Woodbury & Middlebury Open Houses Sept. 26-27: A 1747 Saltbox And A Home With An In-Law Suite

PATCHTOWN, CT — This weekend's Woodbury and Middlebury open houses span almost two centuries. On Saturday, a 1747 saltbox in Woodbury opens its doors. It has original wide-plank floors, twin staircases, a two-bedroom carriage house and a two-story barn that its listing suggests could become a creative studio. On Sunday, a 1936 Middlebury home shows off a private in-law suite, a fire pit and a new floating deck.

Two Woodbury and Middlebury homes are holding open houses Sept. 26-27, with prices from $450,000 to $1,395,000, according to Zillow.com.

Saturday, Sept. 26

509 Weekeepeemee Road, Woodbury, noon to 2 p.m., $1,395,000: Built in 1747 and set on 5.19 acres along what the listing calls a peaceful country lane, this saltbox keeps its original wide-plank wood floors, two fireplaces, twin staircases and authentic built-ins. The kitchen has Viking appliances and granite counters that look out on the gardens. A screened stone-and-timber breezeway leads to an expanded patio with a firepit built from native fieldstone. The grounds include a separate two-bedroom carriage house with a covered porch and an oversized 2.5-car garage, plus a newer 40-by-28-foot, two-story barn and two storage sheds. The three-bedroom, 2.5-bath home has 2,346 square feet, according to Zillow. Listed updates include a new cedar-shingle roof with copper d ownspouts in 2025, new air conditioning, fresh interior paint in 2026 and refinished floors.

Sunday, Sept. 27

106 Country Club Road, Middlebury, 11 a.m. to 1 p.m., $450,000: The main level of this 1936 home includes a private in-law area with its own bedroom, kitchenette, full bath and separate entrance. The listing describes the house as updated and move-in ready, with an updated kitchen and a finished basement that could serve as a family room, playroom or home office. Outside are a fire pit and a newly added Trex floating deck. The four-bedroom, 2.5-bath home has 2,664 square feet on a 0.29-acre lot.

Make a weekend of it: The two open houses fall on different days, so you can see both without rushing. Spend Saturday's noon-to-2 p.m. window walking the Woodbury grounds, from the fieldstone firepit to the barn. Then come back Sunday morning for the Middlebury house and its in-law suite. The two homes are almost 190 years and nearly $1 million apart. Planning ahead? 69 Nonnewaug Road in Woodbury has an open house next weekend, Sunday, Oct. 4, from 10 a.m. to noon.

Listing details from Zillow.com as of Sept. 24, 2026. Open-house schedules can change; check the listing before you go.