Listings in 06762 - NewHaven County, Connecticut
Displaying 1 – 200 of 497 Real estate listings
245 Upper Whittemore Road
Middlebury, CT | Closed
Listed: Apr, 16, 2026
Price: $815,000
Living Area: 2,990 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 16, 2026
Price: $815,000
Living Area: 2,990 Sq. Ft.
283 Whittemore Road
Middlebury, CT | Closed
Listed: Apr, 27, 2026
Price: $519,000
Living Area: 1,300 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 27, 2026
Price: $519,000
Living Area: 1,300 Sq. Ft.
24 Ridgewood Drive 24
Middlebury, CT | Closed
Listed: Jan, 05, 2026
Price: $554,000
Living Area: 2,403 Sq. Ft.
Middlebury, CT | Closed
Listed: Jan, 05, 2026
Price: $554,000
Living Area: 2,403 Sq. Ft.
1 Independence Circle 1
Middlebury, CT | Closed
Listed: May, 21, 2026
Price: $609,000
Living Area: 2,553 Sq. Ft.
Middlebury, CT | Closed
Listed: May, 21, 2026
Price: $609,000
Living Area: 2,553 Sq. Ft.
80 Anawan Avenue
Middlebury, CT | Closed
Listed: May, 13, 2026
Price: $529,900
Living Area: 1,962 Sq. Ft.
Middlebury, CT | Closed
Listed: May, 13, 2026
Price: $529,900
Living Area: 1,962 Sq. Ft.
420 Charcoal Avenue
Middlebury, CT | Closed
Listed: Apr, 20, 2026
Price: $485,000
Living Area: 1,575 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 20, 2026
Price: $485,000
Living Area: 1,575 Sq. Ft.
North Benson Road 62
Middlebury, CT | Pending
Listed: Feb, 05, 2026
Price: $545,400
Living Area: 2,206 Sq. Ft.
Middlebury, CT | Pending
Listed: Feb, 05, 2026
Price: $545,400
Living Area: 2,206 Sq. Ft.
8 Deer Run Road
Middlebury, CT | Pending
Listed: Jun, 08, 2026
Price: $839,900
Living Area: 2,450 Sq. Ft.
Middlebury, CT | Pending
Listed: Jun, 08, 2026
Price: $839,900
Living Area: 2,450 Sq. Ft.
112 Joy Road
Middlebury, CT | Active Under Contract
Listed: Jul, 30, 2026
Price: $499,900
Living Area: 1,900 Sq. Ft.
Middlebury, CT | Active Under Contract
Listed: Jul, 30, 2026
Price: $499,900
Living Area: 1,900 Sq. Ft.
3 Brookside Drive 3
Middlebury, CT | Active Under Contract
Listed: Dec, 27, 2025
Price: $599,900
Living Area: 4,200 Sq. Ft.
Middlebury, CT | Active Under Contract
Listed: Dec, 27, 2025
Price: $599,900
Living Area: 4,200 Sq. Ft.
409 Chestnut Circle 79
Middlebury, CT | Closed
Listed: Oct, 14, 2024
Price: $699,900
Living Area: 2,292 Sq. Ft.
Middlebury, CT | Closed
Listed: Oct, 14, 2024
Price: $699,900
Living Area: 2,292 Sq. Ft.
North Benson Road 55
Middlebury, CT | Pending
Listed: Apr, 07, 2025
Price: $548,828
Living Area: 2,462 Sq. Ft.
Middlebury, CT | Pending
Listed: Apr, 07, 2025
Price: $548,828
Living Area: 2,462 Sq. Ft.
North Benson Road 57
Middlebury, CT | Pending
Listed: Dec, 15, 2025
Price: $561,271
Living Area: 2,206 Sq. Ft.
Middlebury, CT | Pending
Listed: Dec, 15, 2025
Price: $561,271
Living Area: 2,206 Sq. Ft.
North Benson Road 61
Middlebury, CT | Pending
Listed: Sep, 04, 2026
Price: $608,700
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Pending
Listed: Sep, 04, 2026
Price: $608,700
Living Area: 1,950 Sq. Ft.
North Benson Road 41
Middlebury, CT | Closed
Listed: Nov, 22, 2024
Price: $541,566
Living Area: 2,206 Sq. Ft.
Middlebury, CT | Closed
Listed: Nov, 22, 2024
Price: $541,566
Living Area: 2,206 Sq. Ft.
North Benson Road 42
Middlebury, CT | Closed
Listed: Feb, 23, 2025
Price: $499,900
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Closed
Listed: Feb, 23, 2025
Price: $499,900
Living Area: 1,950 Sq. Ft.
2 Arrowwood Court 2
Middlebury, CT | Closed
Listed: Apr, 13, 2026
Price: $599,900
Living Area: 2,256 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 13, 2026
Price: $599,900
Living Area: 2,256 Sq. Ft.
36 Highridge Road 36
Middlebury, CT | Closed
Listed: Mar, 30, 2026
Price: $585,000
Living Area: 1,997 Sq. Ft.
Middlebury, CT | Closed
Listed: Mar, 30, 2026
Price: $585,000
Living Area: 1,997 Sq. Ft.
49 North Benson Road 49
Middlebury, CT | Closed
Listed: May, 14, 2025
Price: $533,416
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Closed
Listed: May, 14, 2025
Price: $533,416
Living Area: 1,950 Sq. Ft.
179 Burr Hall Road
Middlebury, CT | Closed
Listed: Jul, 31, 2026
Price: $675,000
Living Area: 3,938 Sq. Ft.
Middlebury, CT | Closed
Listed: Jul, 31, 2026
Price: $675,000
Living Area: 3,938 Sq. Ft.
28 Hunting Ridge Road
Middlebury, CT | Closed
Listed: Mar, 10, 2025
Price: $729,900
Living Area: 2,466 Sq. Ft.
Middlebury, CT | Closed
Listed: Mar, 10, 2025
Price: $729,900
Living Area: 2,466 Sq. Ft.
