The short answer
The most valuable questions are the ones aimed at the right person. Ask the seller about age of systems, repairs, and disclosures; the association about dues, reserves, assessments, and leasing rules; your inspector about what will need money in the next five years; and your lender about the total payment and cash to close. Ask about insurance early — in Florida it is the answer most likely to change your decision.
- Ask the seller
- History & repairs
- Ask the association
- Dues & assessments
- Ask the inspector
- 5-year cost outlook
- Ask the lender
- All-in payment
01
Questions for the seller or listing agent
- How old are the roof, air conditioning, water heater, and electrical panel?
- What has been repaired or replaced in the last five years, and were permits pulled?
- Has there ever been water intrusion, a roof leak, or a plumbing failure?
- Have any insurance claims been filed on the property?
- How long has it been on the market, and have there been price changes?
- Why is the seller moving, and what is their preferred timeline?
- What is included — appliances, window treatments, storage, parking?
02
Questions about cost of ownership
This is where Florida purchases succeed or fail. Get real numbers, not estimates, and check them against the affordability math in how much house you can afford.
- What will homeowners insurance cost on this specific property?
- Is flood insurance required, and what zone is the property in?
- What will property taxes be at my purchase price, not the seller's assessed value?
- What are the monthly association dues, and what do they include?
- What utility costs has the current owner been paying?
- What maintenance will be due within two years?
03
Questions for a condo or HOA property
Association health is part of the property. Ask before you are emotionally committed, and verify the answers against the documents and the estoppel letter.
| Question | What a bad answer looks like |
|---|---|
| How much is in reserves? | Minimally funded with major work pending |
| Is a special assessment approved or under discussion? | A large assessment with installments past closing |
| Has the milestone inspection or reserve study been completed? | Overdue, or completed with unfunded findings |
| How much have dues risen in three years? | Steep repeated increases with no explanation |
| What are the leasing rules? | A waiting period that blocks your rental plans |
| Is the association involved in litigation? | Active litigation, which can also affect financing |
04
Questions for your inspector
- What here will need real money in the next five years?
- Is anything a safety issue or an insurance problem rather than routine wear?
- Does the roof have remaining insurable life?
- Do you see evidence of past water intrusion or repair covering it?
- Would you recommend a specialist — roofer, electrician, or plumber — for anything?
05
Questions for your lender
Ask about the total picture rather than the rate alone, and confirm the lender is comfortable with your property type. If you are still setting up financing, start with how to get pre-approved.
- What is my total monthly payment including taxes, insurance, and mortgage insurance?
- What is my estimated cash to close?
- Are you comfortable financing this building or property type?
- When can I lock the rate, and how long does the lock last?
- What could still change between now and closing?
06
Questions to ask yourself
The honest ones matter most: how long do you plan to stay, could you cover a surprise assessment or insurance increase, and would you still like this home if nothing about it improved? Pair these with the showing checklist before you write an offer.
If you would rather have someone else ask the hard ones, that is the job. As a real estate office in Hollywood, FL, I put these questions to sellers, associations, and lenders in writing so the answers are documented before your deposit goes hard.
The same rules apply for clients across Weston and Fort Lauderdale and the surrounding South Florida communities.
