Cheshire Real Estate

Cheshire, CT Homes for Sale

Cheshire, CT homes for sale generally range from $325,000 for older capes to over $800,000 for newer colonials on larger lots. Dave Jones Realty has worked this Route 10 corridor for decades, guiding buyers through neighborhoods that mix mid-century construction with subdivisions built since the 1990s. Cheshire sits about 20 minutes north of New Haven and 25 minutes south of Hartford, making it a practical choice for commuters splitting the difference between both cities while staying in a well-regarded school district.

Be the First to Know About New Cheshire Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Cheshire Real Estate Map Search

Home Styles and Price Ranges

Cheshire's housing stock centers on colonial-style homes built between 1970 and 2005, typically listing between $450,000 and $700,000 with 2,000 to 3,200 square feet. Older cape and ranch homes near the town center date to the 1950s and 1960s and price between $325,000 and $450,000. Larger custom colonials on lots of one acre or more, common in the northern and western sections of Cheshire, list from $700,000 to over $1 million.

Neighborhoods

Cheshire Center

The area around South Main Street and Route 10 holds Cheshire's oldest homes, including capes and colonials within walking distance of the town green and Bartlem Park. Lot sizes here average a quarter to a third of an acre with mature trees.

Northern Cheshire

Northern Cheshire near Mixville Road and West Main Street features larger colonials on one-acre-plus lots built since the 1990s. Homes in this section commonly exceed 3,000 square feet and back onto wooded parcels.

Daily Life

Cheshire residents reach Interstate 84 in Southington in about 12 minutes and Interstate 691 in under 10 minutes for connections to New Haven and Hartford. The Farmington Canal Heritage Trail runs directly through town, offering a paved route for walking and cycling. Cheshire High School serves the entire town, and Bartlem Park hosts town recreation programs and summer concerts. Downtown Cheshire along South Main Street holds locally owned restaurants and shops within the historic district.

Working With a Local Agent

Dave Jones Realty has represented buyers and sellers across Cheshire Center and northern Cheshire, offering direct comparison between the town's older core and its newer subdivisions.

Newest Homes for Sale in Cheshire, CT

$499,900
3 Beds 2 Baths 24198101 MLS
***Seller is asking for highest and best Due 12 pm on Tuesday August 18th. *** Welcome to 25 Stacy Court, a well-maintained raised ranch set on 0.92 acres in a desirable Cheshire cul-de-sac. Offered by the original owners after 55 years, this 1,905-square-foot home features three bedrooms, one full and one half baths, hardwood floors throughout the main level and plenty of indoor and outdoor living space. The living room has vaulted ceilings, a wood-burning fireplace and opens to the dining room, where a newer slider leads to the Trex deck. Three bedrooms and one full bath offering a tub, double-sink vanity and granite countertop complete the main level. Downstairs, the carpeted family room features a second wood-burning fireplace, along with a half bath, laundry area and access to the attached two-car with newer doors. Enjoy summer days around the in-ground vinyl pool with concrete surround and pool house. Additional features include a whole-house fan, gutter guards, paver side walk, and nicely landscaped yard. Valuable updates include the driveway in 2023, roof in 2014, pool liner and filter in 2016, chimney repairs and new chimney cap in 2024, boiler servicing in 2025 and a brand-new septic system in 2026. Private well, oil-fired baseboard heat and wooden shake siding. Convenient to Cheshire amenities and the new Barnum Elementary School. A wonderful opportunity to personalize a cherished one-owner home! Owner to find suitable housing.

25 Stacy Ct, Cheshire

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.