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Starting at $1,586
Studio • 1 Bath • 678 Sq Ft
| 1 available unit | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 3107 | $1,586 | 678 | Nov 2 |
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$1,511 – $2,468/mo
14680 Westerly Drive, Winter Garden, FL 34787The Westerly currently lists 9 floor plans across 41 available units, from studio to three-bedroom, starting at $1,511/mo. 1 studio at $1,586/mo (678 sq ft), earliest move-in Nov 2. 14 one-bedrooms from $1,511 to $1,611/mo (724–801 sq ft), earliest move-in Sep 23. 21 two-bedrooms from $1,711 to $1,923/mo (1,085–1,161 sq ft), earliest move-in Sep 23. 5 three-bedrooms from $2,204 to $2,468/mo (1,302–1,408 sq ft), earliest move-in Sep 23. Prices checked September 24, 2026.
Starting at $1,586
Studio • 1 Bath • 678 Sq Ft
| 1 available unit | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 3107 | $1,586 | 678 | Nov 2 |
Starting at $1,511
1 Bedroom • 1 Bath • 801 Sq Ft
| 2 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 3106 | $1,511 | 801 | Sep 23 | |
| 3406 | $1,546 | 801 | Oct 7 |
Starting at $1,513
1 Bedroom • 1 Bath • 724 Sq Ft
| 11 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 2111 | $1,513 | 724 | Sep 23 | |
| 2303 | $1,546 | 724 | Sep 23 | |
| 3103 | $1,551 | 724 | Sep 23 | |
| 6311 | $1,586 | 724 | Sep 23 | |
| 5311 | $1,596 | 724 | Sep 23 | |
| 5411 | $1,606 | 724 | Oct 3 | |
| 4111 | $1,586 | 724 | Oct 8 | |
| 4205 | $1,576 | 724 | Oct 24 | |
| 2103 | $1,551 | 724 | Oct 31 | |
| 3105 | $1,551 | 724 | Nov 18 | |
| 3409 | $1,546 | 724 | Dec 18 |
Starting at $1,611
1 Bedroom • 1 Bath • 771 Sq Ft
| 1 available unit | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 5415 | $1,611 | 771 | Dec 29 |
Starting at $1,711
2 Bedrooms • 2 Baths • 1,085 Sq Ft
| 10 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 6205 | $1,711 | 1,085 | Sep 23 | |
| 5110 | $1,712 | 1,085 | Sep 23 | |
| 1309 | $1,723 | 1,085 | Sep 23 | |
| 4308 | $1,818 | 1,085 | Sep 23 | |
| 6305 | $1,853 | 1,085 | Sep 23 | |
| 5405 | $1,873 | 1,085 | Sep 23 | |
| 5409 | $1,873 | 1,085 | Sep 23 | |
| 2209 | $1,808 | 1,085 | Oct 4 | |
| 5207 | $1,853 | 1,085 | Dec 1 | |
| 6208 | $1,783 | 1,085 | Dec 6 |
Starting at $1,759
2 Bedrooms • 2 Baths • 1,161 Sq Ft
| 10 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 4202 | $1,759 | 1,161 | Sep 23 | |
| 1202 | $1,760 | 1,161 | Sep 23 | |
| 4102 | $1,769 | 1,161 | Sep 23 | |
| 2412 | $1,778 | 1,161 | Sep 23 | |
| 2402 | $1,892 | 1,161 | Sep 23 | |
| 6212 | $1,903 | 1,161 | Sep 23 | |
| 2102 | $1,913 | 1,161 | Sep 23 | |
| 4110 | $1,913 | 1,161 | Oct 11 | |
| 3410 | $1,923 | 1,161 | Oct 17 | |
| 4210 | $1,903 | 1,161 | Nov 7 |
Starting at $1,794
2 Bedrooms • 2 Baths • 1,095 Sq Ft
| 1 available unit | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 5108 | $1,794 | 1,095 | Sep 23 |
Starting at $2,204
3 Bedrooms • 2 Baths • 1,302 Sq Ft
| 2 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 6213 | $2,204 | 1,302 | Sep 23 | |
| 1213 | $2,248 | 1,302 | Nov 13 |
Starting at $2,333
3 Bedrooms • 2 Baths • 1,408 Sq Ft
| 3 available units | Price | Sq ft | Available | Open unit |
|---|---|---|---|---|
| 5135 | $2,388 | 1,408 | Sep 23 | |
| 5235 | $2,468 | 1,408 | Sep 23 | |
| 5228 | $2,333 | 1,408 | Dec 10 |
Rent at The Westerly is $1,511 – $2,468 per month. The security deposit is $500. The earliest listed move-in is Sep 23. Prices checked September 24, 2026.
Rent
$1,511 – $2,468/moSecurity deposit
$500Earliest move-in
Sep 23The Westerly lists 21 amenities, including a gym, a pool, and parking.
