Personal

Second Home First

I’m getting closer to the point where I’m ready to buy my first piece of property. While I can’t wait to build a nice little home for a family, I’m not quite there yet. A big problem with buying a house is that I don’t know where I want to live long term. For now, renting in Connecticut is ideal for me. I love it here for now, but I am not completely committed to the area, which is fine since it’s just a rental.

When I decided to renew my lease for my apartment, I did so knowing that I’m (probably) staying put until I know what my true “next move” is. I added the probably because if I know one thing, I know life can throw unexpected curveballs, so it’s hard to know anything for sure!

With all of that said, the idea of buying a vacation home first keeps popping up to me. I know it sounds kind of nuts to buy a second home before purchasing a first home, but the more I think about it, the more I like the idea. Am I completely crazy???

My dream is to have a house on Nantucket, duh. But that is going to have to remain a (very) long term goal considering I keep losing the Powerball.

Second home first

I have been considering this second home thing for the better part of the past year. The one thing I keep coming back to is buying a small house in Vermont. Ideally, it would be a home I could enjoy year round. I keep having this vision of an expansive yard with the dogs (now) and kids (later) running around all summer. And then a cozy house with a fireplace we can curl up in front of after a day of skiing in the winter.

As life continues to get more hectic, with no signs of slowing down anytime soon, the idea of having a place to escape to on the weekends sounds more and more appealing.

My search has unofficially started. I’ve basically just been poring over real estate listings just to see what’s out there, but I’m probably a year away from making a legitimate commitment. Unless I find the perfect “unicorn” house, in which case, I’ll be dropping everything to make it happen. It’s been fun just to start dreaming.

Some of the things I’ve kept in mind while looking (in case you’re curious):

– At least two bedrooms and at least two full bathrooms. A third bedroom would be a cherry on the cake. A two bedroom house would be perfect for a family, but it would be nice to have an additional room (or two), so extended family could visit too.

An attic or basement that could be converted into a bunk room is my DREAM.

– Speaking of that, the house doesn’t have to be perfect now. Because it would be a second home, I would prefer to do updates and renovations over time than do them right now, at 28, without knowing what is really needed or wanted long term. This also makes it a more affordable choice as any work being done would be the bare minimum at the beginning. (This will not be some sprawling chalet featured in design magazines, haha!)

– Year round activities and usability is my main concern with the house and why I keep coming back to Vermont. If I’m investing in a property, I want it to be something I can use a lot.

– Accessibility is probably going to end up being the biggest hurdle when finding the home. I keep looking at southern Vermont because it’s the easiest to get to from where I think I’ll end up living long term. (If you haven’t been able to tell, I keep leaning farther away from Florida.😓) I don’t want it to be more than four hours away since it’d be a hopefully frequent drive.

//

Once I started to take the idea more seriously, I did do a little research and apparently there are a lot of people who are making the “second home first” choice, especially in/around metropolitan cities where renting is the norm and real estate prices are astronomical. Buying a house is a HUGE decision, and there are obviously a million things I didn’t cover in the post are being considered too like property taxes, maintenance, and insurance. (That is, it’s not just a fluffy dream I’m approaching with a whimsical attitude.)

So what do you think? Have you done it? Has a friend of yours? Am I crazy?

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106 Comments

V.

Hi Carly,
My husband inherited a cottage after his grandparents passed away. It is on a place similar places on Nantucket, but in Canada (I just assume it is similar, because I don’t know that much about it- high property taxes, nobody can build there anymore, cottages are in high demand, you get the idea). Renovations, property tax, etc. Not just fun and games!

It is definitely an expense that will change the way you buy your ‘main’ house. And it will make you think ‘oh, what if I wouldn’t have this additional expense’.

However, cute property where you’ll make memories and look forward to travel to (especially in pretty place like Vermont!) will erase all that and all that matters is that. I wouldn’t trade the cottage for anything and it is place for family from near and far to meet up!

Good luck with finding something great!

