Answers by Jill Helgren

This is a great question and honestly a situation I see quite a bit here in Treasure Island and throughout Florida. I notice you are in a different state and that is why I mention location. Because we are such a transient state, with people relocating in and out all the time, it is very common for a sale and purchase to be connected like this. The key is not just the price, it is making sure the timing is structured so everything lines up. The biggest thing I would be careful of is relying on the seller of the home you want to buy to find something without a clear plan. Since they are not on the market, they do not have any real pressure right now, so I always try to create some structure around that. Basically, making sure there is skin in the game. On your side, you are in a strong position with a cash buyer. That gives you flexibility, which is a great place to be. If I were guiding you through this, I would start by asking your buyer for a slightly extended closing, something like 45 to 60 days instead of a quick close. Most cash buyers are open to that, especially when it is explained that you are coordinating your next purchase and want a smooth transition. This is often a better solution than agreeing to a rent back that you are not comfortable paying for. If they are really set on a rent back, you can still negotiate that. You do not have to agree to cover it fully. You can offer a short period or a fair daily rate so it works for both sides. At the same time, I would not wait to get the home you want under contract. I would move forward with an offer now and structure it with either an extended closing or a contingency that gives the seller time to secure their next home. That way they are committed and actively working toward a solution instead of just thinking about it. The goal is to get both sides moving forward together with realistic timelines, rather than closing your sale and then waiting with no certainty. This is something I navigate often here in the Treasure Island market, and when it is handled this way it usually keeps everyone in a much stronger position and avoids unnecessary stress. Hope that helps.

Congratulations on getting two offers, that is a great position to be in. I get this question a lot here in Florida and it really comes down to net and risk, not just the price on paper. The 400k financed offer looks better at first glance, but you have to factor in the risk of it actually closing. With a mortgage you have financing approval, appraisal, underwriting, and timelines, and if the appraisal comes in low that buyer may try to renegotiate or walk, which puts you back on the market. The 385k cash offer is usually cleaner with no financing, often no appraisal, and typically a quicker, more predictable closing, so that certainty can definitely be worth something. I would try to bring the cash offer up. What I usually look at with my sellers is how much the buyer is putting down and whether they are willing to cover an appraisal gap, along with timelines and contingencies and how much room there is for things to go sideways. That 15k difference is really the risk premium, because if the financed deal falls apart or gets renegotiated, you could easily lose that amount or more in time, price reductions, or missed opportunities.

I’m sorry you’re dealing with this, that is a tough spot to be in. I’m not giving legal advice here, just sharing my experience and opinion as a Realtor in Florida. A Realtor can absolutely help try to move things forward by coordinating the photographer, suggesting clean-out options, and sometimes acting as a neutral third party to keep things calmer and focused on getting the home sold, but if he is refusing access or not complying with what the judge ordered, that really becomes a legal issue and not something a Realtor can enforce. We cannot force entry or make someone cooperate, so in that case it is usually best to loop your attorney back in so they can enforce the court order or tighten it with specific terms around access, showings, and getting the home ready. Hope that helps.