View North Benson Road # 45 Middlebury, CT MLS# 24089121
$525,438
3

Beds

2.1

Baths

1,950

Sq.Ft.

North Benson Road # 45

Middlebury, CT

View 14 Deer Run Road Middlebury, CT MLS# 24088127
$699,000
3

Beds

2.0

Baths

1,877

Sq.Ft.

14 Deer Run Road

Middlebury, CT

View North Benson Road # 55 Middlebury, CT MLS# 24086408
$548,828
3

Beds

2.1

Baths

2,462

Sq.Ft.

North Benson Road # 55

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View North Benson Road # 53 Middlebury, CT MLS# 24086541
$519,900
3

Beds

2.1

Baths

1,950

Sq.Ft.

North Benson Road # 53

Middlebury, CT

View Ferndale Avenue # Middlebury, CT MLS# 24084578
$75,000
Studio

Beds

0.0

Baths

Ferndale Avenue #

Middlebury, CT

View 3 Pine Ridge 23 Middlebury, CT MLS# 24082812
  • Adult Community
1 of 29
$721,000
2

Beds

2.1

Baths

2,290

Sq.Ft.

3 Pine Ridge 23

Middlebury, CT

View 15 Hunting Ridge Road Middlebury, CT MLS# 24079981
  • New Construction
1 of 2
$794,900
3

Beds

2.1

Baths

2,190

Sq.Ft.

15 Hunting Ridge Road

Middlebury, CT

View 28 Hunting Ridge Road Middlebury, CT MLS# 24079497
  • New Construction
1 of 4
$739,900
4

Beds

2.1

Baths

2,466

Sq.Ft.

28 Hunting Ridge Road

Middlebury, CT

View North Benson Road # 64 Middlebury, CT MLS# 24077175
$545,400
3

Beds

2.1

Baths

2,206

Sq.Ft.

North Benson Road # 64

Middlebury, CT

View 19 Deer Run Road Middlebury, CT MLS# 24068681
$274,900
Studio

Beds

0.0

Baths

19 Deer Run Road

Middlebury, CT

View 11 Hunting Ridge Road Middlebury, CT MLS# 24055021
  • New Construction with Virtual Tour
1 of 39
$799,900
4

Beds

2.1

Baths

2,700

Sq.Ft.

11 Hunting Ridge Road

Middlebury, CT

View 66 Artillery Road Middlebury, CT MLS# 24050169
$599,000
4

Beds

3.1

Baths

2,691

Sq.Ft.

66 Artillery Road

Middlebury, CT

View 288 Watertown Road Lot 5 Middlebury, CT MLS# 24050731
$200,000
Studio

Beds

0.0

Baths

288 Watertown Road Lot 5

Middlebury, CT

View 3 Hunting Ridge Road Middlebury, CT MLS# 24032206
  • New Construction with Virtual Tour
1 of 38
$624,900
3

Beds

2.0

Baths

1,700

Sq.Ft.

3 Hunting Ridge Road

Middlebury, CT

View 22 Somerset Drive Middlebury, CT MLS# 24024751
  • New Construction
1 of 7
$925,000
3

Beds

2.1

Baths

2,878

Sq.Ft.

22 Somerset Drive

Middlebury, CT

View 294 Christian Road Middlebury, CT MLS# 170591262
  • New Construction
1 of 8
$899,000
3

Beds

2.1

Baths

2,878

Sq.Ft.

294 Christian Road

Middlebury, CT

About Middlebury

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.

Listings in Middlebury, CT

68

Estimated median home price

$562,877
Middlebury CT Homes for Sale & Properties

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.

Homes for Sale by Price in Middlebury, CT

PriceCount
$0 - 100K2
$100K - 200K2
$200K - 300K2
$300K - 400K6
$400K - 500K8
$500K - 600K23
$600K - 700K8
$700K - 800K9
$800K - 900K3
$900K - 1M2
$1M - Max3

Homes for Sale by Type in Middlebury, CT

Property TypeCount
Single Family39
Townhouse0
Condo24
Commercial0
Rental5
Lots and Land5
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 11/11/2025)

Information deemed reliable but not guaranteed.

Listing information has been assembled from various sources of varying degrees of reliability. Any information critical to a buying decision should be independently verified.

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