Weekend House

If you aren't already familiar with various Hamptons or upstate communities, I'd suggest picking one or the other, renting a place for the summer, and trying it out. Rent in a different community the following year. You'll get a sense of how the drive times can vary (it can take 2 hours just to get from Manhattan to the west edge of Nassau county in bad traffic) and you'll discover what the communities are like, without the significant financial up-front committment of a purchase. Also, depending on the age of your kid(s) your ability to leave the city on the weekends may be limited at times, given their extra-curricular activities and desire to spend time with their friends. I grew up in a family that had a 2nd home, and there were some significant fights over what weekends were spent where, when some people wanted to be by the lake, and others wanted to pursue activities in town.

I had a weekend home in Litchfield County, CT for many years. Beautiful countryside with rolling hills and weekend activities including a bunch of county fairs. Less than 2 hours from Manhattan with little traffic on most weekends. Towns like Litchfield, Washington and Kent have good restaurants. Area became more popular after all the storms hit the Hamptons and Jersey Shore. Aaron is right. Try renting a place for a week or two this summer through vbro, homeaway or airbnb.

As far as I can see, buying in the Hamptons (or Fire Island for that matter) is about wanting to be in a particular Social Circle.

"North Fork is not really an option as far as the drive goes?" I do not understand that comment. My house in Mattituck is 85 miles from my Village apartment. If you learn to plan the traffic, and I suspect that your travel times may be off hours if you own a business here, it can be as little as 1.5 hours, and is rarely more than 2 hours.

Thanks for the advice so far.

I think for me upstate is bit really an option as I love the water and want to be close to it. Also the catskills for example are like a 3 hour drive.

NYC_sport i assumed the north fork is a further drive then that, sorry. What is it like in the norh fork? Is there good food and activities? How does it compare to the Hamptons?

Thanks

Why on earth would a young family want to be saddled with a second home? Trust me. Been there, done that. In your prime years, go off and wander. Visit new places. Do AirBnBs on weekends. A second home, especially one that is not occupied full time, is a guaranteed money pit. It needs upkeep and constant repair in addition to the monthly outlay of utilities, insurance, taxes and a mortgage (if it is financed). Rather than enjoying your time away from the city, you will be doing chores, fixing something that broke, or dealing with some incident (e.g., stolen property, illegal garbage dumping, leaking roof) on the property, going to the hardware store, etc. Perhaps you can hire a gardener or handyperson to keep tabs on things. But then you have to spend time managing the work of this person, which can suck if the person is not doing a good job. Oh, and the 2+ haul out to the Hamptons (3+ in the summer) gets old very, very quickly. Is it really worth all of that hassle and money just so you can boast to your friends that you have a weekend home in the Hamptons? Take it from a 10+ year NYC/Hamptons veteran - you don't want to do this.

hejiranyc is making some very good points about buying a second home. Its certainly not for everyone and many should worry about overexposing themselves to to residential real estate especially a vacation home that may never turn a profit as some have espoused above. I would point out however that owning and renting are two very different experiences each with their positives and negatives.

Ownership defintely has its downside, the most obvious being exposure to negative market influences and high costs. When the housing market crashed in 2008, vacation areas were often hit the hardest. The Litchfield County market took 4-5 years to recover and prices today are still below the peak. I suspect Upstate NY is similar. Also, taxes in some of these markets are quite high and weekenders usually see very little in return for their payments. Insurance is another cost that is difficult to justify for a weekend home especially if you need to insure against flood or storm damage.

But being an inner city apartment dweller for most of my adult life, I thoroughly enjoyed some of the "hassles" described above such as fixing things, making improvements, planting a garden, etc. The peace and quite of a vacation home made living in Manhattan much easier to tolerate and the commute got easier as the years passed.

