Moving to Portland, Maine. Where should we live?
September 23, 2015 9:57 AM   Subscribe

It looks very likely that my spouse and I will be moving to Portland (the first Portland). We are both really excited about the move but don't know where to live. Help us choose a good neighborhood (and maybe a buyer's agent)!

[I will preface this by saying that I have read all the previous Portland, ME AskMe threads.]

Here are the basics: We're two men, early-mid 40s, no kids. We're both active, big readers, and both do some food writing on the side (although less frequently than we used to). We are both very interested in finding a home with some charm, with good restaurants, coffee, and cocktails (if possible) nearby. We like to walk, so for me, an ideal place would be someplace that allows us easy access to the Peninsula on foot. That said, we are also willing to go further afield if the house and neighborhood are great.

For reference, neighborhoods in other North American cities we like are Cobble Hill/Boerum in Brooklyn, SE Portland in Oregon, Mile End in Montreal, and Andersonville & Wicker Park in Chicago.

We have been eyeing West End and Deering, but we are also pretty sure there are neighborhoods we don't know about that are also wonderful. Help us figure out the best neighborhood for us.

Bonus: Since we're looking to buy a house (or condo if the place is amazing), we need a buyer's agent. So if you know a really good, smart, and honest agent in Portland, we'd love his/her name, as well.
posted by yellowcandy to Home & Garden (10 answers total) 6 users marked this as a favorite
Have you ruled out any neighborhoods - I'm assuming you are not looking to be way out of the downtown area (cheaper, but less businesses nearby)? If South Portland (just over the Casco Bay Bridge area) is a possibility someone just posted a great little bungalow.
posted by mikepop at 11:08 AM on September 23, 2015

The first thing I'll say is that Portland varies greatly even street-to-street, so it can be a bit difficult to endorse an entire neighborhood. Also, Portland is quite small, so living a little out of the way is not actually such a big deal. When you hook up with a realtor they can take you around the whole area pretty quickly.

Not knowing your budget, buying a house in the peninsula would probably be unaffordable for me at this point, but I rented on the East End (near the top of Munjoy Hill) and I love it up there. The gentrification has been pretty intense, though, and it's been invaded by cookie-cutter modern condos.

Off-peninsula it's hard for me to pick out one neighborhood because I pretty much like them all! The Deering area around Evergreen Cemetary can be quite charming depending on the street/house. As Mike suggests above South Portland (across the bridge) is charming as well (but again is gentrifying as it slowly gets eaten by Cape Elizabeth).

One thing that might be a strange thing to say: you might want to take a look at some of the sea-level rise maps out there on the internet. Depending on the projection, there are some lower-lying areas around Portland I probably wouldn't buy land on. The city is currently trying to put more big buildings down on Marginal Way, for example (not that you would move into a doctor's office) and I'm pretty sure they're going to live to regret that.
posted by selfnoise at 11:19 AM on September 23, 2015 [1 favorite]

I've lived in Parkside, the East End, and now Willard Square in South Portland. We loved the East End, and can confirm that the gentrification is moving fast. On the flip side, there are some concentrated areas of pretty run down rentals, so I can also confirm that it varies a lot street-to-street. Between the two Ends, the East has more single family homes and the west has more brick (also more mansions). I have friends who live in and love the West, but don't know it as well.

When we last moved, we looked hard in Deering and Deering Center, and there's a lot to like about those areas. Definitely some charming older homes in the area. The houses and lots tend to be quite small, though, and it's a bit of a hike by foot to the peninsula. We also looked in North Deering, which feels more suburby and is full of houses of more recent vintage, but has more space to offer if that matters to you.

We ended up in South Portland because our priorities were a little yard, neighborhood feel, and a few local businesses we could walk to. Lots of the development there was 1920s era, so some charm to be found. We could walk into town, but it wouldn't be quick. The buses are less than ideal, too. It's only about a 10 minute drive, but driving is the best way to get to the peninsula.

I might rank the choices like this based on your question: West End/East End, Deering/Deering Center/Rosemont, Willard Square/Willard Beach, North Deering. I'm sure there are other options I'm forgetting right now.

We loved our Realtor, but he's super, super busy. I'll MeMail you his name and info. Oh, and in general, housing prices are high and rising in the desirable neighborhoods.
posted by that's candlepin at 12:54 PM on September 23, 2015 [1 favorite]

We lived in the Woodford Street area, and East Deering, that is, the area bordered by Woodford, Forest Ave., Stevens Ave. and Brighton Ave. has some really nice homes. Local businesses include Great Lost Bear on Forest Ave. and Big Sky Bread Company on Deering, and the Bayou Kitchen. Also, a few pawn shops and some more restaurants (fish and chips, etc.) up Forest Avenue heading out of town. Stay away from Morrill's Corner on outer Forest Ave., that gets crazy backed up with traffic and if I had to commute through there every night, I would go insane.

I would not live directly on Woodford, too much traffic, and the corner of Woodford and Forest can get backed up at the end of the workday. There is a bus that goes downtown, and the big Hannaford grocery store is 5 minutes away, as well as the trail around the Back Cove. However it's not really an easy walk to the Old Port, with the highway ramps getting in the way of safe foot travel. There is a bus, in case you want to get to the downtown area. However, it's not as artsy and cool as the downtown, and you can't just walk out the door and be at the Friday Night Art Walk like you could if you lived near the Old Port.

