Medalist Diversified, Inc.

What is the purpose of the Annual Meeting?

At the Annual Meeting, our stockholders will be asked to consider and act upon the following matters:

What is a proxy?

A proxy is a person who votes the shares of stock of another person who could not attend a meeting. The term “proxy” also refers to the proxy card or other method of appointing a proxy. When you submit your proxy, you are appointing each of Francis P. Kavanaugh, our President and Chief Executive Officer, and C. Brent Winn, Jr., our Chief Financial Officer, as your proxy, and you are giving each of them permission to vote your shares of common stock at the Annual Meeting. The appointed proxy will vote your shares of common stock as you instruct unless you submit your proxy without instructions. In this case, they will vote FOR the Company’s director nominees in Proposal 1, FOR Proposal 2, FOR

Proposal 3, and FOR Proposal 4. With respect to any other proposals to be voted upon, they will vote in accordance with the recommendation of the Board of Directors or, in the absence of such a recommendation, in their discretion. If you do not submit your proxy, they will not vote your shares of common stock. This is why it is important for you to return the proxy card to us as soon as possible, whether or not you plan on attending the Annual Meeting.

Who is entitled to vote at the Annual Meeting?

Owners of record of shares of our common stock at the close of business on April 10, 2026, the record date for the Annual Meeting (the “Record Date”), are entitled to receive notice of, and vote at, the Annual Meeting.

If you hold your shares through a bank, broker or other holder of record and intend to vote in person at the Annual Meeting, you will need to provide a legal proxy from your bank, broker or other holder of record.

What are the voting rights of stockholders?

Each share of our common stock is entitled to one vote. There is no cumulative voting.

How many shares are outstanding?

At the close of business on the Record Date, there were 1,428,500 shares of our common stock issued and outstanding. There are no other shares of our stock that are entitled to vote at the Annual Meeting.

What constitutes a quorum?

Stockholders holding a majority of the outstanding shares must be present at the Annual Meeting in person or by proxy to constitute a quorum for the transaction of business. Withheld votes, abstentions and broker non-votes count for purposes of determining whether a quorum is present.

What is the difference between a “stockholder of record” and a “street name” holder?

These terms describe how your shares are held. If your shares are registered directly in your name with Pacific Stock Transfer Company, our transfer agent, you are a “stockholder of record.” If your shares are held in the name of a brokerage, bank, trust or other holder of record as a custodian, you are a “street name” holder.

If you are a “street name” holder, you are considered the beneficial owner of shares held in street name and your broker or other holder of record is considered, with respect to those shares, the stockholder of record. As the beneficial owner, you have the right to direct your broker on how to vote your shares. You are also invited to attend the Annual Meeting and vote your shares in person; however, in order to vote your shares in person, you must provide us with a legal proxy from your bank, broker or other stockholder of record.

How do I vote?

If you are a registered stockholder of record, meaning that your shares are registered in your name, you have five voting options. You may vote:

If you hold your shares in “street name,” meaning that your shares are held through a bank, broker or other holder of record, you will receive voting instructions from the holder of record. You must follow the instructions of the holder of record in order for your shares to be voted.

Can I vote my shares in person at the Annual Meeting?

If you are a “stockholder of record,” you may vote your shares in person at the Annual Meeting. If you hold your shares in “street name,” you must obtain a proxy from your broker, bank, trustee or other holder of record, giving you the right to vote the shares at the Annual Meeting.

What do I need to do to attend the Annual Meeting?

Proof of stock ownership and some form of government-issued photo identification (such as a valid driver’s license or passport) will be required for admission to the Annual Meeting in person. If you have questions about attending the Annual Meeting and voting in person, you may contact us at (804) 338-7708.Only stockholders who owned our common stock as of the close of business on April 10, 2026 are entitled to attend the Annual Meeting.

Can I change my vote after I have mailed in my proxy card?

You may change your vote or revoke your proxy before the polls close at the Annual Meeting by doing one of the following:

Please note, however, that if your shares are held in street name and you wish to revoke a proxy, you may need to contact your bank, broker or other holder of record to change any prior voting instructions.

How may I vote for each proposal?

Proposal 1 — You may votefor orwithhold from voting for each individual nominee.

Proposal 2 — You may votefor, against orabstain from voting to approve, in an advisory and non-binding vote, the compensation of our named executive officers as disclosed in this Proxy Statement.

Proposal 3 — You may vote* for, against* orabstain from voting to ratify the appointment of Cherry Bekaert LLP as our independent registered public accountants for the fiscal year ending December 31, 2026.

Proposal 4 — You may vote* for, against* orabstain from voting on the Charter Amendment.

What are the Board of Director’s recommendations on how I should vote my shares?

Proposal 1 —For the Board of Directors’ nominees for election as Class III directors.

