CHESHIRE, CT — Cheshire's open houses this weekend include a Colonial whose great room has exposed beams, walls of windows and a stone fireplace, the original builder's model home in the Cheshire Crossing 55-and-older community, and a 1957 Colonial on nearly 2 acres with a deck across the back.
Four Cheshire homes are holding open houses Saturday, Oct. 17, and Sunday, Oct. 18, with prices from $499,999 to $649,900, according to Zillow.com.
Saturday, Oct. 17
1100 Coleman Road, 10:30 a.m. to 12:30 p.m., $649,000. This 1957 Colonial sits on a private 1.85-acre lot with hardwood floors throughout, according to the listing. The formal living room has a fireplace with a custom mantel, dentil crown molding and built-in bookcases, and the eat-in kitchen and family room share two bay windows and open onto a deck that runs nearly the length of the house. It's a four-bedroom, 2.5-bath home with 2,280 square feet. Its price was cut by $46,000 on Oct. 13.
385 Sir Walter Drive, noon to 2 p.m., $649,900. Listed Oct. 11, this 1961 Colonial on a level acre has a great room with a soaring ceiling, exposed beams, walls of windows and a stone fireplace with a pellet-stove insert that the listing says can heat the whole first floor. The renovated kitchen has quartz counters and a breakfast bar facing a family room with built-ins and a window seat, and the primary bedroom has an updated bath. The listing cites a new roof and updated windows. It's a three-bedroom, 2.5-bath home with 2,214 square feet.
3 Wadsworth Lane, noon to 2 p.m., $649,000. This is the original builder's model home at Cheshire Crossing, which the listing describes as a 55-and-older active-adult community surrounded by woodlands, with sidewalks throughout. The 2006 home has a first-floor office with French doors, a vaulted kitchen open to a vaulted family room with a propane fireplace, a three-season porch, a first-floor primary bedroom and an electric-car charger. It's a three-bedroom, three-bath home with 3,702 square feet; the HOA fee is $394 a month.
Sunday, Oct. 18
268 Eastgate Drive, noon to 2 p.m., $499,999. New to the market this weekend, this 1975 house is in a sidewalked neighborhood next to Highland Elementary, according to the listing. It has hardwood floors, an updated kitchen opening to a 16-by-20-foot deck, a living room with a fireplace, and a walk-out lower level with a rec room, an office and a full bath. Out back is a covered paver patio, and the house is wired for an included generator. It's a three-bedroom, 2.5-bath home with 1,642 square feet on 0.48 acres.
Make a weekend of it: Saturday, start on Coleman Road at 10:30 a.m., then choose between Sir Walter Drive and Cheshire Crossing, which both open at noon. Sunday, Eastgate Drive makes its debut at noon.
Listing details from Zillow.com as of Oct. 14, 2026. Open-house schedules can change; check each listing before you go.
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