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Windermere Property Management

Let us manage your Windermere rental property

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Our Full Service Windermere Property Management is all-inclusive.

For full-service property management in Windermere, consider utilizing Legends Realty. We have licensed professionals who are passionate about helping landlords throughout Florida. We take care of everything, from condition reports to background checks and more. Throughout the rental process and lease period, we represent property owners and their properties. At Legends Realty, we provide peace of mind and exceptional service.

Our services include:

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Tenant education

A successful tenancy relies on the property manager to educate the tenant at the beginning of the lease. Our tenants are also provided with a “tenant handbook”, outlining the laws and regulations of a tenancy.

Professional marketing

Attracting the right tenants is essential. Just like a sales campaign, you’ll want to capture the interest of qualified tenants through professional online copy. Be sure to include quality photos!

Flexible viewing times

Our team works outside of regular hours to ensure maximum opportunities for prospective tenants to view the property. By dedicating their time on the weekends, our staff members attract more potential property occupants.

Long term team

Our team members have been in Windermere property management for numerous years and are loyal to our company. We ensure our landlords that they will receive a personal and professional level of service from our team.


The security of your property is our priority, we require ID at each property showing and accompany the prospective tenant inside.

Condition reports

Our condition reports are completed with attention to detail. Because we use a digital platform, we minimize any misunderstanding of the state of the property prior to the tenant moving in.

Low vacancy rate

This means you won’t have your property vacant and not receiving rent for a long period of time. We make tenant retention a high priority through constant communication and property maintenance.


Successful relationships are mainly based on frequent communication. You will receive weekly updates via email while your property is vacant to provide feedback on the showings and condition of the property. While occupied the communication continues with follow up emails for repairs and maintenance.

Background checks

Our management team is thorough on their reference checks for each individual applicant to ensure we are only accepting the most reliable tenants for your investment.

Highly trained professionals

Our team is trained 5 days a week. We believe to stay at the top we need to have a focus on continuous improvement.

Flexible fee structures

Our commissions are flexible with three options, remembering that the commission comes from the rent, in which our company will negotiate for you, to achieve the highest and best result.

You don’t have to look any further for property management in Windermere. Our experienced team is ready to help you make the most of your rental properties. Contact us today for more information concerning Windermere property management. We pride ourselves on our outstanding service.

Inquire about Our Services

What Will My Property Rent For?

Property Owners - Please complete the above form for a Free Rental Analysis of your home. Our office will forward to you all the necessary documents for your review, will prepare a rental range and one of our Business Developers will contact you for an appointment to view your property. We specialize in the areas of Seminole, Orange and West Volusia counties of Central Florida.

CENTRAL FLORIDA PROPERTY MANAGEMENT in Lake Mary, Deltona, DeBary, Casselberry, Orlando, Longwood, Winter Springs, Oviedo, Sanford, Maitland, Altamonte Springs, Winter Park, Heathrow, Windermere, Winter Garden, Lake Nona, Orange City, Deland, and Apopka, Florida.

For our procedures and more information, visit our FREE Rental Analysis Blog.


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Full Service Management Agreement: *recommended

Our monthly management fee is 8% or $100 whichever is greater of the collected and a one-time fee of 50% of contracted rent once we secure a tenant. The fee comes from the first collected rent.

Lease Only Agreement:

For local owners interested in managing their property, but need assistance in marketing and securing a qualified tenant.
There is a one-time fee of one full month’s rent once we secure a tenant for this service. The fee comes from the first collected rent.

***We offer a 20% discount to our Management Fees listed in our Agreement to Owners/Investors once we list four or more properties under one Tax ID or Social Security number using our Full Service Management Agreement.

Additional Professional Services such as Eviction Protection, detailed Bi-Annual Property Review Reports, direct deposit, initial lease preparation and so much more are offered with Full Management Only

Licenced Realtors

Licensed REALTORS® -

A real estate agent who is a member of the National Association of REALTORS®, which means that he or she must uphold the standards of the association and its code of ethics.

Eviction Protection

Eviction Protection -

We pay for the cost of an eviction if the tenant we procured defaults on the payment of rent.

Rental Value

What will your home rent for? -

We will prepare a rental range for you; forward all the documents for your review then a Business Developer will call you to schedule a time to view your property. Click here Free Rental Analysis

owner statements

Financials and Reporting -

Detailed accounting for all income and expenses for your property is provided on a monthly basis. The timely disbursement of funds to owners is a high priority. We utilize the industry's most advanced property management and accounting program to accomplish this. This program also allows owners to access the system online and obtain property information through the online Owner Portal. Copies of all lease documents, accounting statements, work orders, receipts, and vendor invoices are stored and available for viewing in the Owner Portal at any time. At the end of the year we supply owners with annual statements categorizing all income and expenses for the property and a 1099-MISC for tax purposes. 

