Document:

EX-10.5

 Exhibit 10.5 

EXCLUSIVITY AND RIGHT OF FIRST OFFER AGREEMENT 

This EXCLUSIVITY AND RIGHT OF FIRST OFFER AGREEMENT (this “Agreement”) is entered into as of [•], 2019 by and between
Consolidated-Tomoka Land Co., a Florida corporation (“CTO”), and Alpine Income Property Trust, Inc., a Maryland corporation (“Alpine”). 

RECITALS 
 WHEREAS, in
connection with Alpine’s initial underwritten public offering (the “IPO”) of common stock, $0.01 par value per share, CTO has sold a portfolio of assets to Alpine and a subsidiary of CTO will enter into a Management Agreement
(the “Management Agreement”) with Alpine, effective as of the closing date of the IPO, pursuant to which the CTO subsidiary will act as Alpine’s external manager; and 

WHEREAS, as described in the final prospectus used in connection with the IPO, CTO has agreed to provide certain exclusivity commitments to
Alpine and a right of first offer with respect to the ROFO Properties (as defined below). 
 AGREEMENT 

NOW, THEREFORE, in consideration of the mutual covenants herein contained, and for other good and valuable consideration, the receipt and
sufficiency of which are acknowledged by each signatory hereto, it is agreed as follows: 
 1. Definitions. For purposes of this
Agreement, the following terms shall have the following meanings: 
 “Affiliate” means, with respect to a person, any person
controlling, controlled by or under common control with, the first person. The term “control” shall mean the power to direct the management and policies of a person, whether through the ownership of voting securities, by contract or
otherwise. For the purposes of this Agreement, Alpine and its consolidated subsidiaries shall be deemed not to be Affiliates of CTO and its consolidated subsidiaries and CTO and its consolidated subsidiaries shall be deemed not be Affiliates of
Alpine and its consolidated subsidiaries. 
 “Acceptance Notice” has the meaning set forth in Section 3(b) of this
Agreement. 
 “Agreement” has the meaning set forth in the preamble to this Agreement. 

“Alpine” has the meaning set forth in the preamble to this Agreement. 

“Business Day” means a day on which commercial banks in New York, New York are open for business and that is not a Saturday or
Sunday. 
 “CTO” has the meaning set forth in the preamble to this Agreement. 

 “Incidental Interest” means an opportunity to acquire, directly or
indirectly, (i) an entity that owns a portfolio of commercial income properties that includes, among others, Single-Tenant, Net Leased Properties, or (ii) a portfolio of commercial income properties that includes, among others,
Single-Tenant, Net Leased Properties, in either case, where not more than 30% of the value of such portfolio, as reasonably determined by CTO, in consultation with the independent directors of Alpine, consists of Single-Tenant, Net Leased
Properties. 
 “IPO” has the meaning set forth in the recitals to this Agreement. 

“Management Agreement” has the meaning set forth in the recitals to this Agreement. 

“Opportunity” has the meaning set forth in Section 2(a) of this Agreement. 

“Property” means a fee or leasehold interest in a real property, together with all improvements and fixtures located thereon,
all rights, privileges and easements appurtenant thereto and all tangible and personal property used in connection therewith. 

“Restricted Period” has the meaning set forth in Section 2(a) of this Agreement. 

“ROFO Notice” has the meaning set forth in Section 3(b) of this Agreement. 

“ROFO Property” means each of the Single-Tenant, Net Leased Properties listed on Schedule I attached hereto and any
Single-Tenant, Net Leased Property that is developed and owned by CTO or any of its Affiliates after the closing date of the IPO. 

“Single-Tenant, Net Leased Property” means a Property that is net leased, on a
triple-net or double-net basis, to a single tenant or, if such Property is net leased to more than one tenant, 95% or more of the rental revenue derived from the
ownership and leasing of such Property is attributable to a single tenant. 
 2. Exclusivity. 

(a) Between the date of the closing of the IPO and the expiration or earlier termination of the Management Agreement (the “Restricted
Period”), CTO will not, and will cause each of its Affiliates not to, acquire, directly or indirectly, a Single-Tenant, Net Leased Property (an “Opportunity”), unless: 

(i) CTO has notified Alpine of the Opportunity by delivering a written notice (which may be by email) containing a description
of the Opportunity and the terms of the Opportunity to the chair of the nominating and corporate governance committee (or any successor committee performing one or more of the functions of such committee) of Alpine’s board of directors, and
Alpine has affirmatively rejected in writing (which may be by email) the Opportunity or has failed to notify CTO in writing (which may be by email) within ten Business Days after receipt of CTO’s notice that Alpine intends to pursue the
Opportunity; 
 (ii) the Opportunity involves an Incidental Interest; 

  
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 (iii) the Opportunity involves a property that was under contract for
purchase by CTO or an Affiliate of CTO as of the closing date of the IPO, such contract is not assignable to Alpine and, despite commercially reasonable efforts by CTO, the seller will not agree to an assignment of the contract to Alpine; or 

(iv) the Opportunity involves a property which, prior to the closing of the IPO, has been identified or designated by CTO as a
potential “replacement property” in connection with an open (i.e. not yet completed) like-kind exchange under Section 1031 of the Internal Revenue Code of 1986, as amended. 

(b) The parties recognize that the legal requirements and public policies of the various states of the United States or other applicable
jurisdictions may differ as to the validity and enforceability of covenants similar to those set forth in Section 2(a) of this Agreement. It is the intention of the parties that the provisions of this Agreement be enforced to the fullest extent
permissible under the legal requirements and public policies of each jurisdiction in which enforcement may be sought, and that the unenforceability (or the modification to conform to such requirements or policies) of any provisions of this Agreement
shall not render unenforceable, or impair, the remainder of the provisions of this Agreement. Accordingly, if any provision of this Agreement shall be determined to be invalid or unenforceable, such invalidity or unenforceability shall be deemed to
apply only with respect to the operation of such provision in the particular jurisdiction in which such determination is made and not with respect to any other provision or jurisdiction. 