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Beth

My Aunt and Uncle own a second home in VT right next to Okemo Mountain and it’s a blast. In the winter we are able to ski down the driveway, down the street and onto the mountain. The other seasons were still just as fun, with big feels and hiking! Going to the Vermont Country Store with all my cousins is one of my favorite past times 🙂

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Emily

My grandparents (and my mom since she was born) always summered out in the hamptons on Long Island and that’s where they retired. In the backs of my parents’ mind they always wanted to retire out there. And of course life gets in the way, so after my grandmother passed three years ago, my parents bought a house so when we would visit my grandpa we wouldn’t overwhelm him. My parents were in their early fifties at the time so still early for buying a second home but my dad has probably been looking for a house since he met my mom at 27! No joke. He knows the hamptons real estate market so well. The house is less than a mile away and a complete blessing. We can visit him without being in his way and vice versa. And just two hours away from westchester, if feels like another world. It’s my favorite place to retreat to all year round. Ideally when my parents retire out there, I’d like to buy a invest in a second home there as well. My moms siblings are starting to do the same there so hopefully my cousins will follow suit as well. But I’m not quite there yet, I’ve got some more life steps to do! It never hurts to look!

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Ashley

I love this idea! I’m definitely not in a “permanent” spot at all, but the idea of a house in Vermont sounds amazing. Actually the idea of a weekend house bigger than my apartment & outside the city would be enough for me!

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Jordana @WhiteCabana

While I don’t know anyone who has bought a second home first, I don’t think it’s a bad idea. Especially when you’re so mobile at the moment in terms of your primary residence. Keep looking. When the house is right, you’ll know what decision to make!

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Ammy

Not crazy at all! I live in a big city with crazy high real estate. We can either live in a rental in a nice neighborhood or buy in a not so great area, so we rent. We are currently buying our first piece of vacation property and it has been the best choice!

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Amy

You’re not crazy! We bought a vacation house in NH (granted, this was not our first property) and have found it to be the best thing for our family. One thing to consider though with the north, your carrying costs for things like heating oil/propane, and snow plowing may be a lot more money that you think. An inefficient heating system can easily cost $300/month in the winter just to keep the pipes from freezing. Most plowing companies work on a contract so you pay every winter whether you are there or not… just some things to consider! I love VT and NH!

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Ashley Barker

Carly you aren’t crazy!! I think this is such a lovely idea all around! Vermont sounds like a beautiful choice.

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Taylor

If renting is financially best or your “first home” right now then I completely understand having your first house purchase being your second home. However, I will say that actually living in a house make all the difference. We love owning and even though it can be a lot of work and we are somewhat young (24 & 27) it makes a huge difference. Looking up houses is so much fun though 🙂 I often research houses for our next move even though we have a few years!

Taylor | http://www.livingtaylored.com

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Brittany

Totally understand the appeal! While I managed to find a somewhat affordable condo in DC that I bought three years ago, I, too, have been looking at Virginia mountain houses as a second option. It’s amazing how much prices plummet when you just move out of a metropolitan area.. Anyway, I say go for it. Life is too short to want to do something and not 😉

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Rachel

You are far from crazy… or we both are. I’m the same age as you and I am having the same thoughts. I will be changing jobs soon and most likely ending up in the Boston area. I’d like to spend at least my work week in the city where I’d have to sell my soul for some property. I don’t want a long commute (2 hours each way right now and it’s destroying me) but at the same time I want to be able to escape on weekends. I’m thinking about renting somewhere in or near the city, and buying a small getaway place that may even be a fixer upper as my first actual purchase. I hope you find something that makes you happy!

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Suzanna

Vermont is the most wonderful place ever!! I live here in the Burlington area, but my friend just started renting a place in Southern Vermont and she LOVES it. If you are ever here you should definitely make trips to the Shelburne/Charlotte area. It’s so picturesque with views of the lake and the Adirondack mountains. This is so exciting for you!! I might not be much more help, but if you have any questions don’t hesitate to ask me!

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Nina

A second home sounds great– but don’t be fooled by the struggles of owning property in Vermont. I’m 28, own my primary home in VT, and it’s pretty much a constant struggle dealing with maintaining your property with the weather while also managing taxes, Vermont prices, and changes in politics. Vermont is often romanticized (like in Scandal!), but there’s a reason the people here are so rugged and hard working.

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Erin

A lot of people who never lived in VT (I went to undergrad up there) also aren’t warned about mud-season! It takes a lot to get used to. 😉

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carly

I listen to the Awesome Etiquette podcast (the great grandchildren of Emily Post host it!) and they always talk about the mud season! 🤣

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Sarah

Carly – You aren’t crazy at all! I’ve always been in favor of real estate as an investment. We bought a summer cottage on Cape Cod earlier this year. I would love to add a place in Vermont/Maine/NH too. Good luck with your search!

