A system and method to allow a buyer to reserve a trial occupancy of a residence listed for sale. The buyer submitting a letter of intent to purchase the residence at an offer price and agreeing to sellers trial occupancy conditions in order to reserve the residence. Optionally, the buyer requesting a trial occupancy as a contingent condition to purchase during contract negotiations. The buyer utilizing either a security deposit or insurance policy, or both, to cover damage to residence during the trial occupancy or sellers remedy for stay over tenancy.