Upcoming Open Houses In Woodbury & Middlebury

WOODBURY, CT — Woodbury's history is on display this weekend: a 1747 saltbox compound with a carriage house and barn, and the John Cramer House, a Greek Revival listed on the National Register of Historic Places. A 1940 in-town Colonial and a 2025 Middlebury Colonial round out the four.

Four Woodbury and Middlebury homes are holding open houses Saturday, Oct. 31, and Sunday, Nov. 1, with prices from $529,000 to $1,278,000, according to Zillow.com. Three are in Woodbury and one is in Middlebury.

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Saturday, Oct. 31

509 Weekeepeemee Road, Woodbury, 11 a.m. to 1 p.m. (also Sunday), $1,278,000. This three-bedroom, 2.5-bath saltbox dates to 1747, with original wide-plank floors, two fireplaces and twin staircases, plus a kitchen with Viking appliances. The grounds include a two-bedroom carriage house with a 2.5-car garage, a 40-by-28-foot barn and a fieldstone fire pit, and the listing cites a new cedar-shingle roof with copper downspouts in 2025. It has 2,346 square feet on 5.19 acres.

Sunday, Nov. 1

11 Judson Avenue, Woodbury, 11 a.m. to 1 p.m., $529,000. This three-bedroom, 1.5-bath Colonial was built in 1940 in town, with a front-to-back living room with a fireplace and built-ins, a dining room with a built-in china closet and oak floors. A floored walk-up attic leaves room to expand. It has 2,120 square feet on 1.16 acres.

10 Weekeepeemee Road, Woodbury, noon to 2 p.m., $599,900. This three-bedroom, 1.5-bath home is the John Cramer House, a Greek Revival from 1843 that's listed on the National Register of Historic Places along with its late-19th-century barn, according to the listing. It has chestnut plank floors, nearly 9-foot ceilings and an original fireplace with a beehive oven, and the barn has two horse stalls. It has 2,012 square feet on 3.09 acres.

18 Hunting Ridge Road, Middlebury, noon to 2 p.m., $789,900. This four-bedroom, 2.5-bath Colonial was built in 2025 on a cul-de-sac, with open-beam ceilings, an oversized quartz kitchen island and a 12-by-14-foot dressing room off the primary suite. A main-level bedroom and full bath suit guests, and a wooded hill out back means no rear neighbors, according to the listing. It has 2,700 square feet.

Also open Sunday: 509 Weekeepeemee Road, 11 a.m. to 1 p.m. (see Saturday).

Sunday packs all four in: the 1747 saltbox and Judson Avenue at 11 a.m., then the John Cramer House, also on Weekeepeemee Road, and Hunting Ridge Road at noon.

Listing details from Zillow.com as of Oct. 29, 2026. Open-house schedules can change, so check each listing before you go.