If you're getting three exterior painting estimates in Connecticut, expect three very different numbers — sometimes ranging by 60% on the same scope. The question isn't which is cheapest. It's which contractor is actually proposing the work that will hold up. Here are the ten questions that separate a 10-year repaint from a 4-year repaint.
The 10 questions.
- Are you licensed and insured in Connecticut? Ask for the certificate of insurance and confirm coverage limits. Both general liability AND workers' comp must be in place.
- What's your written workmanship warranty? If it's not in writing, it doesn't exist. Ours is in the contract; many contractors won't put it on paper.
- How long have you been in business? CT exterior weather demands a contractor who has seen 10+ winter cycles in the same market. Less than 5 years and there's no track record.
- What paint product line will you use? "Benjamin Moore" isn't an answer. "Benjamin Moore Aura Exterior in matte finish" is.
- How many coats? Two. The right answer is two. If they say one heavy coat, walk.
- What does your prep include? Soft-wash, hand-scrape, sand, wood repair, spot-prime, full caulk. If any of those aren't listed, they're being skipped.
- Are you RRP-certified for pre-1978 homes? Required by federal law. Ask for the certificate.
- What's the timeline and what happens if weather pauses you? Honest contractors will tell you they pause for weather. Dishonest ones will paint anyway and the result will fail.
- What are the payment terms? The right answer is 'pay when the job is done.' Deposit + payment-on-finish is normal. Full payment up front is a red flag.
- Can I see references and recent project photos in my town? Real contractors have plenty. Vague answers are a red flag.
Red flags that should make you walk.
- Estimate is 30%+ below the next-lowest bid.
- Contract says "we will use premium paint" without naming the line.
- Contract says "two coats" but doesn't specify primer.
- Contractor demands full payment up front.
- No proof of insurance.
- Pressure to sign immediately ("only valid this week").
- No mention of wood repair allowance — meaning any rot found will be a surprise add.
- Contractor cannot explain their cedar shake protocol when asked (if your home has cedar).
- Contractor cannot name the caulk brand they use.
Green flags that signal a real contractor.
- 10+ years in business in your county.
- BBB A+ rating, not just "BBB listed."
- Written, itemized estimate with paint product lines named.
- Workmanship warranty in writing AND transferable.
- Pay-after-work or partial payment terms (not full up-front).
- Owner is on-site at least at the start and end of the project.
- Real recent photos from your town.
The single best question.
If you only ask one question: "Walk me through what you'll do on day one before any paint touches the house." A contractor who can describe soft-wash, scrape, sand, repair, prime, and caulk in detail is going to do that work. A contractor who shrugs and says "we'll prep it" isn't.
