How to Use This Checklist
Work through these questions in the order listed — starting with the financials and working toward lifestyle. The questions are sequenced so that deal-killers (underfunded reserves, roof replacement needed, unaffordable true monthly cost) surface before you invest significant time and emotional energy in a community. Some questions are answered by documents; others require calls with the HOA management company or conversations with current residents. All 40 are worth the effort before a six-figure decision.
Category 1 — True Monthly Cost
- What is the current HOA fee, and what does it cover specifically?Get the itemized breakdown — lawn care, cable, internet, insurance, amenities. A $480 all-inclusive HOA and a $280 fee-only HOA require very different supplemental budgets.
- Is there a CDD (Community Development District) on this property? What is the exact annual amount?Request the prior year tax bill. The CDD appears as a separate line item — not in the HOA. New Osceola County communities commonly run $1,200–$2,400/year.
- What is the property tax for this specific parcel? (Not an estimate — the actual bill.)Listing tax estimates are frequently wrong. Request the prior year tax bill from the seller or pull it from the county property appraiser’s website.
- What will homeowner’s insurance cost on this specific home?Get a bindability quote from a Florida-licensed carrier on the specific address before making an offer. Older homes or those in flood zones may cost significantly more than general estimates.
- Is this property in a FEMA flood zone? If so, what is the flood insurance cost?Lakefront and waterfront lots frequently require flood insurance at $1,500–$5,000+/year. This is not optional and not in the listing price.
- What is the total all-in monthly cost (HOA + CDD/12 + tax/12 + insurance/12)?This is the real number. Add all four lines and compare against your monthly budget before falling in love with a home.
- Have HOA fees increased in the last 3 years? By how much?A community that has raised fees 8–10% annually is signaling either underfunded reserves, management cost pressure, or deferred maintenance catching up. Ask for the last 5 years of HOA fee history.
- Is there a pending HOA fee increase already voted or proposed?Sellers are not always required to disclose pending fee increases. Ask the management company directly: is there a fee increase planned in the next 12 months?
Category 2 — HOA Financial Health
- What is the current reserve fund balance vs the recommended reserve level?A community funded below 70% of recommended reserves is at special assessment risk. Below 50% is a significant red flag.
- When was the last reserve study conducted? Is the community on the recommended funding schedule?Reserve studies should be updated every 3–5 years. A study older than 5 years on a community with aging infrastructure is outdated and may understate actual needs.
- Have there been any special assessments in the last 5 years? What were they for?Past special assessments indicate a pattern. One assessment for an unusual event (hurricane damage) is different from recurring assessments for deferred maintenance.
- Is there any active or pending litigation involving the HOA?Construction defect suits, slip-and-fall liability, vendor disputes — all carry financial exposure. Request disclosure and review with a real estate attorney if anything is found.
- What is the HOA dues delinquency rate?If more than 10% of homeowners are delinquent on HOA fees, the association is collecting less revenue than budgeted — which creates pressure on reserves or services.
- Are there any major capital projects planned in the next 24 months?Pool resurfacing, roof replacement on clubhouse, paving, elevator work — ask the management company what large capital items are on the planning horizon.
- Has the HOA ever failed to fund its reserve requirements?A community that has consistently underfunded reserves is setting up future buyers (you) for special assessments. Ask for the last 5 years of reserve study compliance.
Category 3 — Home Condition (Resale Buyers)
- How old is the roof, and what type is it (tile, shingle, metal)?Florida insurers increasingly decline to bind policies on shingle roofs over 15 years. A roof needing replacement in the next 2–3 years is a $15,000–$25,000 near-term capital item.
- Can you get an insurance bindability quote on this home before going under contract?If a carrier won’t write the policy without a roof replacement, the effective purchase cost is higher than the listing price. Do this before, not after, making an offer.
- How old is the HVAC system? Has it been replaced once already?HVAC systems typically last 12–18 years in Florida’s heavy-use climate. A 15-year-old original HVAC is a $7,000–$12,000 near-term item.
- Has the home been updated, or is it original to build year?Kitchen and bath updates, flooring, and appliances add $30,000–$80,000 to effective purchase cost if needed. A 2001-vintage kitchen may function fine but will likely need updating within 5 years.