Stevens Ave., further down from Morrill's Corner (toward Brighton) has some nice areas on the side streets. Be aware there is a school there and so lots of traffic and giant speed bumps. Due to the schools, I don't know of any bars in that area within walking distance. But, depends on your budget.

I would avoid Parkside and anything near the Post Office (i.e., Park Street), as well as Libbytown (outer Congress Street) and St. John Street (near the Greyhound station and the ball park, which shoots off fireworks and draws huge crowds and traffic).

If you are looking for a Wicker Park sort of vibe, I agree that Munjoy Hill deserves a look. There, you've got the Front Room restaurant, the Blue Spoon, Rosemont Bakery, and the Eastern Prom, with the park and ocean views. Plus it's walking distance to the Old Port, in summer, anyway.

Avoid the area between Washington Ave. and Franklin Street. North Ave. has a nice little park with sunset views. Also, I would avoid anything with steep hills (winter) and make sure it has adequate off-street parking (also, winter). The West End is nice (closer to Danforth Street than the hospital, tho' there are some really lovely homes in the neighborhood near the hospital, it's quieter) and hospital, I mean), but not sure about a lot of single family homes that close to downtown. You might be looking at condos and townhomes in that case.

If I had a million to drop on a house in Portland, I'd go with this one on Sheridan Street (the views!) or this cute little bugger on Congress (only $795,000!).

Known this lady casually on social media for several years, we had a meet-up once and she seems nice and friendly and knowledgable. She's also pretty honest, we were considering buying the house we were renting at the time, and she gave us some good information about how it would not be a good investment (leaky cinder block foundation, etc.), and I later heard from the locals confirmation of her advice. If she can't help you, sure she will be happy to refer you to someone decent. Good luck!
posted by Marie Mon Dieu at 12:58 PM on September 23, 2015 [3 favorites]

We moved to Portland just over a year ago and love it. We rented down near Willard Beach in South Portland before buying a place in North Deering. North Deering is a good area but there isn't the retail you're craving. We chose it because it enabled us to get a nice house with a big fenced in yard which works great for us, small kid and dogs.

Willard is suffering from Cape Elizabeth creep and every house that came up for sale when we were there seemed to go to retiring boomer couples with a golden retriever and wardrobes purchased entirely from L L Bean. That said, having Willard Beach on your doorstep is pretty great.

This was our realtor for buying this house. She was great.
posted by merocet at 3:25 PM on September 23, 2015 [1 favorite]

Totally agree with merocet's realtor rec.
posted by Sukey Says at 8:34 PM on September 23, 2015

My wife and I just purchased a house in Falmouth with help from Linda MacDonald. She was unbelievably outstanding! From being a shrewd negotiator, to having contacts with a bazillion inspectors/contractors, Linda was the complete professional. I've been recommending her to all my friends who are looking to buy a house. (Full disclosure: I currently have exactly one friend looking to buy a house.)
posted by El_Marto at 7:44 AM on September 24, 2015 [1 favorite]

Such wonderful responses (and MeMails) so far, everyone. Thank you so much.

One follow-up: What's the USM/Oakdale area like? I've seen a few places on the MLS in that area, but I am not familiar with that neighborhood at all.
posted by yellowcandy at 9:11 AM on September 25, 2015

USM area is a bit hit-or-miss (in the same way the East End is, really). Some student rentals in there, some single family, some owner-occupied rentals. I have some friends in the Fessenden St. region who are very happy, and it's not a crazy walk from town. But you don't want to be too close to Forrest Ave., IMO. It's traffic mayhem most of the day. And you probably don't want to be in the area between the highway and Falmouth St. either.

Personally, I'd rank it below the East and West Ends, and probably below the Deering/Rosemont zone as well. But the right house on the right street might be ideal.

Are you going to have a chance to visit and drive/walk around? All this advice might be way off if your taste in neighborhoods is totally different than mine.
posted by that's candlepin at 12:19 PM on September 25, 2015 [1 favorite]

I would say USM No. If you are looking to do a neighborhood thing, West End or East End on the Peninsula. Other than that, you are stretching your vibe. The reason I stressed the Deering area is because it is nice, housing wise, less pricey, but close enough to drive or take a bus (5 minutes). But it still has some neighborhood vibe with Great Lost Bear (although totally cut off from the downtown area, as is South Portland, even moreso, but that's their own neighborhood vibe down there).

Seriously, you cannot get a Wicker Park vibe in Portland. But if you want a nice vibe, you have to get onto the East or West End. Otherwise you are going to be driving or busing it to downtown and spending your nights in quiet town or listening to students living it up, seriously don't do that. It's on the way to the hospital as well. If you want a nice vibe, go to Munjoy Hill. If you want a quiet vibe, go to the West End. If you want a cheaper nice vibe, Deering Central or closer to the Back Cove, or even Westbrook.
posted by Marie Mon Dieu at 5:36 PM on September 25, 2015 [1 favorite]

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