58 Shadduck Road
Middlebury, CT | Active Under Contract
Listed: Sep, 02, 2026
Price: $574,900
Living Area: 2,360 Sq. Ft.
Middlebury, CT | Active Under Contract
Listed: Sep, 02, 2026
Price: $574,900
Living Area: 2,360 Sq. Ft.
46 Washington Drive
Middlebury, CT | Active Under Contract
Listed: Aug, 28, 2026
Price: $645,000
Living Area: 1,940 Sq. Ft.
Middlebury, CT | Active Under Contract
Listed: Aug, 28, 2026
Price: $645,000
Living Area: 1,940 Sq. Ft.
133 Algin Drive
Middlebury, CT | Pending
Listed: Aug, 27, 2026
Price: $474,900
Living Area: 1,837 Sq. Ft.
Middlebury, CT | Pending
Listed: Aug, 27, 2026
Price: $474,900
Living Area: 1,837 Sq. Ft.
213 Acme Drive
Middlebury, CT | Withdrawn
Listed: Jul, 06, 2026
Price: $499,000
Living Area: 1,833 Sq. Ft.
Middlebury, CT | Withdrawn
Listed: Jul, 06, 2026
Price: $499,000
Living Area: 1,833 Sq. Ft.
249 South Street
Middlebury, CT | Expired
Listed: May, 24, 2021
Price: $699,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 24, 2021
Price: $699,000
Living Area: 0 Sq. Ft.
66 Artillery Road
Middlebury, CT | Active
Listed: Apr, 13, 2026
Price: $585,000
Living Area: 2,691 Sq. Ft.
Middlebury, CT | Active
Listed: Apr, 13, 2026
Price: $585,000
Living Area: 2,691 Sq. Ft.
54 Falcon Crest Road
Middlebury, CT | Expired
Listed: Apr, 29, 2021
Price: $998,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Apr, 29, 2021
Price: $998,000
Living Area: 0 Sq. Ft.
130 Fairhaven Drive
Middlebury, CT | Closed
Listed: Jul, 22, 2026
Price: $649,900
Living Area: 2,654 Sq. Ft.
Middlebury, CT | Closed
Listed: Jul, 22, 2026
Price: $649,900
Living Area: 2,654 Sq. Ft.
75B Gleneagle Road, Middlebury, CT 06762
Middlebury, CT | Expired
Listed: Jan, 16, 2019
Price: $899,900
Living Area: 3,600 Sq. Ft.
Middlebury, CT | Expired
Listed: Jan, 16, 2019
Price: $899,900
Living Area: 3,600 Sq. Ft.
637 Watertown Road
Middlebury, CT | Closed
Listed: Dec, 19, 2025
Price: $450,000
Living Area: 1,918 Sq. Ft.
Middlebury, CT | Closed
Listed: Dec, 19, 2025
Price: $450,000
Living Area: 1,918 Sq. Ft.
771 Watertown Road
Middlebury, CT | Closed
Listed: Mar, 25, 2026
Price: $3,850
Living Area: 3,079 Sq. Ft.
Middlebury, CT | Closed
Listed: Mar, 25, 2026
Price: $3,850
Living Area: 3,079 Sq. Ft.
321 Artillery Road
Middlebury, CT | Closed
Listed: Feb, 25, 2026
Price: $699,990
Living Area: 3,300 Sq. Ft.
Middlebury, CT | Closed
Listed: Feb, 25, 2026
Price: $699,990
Living Area: 3,300 Sq. Ft.
193 Ridgewood Drive 193
Middlebury, CT | Closed
Listed: Apr, 07, 2026
Price: $649,900
Living Area: 2,658 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 07, 2026
Price: $649,900
Living Area: 2,658 Sq. Ft.
408 Breakneck Hill Road
Middlebury, CT | Closed
Listed: Apr, 13, 2026
Price: $625,000
Living Area: 1,848 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 13, 2026
Price: $625,000
Living Area: 1,848 Sq. Ft.
18 Freedom Road
Middlebury, CT | Closed
Listed: Apr, 06, 2026
Price: $479,000
Living Area: 1,492 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 06, 2026
Price: $479,000
Living Area: 1,492 Sq. Ft.
271 Shadduck Road
Middlebury, CT | Closed
Listed: Apr, 22, 2026
Price: $432,000
Living Area: 1,288 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 22, 2026
Price: $432,000
Living Area: 1,288 Sq. Ft.
24 Highridge Road 24
Middlebury, CT | Closed
Listed: Apr, 22, 2026
Price: $560,000
Living Area: 1,802 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 22, 2026
Price: $560,000
Living Area: 1,802 Sq. Ft.
301 Steinmann Avenue
Middlebury, CT | Closed
Listed: Apr, 26, 2026
Price: $409,900
Living Area: 1,572 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 26, 2026
Price: $409,900
Living Area: 1,572 Sq. Ft.
84 Munson Road
Middlebury, CT | Closed
Listed: Dec, 29, 2025
Price: $689,000
Living Area: 3,254 Sq. Ft.
Middlebury, CT | Closed
Listed: Dec, 29, 2025
Price: $689,000
Living Area: 3,254 Sq. Ft.
541 Benson Road
Middlebury, CT | Closed
Listed: Mar, 23, 2026
Price: $525,000
Living Area: 1,600 Sq. Ft.
Middlebury, CT | Closed
Listed: Mar, 23, 2026
Price: $525,000
Living Area: 1,600 Sq. Ft.
407 Chestnut Circle 78
Middlebury, CT | Closed
Listed: Sep, 26, 2023
Price: $655,500
Living Area: 2,292 Sq. Ft.
Middlebury, CT | Closed
Listed: Sep, 26, 2023
Price: $655,500
Living Area: 2,292 Sq. Ft.
315 Hemlock Lane 74
Middlebury, CT | Closed
Listed: Nov, 28, 2023
Price: $629,000
Living Area: 2,292 Sq. Ft.
Middlebury, CT | Closed
Listed: Nov, 28, 2023
Price: $629,000
Living Area: 2,292 Sq. Ft.
