2023 Best Places to Retire in Massachusetts

Current Resident: Very nice area, lots of beautiful beaches. There are many restaurants and shops line the sidewalks of mainstreet. There are awesome pizza places and the nightlife is better than most of the cape.... Read 4 reviews

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• Population 6,554

Former Resident: Quaint town with ever blooming residents. Serving as an attractive beach town for many vacationers and urban residents, much business revolves around tourism. Locals are also great, and do not treat those who aren't originally from the area any indifferent. North Falmouth, MA is a beautiful, friendly, and growing community.... Read 4 reviews

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• Population 2,375

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• Population 2,703

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• Population 2,119

Current Resident: Wellfleet has a lot of desirable qualities. The most notable ones are obviously the unspoiled beaches in the federally protected National Seashore and the calm waters on the bayside. But there are also endless miles of hiking trails amongst cedar trees, kettle ponds, wildlife sanctuaries, art galleries and a picture-perfect town center. The food scene in the town center rivals that of Boston. Most tourists pass through this town on route 6 do not know what a hidden gem Wellfleet is, and that is just fine for the rest of us who have discovered this place. Wellfleet is a low-key place where people come to find peace and serenity, though I have spotted celebrities in town on more than one occasion. I just love it here.... Read 2 reviews

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• Population 4,305

Current Resident: All of the towns on Cape Cod have their own unique feel but I love West Yarmouth the most as I live there! It's a pretty quiet, fun and great area to live.... Read 10 reviews

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• Population 6,124

• Suburb of Boston, MA

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  Rating 4.14 out of 5  14 reviews

Former Resident: Grew up here and couldn’t have asked for anything more. Was one of if not the top public school in the state when I graduated. It’s got one of the best beaches in Massachusetts and it’s a beautiful town all around with several parks. The people are nice and friendly and the downtown is quaint and charming. A great place to be if you’re a boater as Gloucester and Marblehead are quick shots via boat. There’s also plenty of weekend boating hangouts. Finally, there’s virtually no crime. The only crime is this town isn’t ranked higher.... Read 14 reviews

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• Population 5,382

• Suburb of Boston, MA

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  Rating 4.26 out of 5  19 reviews

Current Resident: I believe the school system is great! I have had very few teachers I did not like which is amazing for a public school. Although, the ratings have gone down and Wayland Public Schools is now not ranked top 10 in the state, when it was previously top 5 I believe. It is a predominantly white town although there is around 30% asians and 5% black students in my high school. Very easy access to 95 and 90 which makes the commute to activities easy. It is expensive but at the cost of good schools. Additionally, as a student there are always places looking for staff and also interns.... Read 19 reviews

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• Population 13,859

Current Resident: South Yarmouth is conveniently close to everything! A five minute drive to the highway or to a grocery store. It is easy to navigate.... Read 2 reviews

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• Population 24,890

Current Resident: Easy to get to Hyannis. Lots of areas for recreation. Family friendly town. Good police and fire services. Good choices for child care. Town run recreation activities for children. Senior Center offers many activities to Seniors.... Read 16 reviews

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• Population 5,872

Current Resident: It is a great town and we don't get a lot of the tourists. There is a large collection of art studios and history. If you want to take it easy and view a lot of culture, this is the best place on the cape. We have the best stuffed Quahogs and Lobster Rolls in Sandwich. You can also go to Sandy Neck Beach. It is really fun and has a snack bar.... Read 4 reviews

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• Population 3,765

Visitor: I had a great time in Eastham, Ma.. Eastham is a quaint little town with a few historical sites to see. I visited the Windmill on the green. How beautiful that was. What I enjoyed most were the biking and hiking trails that were available to me. The hiking trails/boardwalks were closer to the ocean side which gave a great view of the water and even along the way I saw a rock where Indian arrows were sharpened. I loved the fact I could choose to go to the bay or ocean side beaches. A great vacation spot to go. I do not want to forget that fresh lobster roll I at eat Arnolds!... Read 3 reviews

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• Population 5,674

Current Resident: A very charming community! My husband and I moved to the Pinehills a little less than a year ago. We are thrilled with our decision to build a home here! The Pinehills offers a quant community in the midst of Plymouth. It is the type of place where you go to the post office to pick up your mail and the postal workers know everyone by name. The community is active and the restaurants/amenities are an awesome plus. We love eating at Mamma Mia's or the Rye Tavern. Mirabeau is walking distance from our home, and it is perfect for a spa day with friends or relatives. The landscaping everywhere is gorgeous and the architecture throughout each neighborhood is charming and different. We look forward to laying down roots here!... Read 1 review

