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The Westerly 1 of 12

The Westerly

$1,511 – $2,468/mo

14680 Westerly Drive, Winter Garden, FL 34787

What floor plans are available at The Westerly?

The 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.

S1

Starting at $1,586

Studio • 1 Bath • 678 Sq Ft

1 available unitPriceSq ftAvailableOpen unit
3107$1,586678Nov 2

A3

Starting at $1,511

1 Bedroom • 1 Bath • 801 Sq Ft

2 available unitsPriceSq ftAvailableOpen unit
3106$1,511801Sep 23
3406$1,546801Oct 7

A1

Starting at $1,513

1 Bedroom • 1 Bath • 724 Sq Ft

11 available unitsPriceSq ftAvailableOpen unit
2111$1,513724Sep 23
2303$1,546724Sep 23
3103$1,551724Sep 23
6311$1,586724Sep 23
5311$1,596724Sep 23
5411$1,606724Oct 3
4111$1,586724Oct 8
4205$1,576724Oct 24
2103$1,551724Oct 31
3105$1,551724Nov 18
3409$1,546724Dec 18

A2

Starting at $1,611

1 Bedroom • 1 Bath • 771 Sq Ft

1 available unitPriceSq ftAvailableOpen unit
5415$1,611771Dec 29

B1

Starting at $1,711

2 Bedrooms • 2 Baths • 1,085 Sq Ft

10 available unitsPriceSq ftAvailableOpen unit
6205$1,7111,085Sep 23
5110$1,7121,085Sep 23
1309$1,7231,085Sep 23
4308$1,8181,085Sep 23
6305$1,8531,085Sep 23
5405$1,8731,085Sep 23
5409$1,8731,085Sep 23
2209$1,8081,085Oct 4
5207$1,8531,085Dec 1
6208$1,7831,085Dec 6

B2

Starting at $1,759

2 Bedrooms • 2 Baths • 1,161 Sq Ft

10 available unitsPriceSq ftAvailableOpen unit
4202$1,7591,161Sep 23
1202$1,7601,161Sep 23
4102$1,7691,161Sep 23
2412$1,7781,161Sep 23
2402$1,8921,161Sep 23
6212$1,9031,161Sep 23
2102$1,9131,161Sep 23
4110$1,9131,161Oct 11
3410$1,9231,161Oct 17
4210$1,9031,161Nov 7

B4

Starting at $1,794

2 Bedrooms • 2 Baths • 1,095 Sq Ft

1 available unitPriceSq ftAvailableOpen unit
5108$1,7941,095Sep 23

C1

Starting at $2,204

3 Bedrooms • 2 Baths • 1,302 Sq Ft

2 available unitsPriceSq ftAvailableOpen unit
6213$2,2041,302Sep 23
1213$2,2481,302Nov 13

C2

Starting at $2,333

3 Bedrooms • 2 Baths • 1,408 Sq Ft

3 available unitsPriceSq ftAvailableOpen unit
5135$2,3881,408Sep 23
5235$2,4681,408Sep 23
5228$2,3331,408Dec 10

What are the fees and lease terms at The Westerly?

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/mo
  • Security deposit

    $500
  • Earliest move-in

    Sep 23

What amenities does The Westerly have?

The 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


What do the amenities at The Westerly look like?

  • Pool
    3 photos
  • Gym
  • Game room
  • Work space
  • Dog park
    3 photos

Where is The Westerly?

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.

3.70 · 100+ reviews
Overall rating
Positive
Mixed
Neutral
Negative
Management3.3
Amenities and Shared Spaces2.8
Building Quality2.3
Maintenance2.4
Location4.3

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.


Is The Westerly walkable?

The Westerly is car-dependent (grade F) and biking is not bikeable (grade F).

WALK

Car-Dependent

BIKE

Not Bikeable


What is The Westerly like?

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.


How big is The Westerly?

The Westerly is a 352-unit apartment.

  • Building

    Apartment
  • Total units

    352

What schools are near The Westerly?

Water Spring Elementary is 2.8 miles from The Westerly. 10 schools are listed nearby.

SchoolTypeLevelDistance

Water Spring Elementary

Public · Elementary
PublicElementary2.8 mi

Water Spring Middle School-0482

Public · Middle
PublicMiddle3.0 mi

Horizon High School

Public · High
PublicHigh3.1 mi

1702 Lake Roberts Landing DR

Private · High
PrivateHigh4.6 mi

Summerlake Elementary

Public · Elementary
PublicElementary5.5 mi

Independence Elementary

Public · Elementary
PublicElementary6.5 mi

Cranium Academy

Private · Elementary
PrivateElementary9.0 mi

Zion New Life Child Development Center

Private · Preschool
PrivatePreschool10.1 mi

Fmi STEM Academy

Private · High
PrivateHigh10.9 mi

Starchild Academy Winter Garden

Private · Elementary
PrivateElementary11.8 mi

How do I contact The Westerly?

The Westerly is managed by Willow Bridge. Call (833) 661-4907 to tour or ask about availability.