I’m Listing My Home Without a Realtor - And I’m Using AI to Do It Smarter

I haven’t listed my home yet but I’m just weeks away. Instead of hiring an agent I’ve built a deeply data driven and tech supported approach that rivals what most realtors deliver.

Drawing from two decades as a founder and marketing strategist working with startups across NYC, Boston, and Chicago to scale businesses through streamlined operations and strategic efficiencies, I’ve spent the past year diving into the capabilities of different large language models to handle specific tasks whether that’s analyzing data, crafting compelling descriptions, or assessing images. I’ve completed coursework in generative prompt engineering which has been essential for crafting precise and effective inputs to get the best results from AI tools. By pairing the right tools with the right tasks I’ve been able to gather insights and create a workflow that balances accuracy and creativity.

When it comes to pricing, like many, I don’t find Zillow’s Zestimate to be truly accurate. It often falls short because it relies on historical data from the last sale and public records, and those might not reflect recent upgrades or renovations. Zillow’s pricing estamators can’t fully account for unique property features or current market nuances that I think significantly impact value. Instead I am using a more granular, tailored analysis. This includes evaluating price per square foot, days on market, pricing trends, and nuanced property features like lot type, garage condition, and the age and quality of kitchens and bathrooms. For kitchens and baths, I categorized them as luxury, mid-range, or rental grade, and also noted whether they were new, over ten years old, or substantially older. I wanted to see how this impacted not only pricing, but desirability and how fast a property moved on the market. This detailed approach is especially important because there aren’t many comparable sales for two flats with a bonus in-law suite like ours. Many owners hold onto these properties due to ultra low mortgage rates sometimes as low as 2.5% and because these homes build equity quickly and also generate income, owners often choose to stay invested rather than sell.

Beyond the numbers, the presentation matters too. I reviewed hundreds of listing photos with a buyer’s perspective in mind, scoring cleanliness, staging quality, and clutter while cross-checking descriptions against photos to catch exaggerations - a surprisingly common problem that can undermine buyer confidence. Since the property is a two flat, factors like leasing status, vacancy potential, and mechanical updates also played a key role. I layered in location data such as Walk Score, Transit Score, Bike Score, proximity to parks and supermarkets, and crime statistics from local police reports.

Staging was carefully budgeted. I analyzed average costs per room and identified opportunities to stage smaller spaces like bathrooms myself, saving a few hundred dollars. Upgrade decisions were prioritized based on impact to value rather than expense alone.

The language I use in the listing is strategic as well. Terms like "bring your ideas" or "needs work" were scored for buyer reaction, allowing me to refine messaging that attracts interest without deterring buyers.

I mapped out a detailed two month pre-listing schedule covering everything from staging and photography to MLS paperwork and marketing plans. I also assessed Chicago’s flat fee MLS options to select the most effective and reputable platform.

Marketing research into top producing realtors showed me what’s working in 2025 - from photo quality and listing language to ad targeting strategies. With my marketing and automation background, I crafted ad campaigns beyond the MLS on platforms like Google Performance Max and Meta Advantage Plus to reach the ideal buyers efficiently.

To ensure reliability, I ran analyses across multiple AI tools to compare results and avoid errors or “hallucinations.” My multi-tool verification makes this process more thorough and dependable than relying on a single source or algorithm.

While automated valuation models like CoreLogic’s RealAVM are helpful, my approach combines their evolving strengths but with deeper, customized insights. Using a layered, AI-powered strategy helps me price and market the property with far greater precision and confidence than typical real estate estimates or listings.

When the property goes live soon, it will be priced and positioned with insight and care that few traditional listings can match.

While the process has taken time it’s been thorough and effective. When the property goes live soon it will be priced and positioned with more insight and care than many traditional listings. Though the seller’s market remains robust in Chicago, forward-thinking agents who use AI-powered strategies and refined prompt engineering will be equipped to assist sellers more effectively once buyer market dynamics take hold.

For a transparent look at the full selling process and all disclosures, check out Process and Disclosures & Facts.

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