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• Population 4,724

Current Resident: Growing up in Brewster was fantastic. It is very family-oriented and safe, and is part of the fantastic Nauset Public Schools system. It is very quiet, so there aren't many places to go and do things in the wintertime. In the summer however, the nature makes up for all of it. Beautiful beaches and lovely ponds occupy children outdoors all summer long.... Read 14 reviews

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• Population 10,282

Visitor: Absolutely picturesque beach town that can fit the lifestyle of just about anyone. One of the best thing about South Yarmouth is its location on the Cape being 15 minutes to Hyannis and 20 to Chatham. There is a solid mix of homes here with many smaller cottages that are only used in the summers but, also some mansions on Bass River and on the ocean. There is no crime to speak of and for the most part people keep to themselves. Maybe a quarter of the residents are retirees and the vast majority have perfectly manicured yards with sprinkler systems to keep their grass the greenest. The yards are almost in competition between the grass and the hydrangeas.... Read 16 reviews

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• Population 11,696

Current Resident: Sandwich is the perfect little town. I love being able to live here, especially in the summer because the weather is perfect and the beaches warm up quick. There aren't many big national businesses here, which is good because there are a lot of local stores that are being supported. Sandwich is the perfect family-friendly place to live year round, or even to just come visit. The atmosphere is kind and inviting. You really feel at home in Sandwich. This town has everything a family could want or need!... Read 47 reviews

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• Population 20,369

Current Resident: I've lived in Harwich for nearly my whole life! I like it here a lot-you are close to the beach, which is super nice. Living on Cape Cod has a lot of perks! It's kind of secluded here, but you are close to Boston, Providence, even NYC!... Read 5 reviews

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• Population 13,329

Visitor: Orleans is a great town with some of the best and most well-known beaches on the Cape! There is lots of different shops in town and lots of exciting things going on. It is very pretty and lots of tourists come to Orleans in the summer for vacation.... Read 5 reviews

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• Population 6,276

Current Resident: Buzzards Bay is a beautiful place in Cape Cod. Right on the canal there is ice cream near by, shops, fairs, live music. Buzzards Bay has a “homey” feel to it and I recommend anyone that is interested in warm weather and salt air to visit. The tourists are attracted to the Cape Cod nature in Buzzards Bay. For sure a vacation hot spot!... Read 5 reviews

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• Population 3,206

• Town in Massachusetts

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  Rating 3 out of 5  2 reviews

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• Population 1,436

• Suburb of Boston, MA

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  Rating 3.96 out of 5  73 reviews

Current Resident: I have lived in Hingham for 45 years and brought up my two children here. The town is very welcoming and an excellent town to bring up your family. The schools are excellent. The town is only 20 miles from Boston, so very accessible to the arts and restaurants in the city. The town is right on the water, so many opportunities for summer fun. Hingham has so much to offer and it is a beautiful town!... Read 73 reviews

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• Population 24,061

Current Resident: Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. The population was 14,207 at the 2010 census.[1] The town encompasses five distinct villages, each of which has its own post office. These constituent villages are Dennis (including North Dennis), Dennis Port, East Dennis, South Dennis, and West Dennis.[2]... Read 7 reviews

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• Population 14,664

• Town in Massachusetts

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• Population 4,744

Current Resident: My experience living in Teaticket has been a positive one. As a former Mashpee resident, I can appreciate the differences between the two towns. Living in Teaticket has many pros, like the town curb trash pickup and the excellent schools. The town is also beautiful, views of the ocean, vast local farms, woodlands, marshes, and lots of conservation areas. Some cons about life in Teaticket that I'd like to see change is the traffic, the quality of the roads, and the ever-rising price of real estate.... Read 3 reviews

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• Population 1,522

Current Resident: Dennis Port is a great place to live! Its far enough out on the Cape to feel like a coastal area, and close enough to Hyannis to be convenient to most services, stores and restaurants. 16 fantastic beaches (I think), really great conservation/walking hiking areas, cute town center with some really nice shops and restaurants. The library is absolutely amazing! We have lower property taxes than many other towns on Cape Cod. Summers are more crowded and busy, winters are quiet. The most beautiful fall weather anywhere! Spring is a good time to travel off Cape. Year rounders are very friendly and helpful. Most second home owners are really great too. Every now and then there is a visitor bringing the place they left with them. With these folks we are patient but by no means pushovers. Also, the air is wonderful, when I go back over the bridge, I can't wait to get back to the sea breezes. The sky seems bigger because the trees don't grow as tall as in other places. Laid back life style.... Read 15 reviews

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• Population 3,440