It is a positive commandment to count sets of seven years and to sanctify the fiftieth year, as [Leviticus 25:8-10] states: "And you shall count seven years for yourselves... and you shall sanctify the fiftieth year." These two mitzvot are entrusted to the High Court alone.

You shall count off seven weeks of years—seven times seven years—so that the period of seven weeks of years gives you a total of forty-nine years. Then you shall sound the horn loud; in the seventh month, on the tenth day of the month—the Day of Atonement—you shall have the horn sounded throughout your land and you shall hallow the fiftieth year. You shall proclaim release throughout the land for all its inhabitants. It shall be a jubilee for you: each of you shall return to your holding and each of you shall return to your family. That fiftieth year shall be a jubilee for you: you shall not sow, neither shall you reap the aftergrowth or harvest the untrimmed vines, for it is a jubilee. It shall be holy to you: you may only eat the growth direct from the field. In this year of jubilee, each of you shall return to your holding.

(23) But the land must not be sold beyond reclaim, for the land is Mine; you are but strangers resident with Me.

If that person lacks sufficient means to recover it, what was sold shall remain with the purchaser until the jubilee; in the jubilee year it shall be released, so that the person returns to that holding. If any party sells a dwelling house in a walled city, it may be redeemed until a year has elapsed since its sale; the redemption period shall be a year. If it is not redeemed before a full year has elapsed, the house in the walled city shall pass to the purchaser beyond reclaim throughout the ages; it shall not be released in the jubilee. But houses in villages that have no encircling walls shall be classed as open country: they may be redeemed, and they shall be released through the jubilee. As for the cities of Levi, the houses in the cities it holds: Levi shall forever have the right of redemption. Such property as may be redeemed from Levi—houses sold in a city it holds—shall be released through the jubilee; for the houses in the cities of Levi are its holding among the Israelites. But the unenclosed land about its cities cannot be sold, for that is its holding for all time.

From the time the tribes of Reuven and Gad and half the tribe of Menasheh were exiled, [the observance] of the Jubilee year ceased, as [implied by Leviticus 25:10]: "You shall proclaim freedom throughout the land to all of its inhabitants." [One can infer that this commandment applies only] when all of its inhabitants are dwelling within it. [Moreover,] they may not be intermingled, one tribe with another, but rather each tribe is dwelling in its appropriate place.When the Jubilee is observed in Eretz [Yisrael], it should also be observed in the Diaspora, as [implied by the phrase used in the above verse:] "It is the Jubilee," [i.e.,] in every place. [This applies] whether the Temple is standing or whether the Temple is not standing.

[The portions of] Eretz Yisrael that were divided among the tribes can never be sold permanently, as [Leviticus 25:23] states: "The land will not be sold in perpetuity." If one sells the land in perpetuity, both [the buyer and the seller] violate a negative commandment. Their deeds are of no consequence, and the land reverts to its [original] owner in the Jubilee year.

A person should not sell his home or his ancestral field even though it returns to him eventually, unless he becomes impoverished, as [Leviticus 25:25] states: "If your brother becomes indigent and sells his ancestral heritage." One is not permitted to sell [such property] and hold the money in his pocket, engage in commerce with them, or purchase utensils, servants, or livestock. [He is only allowed to] sell to provide himself with sustenance. [Nevertheless,] if one transgressed and sold [such property], the sale is valid.

If a person purchases a field that is an ancestral heritage and plants trees which increase the value [of the field], when it returns [to its original owner] in the Jubilee, we should evaluate the increase in value brought about by the trees in it and the owner of the field must pay this sum to the purchaser. [This is derived from ibid. 25:33]: "A home that was sold shall go out... [in the Jubilee]." [Implied is that the home] is returned, but not the increase in its value.

If a person sold his field to one person, that person sold it to a second, the second to a third - even if there were 100 consecutive sales - in the Jubilee, it returns to its original owner, as [implied by Leviticus 27:24]: "In the Jubilee year, the field will return to the one from whom he purchased it, whose ancestral heritage it was."

Brothers who divide [an inheritance] are considered as purchasers and each one should return his portion to the other in the Jubilee, but their division is not nullified. Similarly, a firstborn and one who performs yibbum with his brother's wife, return the portion that they received in the Jubilee and take another portion instead of it.

