418 CHARLES, WINTER GARDEN, FL 34787

$2,600

Beds: 5

Baths: 3 Full

Sq. Ft.: 1,584 Sq. Ft.

Year Built: 1952

Lot Size: 0.1 Acres

Garage: 2

Pool: No

DOM: 38

Property Overview

Status: Active

Property Type: Residential Lease

MLS #: 7a4797f291dc438df65ae5f0edab5a35

Subdivision: SHADOW LAWN

County: Orange

HOA Fee: N/A

Year Built: 1952

Construction:

Foundation:

Roof:

Cooling: Central Air

Heating: Central

Sewer: Public Sewer

Water Source: Public

Zoning: N/A

Tax Amount: N/A (N/A)

Listed On: Jan 20, 2026

Description

One or more photo(s) has been virtually staged. Golf Cart District Home where charm, culture, and convenience come together in the heart of Downtown Winter Garden! This beautifully maintained 5-bedroom, 3-bathroom home offers space, style, and flexibility in one of Central Florida’s most sought-after and walkable downtown districts. The open-concept floor plan seamlessly connects the living, dining, and kitchen areas—ideal for entertaining or everyday living. The kitchen is thoughtfully designed with granite countertops and stainless steel appliances, blending modern finishes with functionality. Each bedroom is filled with natural light and offers generous closet space, providing comfort and versatility throughout the home. A two-car garage adds convenience and additional storage. What truly sets this home apart is its exceptional location. Just steps away, Downtown Winter Garden offers a vibrant small-town atmosphere with big lifestyle appeal—featuring locally owned boutiques, award-winning restaurants, coffee shops, breweries, and the iconic Plant Street Market. Spend weekends at the popular Winter Garden Farmers Market, enjoy live music and seasonal festivals, or take evening strolls along the historic brick-lined streets. Outdoor enthusiasts will love immediate access to the West Orange Trail, a 22-mile paved trail perfect for walking, jogging, and biking through scenic Central Florida landscapes. With nearby parks, community events, and a strong sense of local culture, Downtown Winter Garden offers a lifestyle that’s both active and relaxed. Despite the charming, hometown feel, the location provides easy access to major highways, making commutes to Orlando, theme parks, and surrounding areas quick and convenient. This is a rare opportunity to enjoy the energy of downtown living while still coming home to modern comfort and space. Resident Benefits Package (RBP) – $59/month All residents are enrolled in our Resident Benefits Package, which includes: Liability insurance Credit building to help boost your credit score with timely rent payments Up to $1M Identity Theft Protection Move-in concierge service for easy utility and home service setup Best-in-class resident rewards program On-demand pest control HVAC air filters And much more (full details provided upon application) Additional Details Security deposit-free option available for qualified tenants through Obligo Application fee: $80 per applicant (18 years and older) One-time admin fee: $295 upon approval

Exterior Features

Sidewalk

Directions

From Florida’s Turnpike, take Exit 272 for FL-50/West Colonial Drive and head west toward Winter Garden. Continue on FL-50 for approximately 3 miles, then turn right onto S Dillard Street. Drive south for about 0.4 miles, then turn left onto Charles Street. Continue down Charles Street, and 418 Charles Street will be located along the left-hand side of the road, just a short distance from downtown Winter Garden.

School Information

Elementary: Maxey Elem

Middle: Lakeview Middle

High: Windermere High School

Location

Get Directions View on Google Maps

Mortgage Estimator

*Estimate includes Principal & Interest (P&I) only. It does not include taxes, insurance, HOA fees, or PMI. Rates and payments may vary. Consult a lender for accurate figures.

Listing Information

Provided Courtesy of:

CANI PROPERTY MANAGEMENT

Listing Agent: Jeremy Porter

Information is deemed reliable but not guaranteed. Information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data last updated: March 6, 2026, 7:53 am UTC

MLS Source: Stellar MLS Copyright © 2026

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