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Erin

My parents have a home in West Dover, VT. If there is one thing I could recommend, it’s – just get the condo on the mountain. At least for now. There are so many things you don’t realize you need to account for with an actual single family home up there (from who is going to plow for you to the view tax for non-primary residents to remembering that you have to keep the heat on all winter to keep pipes from freezing). My parents say that even though they love their (rather over sized) dream home that my dad built himself, they often just wish they had just gotten a really nice slope side condo.

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Maina

I live in Vermont! My college roommate’s family, actually, was looking for a second home, a farmhouse, in northern Vermont for a second home. They ended up loving their second home so much that they sold their house in Acton, Massachusetts and moved to Vermont! Be careful- Vermont has that pulling power 😉

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Hannah @ AndThenWeTried

I’m on the second home hunt too! My fiancé owns the house we live in and while I went through the buying process with him, I don’t currently own any property. But every few weeks or so I check the market on a lake in Northern Michigan that my family has been visiting since I was a kid. I’ve been actively saving for it and hope to make a purchase in the next 5-7 years. It feels kind of frivolous to be saving up for something so extravagant, but it makes me so excited for my future family!

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Heather | Herkentucky.com

We’re looking for a bigger house here in Louisville — our dogs + our stuff are just outgrowing our current home — but honestly the only thing I want to look for right now is a Nashville condo for weekend getaways!!

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Sarah

I highly recommend, as a realtor in the northeast, that you get a preapproval with monthly breakdown before even browsing!! That way you know what you can realistically afford (more specifically than the bankrate.com calculators can tell you) and you don’t fall in love with something you can’t afford and either jump into something that’s too expensive because you love it, or get disappointed!! I see that with SO many of my friends who are first time home buyers.

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Erin Droese

So excited for you! Can’t wait to live vicariously through you! We just bought our first “primary” home and have LOVED doing projects and decorating. So can’t wait to see that process happen for you! Please share your journey – would love to follow along!

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carly

Still (at least) a year away because I don’t want to rush into anything. BUT, I love the idea!

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Alicia Mae

I think this is a lovely idea. I know homebuying can be stressful, but at the same time, it’s fun searching and dreaming. Best of luck to you!

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Emily

As a former Vermonter (and a future one, as I hope to be able to move back one day), I recommend looking in Burke, Vermont. My friend’s parents have a gorgeous rustic home there and the surrounding area has that Vermont quaintness that you are looking for. Burke Mountain, a ski resort, is only a short drive away. Other great areas include Quechee or Woodstock (both close to the NH border). While not in Vermont, Glens Falls, NY has that same New England appeal.

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Emily

Also…I finished the book Ditch the City and Go Country last night and I highly recommend it! While it is more for primary home dwellers in a rural area, it gives wonderful insights into life in small rural towns.

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Liz

Are you planning on buying a fixer upper without a mortgage? Or are you planning on just putting a down payment on something? Houses are expensive upkeep and they have wonderful way of “suddenly” having issues that often have expensive fixes. Even if you have a house with great bones and structural integrity you will still run into unexpected problems. And there will always be little maintenance things to do even when you’re not there (i.e keeping the thermosat/heating set to a specific temp so that pipes don’t freeze and burst in the winter). If you are paying your current rent and other bills on top of a house’s mortgage and bills it will add up quickly. Obviously, I don’t know your entire financial situation but I think the “second-home” idea sounds more like a money trap to me. It’s a huge responsibility to manage a house especially one that could be 3+ hours away! I think a “second-home” makes more sense for when you are married. Not just for the second-income but also having another person that can drive out to the property should something come up. It helps to have another person to share the responsibility with.

Also have you visited Vermont often? I grew up in Massachusetts and the winters can be very intense. Especially in the Vermont and NH areas the winters can be brutal and can bring all sorts expensive problems with them. Cute idyllic towns in vermont are nice in the fall but come winter it can be a different story. You should be prepared for power outages, snow-ins, and roads being closed.