401 Chestnut Circle 75
Middlebury, CT | Closed
Listed: Sep, 11, 2023
Price: $660,500
Living Area: 2,292 Sq. Ft.
Middlebury, CT | Closed
Listed: Sep, 11, 2023
Price: $660,500
Living Area: 2,292 Sq. Ft.
21 Avalon Dr
Middlebury, CT | Canceled
Listed: Apr, 30, 2019
Price: $649,000
Living Area: 3,425 Sq. Ft.
Middlebury, CT | Canceled
Listed: Apr, 30, 2019
Price: $649,000
Living Area: 3,425 Sq. Ft.
294 Christian Road
Middlebury, CT | Active
Listed: Sep, 14, 2026
Price: $995,000
Living Area: 2,878 Sq. Ft.
Middlebury, CT | Active
Listed: Sep, 14, 2026
Price: $995,000
Living Area: 2,878 Sq. Ft.
18 Hunting Ridge Road
Middlebury, CT | Active
Listed: Sep, 02, 2026
Price: $799,900
Living Area: 2,700 Sq. Ft.
Middlebury, CT | Active
Listed: Sep, 02, 2026
Price: $799,900
Living Area: 2,700 Sq. Ft.
North Benson Road 45
Middlebury, CT | Pending
Listed: Apr, 17, 2025
Price: $525,438
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Pending
Listed: Apr, 17, 2025
Price: $525,438
Living Area: 1,950 Sq. Ft.
1140 Southford Road
Middlebury, CT | Active
Listed: Mar, 28, 2026
Price: $399,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Active
Listed: Mar, 28, 2026
Price: $399,000
Living Area: 0 Sq. Ft.
323 Watertown Road
Middlebury, CT | Pending
Listed: Jul, 28, 2026
Price: $539,000
Living Area: 2,067 Sq. Ft.
Middlebury, CT | Pending
Listed: Jul, 28, 2026
Price: $539,000
Living Area: 2,067 Sq. Ft.
62 Yale Avenue
Middlebury, CT | Expired
Listed: Mar, 02, 2021
Price: $359,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Mar, 02, 2021
Price: $359,000
Living Area: 0 Sq. Ft.
9 Whitehall Court
Middlebury, CT | Active
Listed: Sep, 11, 2026
Price: $979,900
Living Area: 4,261 Sq. Ft.
Middlebury, CT | Active
Listed: Sep, 11, 2026
Price: $979,900
Living Area: 4,261 Sq. Ft.
266 Kelly Road
Middlebury, CT | Expired
Listed: Jun, 06, 2022
Price: $775,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 06, 2022
Price: $775,000
Living Area: 0 Sq. Ft.
266 Kelly Road
Middlebury, CT | Expired
Listed: Jun, 06, 2022
Price: $775,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 06, 2022
Price: $775,000
Living Area: 0 Sq. Ft.
58 Shadduck Road
Middlebury, CT | Expired
Listed: Jun, 23, 2022
Price: $523,899
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 23, 2022
Price: $523,899
Living Area: 0 Sq. Ft.
40 Gleneagle Road
Middlebury, CT | Canceled
Listed: Jul, 30, 2021
Price: $120,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jul, 30, 2021
Price: $120,000
Living Area: 0 Sq. Ft.
260 Porter Avenue
Middlebury, CT | Expired
Listed: Aug, 31, 2021
Price: $365,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Aug, 31, 2021
Price: $365,000
Living Area: 0 Sq. Ft.
75B Gleneagle Road
Middlebury, CT | Canceled
Listed: Aug, 14, 2021
Price: $795,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Aug, 14, 2021
Price: $795,000
Living Area: 0 Sq. Ft.
40A Gleneagle Road
Middlebury, CT | Canceled
Listed: Aug, 14, 2021
Price: $795,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Aug, 14, 2021
Price: $795,000
Living Area: 0 Sq. Ft.
51 Pine Hollow Drive
Middlebury, CT | Expired
Listed: Oct, 12, 2021
Price: $464,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Oct, 12, 2021
Price: $464,900
Living Area: 0 Sq. Ft.
3 Colonial Court 3
Middlebury, CT | Canceled
Listed: Jul, 21, 2021
Price: $499,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jul, 21, 2021
Price: $499,900
Living Area: 0 Sq. Ft.
192 Watertown Road
Middlebury, CT | Expired
Listed: Jun, 21, 2022
Price: $1,000,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 21, 2022
Price: $1,000,000
Living Area: 0 Sq. Ft.
7 East Farm Road
Middlebury, CT | Expired
Listed: Nov, 16, 2019
Price: $1,500,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Nov, 16, 2019
Price: $1,500,000
Living Area: 0 Sq. Ft.
7 Winding Trail
Middlebury, CT | Canceled
Listed: Jul, 29, 2022
Price: $469,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jul, 29, 2022
Price: $469,900
Living Area: 0 Sq. Ft.
420 Burr Hall Road
Middlebury, CT | Expired
Listed: Jun, 16, 2021
Price: $1,299,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 16, 2021
Price: $1,299,000
Living Area: 0 Sq. Ft.
8 Highridge Road 8
Middlebury, CT | Expired
Listed: Jun, 14, 2021
Price: $529,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 14, 2021
Price: $529,900
Living Area: 0 Sq. Ft.
34 Kelly Road
Middlebury, CT | Canceled
Listed: Nov, 12, 2021
Price: $344,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Nov, 12, 2021
Price: $344,900
Living Area: 0 Sq. Ft.
49 Tylers Cove
Middlebury, CT | Expired
Listed: Sep, 02, 2021
Price: $1,250,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Sep, 02, 2021
Price: $1,250,000
Living Area: 0 Sq. Ft.
290 Burr Hall Road
Middlebury, CT | Expired
Listed: Sep, 01, 2021
Price: $195,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Sep, 01, 2021
Price: $195,000
Living Area: 0 Sq. Ft.
