Maine Places

Stonington on My Mind

Maine Places

You know that moment when you arrive in a beautiful Maine town and start plotting how you might move there? This phenomenon is not limited to those who live out of state. We locals experience it all the time. I have mentally relocated to coastal villages and mountain towns all over Maine, but the place I return to most frequently is Stonington. “I can write and you can hang a shingle!” I have said to Mark so many times as we’ve strolled along Main Street that he no longer takes me even remotely seriously. But last weekend I had willing participants in my fantasy. Our good friends from Portland came to stay with us at our camp in Deer Isle and, on a cloudy afternoon, we introduced them to Stonington. Within minutes of taking in the lobsterboat-dotted harbor backdropped by 19th century houses arrayed on a steep slope, they were snapping up real estate brochures and mulling properties. As we ambled through the narrow streets terraced into the ledge, we talked through what our lives would be like here and whether we’d feel isolated in the winter. No, we decided, because we’d have each other — and daily access to 44 North Coffee to keep us cheerful and warm. All the while, I was snapping photos of our hypothetical houses, shown below. None of these is for sale, mind you, but a girl (and her friends) can dream.

“Mommy, it’s just another white house,” my son said as I was taking these. But when I examine the images together, I see so much nuanced variation in the rooflines, adornments (or lack thereof), and the way shadows tint the clapboards. To me, each house looks like it was plucked from an Edward Hopper painting and I can’t decide which one I like best. Do you have a favorite? Leave a comment and let me know!


  1. Shane Osborne

    Dear Sarah,

    I feel the exact same way. In fact, my husband and I recently purchased a home in Stonington. I grew up in Bucksport, but have lived out of state for 28 years…the last 19 years in Washington, DC.

    We have the same fears that you do regarding winter. Luckily, we love to read and take winter walks/hikes. We also want to get involved in the community. Sadly, I don’t think 44 North is open in the winter so you’ll have to go to Harbor Cafe or Stonecutter’s Kitchen for coffee.

    Mark and I plan on getting involved in the Stonington Opera House, SPCA, and would love to DJ at WERU, though it is a hike to their studio in Orland. We love WERU’s Sunday Morning Coffee House show. There is also a Saturday morning version. We listen to it all the way from DC.

    There is no doubt that it will be a quieter life and I do have some worry about fitting in with the locals. My husband just retired from the Federal Government (at 56 years old) and I am only 47 and still working. I may just retire early and off we’ll go. The world is so crazy right now, which makes the appeal of hiding away on an island off the coast of Maine even greater. I wouldn’t be surprised if we were both permanently in Stonington by Spring. You only live once….I don’t want to miss another Summer in Maine. Hope to see you there. We’ll have you over for wine.

    • Sarah Stebbins

      Oh my, you will soon be living the dream. Congratulations on your house purchase! Will you keep me posted on your plans? I would love to follow your journey — for inspiration and fodder for someday convincing my husband that this kind of move is a good idea. 🙂 That stinks about 44 North being closed in the winter but the Deer Isle one is open year-round, right? Best of luck with your move and thank you so much for writing.

    • Tim Donovan

      Hi Folks. 44 North will be open year round in Deer Isle Village. I’m a weekender in Stonington (my house is the first in the photos above) and last winter was my first. I spent almost every weekend up there (and some weeks). Its really quite nice and its great to go to the movies on Saturday nights at the Opera House. But yes, its tremendously relaxing… great for reading and writing. And there is always brunch at Aragosta’s on Sundays… not to mention just watching the boats and the fog. Mesmerizing.

      • Sarah Stebbins

        Oh, Tim, words, and the picture I took, cannot begin to express how much I love your house! I circled back a few times to gawk at how beautiful it is. I think I may need to do a follow up post on the people who own these gorgeous houses and how they came to live in Stonington full or part-time. I will be in touch. 🙂 Thank you so much for writing and enjoy fall in your lovely home.

  2. I just spent 2 weeks on Deer Isle and I too want to move there! I love the sense of community,
    the harbor, the Opera House to name just a few places that stole my heart!

    • Sarah Stebbins

      Oh man, if I spent two weeks on Deer Isle, I don’t think I would ever leave. The longest I’ve ever been able to escape for is a week. I’m glad you had a nice trip, Shirley. Enjoy the rest of your summer.

