Cheshire, CT Real Estate & Homes For Sale

36 homes

Real Estate & Homes For Sale Near Cheshire, CT

We found 30 more homes matching your filters just outside Cheshire

Cheshire, CT Real Estate Trends

Learn about the Cheshire, CT housing market through trends and averages.

Affordability of Living in Cheshire, CT

The median home value is $535,956
MonthMedian home value
June 2025$513k
July 2025$516k
August 2025$520k
September 2025$523k
October 2025$526k
November 2025$528k
December 2025$529k
January 2026$530k
February 2026$531k
March 2026$532k
April 2026$534k
May 2026$536k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Cheshire, CT, by Home Size

Currently, there are 10 new listings in Cheshire, CT and 36 homes for sale.
Home SizeHome Value*
1 bedroom (See homes)$219,000
2 bedrooms (3 homes)$349,580
3 bedrooms (12 homes)$494,073
4 bedrooms (10 homes)$664,957
*Home value over the past month

Explore Neighborhoods in Cheshire, CT

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Neighborhood stats provided by third party data sources.

What Locals Say about Cheshire

Review Highlights

Cheshire, CT: steady, family-friendly suburb with top schools, safety, and durable home values. Loved for safe streets, A-rated schools, trails and parks, tight-knit, dog-friendly vibe. Disliked for Route 10 congestion, limited nightlife and shopping; slower commutes.
AI-generated summary of moderated reviews.
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  • Trulia User
    Chesire Village, Cheshire
    "Beautiful respectful peaceful people and neighborhood grate community. Clean and organized and has such a great atmosphere and very family orientated "
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  • Joshua Wendell
    "It’s easy to get to the highway. Though in some parts of town it can take time to get through and make your way towards where you’re going. "
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  • Reneechoquette
    "Great for trick of treating, close to the rail trail for biking, walking, running, or walking the dog! "
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  • Ctbondlynx
    "Yes dog friendly. Dog parks are near by. And plentiful. Many dogs in the Cheshire neighborhoods. Dogs"
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  • Reneechoquette
    "Safe, quiet, friendly, and lots of kids in this neighborhood (great for trick or treating!) Thr elementary school and rail trail (for waking and biking) are all in walking distance. "
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  • Hollie.barclay
    "Amazing school district and great for kids growing up. We drive a vehicle for all our needs and only use a bike for rec purposes. We have walked on a few occasions but not often. "
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  • Reneechoquette
    "My commute is into Hartford and there is public transportation into the city. The drive otherwise is about 45 min. "
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  • Taylor D.
    "Lights of hope, relay for life, town sports and community outreach programs. Fairs and festivals in the fall with small business promotion"
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  • Russell P.
    "about half an hour, I don't work in town. traffic can get pretty bad going south on the highway. back roads offer a good alternative, drivers I. the area tend to be slow though. "
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  • Sheena N.
    "Cheshire is a nice quiet town. Not too much to do, not many restaurants or shopping centers, but close enough to everything where you don’t really mind. "
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  • Janemarques08
    "That there are plenty of walking trails and sufficient sidewalks to safely walk your dog, whether it’s early morning or late at night. Totally safe neighborhood. "
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  • Sheena N.
    "Close to 84 and 691. Not too far from Merritt or 91. Route 10 can be congested at times, but mostly everything is easy to get to"
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  • Stephanie B. P.
    "Dogs are usually seen walking on leashes. Most are friendly and owners greet each other allowing them to engage. "
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  • Mary
    "On my neighborhood street almost everyone has well behaved dogs. The neighbors clean up after their dogs. The street is perfect walking dogs- less traffic and extra wide roads. "
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  • Janemarques08
    "I’ve lived her for two years. I know most of my neighbors. I feel good knowing that my children attend top “A”rated schools and that we live in a safe neighborhood. "
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  • Nelson_sheena
    "The school system in Cheshire is great. They have tons of fun family activities. The community seems safe as well. Kids ride bikes on the trails and always people are walking their dogs. "
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  • Nelson_sheena
    "Route 10 can be a little crowded during rush hour, but its not bad. The roads are clear and cleaned. "
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  • Sjhickok01
    "great safe place, lots of kids, lots of great wildlife. most people walk their dogs 2-3 times a day...almost everyone is friendly. Beautiful area due to all of the different trees and plants. Beautiful holiday lights and halloween is always a favorite. lots of festivals during the spring/summer season."
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  • janemarques08
    "We have movie night with popcorn near my neighborhood. Lots of group support and activities for the children. "
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  • Jcasner
    Chesire Village, Cheshire
    "Safe great schools, best fire department and good police department. Great parks overall one of the best towns in CT. "
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  • Alyss L.
    "Lots of families with kids and a closed loop street. I also grew up here (1985+) and the town has barely changed. Love that I can raise my kids here now."
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  • Sara c.
    "My neighborhood is amazing! It is very quiet and and neighbors are friendly. We have easy access to all major highways."
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  • Nelson_sheena
    "Dogs are always walking all around the neighborhood. Dog friendly for sure. I see more pits and retrievers than any other dog breed"
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  • Dorothy R.
    "I am retired so I don't have a commute. Family member does and has described it as usually uneventful."
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  • Emily M. G.
    "Great neighborhood in a great town, I feel safe. I’ve lived and grew up here for 23 years and I would live in cheshire as an adult"
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  • Nelson_sheena
    "Quiet, farm land, lots to do. Good restaurants and lots to do with the kids. Lots of shops, banks, pretty scenery"
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  • Emily M. G.
    "It’s a small, nice, and safe neighborhood. I’ve lived in the same house my whole life. It’s right next to mixville, I love walking around my neighborhood, everyone’s very nice."
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  • Nelson_sheena
    "Cheshire is a quiet well kept town. The condos I live in are quiet and everyone is respectful. Lots of wildlife too"
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  • adsinsight
    Chesire Village, Cheshire
    "Live near by, wish I lived here! Great place to raise a family and enjoy life's simple pleasures. Community is very close.. "
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