I hope I’m not scaring you! Vermont is a lovely place to vacation and I have also dreamed of having a place in that area. I have a few family friends who have/had vacation homes in New Hampshire and Vermont and we always had a blast going out there for long weekends. It IS a lot of fun to have place to escape to and invite friends to visit (there are so many places to hike, ski, kayak etc.!). But don’t get too caught up in the dream of the sitting by a cozy fire away from life in a cute town. It’s a ton of responsibility to take on for a place you’ll only be spending weekends at. Most likely it would impact how you buy your “main” house and it might be frustrating to have to compromise on a place where you would spend most of your time. I would hate for you to be in a situation where you are stressed about the vacation house so much that you couldn’t even enjoy it. A condo in the mountains might be a better situation because it would eliminate (some) of the maintenance that comes with a house. Also good to do some research on HOA too because some of them are ridiculous and come with a lot of petty drama.

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carly

Definitely brought up a lot of the things I’ve considered/am considering! I would definitely do a mortgage because part of the appeal of a purchasing is being able to establish even better credit. (Same reason why I financed my car!) I know what I can and want to afford in terms of “all in” costs, so that’s been helping me limit my searching.

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Allison

This is my goal currently! I want to own a home in the Madrid area but have no idea where I want to be long term stateside. My priorities are a bit different than yours considering it’s an internataional property but renting “home”‘and buying a second property just makes so much sense, really! Love it!

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Marcella Ryan

Carly, you are not crazy! This is a perfect idea. My husband and I built a home on the beach about 4 years ago and I think this might turn into our vacation home. With kids in college, I’m ready for living in a big city, walking everywhere (since I carpooled for 12 years) and fixing up a brownstone. Sometimes I think I’m nuts but I say follow your heart and you’re only on this earth for a short time so go with what makes you happy. Love your idea!!!!

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Diana Pearl

My best friend is considering doing the same thing! It seems a little nuts at first glance but I think in the city/nearby it’s hard, because real estate prices are so expensive. Also, renting a vacation home is so pricey — sometimes as much as a month’s rent (or more!) for a single week — that owning your vacation home seems more economical in a way. Also you have more freedom, in that you can go to the vacation home at any point, and then you’ll have your rental home base at any time, too. Basically I totally get why you’re thinking this and I think Vermont sounds lovely. (Though I too am dreaming of a Nantucket property to call my own!)

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Becky

I think this is actually a great idea! You can use it as a weekend/summer escape, but also as an income property, and rent it out or AirBnB it while you are not there!
I’ve been a renter since I was 18 (31 now), and have only recently started thinking about buying a condo, but I’m in the same place, where I don’t know where I want to settle down. A vacation home would be a great start, I should maybe start looking around near the lakes!

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Rae

Honestly, my long-term dream is to own a lake home in Minnesota, and then rent apartments in whichever city we feel like living in. I get restless easily and the commitment of owning a home makes me nervous. So no, I don’t think this is crazy at all!

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Marcella

I’m going to be 24 in a couple of months and my parents reallllly want me to buy a small house instead of rent an apartment, I live in San Antonio, TX where houses are still fairly affordable. I just don’t know if I could take on that responsibility yet! Hopefully in a couple of years. Also not sure if you have read this article already, but it’s helpful especially if you’re looking to buy in a rural area: http://www.designsponge.com/2017/09/6-things-i-wish-id-known-before-buying-our-first-home.html

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Sarah

Carly, I so relate to this post! I just bought my first home this summer (my primary residence), but initially I really wanted to buy a vacation home on the Oregon coast first instead. However once I started talking to lenders I learned that I could get a much more affordable loan for a primary residence, since it’s my first mortgage. For vacation homes, the banks required a much higher down payment that I couldn’t afford. It was disappointing at first but now I’m so happy that I own my “everyday” house. It’s such a big investment that it feels good to spend the vast majority of my time in this place that I spent so much hard earned money on. So just a tip to start pricing out options with lenders (if you haven’t already) before getting too invested in the idea 🙂

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Gidel

I think this is so awesome!

Boyfriend just bought his first property… as an investment. He intends to rent it out almost immediately! The next purchase he wants to make is for getaways and business in NYC, so still not even a main home. He has your thoughts exactly – he just doesn’t know where he will be, or what exactly he will be doing and instead of investing in the perfect home and potentially flipping it, he wants to wait until we’re at least married and have some semblance of where we will be!

Congrats on your realization and good luck on your search!