205B Leonard Road
Middlebury, CT | Expired
Listed: Feb, 23, 2021
Price: $49,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Feb, 23, 2021
Price: $49,900
Living Area: 0 Sq. Ft.
208 Bioski Road
Middlebury, CT | Expired
Listed: Mar, 31, 2021
Price: $125,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Mar, 31, 2021
Price: $125,000
Living Area: 0 Sq. Ft.
8 Arrowwood Court 193
Middlebury, CT | Expired
Listed: Oct, 01, 2021
Price: $525,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Oct, 01, 2021
Price: $525,000
Living Area: 0 Sq. Ft.
North Benson Road 64
Middlebury, CT | Closed
Listed: Feb, 27, 2025
Price: $545,400
Living Area: 2,206 Sq. Ft.
Middlebury, CT | Closed
Listed: Feb, 27, 2025
Price: $545,400
Living Area: 2,206 Sq. Ft.
249 South Street
Middlebury, CT | Expired
Listed: May, 02, 2022
Price: $709,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 02, 2022
Price: $709,900
Living Area: 0 Sq. Ft.
317 A Kelly Road 317 A
Middlebury, CT | Expired
Listed: Dec, 03, 2021
Price: $179,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Dec, 03, 2021
Price: $179,900
Living Area: 0 Sq. Ft.
1194339 Richardson Drive
Middlebury, CT | Expired
Listed: May, 19, 2021
Price: $99,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 19, 2021
Price: $99,900
Living Area: 0 Sq. Ft.
1192273 Richardson Drive
Middlebury, CT | Expired
Listed: May, 19, 2021
Price: $99,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 19, 2021
Price: $99,900
Living Area: 0 Sq. Ft.
54 Falcon Crest Road
Middlebury, CT | Canceled
Listed: Aug, 15, 2022
Price: $1,050,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Aug, 15, 2022
Price: $1,050,000
Living Area: 0 Sq. Ft.
1070 Long Meadow Road
Middlebury, CT | Expired
Listed: Apr, 07, 2022
Price: $749,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Apr, 07, 2022
Price: $749,900
Living Area: 0 Sq. Ft.
92 Chesham Drive
Middlebury, CT | Expired
Listed: May, 26, 2022
Price: $1,300,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 26, 2022
Price: $1,300,000
Living Area: 0 Sq. Ft.
1 Fairview Lane 1
Middlebury, CT | Expired
Listed: Apr, 25, 2022
Price: $499,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Apr, 25, 2022
Price: $499,900
Living Area: 0 Sq. Ft.
1 Bristol Road
Middlebury, CT | Expired
Listed: Oct, 28, 2020
Price: $5,600,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Oct, 28, 2020
Price: $5,600,000
Living Area: 0 Sq. Ft.
10 Old Waterbury Road
Middlebury, CT | Expired
Listed: Nov, 02, 2021
Price: $679,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Nov, 02, 2021
Price: $679,900
Living Area: 0 Sq. Ft.
680 Straits Turnpike
Middlebury, CT | Expired
Listed: Aug, 02, 2021
Price: $499,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Aug, 02, 2021
Price: $499,900
Living Area: 0 Sq. Ft.
90 Saint Joseph Avenue
Middlebury, CT | Canceled
Listed: Jul, 16, 2022
Price: $379,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jul, 16, 2022
Price: $379,900
Living Area: 0 Sq. Ft.
1255 Middlebury Road
Middlebury, CT | Canceled
Listed: Mar, 14, 2022
Price: $600
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Mar, 14, 2022
Price: $600
Living Area: 0 Sq. Ft.
77 Crest Road
Middlebury, CT | Active
Listed: Aug, 10, 2026
Price: $749,900
Living Area: 2,674 Sq. Ft.
Middlebury, CT | Active
Listed: Aug, 10, 2026
Price: $749,900
Living Area: 2,674 Sq. Ft.
397 White Deer Rock Road
Middlebury, CT | Closed
Listed: May, 01, 2026
Price: $2,195,000
Living Area: 3,863 Sq. Ft.
Middlebury, CT | Closed
Listed: May, 01, 2026
Price: $2,195,000
Living Area: 3,863 Sq. Ft.
85 Blueberry Knolls
Middlebury, CT | Closed
Listed: Aug, 13, 2026
Price: $550,000
Living Area: 2,156 Sq. Ft.
Middlebury, CT | Closed
Listed: Aug, 13, 2026
Price: $550,000
Living Area: 2,156 Sq. Ft.
10 Dogwood Court 10
Middlebury, CT | Closed
Listed: Aug, 24, 2026
Price: $3,995
Living Area: 2,277 Sq. Ft.
Middlebury, CT | Closed
Listed: Aug, 24, 2026
Price: $3,995
Living Area: 2,277 Sq. Ft.
71 Sandy Beach Road 71
Middlebury, CT | Expired
Listed: Sep, 22, 2023
Price: $599,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Sep, 22, 2023
Price: $599,000
Living Area: 0 Sq. Ft.
292 Park Extension Road
Middlebury, CT | Canceled
Listed: Jul, 01, 2012
Price: $360,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jul, 01, 2012
Price: $360,000
Living Area: 0 Sq. Ft.
7 Laurel Ridge Road
Middlebury, CT | Expired
Listed: Dec, 17, 2007
Price: $449,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Dec, 17, 2007
Price: $449,900
Living Area: 0 Sq. Ft.
372 Tucker Hill Road
Middlebury, CT | Expired
Listed: Oct, 24, 2023
Price: $1,990,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Oct, 24, 2023
Price: $1,990,000
Living Area: 0 Sq. Ft.
429 Mirey Dam Road
Middlebury, CT | Expired
Listed: Oct, 13, 2022
Price: $900,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Oct, 13, 2022
Price: $900,000
Living Area: 0 Sq. Ft.
96 Tucker Hill Road
Middlebury, CT | Expired
Listed: Nov, 02, 2022
Price: $1,400
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Nov, 02, 2022
Price: $1,400
Living Area: 0 Sq. Ft.