I am not sure of the purpose of subjective expressions of individual's views as to the "value" of a second home. Value is an entirely subjective perception. I do not think of my home as a second home, or a vacation home. It is where I live about 25% of the time, including probably 45 weekends out of the year. It is true that, if you do not want to deal with the tasks that come with home ownership, you should stick to apartments, whether for your first home, or your second. For many, that is part of the joy. My wife, for one, has been cursing this weather for weeks because it is delaying the start of her garden. My wine collection is in my basement, and my woodshop is in my garage. Our dog lays in front of the elevator on friday evenings waiting to leave. On weekends she (and I) go for hour-long morning walks unleashed on the beach. On weekdays, she is tugged grudgingly to the local dog run.

I did the NYC/Hamptons for 14 years, and have been on the North Fork for the past 12. In 26 years, the number of times I have had a 3 hour commute (albeit never east of Southampton) can be counted on two hands and maybe a foot or two, and it universally was not east end/long island traffic, but Queens traffic, that is the prime culprit. And, for those who are NOT travelling east of Southampton, the summer/winter traffic dichotomy heading out on friday and back on Sunday is largely non-existent. If anything, once schools close and, even more so, once you get to late July/August vacation season, the traffic in Queens is less of an issue. If you go east of Flying Point Road on Route 27, well, then July and August in the Hamptons is one big, fat traffic jam.

As for the OP's question about the North Fork comparison, the North Fork is to the Hamptons as a new england town is to Miami. Depends what you are looking for. More farm and vineyard than glitz or glamour. The "towns" on the north fork are a sedate block or two of a post office and an eclectic handful of stores, while Southampton and Easthampton towns are several lively, walkable blocks of restaurants and diverse high end retail. If you are looking in the luxury segment, the housing inventory on the north fork is paltry in comparison to south fork. Property values are way lower (particularly for waterfront properties), but price appreciation fairly stagnant at higher end and taxes higher on north fork. There is no summer traffic, and part-time residents are a much smaller segment of the north fork population. September through Columbus Day, on the other hand, has become an apple and pumpkin picking hell, that hopefully will be addressed by the towns. The restaurant inventory, in my view, is superior to the Hamptons, but short on panache. In season, the North Fork is littered with farm stands with local fruits and vegetables, but the Hamptons has much better butchers and specialty food markets. Both have great seafood stores year-round. If you like beaches, nothing on this coast compares to the Hamptons ocean beaches, particularly when you can access the often fairly empty resident-only beaches. The sound and bay beaches on the north fork are pleasant and quiet, but nothing like the south fork (and no waves).

1) just to play Devil's Advocate: one advantage of buying versus renting in a lot of these places is that when you rent, you pay an inflated price for the Prime 3 months and that's all you get, when you own you get use of the property year-round. And while you might not use it nearly as much in the offseason, it's still there if you want a weekend getaway where you don't have to pay for a hotel or whatever.
2) @ximon - I recently read an article about the Resorts International Casino on the old Concord Hotel site in the Catskills which said that property values in the county still have not returned to 2006 levels.

Interesting 30. Over the years, the revitalization of the Catskills has been all talk no action. Even casinos may not help. My brother spent most of his life in Woodstock, NY and the Catskills are truly beautiful. But population is declining in many upstate towns and the "Borsch Belt" and "Irish Alps" are now dead. With discount airfares and the higher disposable income of many Americans, weekend homes for New Yorkers are now in places like Florida, the Carolinas, and the Caribbean. In recent years, the strong US Dollar led many Americans to buy holiday homes in Ireland, Portugal and Spain. Its a different world now.

I have a house in East Hampton. I bought it in 1999 and not because I wanted to be in any particular social circle. I bought it because it is beautiful there, the air is literally rarified and I can walk to the ocean. The ocean is the place to be and while the North Folk is beautiful it doesn't have the ocean.

There are many people there that love outdoor activities. I learned to windsurf there. And there's tennis clubs. The farm fresh food is incredible. There is first rate theatre there. The International film festival was incredible. Some people that first come to the Hamptons are so stunned by its beauty that they move out there immediately.
As far as maintaining my house, it is not all that time consuming. I have a house watcher who is a very good carpenter and he fixes minor problems at a very reasonable price. I have a landscaper who is incredibly reasonable. I also, enjoy doing outdoor work. There is no crime in my area nor am I aware of crime anywhere in the area.
The town is in the process of buying up as much land as they can without any plans to build on it. Not too long ago they bought a parcel of land across the street from me. They simply want to prevent overbuilding. Therefore land prices can only appreciate.

