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$2,500
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Property Description
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**
Full Property Details
Full Property Details for 418 Charles St
General
- Rent: $2,500
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6375338
- Added to Site: 141 day(s) ago
Rental Information
- Lease/Rent Term: 12 Months
Interior
- Number of Rooms: 10
- Interior Features: Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Surface Counters
- Appliances: Cooktop, Dishwasher, Exhaust Fan, Range, Refrigerator
- Furnishings: Unfurnished
- Flooring: Laminate
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Electric Dryer Hookup, In Garage, Washer Hookup
Exterior
- Exterior Features: Sidewalk
- Deck/Patio: None
- Porch/Patio/Deck: None
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: SHADOW LAWN
- Driving 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.
- Direction Faces: East
School Information
- Elementary School: Maxey Elem
- Middle School: Lakeview Middle
- High School: Windermere High School
Community
- Community Name: 34787 - Winter Garden/Oakland
- Community Features: Park, Sidewalks
- Number of Pets: 3
- Pet Restrictions: 150lbs.
- Management Type: Full Time
- Mgmt. Company: Full Time
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Sewer Connected, Water Connected
Structural Information
- Windows: Aluminum Frames, Blinds, Window Treatments
- Stories/Levels: One
- Square Feet: 1,584
- Sq. Ft. Source: Public Records
- Living Area: 1,584 Sq. Ft.
- Year Built: 1952
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 0.1
- Lot Size (Sq. Ft.): 6,797
- Lot Size: 6797
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
Financial Considerations
- Lease Price: $2,500
- Application Fee: $80
- Security Deposit: $2,600
- Pet Deposit: $300
Disclosures and Reports
- APN: 232227794809130
- Property ID: 232227794809130
Listed by Cani Property Management
Sold by Cani Property Management and Baldwin Park Realty Llc
Schools
Schools serving 418 Charles St
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
William S Maxey Elementary School 1100 East Maple Street, Winter Garden, FL 34787 | PK-5 | 0.9 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 1.4 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 1.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 418 Charles St
Date
Details
Price
Change
Source
5/01/2026
Sold
$2,500
—
MLS
3/26/2026
Price Reduced
$2,500
-3.85%
MLS
1/20/2026
Listed
$2,600
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
418 Charles Street, Winter Garden, FL 34787 (MLS# O6375338) is a Single Family property that was sold at $2,500 on May 01, 2026. Want to learn more about 418 Charles Street? Do you have questions about finding other real estate for sale or rent in Winter Garden? You can browse all Winter Garden rentals or contact a Coldwell Banker agent to request more information.

