Chances are that there are some tax advantages to sell it as is and negotiate with the buyer to an appropriate price. The buyer will probably save a little on property taxes because of the lower sale price. You may save a little in capital gains if that comes into play. Also, I believe that some of the sale transaction fees are based on price.

one last item to add to the list of differing opinions:

Roof replacement is considered a capital upgrade, so the cost of the roof can be added to the cost of the house when calculating any capital gains taxes. This aspect is important if the house is NOT your primary residence, or wasn't your primary residence at some point in the last 5 years, or if the size of your gain is larger than the exclusion on your one time primary residence.

There is some terminology / interpretation issues with the answers on the web. . .

The words are "not tax deductible, but can be added to the cost basis of the house."
The correct interpretation of this phrase is that the cost of a new roof does not go against your income, but does go against the capital gains, if any, of the house.

This might be overlooked, uncertain as to the tax situation of your house.

If you sell as is, you may be limiting your buyer pool to cash offers only. . . therefore the sale of your house might take longer, as those with a mortgage will either pass, or want to negotiate down the cost of a new roof. That is fine if you price the house as if the house has a new roof, but if you price the house as needing a new roof, then you have to forgo most if not all non cash offers.

good luck, its a jungle out there.

You are correct that I should have addressed what the OP said. But some posters have alluded to agents who push for upgrades. These agents are trying to benefit themselves, not their client. In my opinion, spending $20K plus on an old patio villa is not money well spent.

We bought a house few months ago that had a 16 year old roof, but new HVAC. We did offer quite a bit under asking to compensate for the replacement and other necessary upgrades. We were still able to get insurance for the 16 year old roof, but it did cost more. We decided to replace the roof a month or so after buying, however. We probably wouldn’t have considered the house if it didn't have the amazing views it has! In a way I am glad we offered less and did the roof ourselves because we were able to ensure it wasn't done cheaply and we were able to get the shingles and color we wanted.

We are currently house shopping and one of the first things I check when considering a house is the age of the roof. I wouldn’t even look at your house with a 20 year old roof. My opinion then is replace the roof and HVAC, and then your house would be moved way higher on my list.

If I was a buyer in the market for a patio villa with so many on the market I would either be ready to pay a little more for those major items to be taken care of or looking at yours as a deal. It better be priced accordingly. There isn’t much that differentiates one patio villa from another, in your case it would have to be price.

But will you pay the extra $20K to $25K for the cost of the upgrades? Some buyers are looking for a lower priced house. It only takes one buyer to make the sale work.

House upgrades presale
 

Former house flipper here. From 2004 to 2021 I bought and sold 20 houses.
I would pay for a home appraisal to determine fair market value "as-is-where-is."
This will establish a base value. Now you negotiate. If a potential buyer is concerned about the roof, consider a buyers allowance for them to get it done. Your appraisal should tell you the remaining useful life for roof, A/C and appliances. If you are a not a good negotiator, hire a real estate agent. Houses listed/sold by agents almost always sell for more than a FSBO. I have sold both ways, using a pro is better.

The issue is that unless the buyer is a cash buyer they cannot get insurance or financing if the roof is over 15 years old. We had an offer on a house and it fell through for this very reason. Your pool of buyers is then very limited.

Another point of view is, when you look at a house, if the roof and or HVAC was just replaced, chances are they installed the cheapest to get the house sold. But if both are a couple of years old, chances are the homeowners did a quality replacement because at the time they weren't considering selling and were planning on living there.

I will also say, many here in the Villages feel their home is worth more than it actually is and if it's been well maintained, they want "top dollar". There is no way you are going to get "top dollar" for your home with a roof or HVAC system that only has a year or two of life left.

When I bought my house here, the first two things I looked at were the roof and the HVAC. The roof was replaced in 2022 and the HVAC was 20 years old. I negotiated the price down enough to cover most the cost of a new HVAC.

Once potential buyers hire an inspector, both those things are going to be red flagged. You could try to sell it as is and let them negotiate the price down, potentially having them pick up at least part of the cost. Unfortunately, it's pretty much a buyers market right now from what I have seen.

Having just bought a house (our fourth in TV) I can tell you that we would not have looked at a house without a new roof. AC not as concerning to us, because it would not affect financing or insurance.

Since when is a 20 year old patio villa determined to be decrepit? Good grief, arguably, the best parts of TV's are the older sections and they are closer to many golf courses and COSTCO, lol. It doesn't take $200,000 to renovate a patio villa unless one is putting diamonds on the toilet flusher. At this age, smaller sq footage is better for maintenance, taxes, cleaning, cooling and heating. We have downsized as we've gone along the aging path. We no longer need 3,000 sq ft, don't want hordes of visiters staying overnight and love the simplicity of living smaller. I'd spend $20,000 on a patio villa in a heartbeat.

I look at homes/villas daily & pass up those needing such repairs. And, while you wait…you’re paying taxes, ins & fees. Just sayin’

You can say in your listing description that the roof will be replaced upon closing. It’s a “subject to” clause in your purchase agreement. Find a roofing company to give you an estimate on replacement And who will take payment upon closing from your proceeds. The title company will set it up for you. I’ve done this several times for clients. The roof goes on a few days before closing once all the contingencies are done and you are clear to close.