- Is there a home inspection contingency in the contract? (The answer must be yes.)Never waive a home inspection on a 15+ year old Florida home. Use the inspection period to assess roof, HVAC, plumbing, electrical, and structural condition.
- Has the home had any water intrusion or mold issues?Florida’s humidity makes water intrusion a common issue in older homes. Ask directly, check disclosure forms, and inspect during the home inspection specifically for moisture indicators.
Category 4 — Healthcare & Location
- What is the nearest hospital, and what level of care does it provide?Community hospital vs regional medical center vs academic medical center are materially different. For buyers managing chronic conditions, the hospital tier matters significantly.
- What is the actual drive time to your specific specialist providers?Don’t use Google Maps defaults. Drive the actual route on a Tuesday afternoon — not a Sunday morning. That is the real drive time you will live with.
- If you are a veteran, what is the drive time to the nearest VA facility?The VA Medical Center at Lake Nona is 5 minutes from VillageWalk and 25 minutes from Twin Lakes, and 40–50 minutes from most Clermont communities. For frequent VA users, this gap is meaningful.
- What is the drive time to Orlando International Airport?For buyers who fly 6–12 times per year, the difference between 10 minutes (Lake Nona) and 45 minutes (Clermont) compounds into real time over a retirement.
- What grocery stores, pharmacy, and primary care are accessible within 10–15 minutes?Daily life logistics matter. Drive the area around the community during a weekday at the time you would typically run errands.
Category 5 — Community Fit & Lifestyle
- Have you visited the community on a weekday (not a weekend or during a model home event)?Sales events are staged. A Tuesday morning shows you the actual community energy level, the real activity, and the genuine resident population.
- Have you talked to current residents — not sales staff — about what they like and don’t like?Sit by the pool. Walk the walking trail. Start a conversation. Current residents will tell you things that no sales presentation will cover.
- Does the activity programming calendar match how you actually want to spend your time?A community with 40 fitness classes per week and no social clubs is the wrong fit for a non-fitness-focused buyer. Review the actual calendar, not the amenity list.
- If you golf, have you played the on-site course (or a nearby course if the community has no golf)?Course condition, design character, and pace of play vary significantly. Play before you commit to living adjacent to it for 20 years.
- Have you visited in summer (not just winter)?An Orlando community in December is very different from the same community in August. The summer heat and humidity are real. Experience them before committing.
- Does the community’s age demographic actually match where you are in life?A 62-year-old who is still active and high-energy may find a community of primarily 75–80-year-olds a poor social fit, and vice versa. Age demographics within 55+ communities vary significantly.
- What is the community’s policy on rentals? How many homes are currently rented?High rental percentages shift community character — renters have different incentives than owners. Ask the management company for the current owner-occupancy rate.
- Are there any rules that conflict with how you plan to use your home?Read the CC&Rs before making an offer. Parking rules, pet restrictions, home business prohibitions, fence restrictions — find the conflict before closing, not after.
Category 6 — New Construction Specific
- What is the projected completion date of the full community, and how far is your home from active construction?Living adjacent to active construction for 3 years is a different product than a finished community. Know what you are buying into.
- What is the builder’s warranty, and what does it specifically cover vs exclude?Structural warranties typically cover 10 years. Mechanical warranties may be 1–2 years. Cosmetic defects are often covered for only 30–90 days. Get the warranty document and read it.
- What is the projected year-two tax bill — not year-one?New construction is taxed on land value only in the construction year. Year two brings full-value assessment. Ask the builder for a year-two tax estimate explicitly.
- What is your total all-in design center budget — and is it firm?Set a firm design center budget before you enter. Design centers are specifically engineered to drive upgrade spending. Buyers who enter without a number routinely spend $50,000–$100,000 over their initial purchase price.
The single most important item on this list: Talking to current residents — not sales staff — on a weekday morning at a pool or walking trail. Every other question on this list can be answered by documents or professionals. The community culture question can only be answered by the people who live there. Budget 2–3 hours for this conversation before making any offer. The information you get will be better than anything in a brochure.