372 Tucker Hill Road
Middlebury, CT | Expired
Listed: Feb, 23, 2024
Price: $1,789,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Feb, 23, 2024
Price: $1,789,000
Living Area: 0 Sq. Ft.
566 Benson Road
Middlebury, CT | Expired
Listed: Sep, 21, 2023
Price: $479,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Sep, 21, 2023
Price: $479,900
Living Area: 0 Sq. Ft.
1255 Middlebury Road 1-2
Middlebury, CT | Canceled
Listed: Jan, 18, 2023
Price: $800
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jan, 18, 2023
Price: $800
Living Area: 0 Sq. Ft.
LOT 1 /high Point
Middlebury, CT | Expired
Listed: Jun, 29, 2005
Price: $349,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 29, 2005
Price: $349,900
Living Area: 0 Sq. Ft.
27 Vidich Lane
Middlebury, CT | Expired
Listed: Jul, 06, 2010
Price: $359,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jul, 06, 2010
Price: $359,000
Living Area: 0 Sq. Ft.
100 North Benson Road
Middlebury, CT | Canceled
Listed: Jun, 19, 2018
Price: $1,799,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jun, 19, 2018
Price: $1,799,900
Living Area: 0 Sq. Ft.
3 Brookside Drive 3
Middlebury, CT | Expired
Listed: Jan, 15, 2023
Price: $639,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jan, 15, 2023
Price: $639,900
Living Area: 0 Sq. Ft.
87 Falcon Crest Road
Middlebury, CT | Canceled
Listed: Jun, 15, 2023
Price: $825,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jun, 15, 2023
Price: $825,000
Living Area: 0 Sq. Ft.
81 Sandy Beach Road
Middlebury, CT | Expired
Listed: Dec, 02, 2022
Price: $449,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Dec, 02, 2022
Price: $449,900
Living Area: 0 Sq. Ft.
315 Hemlock Lane 74
Middlebury, CT | Canceled
Listed: Nov, 08, 2022
Price: $629,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Nov, 08, 2022
Price: $629,000
Living Area: 0 Sq. Ft.
53 Winthrop Drive
Middlebury, CT | Canceled
Listed: Jan, 18, 2023
Price: $299,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jan, 18, 2023
Price: $299,900
Living Area: 0 Sq. Ft.
7 Oakwood Drive 4
Middlebury, CT | Expired
Listed: Jan, 30, 2023
Price: $619,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jan, 30, 2023
Price: $619,000
Living Area: 0 Sq. Ft.
1255 Middlebury Road 2-1
Middlebury, CT | Canceled
Listed: Jun, 12, 2023
Price: $1,600
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jun, 12, 2023
Price: $1,600
Living Area: 0 Sq. Ft.
96 Tucker Hill Road
Middlebury, CT | Expired
Listed: Jun, 15, 2023
Price: $1,650
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 15, 2023
Price: $1,650
Living Area: 0 Sq. Ft.
15 Meadow View Drive
Middlebury, CT | Expired
Listed: Dec, 17, 2007
Price: $459,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Dec, 17, 2007
Price: $459,900
Living Area: 0 Sq. Ft.
7 Winding Trail
Middlebury, CT | Expired
Listed: Jan, 19, 2024
Price: $479,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jan, 19, 2024
Price: $479,900
Living Area: 0 Sq. Ft.
27 Sandy Beach Road
Middlebury, CT | Canceled
Listed: Sep, 15, 2023
Price: $750,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Sep, 15, 2023
Price: $750,000
Living Area: 0 Sq. Ft.
24 Yale Avenue
Middlebury, CT | Pending
Listed: Aug, 01, 2026
Price: $324,900
Living Area: 1,469 Sq. Ft.
Middlebury, CT | Pending
Listed: Aug, 01, 2026
Price: $324,900
Living Area: 1,469 Sq. Ft.
305 Burr Hall Road
Middlebury, CT | Canceled
Listed: Aug, 29, 2022
Price: $1,299,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Aug, 29, 2022
Price: $1,299,900
Living Area: 0 Sq. Ft.
660 Whittemore Road
Middlebury, CT | Expired
Listed: Aug, 03, 2022
Price: $575,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Aug, 03, 2022
Price: $575,000
Living Area: 0 Sq. Ft.
8 Oakwood Drive 10
Middlebury, CT | Expired
Listed: Sep, 29, 2022
Price: $625,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Sep, 29, 2022
Price: $625,000
Living Area: 0 Sq. Ft.
7 Oakwood Drive 4
Middlebury, CT | Expired
Listed: Sep, 30, 2022
Price: $619,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Sep, 30, 2022
Price: $619,000
Living Area: 0 Sq. Ft.
10 Old Waterbury Road
Middlebury, CT | Expired
Listed: Nov, 29, 2022
Price: $499,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Nov, 29, 2022
Price: $499,900
Living Area: 0 Sq. Ft.
70 Pine Hollow Drive
Middlebury, CT | Active
Listed: Jun, 19, 2026
Price: $649,900
Living Area: 3,174 Sq. Ft.
Middlebury, CT | Active
Listed: Jun, 19, 2026
Price: $649,900
Living Area: 3,174 Sq. Ft.
89 Sandy Beach Road 89
Middlebury, CT | Active Under Contract
Listed: Sep, 01, 2026
Price: $409,900
Living Area: 798 Sq. Ft.
Middlebury, CT | Active Under Contract
Listed: Sep, 01, 2026
Price: $409,900
Living Area: 798 Sq. Ft.
28 Pine Hollow Drive
Middlebury, CT | Expired
Listed: May, 05, 2025
Price: $216,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 05, 2025
Price: $216,000
Living Area: 0 Sq. Ft.
372 Tucker Hill Road
Middlebury, CT | Expired
Listed: Nov, 01, 2025
Price: $1,685,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Nov, 01, 2025
Price: $1,685,000
Living Area: 0 Sq. Ft.
225 Crest Road
Middlebury, CT | Expired
Listed: Oct, 17, 2025
Price: $1,085,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Oct, 17, 2025
Price: $1,085,000
Living Area: 0 Sq. Ft.
