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.

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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.

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Newest Homes for Sale in Cheshire, CT

16 Mountaincrest Dr, Cheshire
$1,590,000
5 Beds ⋅ 5 Baths ⋅ 24207532 MLS
Perched high above the landscape of South Cheshire, this extraordinary custom-built Colonial is a residence of uncommon beauty, privacy, and scale. Set against the natural backdrop of Bethany Mountain and surrounded by meticulously maintained, park-like grounds, this exceptional 4/5-bedroom home captures magnificent views, abundant sunshine, and a remarkable sense of tranquility. From the moment you arrive, there is an unmistakable feeling that this is something special. Thoughtfully designed and impeccably cared for, the home combines the timeless elegance of classic Colonial architecture with the openness and amenities expected of today's finest residences. Inside, soaring ceilings, gleaming hardwood floors, and an inviting open floor plan create an effortless connection between the home's gracious living spaces. At its center is a beautifully appointed gourmet kitchen, equally impressive as a gathering place for family and friends or as the culinary heart of sophisticated entertaining. The main level continues with an elegant formal living room, formal dining room, private library, laundry room, and oversized three-car garage, providing an exceptional balance of formal spaces, everyday comfort, and practical convenience.

16 Mountaincrest Dr, Cheshire
1 Mountaincrest Dr, Cheshire
$1,375,000
4 Beds ⋅ 5 Baths ⋅ 24206472 MLS
A timeless, flexible floor plan with all the newest upgrades. Majestically situated on a gentle hill in a South Cheshire neighborhood, this home is designed to capture the country setting.The impressive 4,000+ sqft contemporary colonial is move-in ready. The cook's delight kitchen features stainless steel appliances, a Sub-Zero refrigerator, a 5-burner gas stove with vented hood,Two full size microwaves, Fisher Paykel drawer dishwasher and an expansive granite island w/seating for 5 & opening into the spacious living room with gas fireplace, wet bar and built-in sound system. The familyroom has french doors opening on to an expansive deck & screened gazebo. The private main floor study comes complete with custom built-ins, hardwood floors and glass french doors, this extra first floor room can serve as a multipurpose area as well. A large mudroom with built-ins and a separate laundry room add everyday function. All-new stunning baths and hardwood floors throughout add polish. Upstairs, your private primary retreat awaits, a cozy sitting nook plus spacious marble bath with soaking tub, glass shower, oversized vanity & expansive separate closets. There is a princess bedroom with private marble bath. As well as, a Jack-n-Jill layout bedrooms and bath. Flexible living space on the walk-out lower level ideal for recreation,media, guestroom, gym or just to relax in nature with a wonderful outdoor hot tub. In addition to the 3 car garage there is an EV hook-up!

1 Mountaincrest Dr, Cheshire
885 S Brooksvale Rd, Cheshire
$1,279,000
5 Beds ⋅ 5 Baths ⋅ 24202325 MLS
Discover this truly exceptional custom Colonial home, distinguished by its thoughtful design, custom millwork, architectural details, and masterful craftsmanship both inside and out, situated on a desirable 2.37 acres corner lot in one of South Cheshire's most sought-after areas. Custom wrought iron gates welcome you into this warm, inviting home, flooded with natural light from the abundant large windows, skylights, and French doors. The heart of the home is the beautifully remodeled kitchen, with its expansive center island offering both exceptional functionality and a wonderful gathering space. The kitchen flows into the spacious family room which provides easy access to the covered porch, allowing effortless, comfortable daily living and entertaining. The first-floor primary bedroom provides convenience and privacy, while three large bedrooms upstairs offer generous space for all. Enjoy year-round sunshine in both the four-season terrace room and the separate sunroom, which bring the outdoors in. A versatile finished space with a full bath above the garage offers possibilities for home offices, a studio, a recreation room, and more. The exceptional outdoor setting offers a resort-like experience; the covered rear porch featuring a raised cedar ceiling, skylights, and terracotta tile, provides an inviting gathering space. Follow the path through the gardens to the heated in-ground Gunite swimming pool and hot tub, creating your own retreat for relaxation and entertaining!

885 S Brooksvale Rd, Cheshire
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