Gidel

PS – I just have to say this. I have been a follower for a very long time and have always really liked you. However, in the last few months/maybe year, you have really come into your own. You can tell by the tone in your posts that you have somehow turned a corner and have a lot more optimism and courage and happiness. I hope that is real and not just a technique you are using! You are more beautiful than you ever have been, your writing is stronger, your outfits are edgier, but still classic, classy, and (of course) preppy, and your blog is just overall so much more amazing! I hope this continues! I love seeing you happy and I love following your growth.

I was actually recently inspired by you more than ever – I bit the bullet, and moved to Washington D.C.! I had thought about it for a long time, but finally went for it. It was one of your posts that helped make that decision. And I am happier than ever.

Thank you for being vulnerable with the world. Thank you for being you.

Great job!

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grace c atwood

carly, i think this is a brilliant idea!

two good friends of mine live in the city (in chelsea) in an apartment that they rent. last year, they purchased a home up in hudson valley, new york – it’s amazing. it has a pool, a big garden, patio… all the things. the perfect city escape. if you can do it, you absolutely should!

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Kristen

I couldn’t agree more. As a city dweller and renter for the past 13 years, a second home has been in the forefront of my mind. Southern Vermont is beautiful, my family has a house there and we’ve been going up there (from CT) for years. It’s not to far away for a quick weekend trip but feels like a different world that allows you to turn-off and enjoy nature. Best of luck on your search! Can’t wait to hear more!

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Kara

Good luck! I have been neck deep in real estate for the past 6 months or so. I am extremely particular in where I would like to purchase my first home. When I was just casually looking a home I would fall in love with would sell and I would have this panic that would follow. Deep breaths. When it’s right you will know.

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Ellie

I never would have thought about this idea, but I think it makes perfect sense (and I consider myself to be pretty financially savvy). Your reasons for looking at a second home are sound and your plan makes sense. I’m sure you have the nuts and bolts in a row and will make a good decision. I hope the right spot comes along soon for you and can’t wait to read more about it!!

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CC

Exciting! I grew up in Manchester, Vermont, and it’s the perfect place for you, including a fabulous bookstore (The Northshire), lovely through 4 seasons, and a manageable driving distance from western CT. Bonus: there are direct flights to FL from Albany (just over a hour away). Don’t pick a ski condo — it will lack the wonderful sense of community you will get from a “real” town.

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carly

You had me at “bookstore” haha! I’m definitely not interested in a condo (would rather Airbnb one for a weekend if I needed, you know?).

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Katie

As a current Manchester resident, I completely agree! 10 and 20 minutes away from two great ski mountains, and with great attractions in town like the old Lincoln Family summer home, it’s the perfect place for a vacation home. And who knows, plenty of my friends growing up and I all had vacation homes in VT and then ended up moving here from mainly CT and NYC, it’s perfect year round!

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Natalie

Carly, it’s like the stars have aligned with this post! My husband and I have been talking about and researching the same thing. We have lived in NYC for a few years now and we are itching for somewhere to go outside of the city, especially on nice summer weekends. While I don’t see us leaving the city anytime soon, the idea of buying a permanent place here lacks a lot of appeal. Anything we can afford to buy is so small and we both know we want to move to the ‘burbs once kids come. We’ve started looking at small, fixer-upper properties out on Long Island near the Hamptons. I can’t help but get carried away with fantasies of sitting on a porch, going to the beach, having peace and quiet! But then I get pulled back thinking is this insane? Even though we can afford it, who buys a second home first? It’s so good to hear from you that you’ve been thinking similar thoughts! I’ve always thought you are very financially savvy and I so look forward to following along for this project of yours.

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Carolyn

My husband and I bought a vacation home first too- really for all of the reasons you mentioned. Our house is on the Cape and we love having special that is ours while we continue to rent our primary residence. I highly recommend!

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Jennie

Bought my first home first, but I love this idea. And as someone who had to give up her dream of living where she grew up, I feel you on that one. It’s tough, but I’ve accepted it, and there is so much about where I live (DC) that I love.

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Ellen Villafuerte

Hi Carly! I live in NY but as far east as possible about fifteen minutes from Southern Vermont and I have to say that it is a great place to live. There are things to do all year round and there are some really beautiful properties in my area both on the NY and VT side!

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Julia Callo

Hi Carly,
I was born and raised in Manchester, VT. It’s about a 3.5 hr drive from where you are. It’s a perfect spot where you have access to over 6 ski areas within reasonable distant. Manchester and all of its surroundig towns are largely filled with second homeowners and I couldn’t recommend that area any more! It’s a perfect place with a large variety of year round activities and events. There are also plenty of fixer uppers available that have great potential. If you need any help in your future search please let me know.