34 Breakneck Hill Road
Middlebury, CT | Expired
Listed: Aug, 18, 2023
Price: $824,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Aug, 18, 2023
Price: $824,900
Living Area: 0 Sq. Ft.
1255 Middlebury Road
Middlebury, CT | Canceled
Listed: Jun, 03, 2024
Price: $1,600
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jun, 03, 2024
Price: $1,600
Living Area: 0 Sq. Ft.
7 Highridge Road 7
Middlebury, CT | Expired
Listed: Aug, 27, 2024
Price: $624,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Aug, 27, 2024
Price: $624,000
Living Area: 0 Sq. Ft.
1255 Middlebury Road 2-7
Middlebury, CT | Expired
Listed: Mar, 01, 2024
Price: $800
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Mar, 01, 2024
Price: $800
Living Area: 0 Sq. Ft.
29 Winding Trail 29
Middlebury, CT | Canceled
Listed: Jan, 02, 2025
Price: $565,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jan, 02, 2025
Price: $565,000
Living Area: 0 Sq. Ft.
1 Winding Trail 1
Middlebury, CT | Expired
Listed: Oct, 23, 2024
Price: $689,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Oct, 23, 2024
Price: $689,000
Living Area: 0 Sq. Ft.
29 Winding Trail 29
Middlebury, CT | Canceled
Listed: Feb, 19, 2025
Price: $565,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Feb, 19, 2025
Price: $565,000
Living Area: 0 Sq. Ft.
White Birch Lane
Middlebury, CT | Canceled
Listed: Dec, 12, 2024
Price: $1,299,895
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Dec, 12, 2024
Price: $1,299,895
Living Area: 0 Sq. Ft.
9 White Birch Drive
Middlebury, CT | Canceled
Listed: Nov, 14, 2024
Price: $879,750
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Nov, 14, 2024
Price: $879,750
Living Area: 0 Sq. Ft.
2016 Straits Turnpike A
Middlebury, CT | Canceled
Listed: Sep, 18, 2024
Price: $1,850
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Sep, 18, 2024
Price: $1,850
Living Area: 0 Sq. Ft.
234 East Main Street 2
Waterbury, CT | Expired
Listed: Jul, 11, 2025
Price: $2,400
Living Area: 0 Sq. Ft.
Waterbury, CT | Expired
Listed: Jul, 11, 2025
Price: $2,400
Living Area: 0 Sq. Ft.
80 Pine Hollow Drive
Middlebury, CT | Canceled
Listed: Sep, 24, 2025
Price: $739,999
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Sep, 24, 2025
Price: $739,999
Living Area: 0 Sq. Ft.
281 Watertown Road
Middlebury, CT | Expired
Listed: Oct, 03, 2025
Price: $499,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Oct, 03, 2025
Price: $499,900
Living Area: 0 Sq. Ft.
885 Straits Turnpike
Middlebury, CT | Expired
Listed: May, 02, 2024
Price: $2,750
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 02, 2024
Price: $2,750
Living Area: 0 Sq. Ft.
409 Chestnut Circle 79
Middlebury, CT | Canceled
Listed: Sep, 27, 2023
Price: $669,500
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Sep, 27, 2023
Price: $669,500
Living Area: 0 Sq. Ft.
750 Straits Turnpike
Middlebury, CT | Expired
Listed: Nov, 03, 2023
Price: $14
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Nov, 03, 2023
Price: $14
Living Area: 0 Sq. Ft.
6 White Birch Lane Drive
Middlebury, CT | Expired
Listed: Jan, 30, 2024
Price: $1,249,650
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jan, 30, 2024
Price: $1,249,650
Living Area: 0 Sq. Ft.
2 Deer Run Road
Middlebury, CT | Canceled
Listed: Mar, 05, 2024
Price: $699,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Mar, 05, 2024
Price: $699,000
Living Area: 0 Sq. Ft.
25 Avalon Drive
Middlebury, CT | Canceled
Listed: May, 03, 2024
Price: $800,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: May, 03, 2024
Price: $800,000
Living Area: 0 Sq. Ft.
13 Independence Circle 13
Middlebury, CT | Expired
Listed: Mar, 31, 2024
Price: $725,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Mar, 31, 2024
Price: $725,000
Living Area: 0 Sq. Ft.
440 Lake Shore Drive
Middlebury, CT | Expired
Listed: May, 25, 2023
Price: $109,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 25, 2023
Price: $109,000
Living Area: 0 Sq. Ft.
428 Benson Road
Middlebury, CT | Canceled
Listed: Sep, 07, 2024
Price: $599,750
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Sep, 07, 2024
Price: $599,750
Living Area: 0 Sq. Ft.
372 Tucker Hill Road
Middlebury, CT | Expired
Listed: Jul, 24, 2024
Price: $1,499,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jul, 24, 2024
Price: $1,499,000
Living Area: 0 Sq. Ft.
6 White Birch Lane
Middlebury, CT | Expired
Listed: May, 07, 2025
Price: $1,249,500
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 07, 2025
Price: $1,249,500
Living Area: 0 Sq. Ft.
105 Jericho Road
Middlebury, CT | Canceled
Listed: Oct, 22, 2025
Price: $465,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Oct, 22, 2025
Price: $465,000
Living Area: 0 Sq. Ft.
66 Artillery Road
Middlebury, CT | Canceled
Listed: Oct, 10, 2024
Price: $599,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Oct, 10, 2024
Price: $599,000
Living Area: 0 Sq. Ft.
33 Ridgewood Drive 33
Middlebury, CT | Expired
Listed: Jun, 19, 2025
Price: $689,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 19, 2025
Price: $689,900
Living Area: 0 Sq. Ft.
24 Ridgewood Drive 24
Middlebury, CT | Canceled
Listed: Sep, 02, 2025
Price: $599,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Sep, 02, 2025
Price: $599,900
Living Area: 0 Sq. Ft.
