418 Charles St Winter Garden, FL 34787
Highlights
- View of Trees or Woods
- Solid Surface Countertops
- 2 Car Attached Garage
- West Orange High School Rated A
- No HOA
- 2-minute walk to Maple Street Park
About This Home
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
Listing Agent
CANI PROPERTY MANAGEMENT Brokerage Phone: 321-280-9065 License #3357719 Listed on: 01/20/2026
Home Details
Home Type
- Single Family
Year Built
- Built in 1952
Lot Details
- 6,797 Sq Ft Lot
- East Facing Home
- Level Lot
Parking
- 2 Car Attached Garage
Interior Spaces
- 1,584 Sq Ft Home
- 1-Story Property
- Blinds
- Combination Dining and Living Room
- Laminate Flooring
- Views of Woods
Kitchen
- Cooktop
- Recirculated Exhaust Fan
- Dishwasher
- Solid Surface Countertops
Bedrooms and Bathrooms
- 5 Bedrooms
- 3 Full Bathrooms
Laundry
- Laundry in Garage
- Washer and Electric Dryer Hookup
Schools
- Maxey Elementary School
- Lakeview Middle School
- Windermere High School
Utilities
- Central Heating and Cooling System
- Cable TV Available
Listing and Financial Details
- Residential Lease
- Security Deposit $2,700
- Property Available on 1/20/26
- The owner pays for insurance, management, pest control, repairs, taxes
- 12-Month Minimum Lease Term
- $80 Application Fee
- Assessor Parcel Number 23-22-27-7948-09-130
Community Details
Overview
- No Home Owners Association
- Shadow Lawn Subdivision
Recreation
- Park
Pet Policy
- Pets up to 150 lbs
- Pet Deposit $300
- 3 Pets Allowed
- $25 Pet Fee
- Dogs and Cats Allowed
Map
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 01/20/2026 01/20/26 | For Rent | $2,600 | -8.8% | -- | |
| 09/17/2024 09/17/24 | Rented | $2,850 | 0.0% | -- | |
| 09/05/2024 09/05/24 | Price Changed | $2,850 | -4.2% | $2 / Sq Ft | |
| 08/29/2024 08/29/24 | Price Changed | $2,975 | -0.8% | $2 / Sq Ft | |
| 08/20/2024 08/20/24 | Price Changed | $3,000 | -6.3% | $2 / Sq Ft | |
| 08/16/2024 08/16/24 | For Rent | $3,200 | 0.0% | -- | |
| 11/15/2022 11/15/22 | Sold | $350,000 | -6.7% | $221 / Sq Ft | View Prior Sale |
| 10/15/2022 10/15/22 | Price Changed | $375,000 | -2.6% | $237 / Sq Ft | |
| 10/15/2022 10/15/22 | For Sale | $385,000 | 0.0% | $243 / Sq Ft | |
| 09/25/2022 09/25/22 | Pending | -- | -- | -- | |
| 09/12/2022 09/12/22 | For Sale | $385,000 | -- | $243 / Sq Ft |
Source: Stellar MLS
MLS Number: O6375338
APN: 23-2227-7948-09-130
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
- 330 E Story Rd
- 636 Sigler Dr
- 615 Sigler Dr
- 422 Charlotte St
- 515 9th St
- 375 Regal Downs Cir
- 823 Magnolia Ave
- 282 E Newell St
- 628 Orange Belt Loop
- 851 9th St
- 648 Orange Belt Loop
- 131 Oak Laurel Dr
- 149 S Park Ave
- 634 Burch Ave
- 750 S Park Ave
- 711 Burch Ave
- 241 N Dillard St
- 13905 W Colonial Dr Unit 200
- 764 Klondike Ave
- 344 Eron Way Unit 12
- 420 E Cypress St Unit SI ID1256812P
- 15242 Tribute at Ovation Way
- 521 S Park Ave
- 203 N Dillard St
- 457 Regal Downs Cir
- 125 S Park Ave
- 57 Windtree Ln Unit G
- 584 W Bay St
- 97 Windtree Ln Unit 104
- 391 Floral Dr
- 239 Traditions Dr
- 354 Daniels Pointe Dr
- 216 Jean St
- 427 Tierra Verde Ln
- 467 Sand Lime Rd
- 1301 Eastern Pecan Place Unit 203
- 118 Southern Pecan Cir Unit 101
- 233 Southern Pecan Cir Unit 101
- 220 Valencia Ct
- 431 Southern Pecan Cir Unit 201
Ask me questions while you tour the home.