418 Charles St

1,439 Sq. Ft.
$22 / Sq. Ft.
1,439
Sq. Ft.
$22
per Sq. Ft.

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...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.
  1. Listed by Jeremy Porter • Brokerage DRE #1069169 • CANI PROPERTY MANAGEMENT
    P: (321)-280-9065 C: (321)-280-9065 leasing@canipm.com

Property Details for 418 Charles Street

Subdivision Name
SHADOW LAWN
Garage Spaces
2
View
Trees/Woods
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 01/21/2026 05:26 AM

Property Details for 418 Charles Street

StatusActive
MLS #O6375338
Days on Market6
Rental Incentives-
Available Date01/20/2026
Lease TermLease Length: 12 Months
Furnished-
Compass TypeRental
MLS TypeResidential Lease / Single Family Residence
Year Built1952
Lot Size0.16 AC / 6,797 SF
CountyOrange County

Location

Listing Courtesy of CANI PROPERTY MANAGEMENT, Jeremy Porter
Add your commute

Building Information for 418 Charles Street

Building/Complex418 Charles StFloor-Stories1Pet Policy-Pet Policy DetailsCats OK,Dogs OK,Monthly Pet Fee,Pet DepositYear Built1952Building Size-Lot Size0.16 AC / 6,797 SF

Property Information for 418 Charles Street

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 1839.0
  • Building Area Units: Square Feet
  • Community Features: Park, Sidewalks
  • Direction Faces: East
  • 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.
  • Elementary School: Maxey Elem
  • Middle Or Junior School: Lakeview Middle
  • High School: Windermere High School
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Long Term YN: true
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 418
  • Street Name: CHARLES
  • Street Suffix: STREET
  • State: FL
  • City: WINTER GARDEN
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
Taxes and HOA Information
  • Additional Applicant Fee: $80
  • Additional Pet Fees: $300 pet deposit each $25 monthly pet fee each
  • Association: No
  • Management: Full Time
  • Number Of Pets: 3
  • Pet Deposit Fee: $300
  • Pet Fee Non Refundable: $25
  • Pet Size: Extra Large (101+ Lbs.)
Virtual Tour
Property
Lot Information
  • Lot Features: Level, Sidewalk
  • Parcel Number: 232227794809130
  • Water Access: No
  • Water Extras: No
  • Living Area: 1439
Property and Assessments
  • Year Built Numeric: 1952
  • Building Elevator: No
  • New Construction: No
  • Owner Pays: Insurance, Management, Pest Control, Repairs, Taxes
  • Property Attached: No
  • Dock YN: No
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Exterior Features: Sidewalk
  • Levels: One
  • Patio And Porch Features: None
  • Pool Dimensions: N/a
  • Pool Private: No
  • Pool: None
  • Pool Private: No
  • Security Deposit: $2,700
  • Spa: No
  • Waterfront Feet Total: 0
  • Number Of Stories: 1
Interior Features
  • Bedrooms Total: 3
  • Bathrooms Full: 2
  • Appliances: Cooktop, Dishwasher, Exhaust Fan, Range, Refrigerator
  • Cooling: Central Air
  • Flooring: Laminate
  • Heating: Central
  • Interior Features: Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Surface Counters
  • Laundry Features: Electric Dryer Hookup, In Garage, Washer Hookup
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 8.0
  • Water View: No
  • Window Features: Aluminum Frames, Blinds, Window Treatments
  • Bathrooms Half: 0
Rental
Rental Information
  • Pets Allowed: Cats OK, Dogs OK, Monthly Pet Fee, Pet Deposit
  • Max Pet Weight: 150

Property History for 418 Charles Street

DateEvent & SourcePriceAppreciation
Jan 20, 2026

Listed (Active)

MFRMLS #O6375338

$2,600—
Sep 25, 2024

Withdrawn

MFRMLS #O6217172

—
Sep 17, 2024

Rented

MFRMLS #O6233040

$2,850—
Aug 16, 2024

Listed (Active)

MFRMLS #O6233040

$3,200—
Jun 22, 2024

Listed (Active)

MFRMLS #O6217172

$2,000—
DateEvent & SourcePrice
01/20/2026

Listed (Active)

MFRMLS #O6375338

$2,600
09/25/2024

Withdrawn

MFRMLS #O6217172

—
09/17/2024

Rented

MFRMLS #O6233040

$2,850
08/16/2024

Listed (Active)

MFRMLS #O6233040

$3,200
06/22/2024

Listed (Active)

MFRMLS #O6217172

$2,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 418 Charles Street

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Public - PK to 5
Charter - K to 8
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
William S Maxey Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Lakeview Middle School
Public6 to 8

West Orange High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

418 Charles Street is available for rent in Winter Garden, FL 34787. This property was listed on January 20, 2026 by CANI PROPERTY MANAGEMENT, it's currently listed at $2,600. It has been on the market for a total of 6 days and was last rented on September 17, 2024. This listing's school district is Orange County Public Schools. Nearby schools include William S Maxey Elementary School, Cornerstone Academy Charter and Lakeview Middle School. 418 Charles Street is a 3-bed, 2-bath, 1,439 sqft a property built in 1952.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of CANI PROPERTY MANAGEMENT, Jeremy Porter

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 01/21/2026 05:26 AM