(c) For the avoidance of doubt and notwithstanding anything to the contrary, the terms of this Agreement shall not restrict CTO or any of its
Affiliates from providing financing for a third party’s acquisition of Single-Tenant, Net Leased Properties or from developing and owning any Single-Tenant, Net Leased Property. 

3. Right of First Offer. 

(a) CTO hereby agrees that, during the Restricted Period, neither CTO nor any of its Affiliates shall enter into any agreement with any third
party for the purchase and/or sale of any ROFO Property without first offering Alpine the right to purchase the ROFO Property. 
 (b) If,
during the Restricted Period, CTO or any of its Affiliates proposes to sell a ROFO Property, CTO or such Affiliate shall deliver a written notice (which may be by email) to Alpine (such notice, a “ROFO Notice”), which ROFO Notice
shall set forth the material business terms of such proposal including, without limitation, CTO’s or such Affiliate’s proposed sales price, the square footage of the ROFO Property, the terms of any lease associated with the ROFO Property,
the proposed due diligence period, the proposed closing date, any deposit requirements and any other principal business terms. Alpine shall have the option to purchase the ROFO Property, which Alpine shall exercise by delivering irrevocable notice
to CTO or its Affiliate, as applicable (an “Acceptance Notice”), within ten Business Days of the giving of the ROFO Notice, along with an agreement of sale to purchase the ROFO Property. 

  
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 (c) With respect to any ROFO Property for which a ROFO Notice has been delivered pursuant to
Section 3(b) above, if Alpine declines or fails to exercise its right of first offer within the period provided in Section 3(b) above (such failure being deemed a waiver of any such right of first offer), then CTO or its Affiliate, as
applicable, shall thereafter be free to offer for sale and sell such ROFO Property upon terms similar to those set forth in the ROFO Notice; provided, however, that the sale of such ROFO Property upon terms similar to those set forth in the
ROFO Notice shall be completed by CTO or its Affiliate, as applicable, within 12 months of the date the ROFO Notice is delivered to Alpine; provided further, that if CTO or its Affiliate, as applicable, subsequently offers for sale such ROFO
Property on terms that are materially different from the terms set forth in the ROFO Notice relating to such ROFO Property, then CTO or such Affiliate shall provide Alpine with a revised ROFO Notice in accordance with the terms set forth above and
Alpine shall have all of the same rights as set forth above. Time shall be of the essence as to Alpine’s giving of any Acceptance Notice. The terms upon which CTO or its Affiliate, as applicable, is willing to sell any ROFO Property shall be
deemed materially different if the net effective sales proceeds shall be more than five percent (5.00%) less than the net effective sales proceeds set forth in the initial or any revised ROFO Notice. 

4. Notices. Except as otherwise expressly provided herein, all notices, requests, demands, claims and other communications required or
permitted hereunder will be in writing and will be sent by personal delivery or nationally recognized overnight courier. Any notice, request, demand, claim, or other communication required or permitted hereunder will be deemed duly given, as
applicable, upon personal delivery or one Business Day following the date sent when sent by a reputable overnight courier service, addressed as follows: 
  

	 	(a)	 If to CTO, to: 

Consolidated-Tomoka Land Co. 

1140 N. Williamson Blvd., Suite 140 

Daytona Beach, FL 32114 

Attention: General Counsel 
  

	 	(b)	 If to Alpine, to: 

Alpine Income Property Trust, Inc. 

1140 N. Williamson Blvd., Suite 140 

Daytona Beach, FL 32114 

Attention: Chair, Nominating and Corporate Governance Committee 

with a copy to: 
 Alpine Income
Property Trust, Inc. 
 1140 N. Williamson Blvd., Suite 140 

Daytona Beach, FL 32114 

Attention: General Counsel 
 Any party may
change the address to which notices, requests, demands, claims, and other communications required or permitted hereunder are to be delivered by providing to the other parties written notice in the manner herein set forth. 

  
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 5. Miscellaneous. 

(a) Entire Agreement. The agreement of the parties that is comprised of this Agreement sets forth the entire agreement and understanding
between the parties hereto with respect to the subject matter hereof and supersedes any and all prior agreements, understandings, negotiations and communications, whether oral or written, relating to the subject matter of this Agreement. 

(b) Amendments. This Agreement may be amended or modified, but only by an instrument in writing executed by each of the parties hereto.

 (c) No Third Party Beneficiaries. This Agreement will be binding upon and inure solely to the benefit of the parties hereto, and
nothing in this Agreement, express or implied, is intended to or will be construed to or will confer upon any other person any right, claim, cause of action, benefit or remedy of any nature whatsoever under or by reason of this Agreement. 