297 Whittemore Road
Middlebury, CT | Expired
Listed: Apr, 30, 2025
Price: $579,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Apr, 30, 2025
Price: $579,900
Living Area: 0 Sq. Ft.
75 Gleneagle Road
Middlebury, CT | Expired
Listed: Apr, 24, 2024
Price: $219,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Apr, 24, 2024
Price: $219,900
Living Area: 0 Sq. Ft.
23 Caveson Court 23
Middlebury, CT | Canceled
Listed: Aug, 24, 2025
Price: $579,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Aug, 24, 2025
Price: $579,900
Living Area: 0 Sq. Ft.
105 Jericho Road
Middlebury, CT | Canceled
Listed: May, 14, 2025
Price: $489,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: May, 14, 2025
Price: $489,900
Living Area: 0 Sq. Ft.
122 Crest Road
Middlebury, CT | Closed
Listed: Apr, 19, 2026
Price: $825,000
Living Area: 3,253 Sq. Ft.
Middlebury, CT | Closed
Listed: Apr, 19, 2026
Price: $825,000
Living Area: 3,253 Sq. Ft.
10 Old Waterbury Road 1
Middlebury, CT | Closed
Listed: Jul, 01, 2026
Price: $1,300
Living Area: 500 Sq. Ft.
Middlebury, CT | Closed
Listed: Jul, 01, 2026
Price: $1,300
Living Area: 500 Sq. Ft.
443 Benson Road
Middlebury, CT | Closed
Listed: May, 28, 2026
Price: $2,800
Living Area: 1,766 Sq. Ft.
Middlebury, CT | Closed
Listed: May, 28, 2026
Price: $2,800
Living Area: 1,766 Sq. Ft.
863 Whittemore Road
Middlebury, CT | Closed
Listed: May, 03, 2026
Price: $399,900
Living Area: 1,176 Sq. Ft.
Middlebury, CT | Closed
Listed: May, 03, 2026
Price: $399,900
Living Area: 1,176 Sq. Ft.
403 Chestnut Circle 76
Middlebury, CT | Closed
Listed: Sep, 13, 2023
Price: $665,600
Living Area: 2,292 Sq. Ft.
Middlebury, CT | Closed
Listed: Sep, 13, 2023
Price: $665,600
Living Area: 2,292 Sq. Ft.
552 Breakneck Hill Road
Middlebury, CT | Active
Listed: Aug, 12, 2026
Price: $950,000
Living Area: 4,114 Sq. Ft.
Middlebury, CT | Active
Listed: Aug, 12, 2026
Price: $950,000
Living Area: 4,114 Sq. Ft.
North Benson Road 47
Middlebury, CT | Pending
Listed: May, 29, 2025
Price: $509,900
Living Area: 2,206 Sq. Ft.
Middlebury, CT | Pending
Listed: May, 29, 2025
Price: $509,900
Living Area: 2,206 Sq. Ft.
North Benson Road 60
Middlebury, CT | Pending
Listed: Nov, 04, 2025
Price: $573,584
Living Area: 2,206 Sq. Ft.
Middlebury, CT | Pending
Listed: Nov, 04, 2025
Price: $573,584
Living Area: 2,206 Sq. Ft.
North Benson Road 65
Middlebury, CT | Pending
Listed: May, 20, 2026
Price: $573,572
Living Area: 2,206 Sq. Ft.
Middlebury, CT | Pending
Listed: May, 20, 2026
Price: $573,572
Living Area: 2,206 Sq. Ft.
North Benson Road 66
Middlebury, CT | Pending
Listed: Jul, 01, 2026
Price: $562,350
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Pending
Listed: Jul, 01, 2026
Price: $562,350
Living Area: 1,950 Sq. Ft.
North Benson Road 39
Middlebury, CT | Closed
Listed: Feb, 24, 2025
Price: $505,834
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Closed
Listed: Feb, 24, 2025
Price: $505,834
Living Area: 1,950 Sq. Ft.
36 Independence Circle
Middlebury, CT | Closed
Listed: Jun, 18, 2026
Price: $650,000
Living Area: 3,512 Sq. Ft.
Middlebury, CT | Closed
Listed: Jun, 18, 2026
Price: $650,000
Living Area: 3,512 Sq. Ft.
47 Middlebury Terrace
Middlebury, CT | Active
Listed: Jul, 29, 2026
Price: $474,500
Living Area: 1,953 Sq. Ft.
Middlebury, CT | Active
Listed: Jul, 29, 2026
Price: $474,500
Living Area: 1,953 Sq. Ft.
4 Kimberwick Court 4
Middlebury, CT | Pending
Listed: Jul, 08, 2026
Price: $534,900
Living Area: 2,181 Sq. Ft.
Middlebury, CT | Pending
Listed: Jul, 08, 2026
Price: $534,900
Living Area: 2,181 Sq. Ft.
4 Kimberwick Court 4
Middlebury, CT | Pending
Listed: Jul, 08, 2026
Price: $534,900
Living Area: 2,181 Sq. Ft.
Middlebury, CT | Pending
Listed: Jul, 08, 2026
Price: $534,900
Living Area: 2,181 Sq. Ft.
168 North Farm Road
Middlebury, CT | Active Under Contract
Listed: Jun, 06, 2026
Price: $649,900
Living Area: 3,302 Sq. Ft.
Middlebury, CT | Active Under Contract
Listed: Jun, 06, 2026
Price: $649,900
Living Area: 3,302 Sq. Ft.
271 Steinmann Avenue
Middlebury, CT | Active
Listed: Sep, 19, 2026
Price: $139,999
Living Area: 0 Sq. Ft.
Middlebury, CT | Active
Listed: Sep, 19, 2026
Price: $139,999
Living Area: 0 Sq. Ft.
111 North Street
Middlebury, CT | Closed
Listed: Jun, 01, 2026
Price: $3,400
Living Area: 2,245 Sq. Ft.
Middlebury, CT | Closed
Listed: Jun, 01, 2026
Price: $3,400
Living Area: 2,245 Sq. Ft.