Julia

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Suzanne

Go for it! A small vacation home can be a great investment especially if you watch the market in a particular location and know when to buy! We purchased a 3BR/2.5Bath condo mid-island on Nantucket in 2012 for personal use, we’ve watched its value nearly double over the past 5 years and hope someday to use it as a stepping stone to a larger home there. Good luck!

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Jane

Carly, do it! I purchased my second home “first” last year down the Jersey Shore (I still rent in Manhattan too). It was scary, SO scary actually. But it was so worth it. I love it, and getting to update it as I go is so rewarding. You won’t regret it.

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Erin

I bought my first house just one month ago at the age of 24! It’s incredibly scary but so worth it to not pay rent. My advice: don’t rush into anything, make sure you view the whole house (including crawl space, etc!) before making an offer, and be patient. My current house is the third one I made an offer on and the second one that I had under contract. Be wary of sellers who think too highly of their home; the first house I had under contract was appraised significantly under the price I had agreed upon with the seller, and they refused to come down or even meet in the middle between that and the appraised price. I ended up losing the money I had spent on the appraisal and had to start the house search all over again from square one after a full month of being under contract! It can be frustrating but I was so happy to finally settle into my current home.

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carly

I had looked at a house a few years ago and had the same problem. They had lived there for 20 years and the price was sentimental… not market value!

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Sarah Wilson

I think it’s a great idea! But with your lifestyle now think about how often you will actually use the house. I know it’s something you envision your future family spending time at, but you really don’t know what is in store for your future family. So if you really think you will get enough use out of it right now, then I say go for it!!!

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Marina

Being in the army, I keep having this idea of buying a home at my first duty station (which will be near a coastal place) in order to have that option. It is such a huge goal, but very achievable if you’re adamant about doing it. There is no age limit to doing big things such as buying a home. Be smart, do your research, and accomplish great things.

Marina | Travel + Lifestyle Blogger

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A

I know plenty of people who rent apartments here in NYC, but have second homes they escape to on the weekends mainly in Pennsylvania, around the Delaware Water Gap area. My best friend’s brother bought his vacation home in the Poconos and continued to rent in Brooklyn for a number of years. They eventually moved there full time when they had their third child.

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Mallory W.

Second home first is definitely a great idea and something my husband and I have discussed. With the crazy housing prices in metropolitan areas, you can get priced out of the housing market fairly quickly. But a vacation home in a place you love that’s more financially feasible allows you to buy, build equity and have a great escape from city life. I say do it!

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Kristina

One of my friends & her bf just bought a second home but still rent in the city – they actually got a place on a lake in Connecticut! I don’t think it’s so crazy of an idea. I own that first home, but would love to get a lake house someday 🙂

Kristina does the Internets

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Kate

Carly – I gawked at your IG story because this has been circling in my head for a couple months now! My dream would be a little house on a couple acres of land about an hour or two outside of Dallas where I could keep a horse and host friends on the weekend. Love that I’m not the only one thinking (dreaming) about this!

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Heather

Yes! I’m totally on board with this idea. I live in DC where renting is also the norm, and realizing that a vacation home somewhere in Virginia is far, far less than what I’d pay for for a one bedroom condo here makes this idea sound more and more appealing.

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Kendra

I live in pricey NYC and have considered doing the exact same thing in either the Adirondacks or the Catskills, or maybe even the Pocono. It’s very common around here since property in the city is so expensive. I say go for it. Also, if Nantucket is your dream perhaps consider Cape Cod instead. It’s much more affordable, and you’re just a ferry ride away from ACK. I looked into that, but it the distance is a bit too far for me. Happy House-Hunting!

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carly

My problem with the Cape/Nantucket is that it’s not a year round spot… I don’t want to spend my winters there! I’d prefer to be closer to skiing and other snow activities!

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Lily von Trapp Derbyshire

Hi Carly,
My uncle Chris von Trapp is a real estate agent in Vermont, based mainly in Shelburne and Vergennes but has properties all over the state. Being close if not on Lake Champlain would be my recommendation and it’s not far from Burlington and their international airport. Shoot me an email if you would like more info, I know the state pretty well!

