u/Jolly_Ad_5561

Hi all! Not sure if this sub is the best place to ask this, but we are considering a move to Greenwich, and I’m wondering what the young mom community is like? I’m pregnant with our first, and I really want to be somewhere that has a thriving young mom community. What is that like in Greenwich? We have looked elsewhere in Westchester and found that the majority of parents are dual income and have a nanny, which is not the environment we are personally looking for. Are people open to expanding their friend groups, genuine, sincere, inclusive? Or do they stick to themselves and their family and friends they’ve had for way longer? We are not from the northeast and have no “old friends” or family up here, so this is really important to us.

Bonus question: is it a stupid time to buy a house in Greenwich right now? Do people think prices will come down at all over the next few years?

Curious for opinions from this community on a home purchasing decision.

I work in finance (PE) and am about 4 years from Partner. Feel pretty good about my odds of making it.

Wife and I are young thirties. NW ~7.1M. HHI ~650k per year post tax. Not absolutely laser focused on fat firing, but would like to have it as an option (most likely that would look like continuing to live in NYC area until ~$10-15M then move to the south (where maybe I keep working if there’s something interesting I want to and can do down there) and raise our family there - we don’t have kids yet, but plan to soon).

We left the city 3 years ago for a variety of reasons and have been renting in Westchester county while we have casually perused buying a home (getting to know different areas, etc). If you are familiar with the area, you know the housing market has been insane (way more than the rest of the country) since 2021, and has only gotten worse (for buyers) with each passing year. There’s very limited inventory, lots of very wealthy buyers (or at least they have wealthy grandparents or parents who buy them expensive houses), lots of older homes that need work (which is very expensive because labor costs up here are so high), etc.

We have narrowed our search to Fairfield county (Connecticut for those unfamiliar) because property taxes are way lower than Westchester (New York).

What we are struggling with is if buying a house is really a good financial decision anymore or not. Historically the advice was always to buy as soon as you can (and of course had we bought in 2021, or even since then it would have worked out very well). But now I just look at the market at an all time high (year after year), see that the cheapest homes that wouldn’t require immediate work start around 2M in the area we want to be, and know that we would be taking on huge new costs (beyond a mortgage that would be ~3x our current rent), have to buy and insure a second car, deal with and pay for maintenance, property taxes, etc. Of course, if the market continues to appreciate 5%+ per year, those costs will be offset by the value of the home going up making it “worth it.” But if the market stalls or declines, obviously it’s a whole different story.

On a more personal side - we are plenty content in our 2 bedroom apartment at the moment, but we would like to start having kids next year and do think it would be hard (bulky strollers, car seats, etc) in an apartment (yes I know people make it work all the time). We are pretty confident we will continue to live up here at least 4-5 more years (maybe way beyond that, but can’t say more than 5 more with a lot of conviction at this point due to a desire to raise kids in the south where we are from). So in some ways it almost feels like we would be better off to go ahead and just buy something now versus in 2 years from now and only really be confident about getting 3 years out of it (versus 5 (or more) if we bought now). But also don’t want to make a stupid decision given what feels like an absurd backdrop of the state of the housing market up here.

Ultimately we are trying to balance the right financial decision (the main priority) with a consideration of preferences / quality of life and timeline of the next 5 years.

Would you keep renting (keeping your expenses to ~125k ish a year and building no equity in a (hopefully) appreciating housing asset) for now and buy something in ~2 years (and potentially only own it for 3 years…) OR would you go ahead and buy now and hope that the market continues to appreciate enough to offset the pretty significant increase in annual expenses (one times costs like buying a second car, but also just higher carrying costs moving forward - probably to the tune of 240k annually).

I have modeled this out extensively (including all maintenance, services, taxes, fees involved with both buying and selling, the opportunity cost of the money being in stocks instead (assumed 7%), etc), and it generally shows we would be financially better off (by $18k) versus renting in 5 years so long as the home appreciates 5% per year (and increasingly better off the longer we stay past 5 years and/or the more it appreciates beyond 5% annually). Of course there are tons of assumptions you have to build in, but the home appreciation is of course the biggest one.

What would you do??

For added context, there arent houses all that frequently that get listed that we are interested in because inventory is so bad. So each time we pass on something, it’s months and months and months before something else even partially interesting comes on again. The house we are considering at the moment is a private listing, 2M flat (current owners bought for 1.3m just under 5 years ago so they’d be getting 8%+ CAGR out of it…..), 1,800 SF (so this is very much a starter home), and we could make some improvements over time like adding more square footage (but that’s a whole other question if the money we could put in would actually pay itself off and then some, esp with labor being so pricey here).

I’m sure I’ve missed key things you guys will want to know so I’ll edit the post with helpful info as you flag or I think of it.