[Stylo]

Originally Posted by Henry10

Thats correct, however when somebody bought that 500k home 15 years ago, taxes were probably 5-6k. Now house still worth 500k, but taxes are close to 9 or even 10.

So in ten years, for example you gain 0% appreciation (sometimes even negative) while your taxes have gone up 50% or more.

A 500k home in Old Saybrook has about $6k in taxes. It’s always been pretty low taxes.

[Henry10]

Originally Posted by JayCT

I agree that traffic from New York to the Connecticut shore can be bad but the OP seems to know that and is willing to accept it. It has long been a dream of theirs to own a home near the beach. Some dreams are more important than a few pennies. I know someone that owned a beach house in Old Saybrook years ago but sold it because it did not make financial sense to keep it. They could afford it but they would save money in theory if they sold it. They are kicking themselves now because that home is now worth a lot more than they can afford today. The OP says they can now do this so we should not discourage them. It is their decision. I say go for it. Without a dream, life would be pretty boring. Jay

If OP can EASILY afford that second home -- I am all for that.

From experience -- I would add a few caveats -- first, no sidewalks. Second -- no or minimal yard work. I know you can hire people, but when your contractor does not plow that sidewalk, and you backup guy is in Florida -- you do not want the hassle of driving out there, cleaning it yourself, or getting a fine from the town. Same for yard.

However OP must understand that trivial matters become chores when not living in a house full-time. Some things you just can't outsource.

If house becomes a chore (mine often is) -- it is no longer fun driving to it on Friday. If you have to do it -- then it is not worth it.

Cameras are a must. I also would not recommend anywhere south of Route 1. They all got flooded during Irene and/or Sandy. At least 1 mile away from the train tracks / I-95, due to noise at night.

Here is my take on the towns -- Madison, Guilford leans white-collar. Clinton / Westbrook lean blue-collar. That's not to say that Madison has no blue collar folks, or Clinton has no million dollar homes. Because they do.

Old Saybrook is somewhere in the middle. The outlets in Clinton and Westbrook have no affect on Clinton's or Westbrook's local life. They're right off the exits, and shoppers get off and get on the highway, without venturing into towns.

Madison and Guilford have some hoity-toity shops, while Clinton and Westbrook are more into antiques.

Old Saybrook again, is somewhere in the middle. Sunday drive back is easier than Friday's. 8 pm Friday entering Greenwich is like a switch. Traffic is much better than entering at 7:55. Just from experience.

Actually the more enjoyful drives for me are the off-weekends, like in Feb, March, Nov or mid-Sep. That's where crowds are staying put.

[kidyankee764]

Originally Posted by JayCT

I am not sure that is correct but it was before that. The late 90’s. The house they owned was one house in from a small beach and had water views. They have looked and today a house that close to the water is a lot higher than when they sold. Jay

Yeah, unfortunately (or fortunately?) it’s correct. The median sale price in 03-04 is the same as it is today. It was much cheaper in the 90s.

[Stylo]

Originally Posted by Henry10

I also would not recommend anywhere south of Route 1. They all got flooded during Irene and/or Sandy.

Sorry, but this is really extreme and incorrect advice. CT is not FL, we have a lot of varying elevations near the shoreline. I’m a block from the water, and very much south of Route 1. I’m also about 30’ above sea level, not in a flood zone, and no water came anywhere near my house in those storms. In nearby Morningside, direct waterfront homes are 30 feet or more above sea level on a cliff!

Some other lower lying homes are raised, or in such a low risk area that flood insurance is minimal.

Either way, that’s a blanket statement that isn’t true. You need to consider elevation and flood zones when buying.

[Henry10]

Originally Posted by Stylo

Sorry, but this is really extreme and incorrect advice. CT is not FL, we have a lot of varying elevations near the shoreline. I’m a block from the water, and very much south of Route 1. I’m also about 30’ above sea level, not in a flood zone, and no water came anywhere near my house in those storms. In nearby Morningside, direct waterfront homes are 30 feet or more above sea level on a cliff!

Some other lower lying homes are raised, or in such a low risk area that flood insurance is minimal.

Either way, that’s a blanket statement that isn’t true. You need to consider elevation and flood zones when buying.

You are in Milford. I was talking about the Shoreline East.

[Henry10]

Here is a map of future flooding:



https://www.connecticutmag.com/healt...f13eecce2.html

[NY 915]

Originally Posted by kidyankee764

For lunch, check out “The Place”. It’s an outdoor seafood joint, where you order from a counter and go sit on tree stumps behind the restaurant and eat. Great seafood and I believe you can bring your own drinks (alcoholic and non). If you’re looking to be waited on, it’s not the place to go. .

Back in the early 80's I was living in Ft Lauderdale and decided to take a summer off to just chill and rented an awesome beach house mostly of glass directly on the Long Island sound in Niantic, Ct.....I enjoyed the small town vibe of Niantic and it had a nice main street area...... and I took a number of road trips and during one of them found myself in Guilford and saw that joint "The Place" with the tree stumps you sat on in back of the place.....good grub and a good time. Nice to see you mention it and that it is still there after all these years.

http://theplaceguilford.com/

[jyyanks]

OP here. Great advice from all. As someone who has not had the luxury of owning a second home before, there are a lot of things we haven't considered. It's helpful to hear from those who have the experience and can give advice/best practices - thank you.

We are in the very beginning of our search. We're hoping to narrow down to a town or two, and then a particular area in the town. We may find that we have "champagne taste on a beer budget", in which case, we'll have to re-evaluate. Right now, I'm set on the ocean but if we can't find what we're looking for, then we may consider a lake house or raising our budget and renting etc (Not at that point yet).

The commute is a big factor. I think if we find the right home, in the right town, with a "vacation feel", the drive will be worth it. We will probably leave late Friday (9PM) or early Saturday (8 AM) to avoid traffic. Flooding is a concern but since it's a second home and not our primary, it's a little better and we will be purchasing flood insurance.

Taxes are high in some areas that I looked at, but compared to the utterly ridiculous taxes I pay in Westchester, I'm immune to tax sticker shock. I commute into NYC every day, travel for work a lot, and have crazy long hours so am looking forward to a little piece of heaven. If it doesn't work out after a couple of years, we can always sell it.

I'll be back multiple times with multiple questions so please bear with me. I'm really excited about the possibility -- thanks for helping me on this journey.

[nico7]

If you begin entertaining options not directly on Long Island Sound, consider Essex, which is along the Connecticut River just north of Old Saybrook and LIS, with a beautiful town center. It would be an extra 5 minutes (if that) relative to OS (although I understand this may be too far, as 1.5 hours can be Clinton or Branford depending on traffic). You could have a house near/in the center, within walking distance of the water.


https://www.google.com/search?tbm=is...oq=essex%2C+ct


https://www.zillow.com/homedetails/4...00403274_zpid/

I know it's a different idea, but would offer a large waterfront and nearby ocean access. Essex is very popular with folks who visit the area, and is somewhat of a hidden gem.


You visited Branford, but did you check out Stony Creek? It has its own small "center" and is removed from the hustle and bustle.

https://www.zillow.com/homedetails/3...7895230_zpid/?

[nico7]

One more thing that might not have been apparent: Old Saybrook has an Amtrak station (also serviced by ShoreLine East), which might shorten the travel time and lessen the stress of driving.