Woodbury & Middlebury Open Houses Oct. 10-11: An 1850 Main Street Home, A New Cape And 3 More

WOODBURY, CT — This weekend's open houses in Woodbury and Middlebury include an 1850 antique on Main Street North with a mahogany-floored wraparound porch and a new Cape surrounded by 12 acres of open space. There's also a 14-month-old Colonial in Middlebury's Hunting Ridge Estates.

Five Woodbury and Middlebury homes are holding open houses Saturday, Oct. 10, and Sunday, Oct. 11, with prices from $574,900 to $849,900, according to Zillow.com.

Saturday, Oct. 10

63 Main St. North, Woodbury, 11 a.m. to 1 p.m., $849,900. This 1850 antique with a 2002 addition has a mahogany-floored wraparound porch, oak floors, built-ins and fireplaces, plus an open kitchen and family room with a gas log fireplace and a first-floor bedroom. Out back are stone walls, an outdoor fireplace and a hot tub. It's a four-bedroom, two-bath home with 2,662 square feet. The listing points out that Reader's Digest named Woodbury Connecticut's most charming small town in 2024.

18 Hunting Ridge Road, Middlebury, noon to 2 p.m., $799,900. Built in 2025 in Hunting Ridge Estates, a 23-home subdivision, this Colonial has hardwood floors on both levels and a kitchen with white shaker cabinets, quartz counters, a large island and a walk-in pantry. The family room has a gas fireplace and sliders to a 17-by-15-foot patio. It's a four-bedroom, 2.5-bath home with 2,700 square feet on 1.06 acres. Its price was cut by $19,100 on Sept. 28.

Sunday, Oct. 11

86 Quail Run Road, Woodbury, 10 a.m. to 1 p.m., $765,000. One of four new homes on flat lots on a Quail Run cul-de-sac, this Cape is surrounded by 12 acres of private open space, according to the listing. It has a full front porch, an open floor plan, an attached two-car garage and a lower level set up for future finishing. It's a three-bedroom, 2.5-bath home with 2,060 square feet on 1.24 acres; the HOA fee is $25 a month.

16 Caveson Court #16, Middlebury, noon to 2 p.m., $575,000. This updated Cape in the Steeplechase community has hardwood floors, plantation shutters, an extra room off the eat-in kitchen and a primary suite with two walk-in closets. There's a private deck and a full walkout basement. It's a three-bedroom, 2.5-bath condo with 1,957 square feet; the HOA fee is $277 a month. Its price was cut by $25,000 on Sept. 30.

323 Upper Grassy Hill Road, Woodbury, 1 to 3 p.m., $574,900. This 1986 home has a living room, a great room and a separate dining room, an updated kitchen and a deck. It's a three-bedroom, 2.5-bath home with 3,282 square feet on 0.93 acres. Its price was cut by $14,100 on Sept. 29.

Make a weekend of it: Saturday, see Main Street North at 11 and drive to Hunting Ridge Road at noon. Sunday morning starts at Quail Run, then heads to Steeplechase in Middlebury and back to Upper Grassy Hill Road.

Listing details from Zillow.com as of Oct. 7, 2026. Open-house schedules can change; check each listing before you go.