AI Systems Instructor • Real Estate Technologist
Quick Answer: Research each expired listing specifically, load your Context Card, and use the HOME Framework to generate letters that reference the property's specific issues and offer data-backed solutions. Personalization and market knowledge beat generic prospecting scripts.
Expired listing owners get 15 letters the day their listing expires. Fourteen of them say the same thing: 'I noticed your home didn't sell. I can do better.' This guide shows you how to use AI to write expired listing letters that actually get opened—letters that demonstrate market knowledge, show you've done your homework on their specific property, and offer a specific reason to call you instead of the other 14 agents in their mailbox.
Before you write, spend 5 minutes researching. Check: original list price vs. market value, days on market, number of price reductions, listing photos quality, and competing sold properties in the area. Note one specific thing the previous listing got wrong—pricing, marketing, or staging. This becomes the backbone of your letter.
Tip: Check the listing's photo quality and description. If the photos were bad or the description was generic, that's your angle: 'Your home deserved better marketing.'
Expired listings fail for 3 main reasons: overpricing, poor marketing, or bad timing. Your research should reveal which one. If the home was priced 10% above comparable sales, lead with pricing strategy. If the photos were smartphone quality, lead with marketing. Build your Context Card with your specific approach for each failure type.
Tip: Reference a specific comparable sale in your letter. 'A similar home on Oak Street sold for $480K in 11 days' is infinitely more credible than 'I can get your home sold.'
Hero: You are a real estate agent who specializes in selling homes that previously failed to sell. Outcome: Write a 200-word letter to an expired listing owner that demonstrates research, identifies a specific issue, and offers a concrete solution. Materials: All your research data—original price, days on market, comparable sales, what went wrong. Execute: Direct and honest tone, no false flattery, one specific suggestion, one clear CTA.
Tip: Ask AI to generate 3 letter variations: one focused on pricing, one on marketing, one on market timing. Choose the one that best matches your research.
Review each letter through the OODA Loop. Observe: does it address the real reason this listing expired? Orient: does the tone match a trusted advisor, not a desperate salesperson? Decide: is the CTA specific enough to prompt action? Act: handwrite the address and add a post-it note with one personal detail. The AI wrote the content—you add the human touches that make it stand out in a stack of 15 letters.
Tip: Handwrite a one-line P.S. on each letter. 'P.S. — I drove by your home on Tuesday. The curb appeal is strong. Let's talk about positioning.' A handwritten touch on a professional letter signals effort.
[Context Card loaded] Hero: You are a real estate agent writing an expired listing letter to a homeowner in Brentwood, TN. Outcome: Write a 200-word letter that identifies why their home likely didn't sell and offers a specific solution. Materials: - Property: 567 Ridgewood Dr, Brentwood, 4BR/3BA, 3,100 sf - Original list price: $795K - Days on market: 87 days, 2 price reductions (to $765K, then $749K) - Comparable sold: 890 Hillcrest (3,000 sf, $710K, 14 DOM); 234 Valley View (3,200 sf, $725K, 9 DOM) - Photos: Professional but limited (18 photos, no drone, no video) - My name: Ryan Wanner Execute: Direct and respectful. No 'I noticed your listing expired.' Reference specific data. Include one actionable insight they can use whether they hire me or not. End with a specific CTA. No generic flattery.
Dear Homeowner, Your home at 567 Ridgewood deserves a direct conversation, not another 'I can sell your home!' letter. The data tells a clear story: similar homes on Hillcrest and Valley View sold in under two weeks at $710K-$725K. Your original price of $795K—even after reductions to $749K—put your home in competition with a higher tier of inventory that offers different finishes and lot sizes. That's not a criticism. It's a pricing strategy issue. The home itself is solid. Here's what I'd do differently: position at $719K with a targeted 10-day marketing push—drone photography, video walkthrough, and a broker open on day one. At that price point, you're the best value on Ridgewood and likely generating multiple showings in the first weekend. One thing you can use whether you call me or not: the spring market historically starts in mid-February in Brentwood. If you're considering relisting, the next 30 days are your window. I'd welcome 15 minutes to walk through the comp data with you. No obligation. Ryan Wanner 615-555-0123
Send your letter within 48 hours of expiration. The homeowner is frustrated and actively evaluating options. By day 5, they've either relisted with the same agent or stopped thinking about it.
Include one piece of free advice in every letter. It demonstrates competence and generosity—two things that build trust with frustrated sellers.
Track your response rate by letter type (pricing-focused, marketing-focused, timing-focused). You'll likely find that one angle consistently outperforms the others in your market.
Use AI to batch-generate letters for all expired listings in your farm area each morning. Personalize the Materials section for each property. The Context Card keeps your voice consistent across all letters.
Opening with 'I noticed your listing expired' like every other agent
Fix: Open with a specific insight about their property or market. 'Your home on Ridgewood deserves a direct conversation' is specific. 'I noticed your listing expired' is what 14 other agents already said.
Criticizing the previous agent's work
Fix: Focus on data and strategy, not blame. 'The pricing put your home in competition with a different inventory tier' is professional. 'Your last agent priced it wrong' is unprofessional.
Sending identical letters to every expired listing
Fix: Personalize the Materials section for each property. Reference specific comparable sales, specific marketing gaps, and specific pricing data. Generic letters produce generic results.
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