$571,892Average Value$289Average Price per Sq Ft25Homes For Sale
Cheshire is a suburbanizing town north of New Haven
If you want a Cheshire smile on your face, you may want to check out Cheshire, Connecticut. This suburban New England town is relaxing, idyllic, and has plenty to do. "It's a small friendly town," says Marc Seigel, a Realtor with RE/MAX RISE. "It's got a homey feel and great people. It used to be rural, but it's become more suburban over the years."
Community pride is strong at Cheshire Pizza & Ale.
With wide lawns and covered porches, Cheshire residents have plenty of options to relax and enjoy the weather on a sunny day.
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Cheshire hosts several youth sports teams, from baseball to football
Cheshire is a sports town without a professional sports team; it's mostly the kids and parents playing recreationally. There are plenty of youth leagues that make use of the town's considerable green space. "There are strong sports organizations in town for the kids," Seigel says, "Whether it's baseball, soccer, or football." Bartlem Recreation Area is home to baseball and soccer fields, along with the indoor community pool, where Seigel says you'll often find residents swimming and splashing around. Sports aren't only restricted to kids Cheshire, "As an adult," Seigel says, "I'm playing pickleball or tennis. We have lots of courts available."
Cheshire teams often compete at the fields of Bartlem Recreation Area.
Bikers and hikers enjoy the Farmington Canal Heritage Trail which connects Cheshire to towns all the way from New Haven to Suffield.
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Cheshire's semi-rural homes rarely come on the market
The community found in the parks and sports courts translates back to Cheshire's tidy suburban streets, "You definitely know your neighbors," Seigel says. "People care about having good relationships with each other." Becoming a neighbor in Cheshire can be tough, though. "It's difficult to get a house here," Seigel says. "We have very little inventory. New England is showing scarcity in the housing market." It's not impossible by any means, but if you see a house in Cheshire go up for sale, you'll have to act fast. Homes in town start around $450,000 for three bedrooms and two baths with just under an acre of land. Homes in town top out around $1 million for waterside new builds with four bedrooms and four bathrooms for those looking for plenty of space and a lake in the backyard.
Older homes in Cheshire offer a variety of unique architectural details.
Cheshire has many recently developed areas with large modern homes.
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A local museum attracts comics and cartoons fans
Whether you're a kid or a grownup, the Barker Character Comic and Cartoon Museum is likely to put a wide smile on your face. Open since 1997, the museum is home to over 80,000 pieces of memorabilia centered around American pop culture. You'll find iconic lunch boxes, comic books, and action figures from American cultural touchstones like G.I. Joe, The Incredible Hulk, and Loony Tunes -- but that's not all, folks! The museum owners offer free admission in April for all ages, so if you're looking for the right time to go, you won't feel like an April fool if you head to the museum on April 1. You'll just have some more money in your pocket. Whether you're looking to lace up for a game of pickleball, take the kids to soccer practice, or just find a community where you'll have a friendly relationship with your neighbors, you'll find plenty of reasons to smile in Cheshire.
Popeye, who shares his birthday with museum founder Herbert Barker, is well represented at Cheshire's Barker Character, Comic & Cartoon Museum.
The grounds of Cheshire's The Barker Character, Comic & Cartoon Museum offer countless photo opportunities.
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Students received A-rated educations at Cheshire schools
Students are part of the acclaimed Cheshire Public Schools system, rated with an A on Niche. For kindergarten through sixth grade, students may attend Highland School, which Niche gives an A. Dodd Middle School and Cheshire High School also earn As. High school students can take advantage of career and technical education courses in STEM subjects, hospitality, education and more.
Cheshire Academy has students from 27 countries on its 104-acre campus in Cheshire.
Cheshire High School is a highly rated public school that serves about 1,400 students in town.
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Photography Contributed By
Ed Messenger
Video By
Nathan Allen
Interested in learning more about homes in this area?
Reach out to
Kelly Hill-Mihalyak,
an experienced agent in this area.
On average, homes in Cheshire, CT sell after 55 days on the market compared to the national average of 58 days. The median sale price for homes in Cheshire, CT over the last 12 months is $525,000, up 2% from the median home sale price over the previous 12 months.
