Lookng for ideas for second home

Sherman, CT

Anywhere that is not in the direction i'm going on a Friday -- I'd love to have less traffic as I get out of the city.

Seriously: get a printed map of the tri-state area, use google maps to estimate 2.5 hrs of driving time (or train time), pick several areas, and take weekend trips and check out the locations. Your criteria of "homeowners association" and "hip nyc types" are mutually exclusive. Hipsters don't move into condo developments -- they renovate abandoned industrial buildings -- have you considered Philadelphia?

Good point Aaron about hipsters renovating buildings....Would lazy hipsters who have no desire to shovel snow anymore be more appropriate?...I was hoping for recommendations preferably north of the city...

New Paltz

Rhinebeck, NY

2.5 hrs of driving time on a good day will get you to Kingston, with a little time to spare. There are lots of towns both E & W of the river nearby. Rhinebeck, Rhinecliff, Stone Ridge, Rosendale. The only significant 'lake' is the Ashokan Reservoir, a little ways west. Alternatively, consider the NY/CT border (Amenia, Brewster, NY), or even west CT: Salisbury, Norfolk), or fartuhr south (area just north of Danbury). More populated, and therefore more people to hire to shovel snow.

Yes, Keith is correct. There are still some good deals for homes in that area.

Great Brrington, MA

Freudian slip considering how cold it is up there now ..... Barrington, of course.

North Fork

You could check out Hudson, which is now a hip place, only 2 hrs away on the Amtrak...the best kept secret of the Catskills though is East Durham...it's a 10 minute drive from Hudson (close to Windham mountain, which is very convenient if you are skiing like me and to Zoom Flume for your summer fun). Great deals in huge homes, very low taxes, and a tight Irish community...Their annual Irish Festival is a lot of fun...

Good luck!

There are still some deals to be had in East Hampton where I have my vacation home. Love it there.

NYstate taxes up there are crazy high

If you mean East Hampton, not necessarily the case with the tax situation. I know the market and am a broker.

I think rhinebeck is the best choice. I agree with Keith's suggestion .

Repetitive.

Why not stay local? Chelsea? It's like your own vacation within the city.

You could also consider Tuxedo Park--most homes are very pricey though there are also some cheaper places (currently seem to be three or four listed in your range). The town of Tuxedo (outside the park) is a dump but if you are looking for gated community with homeowners' assoc and lake access--this could work. And it's only about an hour from NYC.

Greenwood Lake on the west side of the river or Putnam County. In lower Putnam County, parts of Garrison and all of Continental Village have access to a swimming lake for a yearly association fee..

Go to the Poconos!Cheap and max 2 hours away!