My house has appreciated a lot. My advice is to buy, you will enjoy it tremendously without having to go through the hassles of using Airbnb. And prices for a short stay or rental have gone up.

As a real estate broker, and a resident, I know the area extremely well; would be happy to advise.

Longtime lurker, first time poster here.

This feels like a top of the bubble thread to me.

I want a weekend house! I understand the allure of being able to have a bunch of stuff in a second place, so that when you're travelling with family, you're not juggling your suitcases and the kids' suitcases and the sports equipment and the scooters... when families of four travel from my building for the weekend, it's like Dunkirk with the logistics.

On the other hand, the desire is strong in me because I sold my beach house ten years ago, and it's taken about that long to forget how high the taxes are in a vacation-oriented town, and how you can't get a plumber in when you need him because everyone else needs him, and how the tree guy has you by the short ones, and how you can't sleep in on Saturday mornings because that's when the landscapers come, and how it wrecks your day job to have to trot out to the beach on a Wednesday because that's the only time you can get a leak fixed.

So I would say: rent for a summer, and if you like the experience, then buy. I wouldn't jump straight into it.

And also, unless they've invented new cars and new traffic laws, East Hampton is three-and-a-half hours from Manhattan any time you would actually want to go there.

On off peak it has taken me two and a half hours to travel to East Hampton.

My taxes are very low. I bought an old house. Even if I build a new one, they will still be low.

Prices in East Hampton are going through the roof.

Streetsmart,

Would you mind sharing your annual maintenance costs? In your opinion, what would be a reasonable/realistic budget for 0.5-0.75 acre including pool maintenance, landscaping, misc. repair for a +/- 2500sq ft house in the Hamptons?
Thanks!

SS: Are you in East Hampton town but not in East Hampton Village?

My very personal opinion is that weekend houses are a bit like boats.

@tribby

As far as landscaping goes, the basics are lawn mowing. This can be about $60 per week depending on the size of your lot.I usually have my landscaper mow every other week in July and August. If your property has a lot of trees like mine then they will need some maintenance like pruning. It's advisable to have an irrigation system if you are going to have hydrangea bushes. So cost of landscaping can vary a lot. I have my landscaper do a spring and fall cleanup, which cost as about $350.00 each time. Many times in the spring I do the cleanup myself.

As far as pool maintenance, I don't have a pool, but I was thinking of putting a pool in. i have interviewed a few pool people and maintenance could be about $1500 a year depending also if you have a heated pool.

As far as plumbing, I have a very good plumber. He winterizes my house meaning he drains the pipes in the winter, then come spring he turns the water back on. I pay him $225.00 total for turning the water on and off.

As far as misc repair, that can vary depending on the condition of the house when you buy. The person who inspected my house when I bought told me the roof needed to be replaced. And I did this and it worked out fine. As for repairs I needed my plumber to remove tree roots that were getting into my septic pipes. This was the first time it happened since I bought and my plumber charged me $175.00. Aside from the roof I needed to replace I haven't needed many repairs. I needed a repair to my fuse box once which cost $800.00. I needed a main fuse that my house watcher was able to purchase on EBay since it was no longer available. Otherwise I would have had to replace the entire fuse box which would have cost $2200.00.

So I haven't had many repairs and I bought the house in 1999. My house watcher maintains the deck, once had to replace my mailbox. I have a wood rail fence that requires new rails every so often. I could remove the fence but it looks nice.

Finding good people is the key to getting good work.

Ali I had to laugh at your comment about Dunkirk! So true, I've often taking pictures of the back of our SUV when we're packed for a long weekend somewhere. Currently I just have one child living with me! I always blame my wife, then when I pack and we get somewhere we're missing like half the things we need! Lol.

