$573,334Average Value$287Average Price per Sq Ft23Homes 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
Delaney Smith,
an experienced agent in this area.
On average, homes in Cheshire, CT sell after 57 days on the market compared to the national average of 54 days. The median sale price for homes in Cheshire, CT over the last 12 months is $525,000, up 7% from the median home sale price over the previous 12 months.
62+ Community. Welcome to Cheshire Hillside Village, a well maintained complex. Heat and hot water included. Assigned parking, and easy access to RT 10 & I-84. No pets are allowed.
Build your own expanded Cape Cod (or bring your own plans) on Blackberry Woods, Cheshire's newest development. 4 bedroom, 2.5 bathroom Maple model with a primary bedroom on the main floor. Oversized family room with fireplace opens to a custom kitchen with island. Formal dining room for get togethers and events. The 1st floor hosts the primary suite with large walk in closet and tile shower, and
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
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
Desirable end-unit townhouse located in the small and sought-after Walden Woods complex. This updated home offers a bright and open living room/dining room combination with hardwood floors and sliders leading to a private deck overlooking a level, wooded backyard-perfect for relaxing or entertaining. The updated eat-in kitchen features a pantry and ample cabinet space. An updated half bath
Your Dream Home in the Heart of Cheshire! Welcome to this stunning 5-bedroom/potential 7 bedroom, 5.5-bath Colonial located in the center of Cheshire. With over 5,000 sq. ft. of living space and set on more than an acre, this masterpiece offers the perfect blend of luxury, comfort, and convenience. The seller has spared no detail in the design and upkeep of this exceptional home. Main Floor
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
Welcome to this charming ranch style single family home, thoughtfully updated and conveniently located just minutes from I84 and Route 8, with easy access to the Merritt Parkway and I91 for an easy commute. From the moment you walk in, you will appreciate the bright and refreshed feel throughout. The kitchen has been updated with quartz countertops, stainless steel appliances, and brand new
886 Coleman Road is a 1.85 acre mostly level and gently wooded parcel with mature trees. It offers natural beauty abundant with wildlife. Located in the South end of Cheshire- it is known as Lot 3 of The Carol Ridge Subdivision. The spot offers a respite from the day- yet it is conveniently located within an easy commute from New Haven, Quinnipiac University and Yale. This makes it well suited
Donna Myjak CRS,SRES,SRSBerkshire Hathaway NE Prop.
15 Philson Court is a 2 acre lightly wooded parcel- also known as Lot 5 of The Carol Ridge Subdivision- which is a quiet established cul de sac in the south end of Cheshire. The location is ideal for those who value convenience and ease of commuting to New Haven, Yale, QU, and Tweed Airport for quick weekend jaunts. The Town of Cheshire has many offerings: Nearby shopping and restaurants
Donna Myjak CRS,SRES,SRSBerkshire Hathaway NE Prop.
BRAND NEW APARTMENTS coming JANUARY 2026!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. Property is under construction at this time. Please contact the Leasing Office to be added to the waitlist.
Move right into this beautifully remodeled one-bedroom apartment set in a peaceful North Cheshire location. This attractive first-floor unit features a slider to a private patio-perfect for easy, one-level living. Enjoy the updated kitchen complete with stainless steel dishwasher, refrigerator, and stove, along with a refreshed bathroom and brand-new laminate flooring throughout. Additional
Ready to embrace vacation-inspired living in Cheshire, Connecticut? Our modern studio, 1 & 2 bedroom apartments offer spacious, pet-friendly floor plans for rent. This quiet suburban oasis is close to endless shops, dining, and recreation destinations. Live it up, wind it down, or take life at whatever pace you desire – Lakeside of Cheshire delivers the lifestyle you’ve been searching for. We
Come view this true oasis of a home right in Cheshire. This unit is the perfect mix of quaint, cozy, and roomy. Offering 2 bedrooms, 1 bathroom, a living space, kitchen, and in-unit laundry. The grounds are well kept and you have access to a beautiful backyard where you can make it your own! The owners have kept this lot meticulous with maintaining the grounds and garden areas. The driveway is a
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
Updated 3-4 Bedroom Home in Prime Cheshire Location Enjoy comfortable living in this newly remodeled home located in a prime area of Cheshire. The home offers 3 bedrooms with the option to use an additional space as a 4th bedroom, home office, or flex room. Inside, you'll find a spacious primary bedroom, 2 full bathrooms, and fresh updates throughout. The home also features all new windows and a
Apartment Living Reinvented For The Twenty First CenturyAt Acclaim at Cheshire, youll discover the lifestyle youve been looking for has never been more within reach. Select your next residence from our spacious one or two-bedroom floor plans. Living at Acclaim at Cheshire offers a modern, efficient, and community-focused lifestyle. Designed with a blend of affordability, sustainability,
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
This property at 610 Ives Row features 3 bedrooms and 2 bathrooms within a total of 1,436 square feet. The living room offers ample space for relaxation and entertainment. The kitchen is equipped with a dishwasher and includes washer/dryer hookups for convenience. Each bedroom provides sufficient storage space, while the bathrooms are designed for functionality. The property is smoke-free,
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
Now available in the quiet and sought-after complex in south Cheshire is this 1,150 sq. ft unit town home! Surrounded by serene woods and minutes from the Farmington Canal Line State Park Trail and Sleepy Giant State Park. Close to I-91\I-95, Rt.10, shopping, & downtown New Haven!!Pets are welcome! (NF Dep applies) - Can be shown with proper notice Available on 4/01/2026 with
Welcome to Maplecroft Village! Nestled in the heart of Cheshire, this ranch-style apartment complex boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments have 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit has beautiful quartz countertops, a
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