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Beds
Baths
Sq.Ft.
283 Whittemore Road
Middlebury, CT
301 Steinmann Avenue
90 Fenn Road
271 Shadduck Road
24 Highridge Road 24
420 Charcoal Avenue
122 Crest Road
245 Upper Whittemore Road
851 South Street
66 Artillery Road
408 Breakneck Hill Road
2 Arrowwood Court 2
64 Watertown Road
192 Breakneck Hill Road
193 Ridgewood Drive 193
18 Freedom Road
6 Brookside Drive
6 Brookside Drive 6
19 Deer Run Road
200 North Farm Road
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 4/27/2026)
Information deemed reliable but not guaranteed.
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