Proposal 2 —For the proposal to approve, in an advisory and non-binding vote, the compensation of our named executive officers as disclosed in this Proxy Statement.

Proposal 3 —For the proposal to ratify the appointment of Cherry Bekaert LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2026.

Proposal 4 —Forthe Charter Amendment.

How many candidates can be elected as directors as the Annual Meeting?

Two Class III directors may be elected to the Board of Directors at the Annual Meeting. The nominees receiving the greatest number of “FOR” votes will be elected as a director, even if the number of votes received is less than a majority of the votes present at the Annual Meeting.

Assuming a quorum is present at the Annual Meeting, what vote is required to approve each item?

None of the proposals, if approved, entitle stockholders to appraisal rights under Maryland law or our Charter.

What does it mean if I receive more than one proxy card?

If you receive more than one proxy card from the Company, it means that you have multiple accounts with our transfer agent and/or with a broker, bank or other holder of record. You will need to vote separately with respect to each proxy card you received. Please vote all of the shares you own.

What if I authorize a proxy without specifying a choice on any given matter at the Annual Meeting?

If you are a stockholder of record as of the Record Date and you authorize a proxy (whether by Internet, mail or otherwise) without specifying a choice on any given matter to be considered at the Annual Meeting, the proxy holders will vote your shares according to the Board of Director’s recommendation on that matter. If you are a stockholder of record as of the Record Date and you fail to authorize a proxy or vote in person at the Annual Meeting, assuming that a quorum is present at the Annual Meeting, it will have no effect on the result of the vote on any matters to be considered at the Annual Meeting.

What if I hold my shares through a broker, bank or other holder of record?

If you hold your shares through a broker, bank or other holder of record, under the rules of the Nasdaq Capital Market, your broker or other holder of record may not vote with respect to certain proposals unless you have provided voting instructions with respect to that proposal. A “broker non-vote” results when a broker, bank or other holder of record properly executes and returns a proxy but indicates that the holder of record is not voting with respect to a particular matter because the holder of record has not received voting instructions from the beneficial owner. A broker non-vote is not considered a vote cast on a proposal; however, shares for which a properly-executed broker non-vote is delivered will be counted as present for purposes of determining whether a quorum is present.

Because a withhold vote or an abstention is not a vote cast, if you instruct your proxy or broker to “withhold authority” or “abstain” on any matter, it will have no effect on the vote on any of the matters to be considered at the Annual Meeting. However, your shares will still be counted as present for purposes of determining whether a quorum is present.

What if I return my proxy card sent by the Company but do not provide voting instructions?

If you return a signed proxy card but do not provide voting instructions, your shares will be voted as follows:

Proposal 1 —For the Company’s nominees for election as Class II directors.

Proposal 2 —For the proposal to approve, in an advisory and non-binding vote, the compensation of our named executive officers as disclosed in this Proxy Statement.

Proposal 3 —For the proposal to ratify the appointment of Cherry Bekaert LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2026.

Proposal 4 —For the Charter Amendment.

What happens if additional matters are presented at the Annual Meeting?

We know of no other matters other than the items of business described in this Proxy Statement that can be considered at the Annual Meeting. If other matters requiring a vote do arise, the person named as proxy will have the discretion to vote on those matters for you.

Who will count the votes?

A representative of our transfer agent, Pacific Stock Transfer Company, will act as the inspector of election and will tabulate votes.

Who pays the cost of this proxy solicitation?

We will pay all of the costs of soliciting the Company’s proxies. Proxies may be solicited on our behalf in person or by telephone, mail or electronic transmission by our directors, officers or employees, who will receive no additional compensation for such solicitation. In addition, proxies may be solicited on our behalf by Morrow Sodali LLC (“Morrow Sodali”), who we have retained to assist in the solicitation of proxies. Morrow Sodali will receive a fee of up to $10,000 plus reasonable out-of-pocket expenses for its services. Morrow Sodali estimates that approximately 20 of its employees will assist in the Company’s proxy solicitation. We will also reimburse brokerage houses and other custodians, nominees and fiduciaries for their reasonable out-of-pocket expenses for forwarding proxy and solicitation materials to our stockholders. Our aggregate expenses in connection with our solicitation of proxies, excluding normal expenses related to a non-contested solicitation of proxies and excluding salaries and wages of our officers and regular employees, are expected to aggregate to approximately $20,000, of which approximately $5,000 has been spent to date.

How do I submit a stockholder proposal for inclusion in the proxy materials for next year’s annual meeting, and what is the deadline for submitting a proposal?