A person who sells a house in a city surrounded by a wall may redeem it throughout a twelve month period from the day he sold it whenever he desires, even on the day he sold it. When he redeems it, he returns all the money he received and does not deduct anything from the purchaser.

When a person sells a home in a settlement or in a city that is not surrounded by a wall in the appropriate manner, he may redeem it according to the advantages that apply with regard to both the redemption of an [ancestral] field and the redemption of a home in a walled city.What is implied? If he desires to redeem [the home] immediately, he may, as is the law with regard to a home [in a walled city]. If the twelve months pass and he does not redeem it, he may redeem it until the Jubilee, as is the law regarding a field. When he redeems it, he makes a reckoning with the purchaser and subtracts the value of the benefit he received. If the Jubilee arrives without having redeemed it, the house returns [to the owner] without payment, as is the law with regard to fields.

Although the tribe of Levi does not have an ancestral portion within Eretz [Yisrael], the Jewish people were commanded to give them cities to dwell in and [additional] residential property. The cities include the six cities of refuge and 42 additional cities. When cities of refuge will be added in the era of Mashiach, all will be given to the Levites.

"And you shall proclaim dror": According to everyone dror refers to freedom, like a tzipor dror, a wild bird that is not under the control of any human. But R. Yehuda adds from the connection between dar and dirah that it means one can live wherever they wish, and dar also teaches about the ability to hawk one's goods in every place.

YOVEIL HI’ (IT IS A JUBILEE)...In my opinion, Scripture does not call the year yoveil with reference to the blowing [of the Shofar], but with reference to “the liberty” [that it brings to the inhabitants of the Land]; for this term is not mentioned in the first verse which states, Then shalt thou make proclamation with the blast of the horn. But when He stated [in the verse before us] and ye shall proclaim liberty throughout the Land unto all the inhabitants thereof, meaning that they shall all be free to reside wherever they please, He continued by saying ‘yoveil hi,’ that it is a year in which every man is “carried away” to his possession, and his feet “transport him” to his family afar off to sojourn...Thus the meaning of it shall be ‘yoveil’ unto you is “it is a year which ‘brings’ [liberty] and it shall be so to all of you, that you shall come and return every man unto his possession, and every man unto his family.”

YOVEL HI. The language of "yovel" references control and freedom, and it's from the language of "mixing" like offerings "mixed with oil," for in the year of the Yovel there is confusion and switching up and mixing of domains, that control of fields and slaves is switched around, and the buyer is like the seller, the slave like the master, the borrower like the lender, one freedom and one domain for everyone, there is no first and last, no one greater or lesser than the other...

And each man shall return to his ancestral land — even if he has no ancestral land he goes back to his main family and all the family heads are gathered together.

A kabbalistic approach to the words יובל היא: The word יובל is derived from the expression ועל יבל ישלח שרשיו, “sending forth its roots by a stream” (Jeremiah 17,8), a hint that all the succeeding generations are traced back to their original roots, to the prime cause which determined their development. This is the reason why the Yovel is called דרור, “freedom,” a reminder of when man was free from sin. All of humankind originated with the pool of souls at G’d’s disposal and eventually this is where the souls will return to.Each one of the seven times periods of a cycle of 7000 years will perform the tasks assigned to the respective day of creation making a total of 49,000 years. When they have completed these 49,000 years the universe will revert to the Tohu Vavohu which preceded the words בראשית ברא (Genesis 1,1).

(2) It is from the roots of the commandment from the angle of the simple understanding that God, may They be blessed, wanted to inform Their nation that everything is Theirs; and in the end everything will return to those to whom They wanted to give it at first - for the earth is Theirs, as it is written (Exodus 19:5), "for all the earth is Mine." And with this commandment of the counting of forty-nine years, they will distance themselves from stealing land of their fellows and they will not covet it in their hearts; in that they know that everything returns to the one that God wishes it to be theirs.

(2) ואל אחזת אבתיו AND UNTO THE POSSESSION OF HIS FATHERS [SHALL HE RETURN] — This means, he shall return to the dignity held by his ancestors and people shall not hold him in low esteem because of this (because he had previously been a slave)