(d) Assignments. This Agreement will be binding upon and inure to the benefit of and be enforceable by the successors and permissible
assigns of the parties hereto. Neither this Agreement nor any rights and obligations hereunder may be assigned, hypothecated or otherwise transferred by any party hereto (by operation of law or otherwise) without the prior written agreement of the
other party. 
 (e) Governing Law. This Agreement, and all claims arising in whole or in part out of, related to, based upon, or in
connection herewith or the subject matter hereof will be governed by and construed in accordance with the laws of the State of New York, without giving effect to any choice or conflict of law provision or rule that would cause the application of the
laws of any other jurisdiction. 
 (f) Jurisdiction. Each party to this Agreement, by its execution hereof, hereby:
(i) irrevocably submits to the exclusive jurisdiction of the state courts of the State of Florida, located in Orlando, or in the United States District Court for the Middle District of Florida, for the purpose of any and all actions, suits or
proceedings arising in whole or in part out of, related to, based upon or in connection with this Agreement or the subject matter hereof; (ii) waives to the extent not prohibited by applicable law, and agrees not to assert, by way of motion, as
a defense or otherwise, in any such action, suit, or proceeding, any claim that it is not subject personally to the jurisdiction of the above-named courts, that its property is exempt or immune from attachment or execution, that any such action
brought in one of the above-named courts should be dismissed on grounds of forum non conveniens, should be transferred to any court other than one of the above-named courts, or should be stayed by reason of the pendency of some other
proceeding in any other court other than one of the above-named courts, or that this Agreement or the subject matter hereof may not be enforced in or by such court; and (iii) agrees not to commence any such action, suit or proceeding other than
before one of the above-named courts nor to make any motion or take any other action seeking or intending to cause the transfer or removal of any such action to any court other than one of the above-named courts whether on the grounds of
inconvenient forum or otherwise. Each party hereby (x) consents to service of process in any such action in any manner permitted by the laws of the State of New York; (y) agrees that service of process made in accordance with clause
(x) will constitute good and valid service of process in any such action; and (z) waives and agrees not to assert (by way of motion, as a defense, or otherwise) in any such action any claim that service of process made in accordance with
clause (x) or clause (y) does not constitute good and valid service of process. 

  
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 (g) Waiver of Jury Trial. TO THE EXTENT NOT PROHIBITED BY APPLICABLE LEGAL
REQUIREMENTS WHICH CANNOT BE WAIVED, EACH OF THE PARTIES HERETO HEREBY WAIVES AND COVENANTS THAT IT SHALL NOT ASSERT (WHETHER AS PLAINTIFF, DEFENDANT OR OTHERWISE) ANY RIGHT TO TRIAL BY JURY IN ANY FORUM IN RESPECT OF ANY ISSUE, ACTION, CLAIM, CAUSE
OF ACTION, SUIT (IN CONTRACT, TORT OR OTHERWISE), INQUIRY, PROCEEDING OR INVESTIGATION ARISING OUT OF OR BASED UPON THIS AGREEMENT OR THE SUBJECT MATTER HEREOF, IN EACH CASE WHETHER NOW EXISTING OR HEREAFTER ARISING. ANY PARTY HERETO MAY FILE AN
ORIGINAL COUNTERPART OR A COPY OF THIS SECTION 5(g) WITH ANY COURT AS WRITTEN EVIDENCE OF THE CONSENT OF EACH SUCH PARTY TO THE WAIVER OF ITS RIGHT TO TRIAL BY JURY. 

(h) Specific Performance. Each of the parties acknowledges and agrees that the other parties would be damaged immediately, extensively
and irreparably and no adequate remedy at law would exist in the event that any of the provisions of this Agreement were not performed in accordance with their specific terms or were otherwise breached or violated. Accordingly, in addition to, and
not in limitation of, any other remedy available to any party, the parties agree that, without posting bond or similar undertaking, each of the other parties shall be entitled to an injunction or injunctions to prevent breaches or violations of the
provisions of this Agreement and to the remedy of specific performance of this Agreement and the terms and provisions hereof in any action instituted in any court having jurisdiction over the parties and the matter in addition to any other remedy to
which such party may be entitled, at law or in equity. Such remedies, and any and all other remedies provided for in this Agreement, will, however, be cumulative in nature and not exclusive and will be in addition to any other remedies to which such
party may be entitled. Each of the parties hereby acknowledges and agrees that it may be difficult to prove damages with reasonable certainty, that it may be difficult to procure suitable substitute performance, and that injunctive relief and/or
specific performance will not cause an undue hardship to any party. Each party further agrees that, in the event of any action for specific performance in respect of any breach or violation, or threatened breach or violation, of this Agreement, it
shall not assert the defense that a remedy at law would be adequate or that specific performance or injunctive relief in respect of such breach or violation should not be available on any other grounds. 

(i) No Waiver. No failure or delay on the part of any party hereto in the exercise of any right hereunder will impair such right or be
construed to be a waiver of, or acquiescence in, any breach of any representation, warranty, covenant or agreement herein, nor will any single or partial exercise of any such right preclude any other or further exercise thereof or of any other
right. No waiver of any provision of this Agreement shall be deemed or shall constitute a waiver of any other provision hereof (whether or not similar), or shall constitute a continuing waiver unless otherwise expressly provided. No waiver of any
right or remedy hereunder shall be valid unless the same shall be in writing and signed by the party against whom such waiver is intended to be effective. 

  
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 (j) Construction. The parties have participated jointly in the negotiation and
drafting of this Agreement. In the event an ambiguity or question of intent or interpretation arises, this Agreement shall be construed as if drafted jointly by the parties and no presumption or burden of proof shall arise favoring or disfavoring
any party by virtue of the authorship of any of the provisions of this Agreement. 
 (k) Counterparts. This Agreement may be executed
in any number of counterparts, and by the different parties hereto in separate counterparts, each of which will be deemed an original for all purposes and all of which together will constitute one and the same instrument. This Agreement may be
executed by facsimile or PDF signature by any party and such signature will be deemed binding for all purposes hereof without delivery of an original signature being thereafter required. 

[Remainder of Page Intentionally Left Blank.] 

  
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 IN WITNESS WHEREOF, the parties have duly executed this Agreement as of the date first
written above. 
  

			
	CONSOLIDATED-TOMOKA LAND CO.

 
			
		
	By:	 	  

 
			
	Name:
	Title:
	
	ALPINE INCOME PROPERTY TRUST, INC.