  • Q: Answers Regarding Funds

    A: When you entered into a management agreement, LEGENDS REALTY established an account for you and your property. LEGENDS REALTY recognizes the importance of accurately collecting and disbursing funds. The bookkeeping program used by LEGENDS REALTY is specialized software designed to handle the many facets of property management and accurate record keeping, and complies with the requirements of the Florida Real Estate Commission.
  • Q: Banking

    A: LEGENDS REALTY holds your account in a trust fund mandated by the state of Florida. This account does not earn interest. LEGENDS REALTY accounts for each owner’s funds separately in the trust account and does not co-mingle funds with broker monies, following the Florida Real Estate Commission requirements.
  • Q: Monthly statements

    A: LEGENDS REALTY sends monthly statements to owners via online owner portal. An email will be sent monthly as a reminder. If you have difficulty reading your monthly statement, please contact your management team. We are happy to assist you and answer your questions.
  • Q: Disbursement of monthly funds

    A: LEGENDS REALTY disburses available funds to owners on the 10th of each month UNLESS either day falls on a Saturday, Sunday or Holiday, in which case disbursements are processed on the following Tuesday. A calendar of scheduled payout process dates is available on our website LEGENDS REALTY does not disburse funds on weekends and holidays. LEGENDS REALTY does NOT issue owner checks unless there are sufficient funds in the owner’s account. It is vital to accurately post rents, pay vendors, and disburse funds for your account. Therefore, it is vital that LEGENDS REALTY adhere to this schedule to ensure servicing every owner’s account.
    LEGENDS REALTY distributes owner funds in two ways:
    • Company check disbursed directly to the owner accompanying their monthly statement.
    • ACH direct deposit – directly disbursed into an owner’s bank account; LEGENDS REALTY mails monthly statements after disbursement. A form to start ACH is included with this information.
  • Q:  End of year procedures

    A: At the end of each year, LEGENDS REALTY is required to file 1099’s for income received over $600. Please note that this amount is for “total income received,” and not the yearly total of owner disbursements. The Internal Revenue Service dictates the “total income received” requirement. Please note that security deposits are not included in this amount.
    It is necessary that you supply LEGENDS REALTY with the necessary Social Security/Tax ID information so the 1099 is accurate. LEGENDS REALTY will send the 1099 for the rent by January 31 for the previous tax year. If there is a change in your tax information such as a new trust or address, please notify us with the Owner Change of Information form. If you need another change form, please contact us.
    LEGENDS REALTY also issues 1099s for disbursements to vendors for work over $600.00. Therefore, owners do not have to issue 1099s for work completed and paid through the LEGENDS REALTY trust account. Owners are responsible for issuing 1099s to any vendor paid through the owner’s personal account.
    The last statement of the year will reflect “total amounts” for income and expenses that have transpired throughout the year, such as management fees, leasing fees, landscape, utilities, repairs and maintenance, etc. The amounts will not reflect any funds issued through the owners personal account. Owners can submit their last statement to their tax person along with other information for income tax reporting. LEGENDS REALTY does not issue statements to the owner’s tax preparers. Please note a copy of the owners 1099 and cash flow report will be available in the owners online portal.

Technology -

New Age Real Estate incorporates the most advanced technology available in the business:

  • Paperless Office
  • Electronic
  • Payments (ACH)
  • Electronic Rent Collection (ACH)
  • Industry Leading
  • Web Based Management and Accounting Program
  • Owner and Tenant Online
  • Web Portals
  • Online Document Signing and Storage
  • Electronic Statements and Reporting
  • Bank Lockbox Service
  • e-fax, VOIP phone system
  • Digital Video Recording Online & Website Advertising
  • Search Engine Placement

We are always looking for new innovations that will better serve our clients.

Example Virtual Tours:

Windermere Area Information

Windermere was established as a residential development in 1889 and chartered in 1925.[citation needed] During late 2007, the Town of Windermere filed a proposal to annex Isleworth and Butler Bay, both wealthy subdivisions. This was met with extensive debate from town residents and an objection from Orange County, which stood to lose millions of dollars of property tax revenue. After lengthy discussions, and battles with the county, Isleworth remained in the county, but Butler Bay was annexed into Windermere, with over 90% of its residents approving annexation via a mail-in ballot. Source Wikipedia

Areas We Serve