I've also had second homes in the Catskills, I was quite Far North near Cobleskill. I love the extra drive up there only because you are really in the country. Forget about any trendy or fancy places to eat, but we weren't looking for that, have plenty of that in NYC. I had one place on a small Lake and another small cabin that I actually built myself on 10 acres with large Pines, a number of apple trees and lots of wild berries.

We are currently looking to buy a place in Old Chatham. Amazing prices and a very trendy community, for lack of a better word. Very beautiful area! And there's a bit of 'civilization' up there. Hudson New York has also become a very popular place for second homes.

At least for me with an income that can be unpredictable, I would just buy something well below your means that will be easy to afford. This way you don't have to stress about it. In most communities Upstate including Woodstock I wouldn't Buy thinking about resale. There are a ton of properties available and many of them sit on the market for 12 months or more before selling, even well priced ones that look pretty amazing. This kind of purchase will be more about consumption then investment returns.

Definitely agree doing some renting via Airbnb For a Season would be an excellent idea. There is no shortage of available properties especially upstate.

Keith Burkhardt

@keith, Old Chatham is lovely! Where is Columbia County when we need him?
@30yrs, that was exactly the line that was running through my head too.

Keith, do you consider Old Chatham an area that could appreciate over the near term? Also, how are taxes? Where else did you look? Thanks for the info.

@front_porch

I am about a quarter of a mile from the village proper. I was going to buy a houseinthe village but I decided on my house since it had more land and room for a pool.

Was thinking about buying a condo in Puerto Rico; prices could be cheap. A nice winter retreat.

Vacation homes are far from stress-free especially if you can't get there to check things out in a timely manner. I was always watching the weather reports to check on rain storms, snow storms, power outages, flooding. Installed a low temp alarm that could call me and my caretaker when house was cold then would call the oil company to make sure they could make a quick delivery. Found a website that reported snow accumulation (not that easy to find) so I could call my plow guy and make sure driveway was clear. Went through 3 caretakers until I found a reliable one. If you find a good contractor, caretaker, plumber, handyman or landscaper, treat them like a king!

@ximon taxes are pretty moderate for upstate. Quite honestly I was just surprised at how high the taxes were when I saw a client that owns a home in Woodstock! I have to say I really like Warwick, but the taxes just turn me off so much. An anchor that will never go away and just keep increasing, not what I want as I move towards simplifying my life.

It's hard to say what kind of appreciation you will get, quite frankly I wouldn't expect much. If I buy a place up there it'll become a generational home for my family. If it turns out to be a decent investment so be it.

Keith

Agree that much of the work and worry of a second home is reduced by having good relationships with the local help, and some monitoring systems that give you peace of mind. I've had an upstate NY home (near Oneonta) for 15+ years. It's got automatic water shutoffs and temperature dectectors, the plow guy has standing orders to plow as necessary (he does several people on my road), and the landscaper has standing orders to mow and cleanup as necessary (though I do a fair amount myself as well). I'm good friends with my neighbors, and if a tree fell on the place, I have no doubt somebody would call. It's a terrible financial investment (particularly given the renovation expenses), but that's not why I bought it, and I can afford some marginal investments. Ultimately, I plan to leave NYC and live there full time.

Thanks so much Streetsmart for detailing your maintenance expense and advice on finding good people. I'm looking at a property to purchase without a pool and also wonder how much it would cost to put in a nice one (36x18 or so) with heater, blue stone surround. If we end up purchasing would LOVE to get some of your contacts for help "out east" (the new Streeteasy website for the Hamptons!)

For others, check this out - further away from the city vs. the Catskills but also beautiful:
https://www.nytimes.com/2018/04/13/realestate/second-homes-berkshires.html?hp&action=click&pgtype=Homepage&clickSource=wide-thumb&module=mini-moth&region=top-stories-below&WT.nav=top-stories-below

Anyone here having lived recently in Great Barrington? Sounds like a great place for food!

@streetsmart,
Your house watch it doesn't have any pennies?