 
			
		
	By:	 	  

	Name:
	Title:

 [Signature Page to Exclusivity and Right of First Offer Agreement] 

 Schedule I 

ROFO Properties 
 [Insert
Schedule of ROFO Properties – To Come] 

  
 Sch. I-1EX-10.13

 Exhibit 10.13 

TAX PROTECTION AGREEMENT 

THIS TAX PROTECTION AGREEMENT (this “Agreement”) is made and entered into as of
[                    ], 2019 by and among Alpine Income Property Trust, Inc., a Maryland corporation (the “REIT”), Alpine Income
Property OP, LP, a Delaware limited partnership (the “Partnership”), Consolidated-Tomoka Land Co., a Florida corporation (“CTO”), and Indigo Group Ltd., a Florida limited partnership (“Indigo” and
together with CTO, the “Initial Protected Partners” and, together with the REIT and the Partnership, the “Parties”). 

RECITALS 
 WHEREAS, the
Initial Protected Partners own, directly or indirectly through entities disregarded as separate from such Initial Protected Partners for federal income tax purposes, fee title to or
tenant-in-common interests in the real property and improvements located at: (i) 50 Central Ave, Lynn, MA 01901; (ii) 3775 Oxford Station Way, Winston-Salem, NC 27103;
(iii) 4954 Town Center Parkway, Jacksonville, FL 32246; (iv) 5064 Weebers Crossings Drive, Jacksonville, FL 32246; and (v) 2699 Country Road D, East Troy, WI 53120 (as further described in those certain contribution agreements, each dated as of
[            ], 2019 (the “Contribution Agreements”), by and among the Initial Protected Partners and the Partnership (collectively, the “Properties”);

 WHEREAS, pursuant to the Contribution Agreements, the Initial Protected Partners are contributing (the
“Contributions”), as applicable, their right, title and interests in and to the Properties to the Partnership in exchange for common partnership units of limited partnership interest in the Partnership
(“Units”); 
 WHEREAS, it is intended for federal income tax purposes that the Contributions for Units will be treated as a
tax-deferred contributions of the Properties to the Partnership for Units under Section 721 of the Internal Revenue Code of 1986, as amended (the “Code”); 

WHEREAS, in consideration for the agreement of the Initial Protected Partners to make the Contributions, the Parties desire to enter into this
Agreement regarding certain tax matters as set forth herein; and 
 WHEREAS, the REIT and the Partnership desire to evidence their agreement
regarding amounts that may be payable in the event of certain actions being taken by the Partnership regarding the disposition of certain of the contributed Properties. 

NOW, THEREFORE, in consideration of the promises and the mutual representations, warranties, covenants and agreements contained herein and in
the Contribution Agreements, the Parties hereby agree as follows: 
 ARTICLE 1 

DEFINITIONS 
 To the extent
not otherwise defined herein, capitalized terms used in this Agreement have the meanings ascribed to them in the Partnership Agreement (as defined below). 

 “Accounting Firm” has the meaning set forth in the
Section 3.2. 
 “Agreement” has the meaning set forth in the Preamble. 

“Cash Consideration” has the meaning set forth in Section 2.1(a). 

“Closing Date” means the date on which the Contributions will be effective. 

“Code” has the meaning set forth in the Recitals. 

“Contributions” has the meaning set forth in the Recitals. 

“Contribution Agreements” has the meaning set forth in the Recitals. 

“Final Determination” means (i) a decision, judgment, decree or other order by any court of competent jurisdiction,
which decision, judgment, decree or other order has become final after all allowable appeals by either party to the action have been exhausted or after the time for filing such appeals has expired, (ii) a binding settlement agreement entered
into in connection with an administrative or judicial proceeding (iii) the expiration of the time for instituting a claim for refund, or if such a claim was filed, the expiration of the time for instituting suit with respect thereto or
(iv) the expiration of the time for instituting suit with respect to a claimed deficiency. 
 “Gain Limitation
Property” means (i) each of the Properties, as described in more detail on Schedule 2 hereto as a Gain Limitation Property; (ii) any direct or indirect interest owned by the Partnership in any entity that owns an interest
in a Gain Limitation Property, if the disposition of that interest would result in the recognition of Protected Gain by a Protected Partner; and (iii) any other property that the Partnership directly or indirectly receives that is in whole or
in part a “substituted basis property” as defined in Section 7701(a)(42) of the Code with respect to a Gain Limitation Property. 

“Indirect Owner” means, in the case of a Protected Partner that is an entity that is classified as a partnership, disregarded
entity or subchapter S corporation or real estate investment trust for federal income tax purposes, any person owning an equity interest in such Protected Partner, and in the case of any Indirect Owner that itself is an entity that is classified as
a partnership, disregarded entity, subchapter S corporation or real estate investment trust for federal income tax purposes, any person owning an equity interest in such entity. 

“Notice Period” means the period commencing on
[                    ], 2019, and ending at 12:01 AM on
[                    ], 2029, provided, however, that with respect to a Protected Partner, the Notice Period shall terminate at such time as such
Protected Partner has disposed of 80% or more of the Units received upon the Contributions in one or more taxable transactions. 

“Parties” has the meaning set forth in the Preamble. 

“Partnership” has the meaning set forth in the Preamble. 

  
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 “Partnership Agreement” means the Amended and Restated Agreement of Limited
Partnership of the Partnership, dated as of [                    ], 2019, as the same may be further amended in accordance with the terms thereof.

 “Partnership Interest Consideration” has the meaning set forth in Section 2.1(a). 

“Properties” has the meaning set forth in the Recitals. 

