Can I ask someone if they are willing to sell their home?

Janice, yes, absolutely, and you are not being a creep. Agents do this constantly. It has a name in the business, and going after a specific street or a specific house is completely normal practice. The thread above has the basic idea right. Here is the part that decides whether it works. Write to the actual owner, not the house. Before you send anything, have an agent pull the county assessor and recorder records for the addresses you want. In Orland Park that is Cook County, and it is public information. Surprisingly often the person living there is not the person who can sell. It is a trust, an LLC, an out of state landlord, or three siblings who inherited it. A letter addressed to the occupant of a rental never reaches anyone who can say yes. A letter addressed to the actual trustee does. Write, do not cold call. A letter is fine. Calling a number you found is a different thing. The National Do Not Call Registry restricts telemarketing calls to registered numbers, and while the rules around a personal inquiry get murky, there is no reason to go anywhere near that line when a letter works better anyway. Handwritten beats printed, by a lot. A short handwritten note with your first name and a real phone number gets read. A slick printed mailer gets thrown out with the investor postcards, because homeowners in nice neighborhoods get several of those a week and have learned to ignore them. Keep it short and specific. Two or three sentences. Something like: my family loves this neighborhood, we have been looking for two years, if you ever think about selling I would love the chance to talk before it goes on the market. That is it. No price, no pressure, no life story. One caution on the life story. Be careful about writing a personal letter that describes your family in detail. Those letters can unintentionally reveal things like religion, familial status, or national origin, and that creates fair housing exposure for the seller who reads it. Keep the letter about the neighborhood and your seriousness, not about who you are. Now the two traps nobody warns buyers about. An unrepresented off market seller usually has no idea what the house is worth. Sometimes that is good for you. Often it is worse, because they anchor on a Zestimate or on what a neighbor bragged about, and there are no competing offers to reality check it. Go in with your own comparable sales analysis, and be prepared to walk if the number is fantasy. Off market does not automatically mean discount. You will still want an inspection, a title search, and normal contingencies. Off market deals go sideways on title issues more than on price. Unrecorded easements, old liens, a deceased spouse still on title, a contractor's lien from a remodel. A title search early is cheap insurance. One update since you asked this in 2023. As of August 17, 2024, if you work with an agent, you sign a written buyer representation agreement before touring homes, and how your agent gets paid is negotiated separately rather than assumed from the listing. On an off market deal there is no listing offering compensation at all, so have that conversation with your agent up front so you know who is paying what. It is very workable, it just needs to be discussed rather than assumed. I am Zoltan Peresztegi and I work in Los Angeles and the South Bay, where this approach is how a lot of the best homes actually trade. I am not licensed in Illinois, but I am glad to help you sketch the letter or think through your target street, and I can connect you with a strong agent in the Orland Park area who will pull those ownership records for you. Zoltan

Janice, this is perfectly acceptable. Keith Jean-Pierre Managing Principal The Dapper Agents Real Estate Operations in ALL 50 States

Yes! It’s called off-market outreach—just be respectful, don’t pressure, and keep it simple (“If you ever consider selling, I’d love the opportunity to talk.”).

Yes you can. You may get mixed responses. If you have a real estate professional -- they can assist you in canvassing the neighborhood you are interested in living in. As long as you are not in a hurry -- this route is viable. Someone may take you up on your offer to buy their property -- try to remember that you may not have a lot of negotiation leverage since you what what they have without putting it on the open market!

Hi Carlos! You could ask people... but I would say the best option is to find a Realtor to work with and then have them assist you in finding an off-market property in the neighborhood you like. First, find a local Realtor - I would recommend interviewing 2-3 and and then choosing the one that you think you will get along with best, and one that will work with your real estate goals. I have done this for some of my clients in the past, and we have had a pretty good response rate. We send out a letter to a specific neighborhood on their behalf, explaining that we have a client interested in purchasing in this area and asking if they are looking to sell. Good luck!