cheapest 2 BedroomThis is the cheapest 2 Bedroom at this PropertyModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit View Details June 3, 2026 2105 1093 $250 June 5, 2026 1313 1093 $250 August 5, 2026 1221 1093 $250 Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable June 3, 2026![]()
Cypress B2 - Floorplan Apartment Unit: 2105Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable June 3, 2026Apartment Unit: 1313Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable June 5, 2026Apartment Unit: 1221Apartment Model: Cypress B22 Bedroom, 2 Bath, 1093 sq ftAvailable August 5, 2026Magnolia B5
2 Beds, 2 Baths, 1118 sq ftAvailable Jun 10Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit June 10, 2026 1423 1118 $250 Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftAvailable June 10, 2026![]()
Magnolia B5 - Floorplan Apartment Unit: 1423Apartment Model: Magnolia B52 Bedroom, 2 Bath, 1118 sq ftAvailable June 10, 2026Laurel B3
2 Beds, 2 Baths, 1198 sq ftAvailable Jun 24Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit June 24, 2026 1406 1198 $250 Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable June 24, 2026![]()
Laurel B3 - Floorplan Apartment Unit: 1406Apartment Model: Laurel B32 Bedroom, 2 Bath, 1198 sq ftAvailable June 24, 2026Avalon B4
2 Beds, 2 Baths, 1270 sq ftAvailable Jul 19Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit July 19, 2026 2133 1270 $250 Apartment Model: Avalon B42 Bedroom, 2 Bath, 1270 sq ftAvailable July 19, 2026![]()
Avalon B4 - Floorplan Apartment Unit: 2133Apartment Model: Avalon B42 Bedroom, 2 Bath, 1270 sq ftAvailable July 19, 2026Newport 2-Car Garage Townhome
2 Beds, 3 Baths, 1553 sq ftAvailable Jul 7Largest 2 BedroomThis is the largest 2 Bedroom at this PropertyModel Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit July 7, 2026 6 1553 $250 Unit 6 Amenities and Features
Unique Features
- Luxury Townhomes Include a Ring Video Doorbell
Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftAvailable July 7, 2026![]()
Newport 2-Car Garage Townhome - Floorplan Apartment Unit: 6Apartment Model: Newport 2-Car Garage Townhome2 Bedroom, 3 Bath, 1553 sq ftAvailable July 7, 20263 Bedrooms
Sycamore C2
3 Beds, 2 Baths, 1501 sq ftAvailable Jun 5Model Gallery
Floorplans
Availability Details
Availability Date Unit Sq Ft Deposit View Details June 5, 2026 1202 1501 $250 June 5, 2026 1330 1501 $250 June 27, 2026 2201 1501 $250 Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable June 5, 2026![]()
Sycamore C2 - Floorplan Apartment Unit: 1202Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable June 5, 2026Apartment Unit: 1330Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable June 5, 2026Apartment Unit: 2201Apartment Model: Sycamore C23 Bedroom, 2 Bath, 1501 sq ftAvailable June 27, 2026
Property Information
- Built in 2023
- 232 Units
- 4 Stories
Lease Terms
- 12 - 15 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
Other Fees and Policies
Pet Fees
- Cat
- Cat FeeiCharged Per Pet.$300.00
- Cat RentiCharged Per Pet.$20.00/mo
- Dog
- Dog FeeiCharged Per Pet.$300.00
- Dog RentiCharged Per Pet.$20.00/mo
Breed restrictions apply. See the Aura Leasing Team for details.
Breed restrictions apply. See the Aura Leasing Team for details.
Pets are welcome! No weight limit and maximum limit of 3 pets.
Parking Info and Fees
- Surface Lot
- Garage Parking
- Other
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 | $1,588 | $1,383 | $1,724 |
| Winter Garden 1 Bedroom Apartments | $1,863 | $1,330 | $2,953 |
| Winter Garden 2 Bedroom Apartments | $2,283 | $1,479 | $10,000+ |
| Winter Garden 3 Bedroom Apartments | $2,698 | $1,877 | $4,332 |
| Winter Garden 4 Bedroom Apartments | $2,621 | $2,615 | $2,627 |
Nearby Apartments
Nearby Homes
Did You Know?
The months of July-August show the most apartment renter searches in Winter Garden.

















Pets are welcome! No weight limit and maximum limit of 3 pets.