In order for a stockholder proposal to be properly submitted for presentation at our 2027 annual meeting of stockholders (the “2027 Annual Meeting”), we must receive written notice of the proposal at our executive offices no earlier than December 16, 2026 and no later than 5:00 PM, Eastern Time, on January 15, 2027. In order for a stockholder proposal to be properly submitted for inclusion in our proxy statement for the 2027 Annual Meeting, we must receive written notice of the proposal at our executive offices no later than 5:00 PM, Eastern Time, on January 15, 2027. However, if we hold the 2027 Annual Meeting before May 17, 2027 or after July 16, 2027, stockholders must submit proposals (a) no earlier than 150 days prior to the 2026 Annual Meeting date, and (b) no later than 5:00 PM, Eastern Time, on the later of (i) 120 days prior to the 2027 Annual Meeting date or (ii) ten (10) days after public announcement of the 2027 Annual Meeting date. Stockholders intending to solicit proxies for the 2027 Annual Meeting in support of director nominees other than the Company’s nominees must provide notice that sets forth the information required by Rule 14a-19 under the Exchange Act no later than April 19, 2027, or if the 2027 Annual Meeting is more than 30 days before or after June 16, 2027, then no later than the later of 60 days prior to the 2027 Annual Meeting or the 10 th day following the day on which public announcement of the date of the 2027 Annual Meeting is first made by the Company. All proposals must contain the information specified in, and otherwise comply with, our Bylaws. Proposals should be sent via registered, certified or express mail to: P.O. Box 8436, Richmond, Virginia 23226, Attention: Francis P. Kavanaugh, Secretary.

If I share my residence with another stockholder, how many copies of the 2025 Annual Report and Proxy Statement should I receive?

We are sending only a single set of the 2025 Annual Report and Proxy Statement to any household at which two or more stockholders reside if they share the same last name or we reasonably believe they are members of the same family, unless we have received instructions to the contrary from any stockholder at that address. This practice is known as “householding” and is permitted by rules adopted by the Securities and Exchange Commission (“SEC”). This practice reduces the volume of duplicate information received at your household and helps us to reduce costs. Each stockholder will continue to receive a separate proxy card. We will deliver promptly, upon written request or oral request to the address or telephone number set forth below, a separate copy of the 2025 Annual Report or Proxy Statement, as applicable, to a stockholder at a shared address to which a single copy of the documents were previously delivered. If you received a single set of these documents for your household for this year, but you would prefer to receive your own copy, you may direct requests for separate copies in the future to the following address: P.O. Box 8436, Richmond, Virginia 23226, Attention: Francis P. Kavanaugh, Secretary, or by calling 804-338-7708. If you are a stockholder who receives multiple copies of our proxy materials, you may request householding by contacting us in the same manner and requesting a householding consent form.

What if I consent to have one set of materials mailed now but change my mind later?

You may withdraw your householding consent at any time by contacting us at the address or telephone number provided above. We will begin sending separate copies of stockholder communications to you within 30 days of receipt of your instructions.

The reason I receive multiple sets of materials is because some of the shares belong to my children. What happens if they move out and no longer live in my household?

When we receive notice of an address change for one of the members of the household, we will begin sending separate copies of stockholder communications directly to the stockholder at his or her new address. You may notify us of a change of address by contacting us at the address provided above.

Other Information

Our 2025 Annual Report accompanies this Proxy Statement. However, the Annual Report forms no part of the material for the solicitation of proxies.

PROPOSAL NO. 1. ELECTION OF DIRECTORS

Our Bylaws provide that the number of directors shall be fixed by a majority of the Board of Directors, provided that there shall never be less than the minimum number required by Maryland law, nor more than 15. On December 28, 2023, the Board of Directors approved a resolution to elect for the Company to be subject to Section 3-803 of Subtitle 8 of the Title 3 of the Maryland General Corporation Law. As a result of this election, the Board of Directors is classified into three separate classes of directors. The term of office of one of the three classes of directors expires each year, and each class is elected for a three-year term.

The Board of Directors has fixed the number of directors at five. The Board of Directors, upon the recommendation of its nominating and corporate governance committee, has nominated our Class III directors¾ Francis P. Kavanaugh and Neil Farmer¾for election at the Annual Meeting for a three-year term to expire at the annual meeting of stockholders in 2029 and until their successors are elected and qualified. Mr. Kavanaugh was appointed to our Board of Directors as a Class III director on May 24, 2023. Mr. Farmer was appointed to our Board of Directors on April 28, 2017, and was classified as a Class III director by our Board of Directors on December 8, 2023.

THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE “FOR”

THE BOARD OF DIRECTORS’ NOMINEES NAMED IN PROPOSAL NO. 1.

It is the intention of the proxy holders named in the enclosed proxy, in the absence of a contrary direction, to vote for the election of the Company’s nominees named in Proposal No. 1. Should any of the Company’s nominees become unable or refuse to accept nomination or election as a director, the persons named as proxies intend to vote for the election of such other person as the nominating and corporate governance committee may recommend. The Board of Directors knows of no reason why the Company’s nominees might be unable or refuse to accept nomination or election. There is no family relationship between any director or executive of the Company.

