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$2,600 Just Listed
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Property Description
One or more photo(s) has been virtually staged. Live where charm, culture, and convenience come together in the heart of Downtown Winter Garden! This beautifully maintained 3-bedroom, 2-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 ?? Important Access Notice: Resident will have access only to the 3-bedroom, 2-bathroom, 2-car garage portion of the home. The right-hand side of the home is not included and is not accessible to the resident.
Full Property Details
Full Property Details for 418 Charles St
General
- Rent: $2,600
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6375338
- Updated: 1/20/2026
- Added to Site: 1 day(s) ago
Rental Information
- Lease/Rent Term: 12 Months
Interior
- Number of Rooms: 8
- 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: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
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: 1,439
- Sq. Ft. Source: Public Records
- 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: $2,600
- Application Fee: $80
- Security Deposit: $2,700
- Pet Deposit: $300
Disclosures and Reports
- APN: 232227794809130
- Property ID: 232227794809130
Listed by Cani Property Management
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 Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 418 Charles St
Date
Details
Price
Change
Source
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 with 3 bedrooms and 2 full bathrooms. 418 Charles Street is currently listed for rent at $2,600 and was received on January 20, 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.

