2023 Best Places to Retire in Connecticut

Current Resident: Mystic is a small, beautiful town with many attractions. It's most famous being the Mystic "drawbridge" which is actually a bastille bridge due to the weights that help it go up. You can walk through the town and enjoy the many shops and delicious food in the area. If you are a fan of seafood, this is the place for you. Fresh local oysters and clams are served at most restaurants in the area. If you are looking for fun activities to fill your day, visit the Mystic Seaport for a glimpse into the past, or visit the Mystic Aquarium to see animals from all over the world all in one place. Kayaking and paddle-boarding down the river are also popular options for tourists. Overall, Mystic is a beautiful town with many attractions.... Read 22 reviews

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• Population 4,354

Current Resident: We have lived in Heritage Village twelve years and love it here. There are more activities than any one can be in. Or you can just stay home. Walks are shoveled, grass is cut. Great place to live.... Read 2 reviews

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• Population 4,232

Current Resident: Woodmont on the sound is a wonderful beach community. Family friendly, great neighbors, and beautiful beaches. Wouldn't change anything!... Read 2 reviews

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• Population 1,614

Current Resident: Orange is a great place to raise a family. Excellent schools, convenient shopping, tons of activities, a large variety of restaurants and a car or train ride to Boston and New York. Orange also has more than 1000 acres of open space for recreational activities. Housing is expensive and taxes are moderate. As we say, “Orange is appealing!”... Read 48 reviews

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• Population 14,225

• Suburb in Connecticut

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  Rating 3.5 out of 5  2 reviews

Current Resident: I moved from the Lake Hills section of Fairfield to Southport about 13 years ago, and I love it here! There is a great sense of community and it feels like you are back in time when you enter the Southport Historic District. Everything is walking or biking distance away, which is a great plus. The restaurant scene is very nice with the Artisan and the Gray Goose representing the posh side of Southport. Southport cares a lot about the environment and nature, with Southport Park being a great little destination, and there is an ecological restoration taking place east of Pease Ave, South of Mill Hill Terrace, and north of I-95.... Read 2 reviews

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• Population 1,719

Nearby Resident: Small town, feels very safe, good schooling system. Only problem is that prices are very expensive. Good for retirement or families, but not good if you want to party.... Read 4 reviews

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• Population 3,619

• Suburb of Hartford, CT

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  Rating 5 out of 5  1 review

Current Resident: Very good place to live because it is so close to the center of town where everything is happening. The stores in the center are great and the food places are fun to hang around in. 10/10 great neighborhood as well.... Read 1 review

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• Population 8,187

Current Resident: I liked going downtown, it is a very scenic place. I loved walking around and hanging out with friends and family in the spring.... Read 7 reviews

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• Population 3,475

Current Resident: A unique and interesting town. The town of Southbury is comprised of 39 square miles and set in rural CT. The 20,000 residents are a variety young growing families, empty-nesters, business owners, entrepreneurs and retirees. The rural character is balanced by a variety of popular shops on Main Street. People are eager to move to Southbury for their excellent public schools, activities, overall safety, wonderful parks and hiking trails. Its a beautiful town to grow up in. Southburians are proud of their town's history and work towards creating a balance between the characteristics that make our town charming and keeping the town modern. Over the years the town has grown tremendously but keeps its farms, parks and natural preserves in tact. I have enjoyed growing up in Southbury. I always feel safe and have the parks, hiking trails, shopping, farmland and excellent schools. It may seem far from large cities which is part of Southbury's unique charm. It is a hidden gem!... Read 57 reviews

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• Population 19,866

• Town in Connecticut

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  Rating 3.9 out of 5  31 reviews

Current Resident: I love Milford so much. This has been my home for the past 20 year and I would not have traded it for any other place. I grew up in the school system and while my family was not upper middle class as most of the town is, I was welcomed and cared for by the community. I appreciated as I got older the opportunities Milford gave me. I was able to have safe and efficient transportation to school in college, I was granted various scholarships from community businesses, and the proximity to everything has been such an amazing experience.... Read 31 reviews

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• Population 50,694

Current Resident: Simply stated: The perfect New England town. No place on Earth I would rather live. Moved here in 2020. Absolutely love it.... Read 28 reviews

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• Population 6,725

• Suburb in Connecticut

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  Rating 5 out of 5  2 reviews

Current Resident: A very nice area filled with trees, along with a great park that includes a dog run, a baseball diamond, tennis/basketball court, and playground for kids. There are some local restaurants and shops, and it's pretty safe.... Read 2 reviews

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• Population 3,293

Current Resident: Small coastal town with all the great things! Just enough stores to keep you local and perfect approximation to anything else you will ever need. The people are friendly and very welcoming!... Read 36 reviews

