$569,725Average Value$287Average Price per Sq Ft30Homes 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
Anthony D'Amore,
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 55 days. The median sale price for homes in Cheshire, CT over the last 12 months is $525,000, up 6% from the median home sale price over the previous 12 months.
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
Located in desirable Beacon Hill neighborhood, this custom-built oversized Cape Cod offers exceptional craftsmanship + thoughtful updates. Featuring hardwood flooring throughout most of the home, the layout blends classic charm with modern amenities. The beautifully remodeled 2020 kitchen is a standout with soapstone countertops, farmhouse sink, AGA gas stove with copper range hood, Big Chill
Completely updated Cape Cod-style ranch, custom built with quality craftsmanship throughout! This beautifully maintained home features Marvin Windows and hardwood floors. The formal living room is an inviting space with a fireplace and a beautiful bay window that fills the room with natural light. The stunning kitchen features granite countertops, and stainless steel appliances including a
Welcome to your bright and airy custom home inspired by the peaceful French countryside. Tucked away at the end of a private cul-de-sac, this sun-drenched home offers the perfect blend of class, comfort, and space. Step into the foyer and fall in love with the gleaming natural hardwood floors that flow throughout the main living areas. The living room impresses with soaring vaulted ceilings, a
The Carriage Home offers 2,450 square feet of thoughtfully designed space with 3 bedrooms, 2.5 baths, and bright, open living areas made for modern comfort. The first-floor primary suite provides convenience and privacy, while the airy great room and designer kitchen with a large island and hardwood flooring create a welcoming flow for everyday living. Upstairs, a spacious loft adds versatility
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 Mountaincrest neighborhood. A dramatic two-story marble foyer with a sweeping staircase welcomes you into elegant formal spaces, including a private office with glass
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
SOLD OUT! The Townhouse offers 1,850 square feet of thoughtfully designed space with 2 bedrooms upstairs and 2.5 baths. The main level features hardwood flooring, a luxury kitchen with a large island and premium finishes, and open living and dining areas filled with natural light. Expansive windows and carefully considered details throughout create a bright, inviting atmosphere that blends style
Welcome to Blackberry Woods, Cheshire's newest development. Consider The Willow, with its 3,029 sqft of Living Space on just over 1.36 Acres of Land. Fabulous Floor Plan includes an impressive 2 Story Foyer, First-Floor Full Bath, Large Kitchen Pantry, and Private Office on the Main Level. The Master Suite will "WOW" You with a Walk-In Closet, Double Vanities, Water Closet, and a Luxurious
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
Welcome to Blackberry Woods. Enjoy the Frasier model with 2,821 sqft of living space , w/ 4 Bedrooms and 2 1/2 Baths. This both elegant and practical model features a spacious Foyer with double coat closets, Mudroom and Half Bath off garage entry, open floor plan between the Family Room, Dinette & Kitchen, Gas Log Fireplace, Kitchen Pantry, and a backyard Patio with built-in Firepit! The formal
Blackberry Woods presents the gracious Charter Oak model which provides 2,459 sqft of thoughtful living space with 4 Bedrooms and 2 1/2 Baths. Desirable features of this plan include a spacious foyer entry with coat closet, mudroom off the garage entry w/ half bath and laundry, an open floor plan including a custom kitchen, dinette & family room, gas log fireplace, kitchen pantry, and sliders to
Located in desirable Beacon Hill neighborhood, this custom-built oversized Cape Cod offers exceptional craftsmanship + thoughtful updates. Featuring hardwood flooring throughout most of the home, the layout blends classic charm with modern amenities. The beautifully remodeled 2020 kitchen is a standout with soapstone countertops, farmhouse sink, AGA gas stove with copper range hood, Big Chill
Hillside Village, age restricted community 62+. One level living, 1 bedroom with an additional living space that could be used as a 2nd bedroom (no closet). Slider to patio and yard area, stackable washer/dryer. Condo fees include heat and hot water. Close to restaurants, shopping, public library, and highways. Sold in as is condition, needs work and updating.
Pride of ownership shines in this beautifully maintained Colonial. A spacious foyer with hardwood floors welcomes you into a thoughtfully designed eat-in kitchen featuring a cherry wood island with leathered granite, abundant cabinetry, stainless steel appliances, and under-cabinet lighting. The sun-filled family room offers vaulted ceilings and a brick wood-burning fireplace with a rustic barn
Welcome to 566 West Main Street-where charm meets comfort with a fresh, inviting feel for the season. This well maintained 3-bedroom, 1-bath first floor space features wide plank hardwood floors, a spacious sun-filled living room, and timeless character throughout. Natural light pours into every room, creating a warm and airy atmosphere that feels just right for easy everyday living. The
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
BRAND NEW APARTMENTS!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.
Now through April 30th - Special promotion on new 12-month leases only: New tenants get the choice of ONE of the following: A) Free storage unit for a year (any size, subject to availability), B) $1,000 flexible spending credit immediately applied to the tenant account (use toward rent, storage, pet fees at whatever time period tenant wants to use it during the lease - but does not apply to
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 step inside, 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.
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
Now through April 30th - Special promotion on new 12-month leases only: New tenants get the choice of ONE of the following: A) Free storage unit for a year (any size, subject to availability), B) $1,000 flexible spending credit immediately applied to the tenant account (use toward rent, storage, pet fees at whatever time period tenant wants to use it during the lease - but does not apply to
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
Available for occupancy June 1st, 2026, this move-in ready 3-bedroom, 2-bath Ranch in Cheshire, CT blends modern convenience and classic charm. Inside, you'll find a versatile room with a wall of windows, ideal for a guest room or home office. The spacious living room features built-ins and wood floors, leading to a renovated kitchen with stainless steel appliances, stone backsplash, and
This 3-bedroom, 2-bathroom home located at 1941 Peck Ln offers 1,300 square feet of living space. The living room provides ample room for relaxation and entertainment, while the kitchen includes all the necessary appliances, washer/dryer hookups for added convenience. Each bedroom is designed for comfortable living, and the bathrooms feature both tub and shower options. Additional amenities
Location! Location! Small 1 bedroom apartment , updated kitchen and bathroom. Unit is located on 2nd floor of 4 family residential home with off street parking. Laundry hook ups and secured storage unit located in basement. Beautiful private backyard can be used for BBQ. Walking distance to restaurants and shops. Small dog or cat considered with Landlord approval and additional pet deposit. 1
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