Upcoming Open Houses In Woodbury & Middlebury

WOODBURY, CT — This weekend's open houses in Woodbury and Middlebury include a 1790 Colonial with a separate studio its listing pitches to an artist, a Craftsman in Middlebury's Historic District beside the Crest Preserve and a Woodbury estate with a steel-and-concrete barn for six to eight cars.

Six Woodbury and Middlebury homes are holding open houses Saturday, Nov. 7, and Sunday, Nov. 8, with prices from $359,900 to $2,149,900, according to Zillow.com.

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Saturday, Nov. 7

700 Watertown Road, Middlebury, 11 a.m. to 1 p.m., $590,000. This four-bedroom, three-bath Colonial dates to 1790, per Zillow, and sits on 1.25 landscaped acres with stone walls and patios. The eat-in kitchen has a fireplace with a pellet stove insert, there's a sunroom and a finished attic, and a separate outbuilding studio is, the listing says, perfect for an artist or office. It has 2,528 square feet, and the price was cut $25,000 on Aug. 4.

35 Woodbury Hill #35, Woodbury, 11 a.m. to 1 p.m. (also Sunday, 1 to 3 p.m.), $510,000. This two-bedroom, 2.5-bath condo is in Woodbury Hill, a complex of 78 condos with a saltwater pool and a tennis and pickleball court. It has a vaulted living room with a wood-burning fireplace, a main-level primary suite, a deck with a view and a lower-level family room. It has 1,796 square feet and a $654 monthly HOA fee, per Zillow.

36 Atwood Road, Woodbury, 11 a.m. to 2 p.m., $375,000. This three-bedroom, one-bath ranch sits on a quiet country road, with hardwood floors, a white kitchen, a newer deck and a landscaped backyard with perennial gardens. The listing cites a brand-new septic system and newer heating, cooling and roof. It has 1,008 square feet on 0.54 acres.

77 Crest Road, Middlebury, noon to 2 p.m., $699,900. This four-bedroom, 3.5-bath Craftsman is in Middlebury's Historic District, bordering the 9-acre Crest Preserve, with original hand-carved staircases, reading nooks and a chef's kitchen with double ovens. The backyard has bluestone patios and a renovated gunite saltwater pool. It has 2,674 square feet on 1.5 acres, and the price was cut $50,000 on Nov. 2.

Sunday, Nov. 8

348 Weekeepeemee Road, Woodbury, noon to 2 p.m., $2,149,900. This five-bedroom, 4.5-bath Colonial sits well back from the road on 9.48 acres, with a kitchen opening to a covered porch over a patio and gunite pool. For car collectors, there's a heated three-car garage, a lower-level garage and a detached steel-and-concrete barn for six to eight more cars, according to the listing. It has 5,973 square feet.

555 Middle Road Turnpike, Woodbury, 1 to 3 p.m., $359,900. This two-bedroom, one-bath ranch sits on a level lot of nearly half an acre, with a living room fireplace and an oversized back deck over a small seasonal brook. It has 990 square feet.

Also open Sunday: 35 Woodbury Hill #35, Woodbury, 1 to 3 p.m. (see Saturday).

Saturday covers three homes at 11 a.m. and Crest Road at noon. Sunday adds the Weekeepeemee Road estate at noon and Middle Road Turnpike at 1.

Listing details from Zillow.com as of Nov. 5, 2026. Open-house schedules can change, so check each listing before you go.