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• Population 10,506

• Suburb of Hartford, CT

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  Rating 4.75 out of 5  12 reviews

Current Resident: Peaceful, Rural feeling but equally close to Simsbury proper and Avon, Canton. Absolutely the best part of Simsbury.... Read 12 reviews

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• Population 3,005

• Suburb of Hartford, CT

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  Rating 3.69 out of 5  65 reviews

Current Resident: Avon is a wonderful town with lots of fun things to do. The views of hills and mountain landscapes are breathtaking and never get old. It’s not too busy of a city, but not too remote either. I have enjoyed the past few years of living in Avon!... Read 65 reviews

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• Population 18,821

Current Resident: Quaint artsy New England town. Great place to raise a family. Amazing school system! Great restaurants and local shopping.... Read 12 reviews

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• Population 3,787

Current Resident: Sherman, Connecticut is the tiniest town I have ever lived in. This town is so little, but it has everything a kid and adult would want. The landscape is beautiful, and the outdoors are the most peaceful place ever! Sherman has all the necessitates, a library, beach, playgrounds, and a cute store for all of your needs. Although, one change to be made is a gas station; even if one is just 10/15 minutes away. This town is perfect for a family with kids, growing up in Sherman is the closest thing to perfect. The school teaches respect and courage. Although there is not a ton of entertainment, this town is amazing and overall the best.... Read 19 reviews

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• Population 3,545

Current Resident: A safe and reliable town to grow up in. Public schools are great in the area and access to major highway is as well. Yet, for experiences, Middlebury constantly lacks. Our one major attraction is a small lake where the entire town gathers. Our major streets lack sidewalks, and our restaurant selection consists of 3 places to get dinner, yet their hours are quite confusing. Yet, the clse knit community relationship you would expect from a small town does not exist in Middlebury. Everyone seems distant, and judgmental a majority of the time.... Read 27 reviews

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• Population 7,617

• Town in Connecticut

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• Population 1,592

Current Resident: Woodbridge is great if you like room (no postage stamp size land), you enjoy nature (lots of woods, trails, animals), like the quiet, enjoy high-minded conversations (lots of PhDs, Masters), have kids (schools are excellent), enjoy small town life (there's stuff to do but not much - PTO, school sports, library, some clubs...). Woodbridge is not great if you can't afford it (real estate is expensive, property taxes are high, you have to drive everywhere, etc.), if you like the night life (there is none, or you have to drive to New Haven), are politically conservative (I think I can think of maybe eight houses with GOP signs this past year), have no kids or not expecting any, like big town celebrations (Halloween is the only one I can think of that the town makes any fuss over). I love that my neighbors are from China, Argentina, Peru, and Lebannon - mostly Yale professors. Makes for fun experiences for myself and the kids. Wouldn't trade it - and the solitude is nice, too.... Read 29 reviews

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• Population 9,073

Current Resident: Stonington is a very nice town; When it comes to views, it is one of the most beautiful areas on the Connecticut coast. With this, there is a lot to do in the town during the summer months from concerts to food events to festivals. This comes with a downside, that in the winter, there is not much going on. Overall a great place to live!... Read 18 reviews

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• Population 18,354

• Town in Connecticut

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  Rating 4.13 out of 5  194 reviews

Current Resident: The reviews on Niche for West Hartford helped tremendously in helping us decide to move here back in 2018, and now that we’ve celebrated our 5 year anniversary, it felt only right to hop back on here and write a review of my own! I absolutely LOVE this town. WeHa seriously has it all : amazing restaurants, culture, great schools, shopping, concerts/theatre, parks, trails (bike and walking) - but most importantly, community. That was big on our list. Everyone is so welcoming, supportive and neighborly. I also love that it’s a walkable town. Moving from NYC, that was a big deal for us. Don’t think twice about moving here. Just do it!... Read 194 reviews

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• Population 64,034

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• Population 1,412

Current Resident: Branford, CT is one of those quintessential New England towns. It is a wonderful place to live and raise a family. It has a strong community feel, which comes from the many amazing aspects of the town including 1) its many parks, beaches, trails and ponds that are beautifully maintained and upgraded 2) the Main Street has great restaurants, coffee shops, salons, art, shopping etc. 3) the town green is a central place to meet for the annual Tree Lighting, parades, live music in the summer, scare crow contests in the fall, etc. 4) people who move here, stay here. Branford is a wonderful place to be.... Read 72 reviews

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• Population 28,230

Current Resident: It's an amazing, small, family friendly town. Everyone knows everyone. You feel safe and secure in this town. There isn't much to do or many restaurants but there is plenty in neighboring towns.... Read 8 reviews

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• Population 7,582