Welcome to a home that perfectly balances proportions w/the warmth of a true family home!Built just 4years ago this stunning Cont/Col offers a new construction feel with all the extras usually added after closing!Step inside to find gleamingHW floors that flow seamlessly throughout.The dramatic two-story greatrm serves as the centerpiece,anchored by a cozy gas FP & flooded with natural light.It
Build your dream Carriage Home from the ground up at The Reserve at Stonebridge Crossing-Cheshire's premier low-maintenance community by EG Home. This spacious 2,450 sq ft floor plan offers the perfect blend of comfort, flexibility, and energy efficiency, with the opportunity to personalize every detail. Create your ideal kitchen by selecting from EG Home's curated layouts, including our Pro
Charming 4 bedroom, 2.1 bath Colonial located on a desirable sidewalk-lined cul-de-sac in sought-after South Cheshire. This classic center-hall floor plan offers a light and bright kitchen, spacious living and dining rooms with hardwood floors throughout, and an expansive family room featuring a beautiful custom fireplace mantelpiece. Finished lower level adds additional living space with a
Majestically situated on a gentle hill designed to capture sweeping views of horses mountains and the picturesque countryside. This impressive 4,701 sq ft contemporary colonial is located in the highly sought after South Cheshire neighborhood. A dramatic two-story marble foyer with a sweeping staircase welcomes you into elegant formal spaces, including a private office with glass French doors and
Welcome to a home that perfectly balances proportions w/the warmth of a true family home!Built just 4years ago this stunning Cont/Col offers a new construction feel with all the extras usually added after closing!Step inside to find gleamingHW floors that flow seamlessly throughout.The dramatic two-story greatrm serves as the centerpiece,anchored by a cozy gas FP & flooded with natural light.It
Welcome to this meticulously well-kept ranch, where comfort meets style in every corner! This delightful home boasts 3 bedrooms and 2.5 updated bathrooms, offering plenty of room for relaxation and family life. Step into the updated kitchen, complete with gorgeous granite countertops and stainless-steel appliances. Every bathroom in the house has been thoughtfully renovated, and the recently
Sophisticated elegance defines this 4,437 sq ft architect-designed Contemporary Colonial, featuring a luxurious first-floor primary suite with a custom closet, walk-in limestone shower, and separate soaking tub. The chef will appreciate the beautifully designed kitchen with a stainless-steel six-burner Viking gas range, double ovens, and expansive thick granite counters with seating. A charming
Beautifully renovated ranch-style condo offering approximately 900 sq. ft. of total living space. This bright and spacious 2-bedroom condo features an open floor plan, refinished hardwood floors, abundant natural light, and a stunning new kitchen completed in 2025 with slow-close cabinetry, oversized pantry, Bosch French-door refrigerator, Whirlpool appliances, hidden-panel dishwasher, and modern
A rare find!Brand new farmhouse style contemporary Colonial being constructed at the south end of town in a picturesque country setting close to shopping & easy highway access.The home is available to customize & make changes while under construction & should be ready for late summer occupancy.The home offers HW floors on the main level & landing,2zone gas heat & central air,9' ceilings on the
Build your dream Carriage Home from the ground up at The Reserve at Stonebridge Crossing-Cheshire's premier low-maintenance community by EG Home. This spacious 2,450 sq ft floor plan offers the perfect blend of comfort, flexibility, and energy efficiency, with the opportunity to personalize every detail. Create your ideal kitchen by selecting from EG Home's curated layouts, including our Pro
Welcome to the opportunity to build your dream home in a highly desirable location. Nestled on a secluded rear lot that is just under an acre, this thoughtfully designed 4-bedroom, 2.5-bath Colonial will offer 2,792 square feet of beautifully crafted living space with the perfect blend of privacy and modern comfort. Designed with today's lifestyle in mind, the open concept layout will seamlessly
Unique Multi-Home Property on Over 3 Private Acres! A rare opportunity to own two homes on one beautiful property in a peaceful, private setting. Property Highlights: Over 3 acres of land R-40 zoning - ideal for farming, gardening, horses, or hobby farm potential Quiet country setting surrounded by nature Endless possibilities for multi-generational living, rental income, or guest house Main
Investors and long term planners, welcome to Hitchcock Lake! This home is currently leased until Oct 2026, and the next 6 months of rent can be yours to collect to offset your purchase. After that, enjoy lakefront living at its finest! Photo's were taken prior to tenants moving in! This home has been meticulously maintained in all ways, and has almost too many great features to mention on one
