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Beds
Baths
Sq.Ft.
16 Winding Trail 16
Middlebury, CT
1 Arrowwood Court 1
321 Artillery Road
428 Breakneck Hill Road
3 Hunting Ridge Road
775 South Street
Lots 12,13, 14 Mirey Dam Road
North Benson Road # 62
75 Gleneagle Road
35 Nutmeg Road Apt D1
61 Sandy Hill Road
24 Ridgewood Drive 24
117 Crest Road
84 Munson Road
3 Brookside Drive 3
152 Glenwood Avenue
637 Watertown Road
North Benson Road # 57
292 Park Rd Extension
Middlebury claims a rural character that is largely based on a history of livestock breeding. Many residents were able to raise saddle horses as a sideline in this bedroom community surrounded by Waterbury, Southbury, and Woodbury. The town is also home to an impressive and thriving corporate sector that includes household names like Timex and Uniroyal. For over 90 years, the family owned Quassy Amusement Park has been a popular destination along the shoreline of sparkling Lake Quassapaug.
Weichert Realtors is one of the nation's leading providers of Middlebury, Connecticut real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Middlebury, CT.
(Data as of 3/5/2026)
Information deemed reliable but not guaranteed.
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