29 Cambridge Court
Middlebury, CT | Pending
Listed: Aug, 25, 2026
Price: $829,900
Living Area: 2,796 Sq. Ft.
Middlebury, CT | Pending
Listed: Aug, 25, 2026
Price: $829,900
Living Area: 2,796 Sq. Ft.
51 North Benson Road 51
Middlebury, CT | Closed
Listed: Aug, 06, 2025
Price: $523,920
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Closed
Listed: Aug, 06, 2025
Price: $523,920
Living Area: 1,950 Sq. Ft.
50 North Benson Road 50
Middlebury, CT | Closed
Listed: Aug, 12, 2025
Price: $509,900
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Closed
Listed: Aug, 12, 2025
Price: $509,900
Living Area: 1,950 Sq. Ft.
125 Shadduck Road
Middlebury, CT | Active Under Contract
Listed: Jul, 23, 2026
Price: $324,900
Living Area: 1,008 Sq. Ft.
Middlebury, CT | Active Under Contract
Listed: Jul, 23, 2026
Price: $324,900
Living Area: 1,008 Sq. Ft.
22 Washington Drive
Middlebury, CT | Expired
Listed: May, 16, 2021
Price: $497,870
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: May, 16, 2021
Price: $497,870
Living Area: 0 Sq. Ft.
155 Ridgewood Drive Road 248
Middlebury, CT | Expired
Listed: Jun, 22, 2020
Price: $422,188
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jun, 22, 2020
Price: $422,188
Living Area: 0 Sq. Ft.
17 Westwood Drive
Middlebury, CT | Canceled
Listed: Jul, 14, 2021
Price: $419,000
Living Area: 0 Sq. Ft.
Middlebury, CT | Canceled
Listed: Jul, 14, 2021
Price: $419,000
Living Area: 0 Sq. Ft.
28 Pine Hollow Drive
Middlebury, CT | Expired
Listed: Jan, 22, 2021
Price: $149,900
Living Area: 0 Sq. Ft.
Middlebury, CT | Expired
Listed: Jan, 22, 2021
Price: $149,900
Living Area: 0 Sq. Ft.
10 Old Waterbury Road
Middlebury, CT | Active
Listed: Sep, 15, 2026
Price: $699,900
Living Area: 2,345 Sq. Ft.
Middlebury, CT | Active
Listed: Sep, 15, 2026
Price: $699,900
Living Area: 2,345 Sq. Ft.
327 Steinmann Avenue
Middlebury, CT | Active
Listed: Sep, 08, 2026
Price: $280,000
Living Area: 676 Sq. Ft.
Middlebury, CT | Active
Listed: Sep, 08, 2026
Price: $280,000
Living Area: 676 Sq. Ft.
52A Gleneagle Road, Middlebury, CT 06762
Middlebury, CT | Expired
Listed: Jan, 16, 2019
Price: $759,900
Living Area: 3,100 Sq. Ft.
Middlebury, CT | Expired
Listed: Jan, 16, 2019
Price: $759,900
Living Area: 3,100 Sq. Ft.
75A Gleneagle Road, Middlebury, CT 06762
Middlebury, CT | Expired
Listed: Jan, 16, 2019
Price: $849,900
Living Area: 3,216 Sq. Ft.
Middlebury, CT | Expired
Listed: Jan, 16, 2019
Price: $849,900
Living Area: 3,216 Sq. Ft.
72 E Farms Road, Middlebury, CT 06762
Middlebury, CT | Expired
Listed: Jul, 09, 2019
Price: $995,000
Living Area: 9,080 Sq. Ft.
Middlebury, CT | Expired
Listed: Jul, 09, 2019
Price: $995,000
Living Area: 9,080 Sq. Ft.
54 Falcon Crest Road, Middlebury, CT 06762
Middlebury, CT | Canceled
Listed: Apr, 14, 2005
Price: $1,479,000
Living Area: 6,000 Sq. Ft.
Middlebury, CT | Canceled
Listed: Apr, 14, 2005
Price: $1,479,000
Living Area: 6,000 Sq. Ft.
59 E Farm Road, Middlebury, CT 06762
Middlebury, CT | Canceled
Listed: Oct, 31, 2005
Price: $1,995,000
Living Area: 6,048 Sq. Ft.
Middlebury, CT | Canceled
Listed: Oct, 31, 2005
Price: $1,995,000
Living Area: 6,048 Sq. Ft.
54 Falcon Crest Road, Middlebury, CT 06762
Middlebury, CT | Expired
Listed: Apr, 20, 2006
Price: $1,479,000
Living Area: 6,000 Sq. Ft.
Middlebury, CT | Expired
Listed: Apr, 20, 2006
Price: $1,479,000
Living Area: 6,000 Sq. Ft.
59 E Farm Road, Middlebury, CT 06762
Middlebury, CT | Expired
Listed: Apr, 20, 2006
Price: $1,995,000
Living Area: 6,049 Sq. Ft.
Middlebury, CT | Expired
Listed: Apr, 20, 2006
Price: $1,995,000
Living Area: 6,049 Sq. Ft.
North Benson Road 58
Middlebury, CT | Pending
Listed: Aug, 05, 2026
Price: $608,000
Living Area: 2,582 Sq. Ft.
Middlebury, CT | Pending
Listed: Aug, 05, 2026
Price: $608,000
Living Area: 2,582 Sq. Ft.
10 Old Waterbury Road 3
Middlebury, CT | Closed
Listed: May, 14, 2026
Price: $1,050
Living Area: 450 Sq. Ft.
Middlebury, CT | Closed
Listed: May, 14, 2026
Price: $1,050
Living Area: 450 Sq. Ft.
North Benson Road 44
Middlebury, CT | Pending
Listed: Jul, 15, 2026
Price: $559,250
Living Area: 1,950 Sq. Ft.
Middlebury, CT | Pending
Listed: Jul, 15, 2026
Price: $559,250
Living Area: 1,950 Sq. Ft.