“Protected Gain” shall mean the gain that would be allocable to and recognized by a Protected Partner for federal income tax
purposes under Section 704(c) of the Code in the event of the sale of a Gain Limitation Property in a fully taxable transaction. The initial amount of Protected Gain with respect to each Protected Partner shall be determined as if the
Partnership sold each Gain Limitation Property in a fully taxable transaction on the Closing Date for consideration equal to the Section 704(c) Value of such Gain Limitation Property on the Closing Date, and is set forth on Schedule 2
hereto. Gain that would be allocated to a Protected Partner upon a sale of a Gain Limitation Property that is “book gain” (for example, any gain attributable to appreciation in the actual value of the Gain Limitation Property following the
Closing Date or any gain resulting from reductions in the “book value” of the Gain Limitation Property following the Closing Date) shall not be considered Protected Gain. As used in this definition, “book gain” is any gain that
would not be required under Section 704(c) of the Code and the applicable regulations to be specially allocated to the Protected Partners for federal income tax purposes. 

“Protected Partner” means those persons, as set forth as Protected Partners on Schedule 1, and any
person who (i) acquires Units from a Protected Partner in a transaction in which gain or loss is not recognized in whole or in part and in which such transferee’s adjusted basis for federal income tax purposes is determined in whole or in
part by reference to the adjusted basis of the Protected Partner in such Units, (ii) has notified the Partnership of its status as a Protected Partner and (iii) provides all documentation reasonably requested by the Partnership to verify
such status, but excludes any person that ceases to be a Protected Partner pursuant to this Agreement. 

“Section 704(c) Value” means the fair market value of any Gain Limitation Property as of the Closing Date,
as determined by the Partnership and as set forth next to each Gain Limitation Property on Schedule 3 hereto. Notwithstanding the preceding sentence, with respect to each Gain Limitation Property, the Section 704(c) Value shall
not exceed the “Agreed Maximum Value” set forth next to each Gain Limitation Property on Schedule 3 hereto. 

“Subsidiary” means any entity in which the Partnership owns a direct or indirect interest that owns a Gain Limitation
Property on the Closing Date or that thereafter is a successor to the Partnership’s direct or indirect interests in a Gain Limitation Property. 

“Tax Protection Period” means the period commencing on the Closing Date and ending at 12:01 AM on
                    , 2029, provided, however, that with respect to a Protected Partner, the Tax Protection Period shall terminate at such time as
(i) such Protected Partner has disposed of eighty percent (80%) or more of the Units received upon the Contributions in one or more taxable transactions or (ii) there is a Final Determination that no portion of the Contributions qualified
for tax-deferred treatment under Section 721 of the Code. 

  
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 “Units” has the meaning set forth in the Recitals. 

ARTICLE 2 
 RESTRICTIONS
ON DISPOSITIONS OF 
 GAIN LIMITATION PROPERTIES 

2.1    Restrictions on Disposition of Gain Limitation Properties. 

(a)    The Partnership agrees for the benefit of each Protected Partner, for the term of the Tax Protection
Period, not to directly or indirectly sell, exchange, transfer, or otherwise dispose of a Gain Limitation Property or any interest therein, without regard to whether such disposition is voluntary or involuntary, in a transaction that would cause any
Protected Partner to recognize any Protected Gain. 
 Without limiting the foregoing, the term “sell, exchange, transfer, or otherwise
dispose of a Gain Limitation Property” shall be deemed to include, and the prohibition shall extend to: 
  

	 	(i)	 any direct or indirect disposition by any direct or indirect Subsidiary of any Gain Limitation Property or any
interest therein; 

  

	 	(ii)	 any direct or indirect disposition by the Partnership of any Gain Limitation Property (or any direct or
indirect interest therein) that is subject to Section 704(c)(1)(B) of the Code and the Treasury Regulations thereunder; and 

  

	 	(iii)	 any distribution by the Partnership to a Protected Partner that is subject to Section 737 of the Code and
the Treasury Regulations thereunder. 

 Without limiting the foregoing, a disposition shall include any transfer,
voluntary or involuntary, by the Partnership or any Subsidiary in a foreclosure proceeding, pursuant to a deed in lieu of foreclosure, or in a bankruptcy proceeding. 

Notwithstanding the foregoing, this Section 2.1 shall not apply to a voluntary, actual disposition by a Protected
Partner of Units in connection with a merger or consolidation of the Partnership pursuant to which (1) the Protected Partner is offered as consideration for the Units either cash or property treated as cash pursuant to Section 731 of the
Code (“Cash Consideration”) or partnership interests and the receipt of such partnership interests would not result in the recognition of gain for federal income tax purposes by the Protected Partner (“Partnership Interest
Consideration”); (2) the Protected Partner has the right to elect to receive solely Partnership Interest Consideration in exchange for his Units, and the continuing partnership has agreed in writing to assume the obligations of the
Partnership under this Agreement; (3) no Protected Gain is recognized by the Partnership as a result of any partner of the Partnership receiving Cash Consideration; and (4) the Protected Partner elects or is deemed to elect to receive
solely Cash Consideration. 
 (b)    Notwithstanding the restriction set forth in this
Section 2.1, the Partnership and any Subsidiary may dispose of any Gain Limitation Property (or any interest therein) if such 

  
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disposition qualifies as a “like-kind exchange” under Section 1031 of the Code, or an involuntary conversion under Section 1033 of the Code, or other transaction (including,
but not limited to, a contribution of property to any entity that qualifies for the non-recognition of gain under Section 721 or Section 351 of the Code, or a merger or consolidation of the
Partnership with or into another entity that qualifies for taxation as a “partnership” for federal income tax purposes) that, as to each of the foregoing, does not result in the recognition of any taxable income or gain to any Protected
Partner with respect to any of the Units; provided, however, that in the case of a “like-kind exchange” under Section 1031 of the Code, if such exchange is with a “related party” within the meaning of Section 1031(f)(3)
of the Code, any direct or indirect disposition by such related party of the Gain Limitation Property or any other transaction prior to the expiration of the two (2) year period following such exchange that would cause Section 1031(f)(1)
of the Code to apply with respect to such Gain Limitation Property (including by reason of the application of Section 1031(f)(4) of the Code) shall be considered a violation of this Section 2.1 by the Partnership. 