24/7 Fitness Center
24/7 Package Receiving And Retrieval
Attached Garages Available
Clubhouse Containing Function Space, Game Room And Catering Kitchen
Dedicated Studio Space For Fitness Classes
Elevator
Grilling Area
High Speed Internet
Leed Green Designed
NóS Falamos PortuguêS
Off Street Parking
On-Site Maintenance
On-Site Management
Outdoor Recreation Area With Bocce, Ping Pong, And Swings
Outdoor Wellness Park Featuring Trails And Fitness Equipment
Pet Park
Pet Spa
Private Pool With Elevated Deck And Sunshelf
Sauna
Se Habla EspañOl
Smoke-Free Community
The Westerly is at 14680 Westerly Drive, Winter Garden, FL 34787.
14680 Westerly Drive, Winter Garden, FL 34787
Residents give The Westerly a C grade (about 3.7 out of 5) from 100+ reviews. The Westerly Apartments offers beautiful, well-maintained units in a convenient location with strong community events and responsive leasing staff. However, residents report persistent operational challenges including unresponsive management communication, unresolved maintenance issues, package room disorganization and security concerns, and inconsistent fee practices.
The Westerly Apartments offers beautiful, well-maintained units in a convenient location with strong community events and responsive leasing staff. However, residents report persistent operational challenges including unresponsive management communication, unresolved maintenance issues, package room disorganization and security concerns, and inconsistent fee practices. While positive experiences highlight staff professionalism and amenities, negative reviews consistently cite delayed repairs, difficulty reaching management, and concerns about building access and security.
Management responsiveness and communication are inconsistent across the property, with residents reporting difficulty reaching staff by phone or email and experiencing delayed responses to maintenance and administrative issues. While some residents praise individual staff members for professionalism and attentiveness, others describe a pattern of unresolved concerns, temporary fixes presented as permanent solutions, and inadequate follow-up on requests. Package room security and organization, building access issues (broken key fobs and doors), and post-move-out billing disputes are recurring operational concerns. Recent management changes appear to have improved service quality for some residents, though experiences vary significantly.
The property offers well-regarded amenities including a 24-hour gym, pool, and clubhouse that residents appreciate. However, common-area maintenance and package management are significant concerns, with recurring reports of unaddressed animal waste in hallways, disorganized and unsecured package rooms, and inconsistent upkeep. Parking availability and elevator maintenance issues have also been noted, alongside communication gaps between management and residents regarding maintenance requests and service failures.
Residents report significant building maintenance and cleanliness concerns, particularly pest infestations, broken doors and elevators, and hallway cleanliness issues. Noise disturbances have increased over time, with reports of music and TV noise during quiet hours. While amenities are noted as convenient, the gap between initial move-in condition and current upkeep has disappointed many residents.
Maintenance response times and follow-through are inconsistent, with several residents reporting delayed repairs, temporary fixes presented as permanent solutions, and issues remaining unresolved for extended periods. Communication gaps between residents and management are a recurring concern, including unresponsive phone lines and emails, lack of notice for after-hours maintenance work, and difficulty scheduling repairs. While some residents report positive experiences with responsive and professional maintenance staff, the majority of feedback indicates systemic issues with building access, appliance repairs, HVAC service, and overall property upkeep.
The property benefits from a highly convenient location near shopping, dining, and entertainment venues, with multiple reviews highlighting proximity to stores, restaurants, and Disney access. Most residents praise the walkable area and nearby amenities as a major advantage. However, location convenience alone does not address all resident concerns, as some issues with building maintenance and community standards have been noted.
The Westerly is car-dependent (grade F) and biking is not bikeable (grade F).
F
Car-Dependent
F
Not Bikeable
Experience contemporary bliss in a beautifully designed luxury apartment at The Westerly. These studio, one, two, and three bedroom apartments, carefully crafted with your lifestyle in mind, offering bright and open living spaces complemented by hardwood-style flooring, quartz countertops, and stainless steel appliances.
Experience contemporary bliss in a beautifully designed luxury apartment at The Westerly. These studio, one, two, and three bedroom apartments, carefully crafted with your lifestyle in mind, offering bright and open living spaces complemented by hardwood-style flooring, quartz countertops, and stainless steel appliances. Modern conveniences like programmable thermostats, Bluetooth entry, and full-size washer and dryer sets will make daily living efficient, while the wealth of amenities that await you right outside your front door will help you relax and unwind.
The Westerly is a 352-unit apartment.
Building
ApartmentTotal units
352Water Spring Elementary is 2.8 miles from The Westerly. 10 schools are listed nearby.
| School | Type | Level | Distance |
|---|---|---|---|
Water Spring Elementary Public · Elementary | Public | Elementary | 2.8 mi |
Water Spring Middle School-0482 Public · Middle | Public | Middle | 3.0 mi |
Horizon High School Public · High | Public | High | 3.1 mi |
1702 Lake Roberts Landing DR Private · High | Private | High | 4.6 mi |
Summerlake Elementary Public · Elementary | Public | Elementary | 5.5 mi |
Independence Elementary Public · Elementary | Public | Elementary | 6.5 mi |
Cranium Academy Private · Elementary | Private | Elementary | 9.0 mi |
Zion New Life Child Development Center Private · Preschool | Private | Preschool | 10.1 mi |
Fmi STEM Academy Private · High | Private | High | 10.9 mi |
Starchild Academy Winter Garden Private · Elementary | Private | Elementary | 11.8 mi |
The Westerly is managed by Willow Bridge. Call (833) 661-4907 to tour or ask about availability.