Much-loved home for over 40 years. But it's time to move on. This 4 bedroom 2.5 bath colonial is located in a neighborhood of more expensive homes. Kitchen includes a stainless steel gas range with double ovens, Stainless refrigerator and wood top island. The bright sunroom entered from the kitchen and family room is heated by passive solar. The bedrooms are spacious with hardwood flooring. The
Unique opportunity to own Waterfrontage in Cheshire. This one of a kind planned unit development, sitting on the pristine Lake Percival with an exquisite waterfall is offering a 1-acre lot available to build your dream home. The location of the former Percival Estate home boasts vast views of the pond from the building area, with no flood insurance required, bring your contractor to lay out your
Beautifully maintained condo located in quiet condominium community, conveniently located close to town center. The kitchen offers granite counter tops, pantry closet and an island, with a door to the shared back yard. There is a half bathroom on this level as well. The kitchen opens to an large living room/dining room combination. There are two spacious bedrooms and a full bathroom upstairs. The
Highland Farms combines a comfortable suburban location with access to nearby restaurants and services. Located less than a mile from The Shops at Stone Bridge, a brand new shopping center offering grocery, retail, and more. Please contact the Leasing Office for availability.
Nestled in a prime, central location in the heart of Cheshire, these apartments are crafted to offer a harmonious blend of style and functionality. From the moment you enter, you'll be greeted by spacious layouts adorned with upscale finishes and contemporary touches.The open-concept living areas provide the perfect backdrop for entertaining guests or unwinding after a long day. Each
Why compromise when you can have it all at Acclaim at Cheshire? Our affordable housing in Cheshire brings you the perfect blend of budget-friendly rates, modern amenities, and a convenient location. Whether you're seeking relaxation, exercise, or local exploration, our community has you covered. Beyond our apartments, you'll find close access to public transportation and an array of shopping,
Riverpointe Cheshire encompasses 300 apartment homes within 10 buildings spread amongst beautifully manicured landscape. This stunning community features studios, one-bedroom (with option for a den), two-bedroom, and three-bedroom residences. The community will be completed with sophisticated unit and common area finishes as well as a robust amenity program for all residents to enjoy.Riverpointe
Amazing property and a great place to make a home-- Check for Available units as we DO NOT HAVE ANYTHING AT THIS TIME!!! AUGUST 2026 IS THE NEXT APARTMENT. Don't wait to get in touch with us about these Great units in a fantastic location- No smoking, No pets-- Good credit and Good income needed to qualify. Heat and Hot water, cold water, sewer, trash included in the rent. Super onsite, ample
A rare opportunity to rent a fully updated 3 br 1.5 bath home in Cheshire. Spacious and bright open floor plan for easy and functional everyday living. A lovely updated kitchen with stainless appliances and convenient laundry. Hardwood flooring. Combination living room and dining room with additional space for work area . Oversized 2 car garage included. A fenced in backyard perfect for a furry
Donna Myjak CRS,SRES,SRSBerkshire Hathaway NE Prop.
Welcome to Maplecroft Village! Nestled in the heart of Cheshire, our ranch-style apartment complex, built in 2024, boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments offer 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit offers beautiful
Beautiful 4 Bedroom House *w/ an In-Law* in Cheshire! Garage Parking, Central Air, & a Beautiful Backyard Main House Features: - 3 bedrooms - 2 bathrooms - Bright, open floor plan kitchen/living room with dining nook - Big kitchen with tons of prep space & newer appliances, perfect for any occasion! - Primary bedroom w/ an en-suite bathroom - Finished basement with 4th bedroom, bonus room, and
Welcome to Maplecroft Village! Nestled in the heart of Cheshire, our ranch-style apartment complex, built in 2024, boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments offer 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit offers beautiful
For Rent - Luxury Carriage House at The Reserve at Stonebridge Crossing. This stunning three-bedroom, 2.5-bath residence offers the perfect blend of modern design and luxury finishes in one of the area's most desirable communities. Step inside to discover expansive tall ceilings, gleaming hardwood floors, and an open-concept floor plan ideal for both everyday living and entertaining. The gourmet
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