ARTICLE 3 
 REMEDIES FOR
BREACH 
 3.1    Monetary Damages. In the event that the Partnership breaches its obligations set forth in
Article 2, with respect to a Protected Partner, the Protected Partner’s sole remedy shall be to receive from the Partnership, and the Partnership shall pay to such Protected Partner as damages, an amount equal to (a) the aggregate
federal, state, and local income taxes incurred by the Protected Partner or an Indirect Owner with respect to the Protected Gain that is allocable to such Protected Partner under the Partnership Agreement as a result of the disposition of the Gain
Limitation Property plus (b) the aggregate federal, state, and local income taxes payable by the Protected Partner or an Indirect Owner as a result of the receipt of any payment required under this Section 3.1. 

For the avoidance of doubt, the Partnership shall have no liability pursuant to this Section 3.1 if the Partnership
merges into another entity treated as a partnership for federal income tax purposes or the Protected Partner accepts an offer to exchange its Units for equity interests in another entity treated as a partnership for federal income tax purposes so
long as, in either case, such successor entity assumes or agrees to assume the Partnership’s obligations pursuant to this Agreement. 

For purposes of computing the amount of federal, state, and local income taxes required to be paid by a Protected Partner (or Indirect Owner),
(i) any deduction for state income taxes payable as a result thereof actually allowed in computing federal income taxes shall be taken into account, and (ii) a Protected Partner’s (or Indirect Owner’s) tax liability shall be computed
using the highest federal, state and local marginal income tax rates that would be applicable to such Protected Partner’s (or Indirect Owner’s) taxable income (taking into account the character and type of such income or gain) for the year
with respect to which the taxes must be paid, without regard to any deductions, losses or credits that may be available to such Protected Partner (or Indirect Owner) that would reduce or offset its actual taxable income or actual tax liability if
such deductions, losses or credits could be utilized by the Protected Partner (or Indirect Owner) to offset other income, gain or taxes of the Protected Partner (or Indirect Owner), either in the current year, in earlier years, or in later years.

  
 5 

 3.2    Process for Determining Damages. If the Partnership has
breached or violated any of the covenants set forth in Article 2 (or a Protected Partner asserts that the Partnership has breached or violated any of the covenants set forth in Article 2), the Partnership and the Protected Partner (or
Indirect Owner) agree to negotiate in good faith to resolve any disagreements regarding any such breach or violation and the amount of damages, if any, payable to such Protected Partner (or Indirect Owner) under
Section 3.1. If any such disagreement cannot be resolved by the Partnership and such Protected Partner (or Indirect Owner) within sixty (60) days after the receipt of notice from the Partnership of such breach and the
amount of income to be recognized by reason thereof (or, if applicable, receipt by the Partnership of an assertion by a Protected Partner that the Partnership has breached or violated any of the covenants set forth in Article 2), the
Partnership and the Protected Partner shall jointly retain a nationally recognized independent public accounting firm (an “Accounting Firm”) to act as an arbitrator to resolve as expeditiously as possible all points of any such
disagreement (including, without limitation, whether a breach of any of the covenants set forth in Article 2, has occurred and, if so, the amount of damages to which the Protected Partner is entitled as a result thereof, determined as set
forth in Section 3.1). All determinations made by the Accounting Firm with respect to the resolution of any breach or violation of any of the covenants set forth in Article 2 and the amount of damages payable to the
Protected Partner under Section 3.1 shall be final, conclusive and binding on the Partnership and the Protected Partner. The fees and expenses of any Accounting Firm incurred in connection with any such determination shall
be shared equally by the Partnership and the Protected Partner, provided that if the amount determined by the Accounting Firm to be owed by the Partnership to the Protected Partner is more than five percent (5%) higher than the amount proposed by
the Partnership to be owed to such Protected Partner prior to the submission of the matter to the Accounting Firm, then all of the fees and expenses of any Accounting Firm incurred in connection with any such determination shall be paid by the
Partnership and if the amount determined by the Accounting Firm to be owed by the Partnership to the Protected Partner is more than five percent (5%) less than the amount proposed by the Partnership to be owed to such Protected Partner prior to the
submission of the matter to the Accounting Firm, then all of the fees and expenses of any Accounting Firm incurred in connection with any such determination shall be paid by the Protected Partner. 

3.3    Required Notices; Time for Payment. In the event that there has been a breach of Article 2, the
Partnership shall provide to each affected Protected Partner notice of the transaction or event giving rise to such breach not later than at such time as the Partnership provides to the Protected Partners the IRS Schedule K-1s to the
Partnership’s federal income tax return for the year of such transaction. All payments required to be made under this Article 3 to any Protected Partner shall be made to such Protected Partner on or before April 15 of the year
following the year in which the gain recognition event giving rise to such payment took place; provided that, if the Protected Partner is required to make estimated tax payments that would include such gain (taking into account all available safe
harbors), the Partnership shall make a payment to the Protected Partner on or before the due date for such estimated tax payment and such payment from the Partnership shall be in an amount that corresponds to the amount of the estimated tax being
paid by such Protected Partner at such time as a result of the gain recognition event. In the event of a payment made after the date required pursuant to this Section 3.3, interest shall accrue on the aggregate amount
required to be paid from such date to the date of actual payment at a rate equal to the “prime rate” of interest, as published in the Wall Street Journal (or if no longer published there, as announced by Citibank) effective as of the date
the payment is required to be made. 

