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The Westerly 1 of 8

The Westerly

$1,586 – $2,743/mo

14680 Westerly Drive, Winter Garden, FL 34787

What floor plans are available at The Westerly?

The Westerly currently lists 10 floor plans across 39 available units, from studio to three-bedroom, starting at $1,586/mo. 1 studio at $1,586/mo (678 sq ft), earliest move-in Nov 2. 15 one-bedrooms from $1,666 to $1,811/mo (724–803 sq ft), earliest move-in Oct 1. 18 two-bedrooms from $1,901 to $2,148/mo (1,085–1,161 sq ft), earliest move-in Oct 1. 5 three-bedrooms from $2,458 to $2,743/mo (1,302–1,408 sq ft), earliest move-in Oct 1. Prices checked October 2, 2026.

S1

Starting at $1,586

Studio • 1 Bath • 678 Sq Ft

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

A1

Starting at $1,666

1 Bedroom • 1 Bath • 724 Sq Ft

11 available unitsPriceSq ftAvailableOpen unit
2111$1,666724Oct 1
2303$1,703724Oct 1
3103$1,751724Oct 1
6311$1,786724Oct 1
5311$1,796724Oct 1
5411$1,806724Oct 3
4111$1,786724Oct 8
4205$1,776724Oct 24
2103$1,751724Oct 31
3105$1,751724Nov 18
3409$1,746724Dec 18

A3

Starting at $1,711

1 Bedroom • 1 Bath • 801 Sq Ft

2 available unitsPriceSq ftAvailableOpen unit
3106$1,711801Oct 1
3406$1,746801Oct 7

A4

Starting at $1,776

1 Bedroom • 1 Bath • 803 Sq Ft

1 available unitPriceSq ftAvailableOpen unit
6410$1,776803Nov 4

A2

Starting at $1,811

1 Bedroom • 1 Bath • 771 Sq Ft

1 available unitPriceSq ftAvailableOpen unit
5415$1,811771Dec 29

B1

Starting at $1,901

2 Bedrooms • 2 Baths • 1,085 Sq Ft

10 available unitsPriceSq ftAvailableOpen unit
1309$1,9011,085Oct 1
5110$1,9131,085Oct 1
4308$2,0001,085Oct 1
6305$2,0841,085Oct 1
5409$2,0851,085Oct 1
5405$2,1041,085Oct 1
2209$2,0331,085Oct 6
5407$2,0981,085Oct 10
5207$2,0781,085Dec 1
6208$2,0081,085Dec 6

B4

Starting at $1,972

2 Bedrooms • 2 Baths • 1,095 Sq Ft

1 available unitPriceSq ftAvailableOpen unit
5108$1,9721,095Oct 1

B2

Starting at $1,973

2 Bedrooms • 2 Baths • 1,161 Sq Ft

7 available unitsPriceSq ftAvailableOpen unit
1202$1,9731,161Oct 1
4202$1,9731,161Oct 1
2402$2,0701,161Oct 1
2102$2,1051,161Oct 1
6212$2,1341,161Oct 1
3410$2,1481,161Oct 17
4210$2,1281,161Nov 7

C1

Starting at $2,458

3 Bedrooms • 2 Baths • 1,302 Sq Ft

2 available unitsPriceSq ftAvailableOpen unit
6213$2,4581,302Oct 1
1213$2,5231,302Nov 13

C2

Starting at $2,608

3 Bedrooms • 2 Baths • 1,408 Sq Ft

3 available unitsPriceSq ftAvailableOpen unit
5135$2,6631,408Oct 1
5235$2,7431,408Oct 1
5228$2,6081,408Dec 10

What are the fees and lease terms at The Westerly?

Rent at The Westerly is $1,586 – $2,743 per month. The security deposit is $500. The earliest listed move-in is Oct 1. Prices checked October 2, 2026.

  • Rent

    $1,586 – $2,743/mo
  • Security deposit

    $500
  • Earliest move-in

    Oct 1

What amenities does The Westerly have?

The Westerly lists 40 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

  • 10 Foot Ceilings Available

  • Ceiling Fans

  • Conservation Area View

  • Energy Efficient Stainless Steel Appliances

  • Full Sized Washer Dryers

  • Garbage Disposal

  • Glass Stall Showers

  • Hardwood Style Floors

  • Large Corner Balcony

  • Led Energy Efficient Lighting

  • Light Colored Flooring

  • Oversized Soaking Tubs

  • Patios And Balconies Available

  • Pool View

  • Quartz Countertops In Kitchen And Bathrooms

  • Screened In Balcony

  • Smart Home Technology Featuring Programmable Thermostat And Keyless + Bluetooth Entry

  • Two-Inch Wood Blinds

  • Walk-In Closets


What do the amenities at The Westerly look like?

  • Pool
  • Gym

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 and biking is not bikeable.

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?

Independence Elementary is 6.5 miles from The Westerly. 10 schools are listed nearby.

SchoolTypeLevelDistance

Independence Elementary

Public · Elementary
PublicElementary6.5 mi

Cranium Academy

Private · Elementary
PrivateElementary9.1 mi

Zion New Life Child Development Center

Private · Preschool
PrivatePreschool10.1 mi

Sunridge Elementary School

Public · Elementary
PublicElementary11.4 mi

SunRidge Middle School

Public · Middle
PublicMiddle11.4 mi

Star Child Academy Of Winter Garden

Private · Elementary
PrivateElementary11.8 mi

Star Child Academy-Winter Garden

Private · Preschool
PrivatePreschool11.8 mi

Bright Horizons Dc-Wntr Garden

Private · Preschool
PrivatePreschool11.9 mi

UCP West Orange Charter

Charter · Elementary
CharterElementary11.9 mi

Esteem Academy

Public · High
PublicHigh12.0 mi

How do I contact The Westerly?

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