  3. bob

    hi sarah,
    wonderful article. i was asked to repair a bluestone patio for friends of mine that own waterfront property in brooklin maine. i could not believe how beautiful and magical this place was. i fell in love with the area and the surrounding towns. i actually live on the ocean in a big old beach house in old orchard and i still would rather live up there. it’s the true downeast. the people i met were all very welcoming and the wide variety of different restaurants to explore is always fun. i like all the homes that have a wraparound porch. i’ll look you up if i a ever move up there and of course if we ever had breakfast, lunch or dinner together the menu would be blueberry waffles, crabmeat rolls and steak and lobster respectively. ha, ha!!! can’t wait.

    • Sarah Stebbins

      Ha, that sounds amazing Bob. A beach house in Old Orchard sounds divine too, but I know what you mean. Thank you so much for the kind words and hope to see you Down East. 🙂

  4. Hi Sarah,
    I so enjoyed yet another one of your wonderful articles that are so warm and relatable! I’ve never commented before but after following your kitchen reno with your adorable boys and all your other articles I just wanted to give you kudos for your great work. We just spent 6 months in Harpswell and that solidified my goal of retiring to Maine and building a small, green home by the water. After 40 years of trying to convince my husband that this is a good plan, I think we are almost there! Thank you for your great articles! ?

    • Sarah Stebbins

      Aw, thank you so much for the kind words, Judy — they really mean a lot. Six months in Harpswell sounds amazing. Please keep me posted on your retirement plans — how exciting!!

  5. Barbara Martin

    These houses are all lovely! But you should stay right where you are. 🙂

    • Sarah Stebbins

      Ha, I know, our hood is amazing too. Thanks so much for reading. xo

  6. Gretchen Jost

    Hi Sarah, I too felt the way you did, so I moved here from Texas 25 years ago. Now I fortunately live in one of the photos you posted! White and green with the mansard roof and amazing hydrangea. Nice article.

  7. Sarah Stebbins

    Oh, wow, Gretchen, lucky you. I LOVE your house so much I posted it here before:
    But when I saw that hydrangea in bloom I had to take another photo. I’ll look for you the next time I’m in town. 🙂 Thank you for the kind words.

  8. Gretchen Jost

    Better yet, message me on FB(am changing e-mail) and let me know when you are coming. We can sit on the porch, watch the ever changing harbor, and have margaritas(my specialty) He he.

    • Sarah Stebbins

      That sounds amazing Gretchen! I’m not sure if we’ll be up again this year, but I hope so. Thank you!

    • Sarah Stebbins

      Hi Gretchen, I have a question for you and sent it to the e-mail address you used here. I am hoping you can still check that account and reply from your new account. Thanks so much and talk soon! – Sarah

  9. Karin Brush

    I love them all but would prefer a water view!!!!! My family comes to maine every summer and are.considering a move.up there from Florida!

    • Sarah Stebbins

      Oh Karin, I hope you can make your move happen. Good luck!

  10. Rockyrd

    I loved this article. LOVED your house photos- each one is great. I could not choose.
    It brought back memories from years ago- only about a dozen.
    We were looking to buy a house or property in Stonington after we had rented in several surrounding areas for a few years. We were still both working so wanted to live in it about 6 mos of the year till we fully retired.
    Our realtor told us we could buy something there BUT not to expect it to be there when we returned after the winter. He told us the locals would not like us because we were from “away” and they would probably burn it down! I swear he said that. He was a well respected real estate agent from a fairly large firm too. We were shocked.

    We ended up moving along the coast a bit farther.

    • Sarah Stebbins

      Thank you so much for the kind words and, oh man, I’m sorry you had this experience. I’m glad it didn’t stop you from moving to Maine though and I hope you love your coastal town. Thank you for reading!

  11. Nancy W

    I’m dreaming of moving to Maine in a few short years. Florida has just gotten too hot to handle and the hurricanes are wearing us down. Missing snowy climes and a place where you can get out and enjoy the great outdoors in the summer without melting! Thanks for the inspiration!

  12. Jennie Brooks

    I’ve vacationed in Maine four consecutive years and fell it love instantly. I always come for the amazing fall foliage. I love the coast but after two years I finally made myself venture inland to the Greenville and Rumford areas. SO much more foliage there. This year we visited Stonington. Loved our picture perfect room at Boyce’s Motel. I will have to go back though as this trip was interrupted by a terrible respiratory virus. One of our days was spent in the Blue Hill ER. A very nice ER but not what we’d planned. ; ) So we saw little of Stonington but I do remember the last house pictured. Blues and greens are some of my favorite colors so you can imagine how the trim caught my eye. I do hope to return some day. Living in Maine 6 months of the year would be a dream come true.

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