  
 6 

 ARTICLE 4 

NOTICE OF INTENTION TO SELL GAIN LIMITATION PROPERTY DURING NOTICE PERIOD 

During the Notice Period, if the Partnership intends to dispose of a Gain Limitation Property in a taxable transaction, the Partnership shall
use commercially reasonable efforts to provide at least 90 days’ prior written notice (prior to the closing of such disposition) to the Protected Partners. 

ARTICLE 5 
 SECTION
704(C) METHOD AND ALLOCATIONS 
 Notwithstanding any provision of the Partnership Agreement, the Partnership shall use the
“traditional method” under Treasury Regulations Section 1.704-3(b) for purposes of making all allocations under Section 704(c) of the Code with respect to any Gain Limitation Property. 

ARTICLE 6 
 AMENDMENT OF
THIS AGREEMENT; WAIVER OF CERTAIN PROVISIONS 
 6.1    Amendment. This Agreement may not be amended, directly
or indirectly (including by reason of a merger between either the Partnership or the REIT and another entity) except by a written instrument signed by the REIT, the Partnership, and each of the Protected Partners to be subject to such amendment,
except that the Partnership may amend Schedule 1 upon a person becoming a Protected Partner as a result of a transfer of Units. 

6.2    Waiver. Notwithstanding the foregoing, upon written request by the Partnership, each Protected Partner, in
its sole discretion, may waive the payment of any damages that is otherwise payable to such Protected Partner pursuant to Article 3 hereof. Such a waiver shall be effective only if obtained in writing from the affected Protected Partner. 

ARTICLE 7 
 MISCELLANEOUS

 7.1    Additional Actions and Documents. Each of the Parties hereby agrees to take or cause to be taken
such further actions, to execute, deliver, and file or cause to be executed, delivered and filed such further documents, and will obtain such consents, as may be necessary or as may be reasonably requested in order to fully effectuate the purposes,
terms and conditions of this Agreement. 
 7.2    Assignment. No Party shall assign its or his rights or
obligations under this Agreement, in whole or in part, except by operation of law, without the prior written consent of the other Parties, and any such assignment contrary to the terms hereof shall be null and void and of no force and effect. 

7.3    Successors and Assigns. This Agreement shall be binding upon and shall inure to the benefit of the Protected
Partners and their respective successors and permitted assigns, whether so expressed or not. This Agreement shall be binding upon the REIT, the Partnership, and any entity that is a direct or indirect successor, whether by merger, transfer, spin-off or otherwise, to 

  
 7 

 
all or substantially all of the assets of either the REIT or the Partnership (or any prior successor thereto as set forth in the preceding portion of this sentence), provided that none of the
foregoing shall result in the release of liability of the REIT and the Partnership hereunder. The REIT and the Partnership covenant with and for the benefit of the Protected Partners not to undertake any transfer of all or substantially all of the
assets of either entity (whether by merger, transfer, spin-off or otherwise) unless the transferee has acknowledged in writing and agreed in writing to be bound by this Agreement, provided that the foregoing
shall not be deemed to permit any transaction otherwise prohibited by this Agreement. 
 7.4    Modification;
Waiver. No failure or delay on the part of any Party in exercising any power or right hereunder shall operate as a waiver thereof, nor shall any single or partial exercise of any such right or power, or any abandonment or discontinuance of steps
to enforce such a right or power, preclude any other or further exercise thereof or the exercise of any other right or power. The rights and remedies of the Parties are cumulative and not exclusive of any rights or remedies which they would
otherwise have. No modification or waiver of any provision of this Agreement, nor consent to any departure by any Party therefrom, shall in any event be effective unless the same shall be in writing, and then such waiver or consent shall be
effective only in the specific instance and for the purpose for which given. No notice to or demand on any Party in any case shall entitle such Party to any other or further notice or demand in similar or other circumstances. 

7.5    Representations and Warranties Regarding Authority; Noncontravention. Each of the REIT and the Partnership
has the requisite corporate or other (as the case may be) power and authority to enter into this Agreement and to perform its respective obligations hereunder. The execution and delivery of this Agreement by each of the REIT and the Partnership and
the performance of each of its respective obligations hereunder have been duly authorized by all necessary trust, partnership, or other (as the case may be) action on the part of each of the REIT and the Partnership. This Agreement has been duly
executed and delivered by each of the REIT and the Partnership and constitutes a valid and binding obligation of each of the REIT and the Partnership, enforceable against each of the REIT and the Partnership in accordance with its terms, except as
such enforcement may be limited by (i) applicable bankruptcy or insolvency laws (or other laws affecting creditors’ rights generally) or (ii) general principles of equity. The execution and delivery of this Agreement by each of the
REIT and the Partnership do not, and the performance by each of its respective obligations hereunder will not, conflict with, or result in any violation of (i) the Partnership Agreement or (ii) any other agreement applicable to the REIT
and/or the Partnership, other than, in the case of clause (ii), any such conflicts or violations that would not materially adversely affect the performance by the Partnership and the REIT of their obligations hereunder. 

7.6    Captions. The Article and Section headings contained in this Agreement are inserted for convenience of
reference only, shall not be deemed to be a part of this Agreement for any purpose, and shall not in any way define or affect the meaning, construction or scope of any of the provisions hereof. 

