One or more photo(s) has been virtually staged. Nestled in the highly desirable **Golf Cart District**, this charming home offers the perfect blend of character, culture, and convenience in the heart of **Downtown Winter Garden**. This beautifully maintained **5-bedroom, 3-bathroom** residence provides an ideal combination of space, style, and flexibility in one of Central Florida’s most walkable and sought-after communities. Inside, the **open-concept floor plan** creates a seamless flow between the living, dining, and kitchen areas, making the home perfect for both everyday living and entertaining. The kitchen is thoughtfully appointed with **granite countertops** and **stainless steel appliances**, offering a modern, functional space for cooking and gathering. Each bedroom is filled with natural light and features generous closet space, providing comfort and versatility throughout the home. A **two-car garage** adds convenience and extra storage. A standout feature of the home is the **private in-law suite** located on the right side of the property, offering an excellent setup for **extended family, elderly parents, or teens seeking their own space and privacy**. What truly makes this home special is its unbeatable location. Just steps away, **Downtown Winter Garden** offers a vibrant yet welcoming atmosphere filled with **locally owned boutiques, award-winning restaurants, cozy coffee shops, breweries, and the beloved Plant Street Market**. Spend your weekends exploring the renowned **Winter Garden Farmers Market**, enjoying live music and seasonal events, or taking relaxing evening strolls along the historic brick-lined streets. For outdoor enthusiasts, the home offers immediate access to the **West Orange Trail**, a scenic **22-mile paved trail** ideal for walking, jogging, and biking through beautiful Central Florida surroundings. With nearby parks, community events, and a strong sense of local charm, Winter Garden delivers a lifestyle that is both active and relaxed. Despite its quaint hometown feel, this location also offers **easy access to major highways**, making commutes to **Orlando, area theme parks, and surrounding communities** both quick and convenient. This is a rare opportunity to enjoy the excitement of downtown living while coming home to comfort, space, and modern amenities. **Resident Benefits Package (RBP) – $59/month** All residents are enrolled in the Resident Benefits Package, which includes: * Liability insurance * Credit building to help improve your credit score with on-time rent payments * Up to $1 million in 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 filter delivery * And 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**
- Built in 1952
- 2 garage spaces
- Lot size: 6,797 sqft
- 101 days on market
- 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.
- County: Orange
- Geo subdivision: SHADOW LAWN
Nearby Schools
Maxey Elem
Lakeview Middle
Windermere High School
Features
Interior
Exterior
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Pets, Accessibility & Amenities
Financial
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Let's get in touch!
Let's get in touch!

Kimberly Ann Pfeiffer
🇺🇸🇧🇷 Bilingual REALTOR®
- Source: Stellar MLS
- MLS #: O6375338
Listing updated: May 1, 2026 at 3:10PM
Listing provided by: Jeremy Porter, CANI PROPERTY MANAGEMENT
Last checked 23 hours ago
Listing provided by: Jeremy Porter, CANI PROPERTY MANAGEMENT
Last checked 23 hours ago
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