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

644 S Brooksvale Rd, Cheshire
$1,630,000
5 Beds ⋅ 5 Baths ⋅ 24207257 MLS
Nestled on 2.26 beautifully landscaped acres and set well back from the road, this exceptional contemporary Colonial offers a rare blend of privacy, elegance, craftsmanship, and resort-style living. With more than 6,300 square feet of above-grade living space and views of Cheshire Land Trust property, the home enjoys a peaceful natural setting while delivering an extraordinary collection of indoor and outdoor amenities. Natural light fills the home from every angle, beginning in the dramatic two-story foyer, where soaring floor-to-ceiling windows, a striking brick accent walls, elegant chandelier, and pellet stove create a grand first impression. The expansive first level features radiant floor heating and remarkable flexibility, offering a spacious family room, private office, full bath, and an impressive 43' x 15' room with endless possibilities. Walkout access leads to a covered deck and the private grounds beyond, making this level ideal for entertaining, a fitness studio, guest accommodations, an in-law suite, or multi-generational living. Upstairs, the main living spaces are both sophisticated and inviting. The gourmet kitchen showcases rich custom cherry cabinetry, granite countertops, custom stainless steel appliances, a center island, and a sun-drenched breakfast area overlooking the surrounding landscape. Formal living and dining rooms provide elegant entertaining spaces, while the vaulted Great Room with pellet stove serves as a warm and welcoming gathering place.

644 S Brooksvale Rd, 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.

How much is your home worth?

Get instant property value now!