7.7    Notices. All notices and other communications given or made pursuant hereto shall be in writing, shall be
deemed to have been duly given or made as of the date delivered, mailed or transmitted, and shall be effective upon receipt, if delivered personally, mailed by registered or 

  
 8 

 
certified mail (postage prepaid, return receipt requested) to the Parties at the following addresses (or at such other address for a Party as shall be specified by like changes of address) or
sent by electronic transmission to the telecopier number specified below: 
  

	 	(a)	 if to the Partnership or the REIT, to: 

Alpine Income Property Trust, Inc. 

1140 N. Williamson Blvd., Suite 140 

Daytona Beach, Florida 32114 

Attention: Daniel E. Smith 
  

	 	(b)	 if to a Protected Partner, to the address on file with the Partnership. 

Each Party may designate by notice in writing a new address to which any notice, demand, request or communication may thereafter be so given, served or sent.
Each notice, demand, request, or communication which shall be hand delivered, sent, mailed, telecopied or telexed in the manner described above, or which shall be delivered to a telegraph company, shall be deemed sufficiently given, served, sent,
received or delivered for all purposes at such time as it is delivered to the addressee (with the return receipt, the delivery receipt, or (with respect to a telecopy or telex) the answerback being deemed conclusive, but not exclusive, evidence of
such delivery) or at such time as delivery is refused by the addressee upon presentation. 
 7.8    Counterparts.
This Agreement may be executed in two or more counterparts, all of which shall be considered one and the same agreement and each of which shall be deemed an original. 

7.9    Governing Law. The interpretation and construction of this Agreement, and all matters relating thereto,
shall be governed by the laws of the State of Maryland, without regard to the choice of law provisions thereof. 

7.10    Consent to Jurisdiction; Enforceability. 

(a)    This Agreement and the duties and obligations of the Parties shall be enforceable against any of the other Parties
in the courts of the State of Maryland. For such purpose, each Party and the Protected Partners hereby irrevocably submits to the nonexclusive jurisdiction of such courts and agrees that all claims in respect of this Agreement may be heard and
determined in any of such courts. 
 (b)    Each Party hereby irrevocably agrees that a final judgment of any of the
courts specified above in any action or proceeding relating to this Agreement shall be conclusive and may be enforced in other jurisdictions by suit on the judgment or in any other manner provided by law. 

7.11    Severability. If any part of any provision of this Agreement shall be invalid or unenforceable in any
respect, such part shall be ineffective to the extent of such invalidity or unenforceability only, without in any way affecting the remaining parts of such provision or the remaining provisions of this Agreement. 

  
 9 

 7.12    Costs of Disputes. Except as otherwise expressly set
forth in this Agreement, the nonprevailing Party in any dispute arising hereunder shall bear and pay the costs and expenses (including, without limitation, reasonable attorneys’ fees and expenses) incurred by the prevailing Party or Parties in
connection with resolving such dispute. 
 [no further text on this page—signature page follows] 

  
 10 

 IN WITNESS WHEREOF, the parties hereto have executed and delivered this Agreement by their
respective officers, general partners, or delegates thereunto duly authorized all as of the date first written above. 
 REIT: 

ALPINE INCOME PROPERTY TRUST, INC., 

a Maryland corporation 
  

					
		 	 By:
	 	  

	                    	 	 Name:
	 	  

		 	 Title:
	 	  

 PARTNERSHIP: 

ALPINE INCOME PROPERTY OP, LP, 
 a Delaware limited
partnership 
  

					
		 	 By:    
	 	ALPINE INCOME PROPERTY GP, LLC,
	                        	 		 	 a Delaware limited liability company,
 its
General Partner
  

By: ALPINE INCOME PROPERTY TRUST, INC.,

     a Maryland corporation,
its sole member

 

					
		 	 By:
	 	
                     
                                

	                                      
     	 	 Name:
	 	  

		 	 Title:
	 	  

 CTO: 

CONSOLIDATED-TOMOKA LAND CO., 
 a Florida corporation 

 

					
		 	 By:
	 	  

	                    	 	 Name:
	 	  

		 	 Title:
	 	  

 INDIGO: 

INDIGO GROUP LTD., 
 a
Florida limited partnership 
  

					
		 	 By:
	 	INDIGO GROUP INC.,
	                    	 		 	a Florida corporation,

  
 11 

					
	                                      
	 	its General Partner

					
			
	                                	 	By:	 	 

			
	 

                          
  
	 	 Name: Daniel E. Smith

Title: Senior Vice President

  
 12 

 Schedule 1 

List of Protected Partners 

Consolidated-Tomoka Land Co. 
 Indigo Group Ltd. 

  
 13 

 Schedule 2 

Gain Limitation Properties and 

Estimated Maximum Protected Gain for Protected Partners as a Group 

 

									
	 Name of Protected Property
	  	Closing Date Built In
Gain
(Aggregate)	 	  	Maximum Protected
Gain
(Aggregate)	 
	 Family Dollar, Lynn, MA
	  	$	             	 	  	$	             	 
	 Hobby Lobby, Winston-Salem, NC
	  	$	 	 	  	$	 	 
	 Cheddar’s, Jacksonville, FL
	  	$	 	 	  	$	 	 
	 Scrubbles, Jacksonville, FL
	  	$	 	 	  	$	 	 
	 Alpine Valley Music Theatre East Troy, WI
	  	$	 	 	  	$	 	 

  
 14 

 Schedule 3 

Maximum 704(c) Value to be Used in Computing Protected Gain 

 

					
	 Name of Protected Property
	  	Agreed Maximum Value	 
	 Family Dollar, Lynn, MA
	  	$	             	 
	 Hobby Lobby, Winston-Salem, NC
	  	$	 	 
	 Cheddar’s, Jacksonville, FL
	  	$	 	 
	 Scrubbles, Jacksonville, FL
	  	$	 	 
	 Alpine Valley Music Theatre East Troy, WI
	  	$	 	 

  
 15

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