Upcoming Open Houses In Woodbury & Middlebury

MIDDLEBURY, CT — This weekend's open houses include a Contemporary Craftsman in Middlebury's Historic District that borders the Crest Preserve, an antique within walking distance of Lake Quassapaug and a remodeled condo in Woodbury.

Five homes in Woodbury and Middlebury are holding open houses Saturday, Oct. 24, and Sunday, Oct. 25, with prices from $199,900 to $749,900, according to Zillow.com.

Saturday, Oct. 24

77 Crest Road, Middlebury, 11 a.m. to 1 p.m. (also Sunday, noon to 2 p.m.), $749,900. In Middlebury's Historic District and bordering the 9-plus-acre Crest Preserve, this 1935 Contemporary Craftsman has original hand-carved staircases, hardwood floors, a finished attic, a chef's kitchen with quartz counters and a renovated Gunite saltwater pool, according to the listing. It's a four-bedroom, 3.5-bath home with 2,674 square feet on 1.5 acres.

314 Porter Ave., Middlebury, 11 a.m. to 3 p.m., $485,000. Renovated top to bottom, this 1941 Cape has new bamboo floors in the kitchen, refinished original hardwood in the living and dining rooms, custom cabinetry and a finished lower level with a second living room, according to the listing. It's a three-bedroom, two-bath home with 1,440 square feet on 0.34 acres.

70 Pine Hollow Drive, Middlebury, noon to 2 p.m., $619,900. Maintained by its original owners on 1.22 park-like acres, this 1978 home has a sunken living room with a fireplace, a family room with another fireplace, a finished room with a wet bar, a 54-foot deck and three oversized garages, according to the listing. It's a three-bedroom, 2.5-bath home with 3,174 square feet. Its price was cut by $19,100 on Oct. 21.

Sunday, Oct. 25

802 Charcoal Ave., Middlebury, 11 a.m. to 1 p.m., $499,900. Within walking distance of Lake Quassapaug on more than 2 acres, this antique, which Zillow lists as built in 1700, has wide board floors and plaster walls, plus a detached oversized two-car garage with a workshop and a finished artist's loft, according to the listing, which pitches it to buyers who want to restore it. The house isn't air-conditioned. It's a four-bedroom, 2.5-bath home with 1,911 square feet. Its price was cut by $50,100 on Oct. 22.

229 Bacon Pond Road #312, Woodbury, noon to 2 p.m., $199,900. In the Town In Country complex, this condo has been remodeled top to bottom, according to the listing, with a new kitchen with quartz counters and stainless appliances, new flooring and central air. It's a two-bedroom, one-bath condo with 913 square feet; the HOA fee is $500 a month.

Also open Sunday: 77 Crest Road, Middlebury (noon to 2 p.m.).

Make a weekend of it: Saturday, Crest Road and Porter Avenue open at 11 a.m. and Pine Hollow Drive at noon. Sunday, see Charcoal Avenue at 11, then the Woodbury condo or a second look at Crest Road from noon.

Listing details from Zillow.com as of Oct. 22, 2026. Open-house schedules can change; check each listing before you go.