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Rachel

Local Vermonter here – yes he is. The Von Trapp family moved to Vermont after leaving Austria and established a ski resort. They still live in the area and yes, Chris Von Trapp is of that family.

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Lily von Trapp Derbyshire

Hi Carly,
Yes, we are that von Trapp family :)!

Manchester area is gorgeous – I have friends in the Arlington area. Good luck!

-Lily von Trapp Derbyshire

Jane

I live in a part of Canada where many people have homes and cottages. It can be stressful having to deal with two bills for lighting, electric, plus having to check up on the property and deal with unexpected problems such as roof leaks and water damage. If you’re doing this alone it’s a lot to take on. Why not a condo as a first purchase?

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Lauren

I think a second home first sounds like the a great idea! And if you think about it, it makes sense – you’re young, not married yet, and can put off buying the ‘first home’ till later. Plus, it would be fun to have spur of the moments vacations and you could always rent it out when you’re not using it and put that money towards the first home or something fun!

Lauren,
http://www.atouchofsoutherngrace.com

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Amy

I think you are very financially savvy and I’m sure you wouldn’t be thinking about this if it was something you couldn’t realistically do. Just two comments: Use a real estate attorney for contract/closing even if Vermont doesn’t require one; and hire a professional home inspector. I’m excited for you. I love Vermont! It’s a beautiful state!

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Joslyn

I’ve been toying with this idea for about a year now, glad I’m not the only one! I’m 30, not married and not exactly sure I want to stay where I live forever, but I am sure that I want a beach house! I’m planning to look at some properties in the off season and maybe bite the bullet. If it makes sense financially I say go for it 🙂

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Olivia Gould

This is a unique idea (or maybe not so unique because after reading comments, it seems more common) – and I love it!

My husband and I rent in DC, and we have no idea when we want to buy. We are in our mid-late 20s and no kids yet. As we all know, buying in a good neighborhood in DC is usually only for the very fortunate. However, we did buy a Disney Vacation Club timeshare that’s a 50 year commitment – so now we always have a place to stay at one of their best resorts on property. We are THOSE crazy Disney folks. We can also use our timeshare to visit other non-Disney resorts all over the world. It’s called a “second home” for all of us who have this timeshare, so I guess I’ve done this second home first as well! Haha. In fact, most people don’t buy into a timeshare until they’re a little older and more established.

Good luck with your journey into hopefully buying a new home at some point! Can’t wait to see updates. 🙂

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Melissa

My husband and I are 26, and we currently own a small townhouse in Pittsburgh close to our jobs. It’s great to have a smaller home that we are building equity on and could one day use as a rental property. Most of our friends our age are renting or have a townhouse like us. However, the “next move” conversation comes up quite frequently. We’ve thought about buying a small second home in Colorado. We’ve thought about buying an RV and traveling around the country whenever we wanted. (I work remotely.) We’ve also thought about investing in a bigger home in the same area we’re in now in a good school district. I feel like you have to figure out what is most important to you, decide what is the most practical choice for your life, and know that there’s a plan for your life that you can’t always control. I’ve stuck to Oprah’s advice of “making the next RIGHT move” from wherever you are. Right now, for me, that means learning patience and waiting it out to see what life brings. Good luck with the home search!

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sophie

this is a great idea! my husband and i purchased our vacation home in bellport, ny – and are still renting in brooklyn. we definitely have plans to buy a “first” home at some point … but having the weekend getaway works for us at this point – and is a great investment for the future.

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Jen

A friend of mine bought a second home out in the Berkshires this year, while still renting in the Boston area. Houses are crazy expensive here in the Boston area, but she was able to afford a decent sized home in the Berkshires. She plans to rent it out during the winter (since it’s near a ski resort) and make a little extra money that she can use towards her mortgage payments.

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Annie

This is too funny because I’ve been thinking the same thing! We live in Chicago and are thinking about buying, but property taxes here are crazy and the state of Illinois is a hot mess. I’ve been throwing out the idea of buying a small cabin on a lake in Wisconsin – a fixer upper so we can increase the value. Plus getting away to the lake is my favorite activity. I totally get where you are coming from on this! My vote is yes! 🙂

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Amy

You should leave Illinois and buy in Indiana. Loads of people are doing it. Property taxes are super low and homes are nice. Plus, you could still afford a small lake home in Michigan or Wisconsin. Indiana is hot!!!

