My Search Tools:

$2,600 - 418 Charles Street, WINTER GARDEN

3
Bedrooms
2
Baths
1,439
SQ. Feet
0.1
Acres

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.

Essential Information

  • MLS® #:
    O6375338
  • Price:
    $2,600
  • Bedrooms:
    3
  • Bathrooms:
    2.00
  • Full Baths:
    2
  • Square Footage:
    1,439
  • Acres:
    0.10
  • Year Built:
    1952
  • Type:
    Residential Lease
  • Sub-Type:
    Single Family Residence
  • Status:
    Active

Community Information

  • Address:
    418 Charles Street
  • Area:
    Winter Garden/Oakland
  • Subdivision:
    SHADOW LAWN
  • City:
    WINTER GARDEN
  • County:
    Orange
  • State:
    FL
  • Zip Code:
    34787

Amenities

  • # of Garages:
    2
  • View:
    Trees/Woods

Interior

  • Interior Features:
    Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Surface Counters
  • Appliances:
    Cooktop, Dishwasher, Exhaust Fan, Range, Refrigerator
  • Heating:
    Central
  • Cooling:
    Central Air
  • # of Stories:
    1

Exterior

  • Exterior Features:
    Sidewalk
  • Lot Description:
    Level, Sidewalk, Paved

School Information

  • Elementary:
    Maxey Elem
  • Middle:
    Lakeview Middle
  • High:
    Windermere High School

Additional Information

  • Days on Market:
    6

Listing Details

  • Listing Office:
    Cani Property Management

Listing information courtesy of Cani Property Management.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on January 26th, 2026 at 9:50am EST.