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My brother recently put in an offer for a home in Chelmsford. There are about 20 other offers and several over asking. It’s still very much a seller’s market and I don’t see it changing in MA for the foreseeable future.
Rising Star
Yeah...the house my parents got below was their fourth bid, with 100K over asking, majority cash, and no mortgage contingency. They wouldn’t have dreamed of offering those terms just a few months ago (and the winning offers back then were really only a few thousand over asking price vs the 10%+ that’s been more customary now).
Just bought a home. Can confirm it’s a seller’s market. Every single offer I made had minimum 3 competing, many with all cash or absurd provisions.
Timing a very long term purchase based on short and mid term trends is going to be frustrating for sure
Rising Star
Sellers market in the suburbs - at least in strong school districts. My parents paid 10% over asking with 70% cash and beat out 7 other bids, also had a strong letter of interest...
The season is pretty much over though, so there’s even less good inventory now than there was during the Covid peak (which is what led to the price inflation). What’s left are blah goods that are overpriced with owners trying to capitalize on buyer demand (but need to recognize that buyers won’t pay the Covid premium if it’s not move-in-ready or well maintained/updated). Definitely wait until next spring for more supply; I don’t think the market will soften much, if at all, for a while in the suburbs given that people want more space. Like someone else mentioned, 09 didn’t see much of a dip (though the 05/06 prices were definitely inflated in some cities).
For the city, I’d also wait, given the usual lag on housing prices after an economic crash with eviction moratoriums and such. I think more supply will hit the market over the next few months (if not all once come spring) and be more attractive price-wise. Next spring should give your more optionality, so you see the full impact of the downturn / get more choices in what you can buy.
Regardless, talk to a broker about very specific neighborhoods (not just cities), recession impact in 08/09, what they suspect will happen over the next few months (no one knows but helpful to hear different takes) before you figure out what to do.
Chief
Buying suburbs or in Boston proper? Suburbs is definitely a sellers market - Boston might be a different story, as I have several friends who are thinking hard about selling their apartments/condos.
I just bought in North Dorchester, it was less competitive than it sounds like the burbs are experiencing.
The market here didn’t really soften that much in 2008 so I wouldn’t expect it to now. We went the pre/ new construction route which carries its own risks, but I really didn’t want to write some BS letter to a current owner convincing them to take my mortgage/down payment offer over cash 🤣 We had to wait on some delays but have been really happy otherwise! Would definitely recommend if you want to bypass the offer dance 
The broker told me the seller picked me over other cash offers because my letter said 1) I was a vet and the seller had been in the service, 2) I said my wife and I were planning to put roots down and have kids and the seller had the home in his family for generations wanted to sell to a couple who were putting down roots, 3) I said I couldn’t wait for my dog to have a big yard and the seller loves dogs, 4) said I would fit in the neighborhood for xyz reasons and the seller had a vested interest in that because was friends with all his neighbors.
What are you buying?
2-3 bed, 2 bath. Don't care if it's condo or house.