@Keith,
Hudson New York has become much less interesting since they got rid of all the brothels, gambling, and bootlegging.

Tribby, thanks for the NYT link.

“There are new distilleries, breweries and farm-to-table restaurants — it’s such a movement,” said Mr. Firth, of the Prairie Whale. “People are doing this stuff because it makes them feel good. And feeling good is the new rich.”

I love this quote! This is exactly what is happening in Litchfield County and places like Hudson, NY. New restaurants are not just good but excellent - and expensive! I think that the local economies are becoming more and more tourist and weekend oriented with more and more vacation homes instead of year-round residences.

Taxes are stupid high for what you get. I did not have sidewalks, sewers or public water and most of my property taxes went to the school district which was of course a waste of money for weekenders like me. Its a problem that these towns remain controlled by local residents who have little to no inventive to keep taxes low for weekenders who have little political power e.g. our town hall closed 12 noon on Fridays. Assessed values for lake houses and country estates were of course much higher than for the average town home.

@ 30 years you can say the same about Soho.

Laughed at the boat comment! But I don't think a second home is quite as bad.

@streetsmart I grew up in the South, and I miss having a pool! (though not priming the pump and skimming the leaves...)

Soho was never really big on that stuff, more on The Bowery - like McGurk's Suicide Hall (which a friend of mine actually lived above), Spanish Mamie's, Flynn's Black Hole, etc. Although there was a sprinkle of "Gentlemen's Houses" sprinkled through Soho.
https://cityroom.blogs.nytimes.com/2011/01/26/on-the-records-a-well-preserved-roadmap-to-perdition/

I remember in the early '80's going to an after hours club in Soho just off Houston that frisked you on the way in and had an anything goes policy once you were inside. There were a bunch of places like that in lower Manhattan back then. I wonder where NYC restaurant and bar workers go these days to relax after a long night of work?

Lol, a few years back I ran a once a week after-hours event specifically years towards those in the hospitality industry. "Employees Only" used to be the a spot geared towards this, but I don't think it is any longer.

Ha! I tried to get into a place like once that but my friend was a bad liar so we were tossed. A bar in college used to simply shut off the outside lights and pull the shades down. Walking out of a bar at dawn was a "walk of shame".

Remember a 'club' called a7? Just a red light above the door. That's where I cut my teeth as a punk in 1981. I have many stories of all sorts of clubs from those days. Just walking home from the Mudd Club to my first apartment on Norfolk Street and Houston was quite an adventure back then...Rent paid $200 per month divided by 3 roommates.

Norfolk and Houston was definitely pioneering in 1981. I lived in a Mitchell Lama on Columbia and Rivington back in the mid-1980s. The walk from Delancey Street subway was always an adventure. Yellow taxis would never come through the area so I used the Hispanic car service on Houston to get around.

TFW a bunch of friends tried to get into Area by hiring a limo, and it still didn't work.

http://nymag.com/news/features/area-nightclub-2013-11/

@30yrs

Do not follow your question about the house watch and pennies???

Streetsmart,
The very well known but also extremely dangerous fix for blown fuses is just sticking a penny in.

Re: getting into after hours spots: There is a fairly infamous guy who is one of the last still running after hours spots. A couple of years ago he had a spot on the second floor of a warehouse in LIC. One night I got there just before 4AM when they open and there was already a line of about 100 people (the oldest of which was probably half my age), the guy opens the door, sees the line, and screams out "NO ONE'S GETTING IN FOR FREE TONIGHT", but then saw me and added "EXCEPT FOR THAT GUY" and pointed at me all the way at the back of the line. I wish I could have taken some pictures of the looks on all those Millennial's faces.
Chalk up one in the win column for us alter cockers.

If you have not yet seen it, New York Times Style Magazine recently published a quite detailed look at life in New York City in the early 1980's:

https://www.nytimes.com/interactive/2018/04/17/t-magazine/new-york-1980s-culture.html?action=click&module=MoreInSection&pgtype=Article&region=Footer&contentCollection=T%20Magazine