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Krystal // The Krystal Diaries

I don’t think it’s a crazy idea but I do think I’m one of the few people who doesn’t love the idea of a second home for myself. I used to want one but after being a homeowner for five years now (not that long at all!) I don’t want the hassle of a second property to maintain, hire maintenance people or pay taxes on. However, I would buy a second property to rent out if I could make a good profit off of it.

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Kelly Golightly

Not crazy at all! That’s what we did. Instead of buying in LA which is overpriced, we bought in Palm Springs (our favorite place in the world) and then rented a smaller place in LA. The PS house + Beverly Hills apartment cost less than the house we had been renting in Silver Lake in LA. I say go for it!

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Amanda

This doesn’t sound crazy to me at all! In fact, I dream about doing the same. I used to live in NYC and now live in SF, two of the most expensive cities in the US, making it nearly impossible to own (also, I do NOT want to spend 1 million dollars on a one bedroom, eek). I’d much rather invest in a city-escape type getaway. Looking forward to seeing where your vacay home buying journey takes you (I love vermont!)

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Jessica Alvarez

I read this post the day you published it and LOVED it. I think it’s so original and personal yet practical for a blogger to write about at this stage of life. I figured it would attract a lot of comments, so I’m back a few days later just to read what others had to say! So helpful! 🙂

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Allie

I live in Vermont! Close to Killington Moutain.
I highly suggest Chittenden VT and Middlebury, both beautiful places, close to mountains and lakes.

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Emily Richey

Not crazy at all! I love this idea! Also, my husband’s family has a house at Stratton (we are actually headed up tomorrow after I pick him up from a 7 month deployment!!) and we looove the area. The houses on the mountain itself aren’t really what you are looking for I don’t think, but that area of southern Vermont has so many lovely old farm properties that just need a little TLC. We dream of having one ourselves! Queue all of the wood-burning fires, red wine drinking, skiing, hiking, snow-shoeing, apple picking! xx

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Anna

Hey Carly, you should look in and around Manchester, VT. My family has owned a house on Bromley Mountain since the late 70s, and we use it in every season. Summer in VT is absolutely beautiful, and cooler than Philly where I am from but still warm enough to swim in the nearby Dorset Marble Quarry (beautiful clear cool spring water that filled in the oldest marble quarry in the US!) The town itself is super cute and quaint but with a normal grocery store, good shopping, and the most swoon worthy bookstore on the planet. You would LOVE it, its our favorite place in town. It is close to CT as its in south western VT and many of our neighbors are from there. It is also close to skiing at multiple mountains: Stratton, Okemo, Magic and Bromley are all within a half hour. I think you would LOVE it and this time of the year is seriously gorgeous. Have fun looking!

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Anna

That is so exciting! I’ve been reading your blog for about 5 years now and would love to grab coffee in town sometime if (and when!) you buy in Manchester. It really is the best 🙂

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Meg Zuehl

You sound like you have put a lot of thought into this and that a second home would add major quality to your life. I admire that you are not falling prey to what “everyone” does but are doing what’s right for you. I think a cabin in Vermont sounds absolutely heavenly and I bet your dogs do too 😉

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Emily

I love your idea of buying a property in Vermont! My family rented a house up there for a few winters and those are some of my best memories from growing up! We rented in New Egypt, which is right next to Manchester (SUCH a cute town) and 10 minutes from Bromley mountain. It was towards the south and exactly a 4 hour drive from our house in NJ. If I could buy a house in Vermont this second, I would! Good luck!

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Kristin

I love this idea! When we were renting in New York, this was actually our plan, also. We ended up moving to Vermont full time last year and just bought our first house this summer. It’s a much more affordable area than New York or Connecticut, but still close enough that it would make the perfect weekend getaway. Now our plans for a weekend house have been pushed back a bit, but we’re hoping for something near the shore, hopefully in the next 10 years or so.

I think your idea of buying in southern Vermont is a great one. Parts of VT are actually only two hours from the city or CT, so that would be an easy weekend commute. We’re in the Upper Valley now, which is also spectacular, but a little more expensive and a little further afield than you might want to travel.

We had an arduous but ultimately really fruitful experience buying our first house and we’re renovating it little by little. Feel free to email me if you want more specifics or just want someone to chat about ideas with, since I love talking real estate!

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Catemann

Carly– check out the Brattleboro area…southern VT, especially the perfect VT village of Newfane! Good luck with the 2nd house search!

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