Nominees for Election

Francis P. Kavanaugh, President and Chief Executive Officer, Secretary and Treasurer. Mr. Kavanaugh, age 66, is our President and Chief Executive Officer, Secretary and Treasurer. Mr. Kavanaugh has served as our President and Chief Executive Officer since October 19, 2023. He was appointed to our Board of Directors as a Class III director on May 24, 2023 and his current term expires at the 2026 annual meeting. Mr. Kavanaugh is the co-founder of Fort Ashford Funds, LLC, a privately held investment firm, and has served as its Managing Director since its inception in 2004. Mr. Kavanaugh received his B.S. in Information and Computer Science from the University of California Irvine in 1985 and his MBA from Pepperdine University in 2003. Mr. Kavanaugh has more than 30 years of diverse experience in real estate investment, business restructuring and operational leadership. He has been actively involved with the restructuring of over 20 businesses in the public and private sectors and is adept at navigating complexity and implementing strategic changes. The Board of Directors believe Mr. Kavanaugh’s experience significantly contributes to the Company, especially with respect to his strong operational leadership and vision for strategic changes and make him a valuable member of the Board of Directors.

Neil P. Farmer, Lead Independent Director and Independent Director. Mr. Farmer, age 69, is an independent Class III director who was appointed to our Board of Directors on April 28, 2017 and his current term expires at the 2026 annual meeting. Mr. Farmer founded Farmer Properties, Inc., a real estate development firm located in Richmond, Virginia in 1983. Mr. Farmer has served as the President of Farmer Properties since its founding, with responsibility over the entirety of its real estate development business. He received his B.A. in Government and Foreign Affairs from Hampden-Sydney College in 1978. Mr. Farmer has been in the commercial real estate and residential real estate business for over 30 years, and the Company’s Board believes he provides the Company with real estate expertise gained in his career, especially with regard to renovations and large capital projects.

Directors Continuing in Office

*Marc Carlson, Independent Director.*Mr. Carlson, age 65, is an independent Class II director who was appointed to our Board of Directors on January 30, 2025. His current term expires at the 2028 annual meeting. Mr. Carlson is the

Managing Director of 3 Points Partners, a position he has held since 2010, serving as a CEO advisor, coach and board member to several technology companies. Since 2023, he has also served as a member of the board of directors and a senior advisor to the Krach Institute for Technology Diplomacy at Purdue University. Mr. Carlson served as a senior advisor to the Under Secretary of State for the Economy, Energy and Environment from 2019 – 2021. From 2011 until 2018, Mr. Carlson was the Vice President of Enterprise Sales and the Chief Customer officer of Docusign. Prior to Docusign, Mr. Carlson served as the CEO of Microposite, a clean technology materials business, and was an early employee of Ariba (now SAP). Mr. Carlson has extensive personal real estate investment experience and manages a multi-state portfolio of industrial, medical and land investments. The Company’s Board believes his broad experience in technology and real estate makes Mr. Carlson a valuable addition to our Board of Directors.

Emanuel D. Neuman, Independent Director. Mr. Neuman, age 46, is an independent Class II director who was appointed to our Board of Directors on July 19, 2023. His current term expires at the 2028 annual meeting. Mr. Neuman co-founded Spandrel Development Partners in 2013, where he currently leads the firm’s investment strategy, capital markets, deal structuring and strategic growth initiatives. From 2008 to 2012, he was the co-portfolio manager at Unterberg Capital LLC, a long-only investment fund, and from 2005 to 2008, he was a Vice President in the investment banking division of Collins Stewart, LLC, where he led the origination, execution and marketing of a wide range of public and private equity offerings and merger and acquisition transactions. Mr. Neuman received his B.S. in Accounting from Babson College in 2002. Mr. Neuman has 20 years of investment banking, investment management and real estate development experience, and management believes this experience makes Mr. Neuman a valuable addition to our Board of Directors.

*David Lunin, Independent Director.*Mr. Lunin, age 45, is an independent Class I director who was appointed to our Board on September 19, 2023. His current term expires at the 2027 annual meeting. Mr. Lunin has served as the Executive Vice President and Chief Financial Officer of Calumet, Inc., a specialty product and renewable fuel producer, since 2023. Prior to joining Calumet, Mr. Lunin was a Managing Director at Goldman Sachs from 2010 to 2023, where he held various investment banking roles with a focus on executing mergers & acquisitions and capital markets transactions. He is a graduate of George Washington University with a Bachelor's degree in Business Administration. He also holds an MA in Applied Economics from Johns Hopkins University and an MBA from Columbia Business School. The Company’s Board believes that Mr. Lunin’s capital markets and investment banking experience and his experience as the Chief Financial Officer of a publicly traded company make Mr. Lunin a valuable addition to our Board of Directors.