View North Benson Road # 48 Middlebury, CT MLS# 24129196
$603,780
3

Beds

2.1

Baths

2,706

Sq.Ft.

North Benson Road # 48

Middlebury, CT

View 6 Brookside Drive Middlebury, CT MLS# 24164000
  • Virtual Tour
1 of 40
$599,995
4

Beds

3.1

Baths

3,745

Sq.Ft.

6 Brookside Drive

Middlebury, CT

View 6 Brookside Drive 6 Middlebury, CT MLS# 24159958
$599,995
4

Beds

3.1

Baths

3,745

Sq.Ft.

6 Brookside Drive 6

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 10 Old Waterbury Road Middlebury, CT MLS# 24143678
$599,900
5

Beds

4.0

Baths

2,345

Sq.Ft.

10 Old Waterbury Road

Middlebury, CT

View 3 Brookside Drive 3 Middlebury, CT MLS# 24145711
$599,900
4

Beds

2.2

Baths

4,200

Sq.Ft.

3 Brookside Drive 3

Middlebury, CT

View 3 Brookside Drive 3 Middlebury, CT MLS# 24146182
$599,900
4

Beds

2.2

Baths

4,200

Sq.Ft.

3 Brookside Drive 3

Middlebury, CT

View 428 Breakneck Hill Road Middlebury, CT MLS# 24155123
$599,900
2

Beds

1.1

Baths

1,749

Sq.Ft.

428 Breakneck Hill Road

Middlebury, CT

View 2 Arrowwood Court 2 Middlebury, CT MLS# 24163914
  • Recently Listed
1 of 32
$599,900
3

Beds

2.1

Baths

2,256

Sq.Ft.

2 Arrowwood Court 2

Middlebury, CT

View 36 Highridge Road 36 Middlebury, CT MLS# 24163482
$585,000
3

Beds

2.1

Baths

1,997

Sq.Ft.

36 Highridge Road 36

Middlebury, CT

View 66 Artillery Road Middlebury, CT MLS# 24164662
$585,000
4

Beds

3.1

Baths

2,691

Sq.Ft.

66 Artillery Road

Middlebury, CT

View 292 Park Rd Extension Middlebury, CT MLS# 24141966
$574,900
5

Beds

2.0

Baths

1,924

Sq.Ft.

292 Park Rd Extension

Middlebury, CT

View North Benson Road # 60 Middlebury, CT MLS# 24138018
$573,584
3

Beds

2.1

Baths

2,206

Sq.Ft.

North Benson Road # 60

Middlebury, CT

View 1 Arrowwood Court 1 Middlebury, CT MLS# 24155854
$569,500
3

Beds

2.1

Baths

2,295

Sq.Ft.

1 Arrowwood Court 1

Middlebury, CT

View North Benson Road # 59 Middlebury, CT MLS# 24116892
$568,564
3

Beds

2.1

Baths

2,206

Sq.Ft.

North Benson Road # 59

Middlebury, CT

View North Benson Road # 57 Middlebury, CT MLS# 24145034
$561,271
3

Beds

2.1

Baths

2,206

Sq.Ft.

North Benson Road # 57

Middlebury, CT

View North Benson Road # 52 Middlebury, CT MLS# 24100213
$560,753
3

Beds

2.1

Baths

2,206

Sq.Ft.

North Benson Road # 52

Middlebury, CT

View 24 Highridge Road 24 Middlebury, CT MLS# 24169215
  • Recently Listed with Virtual Tour
1 of 40
$560,000
3

Beds

2.1

Baths

1,802

Sq.Ft.

24 Highridge Road 24

Middlebury, CT

View North Benson Road # 44 Middlebury, CT MLS# 24109951
$555,888
3

Beds

2.1

Baths

2,252

Sq.Ft.

North Benson Road # 44

Middlebury, CT

View 24 Ridgewood Drive 24 Middlebury, CT MLS# 24147226
$554,000
3

Beds

3.1

Baths

2,879

Sq.Ft.

24 Ridgewood Drive 24

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

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

70

Estimated median home price

$574,242
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 - 100K1
$100K - 200K1
$200K - 300K3
$300K - 400K2
$400K - 500K5
$500K - 600K33
$600K - 700K8
$700K - 800K9
$800K - 900K5
$900K - 1M2
$1M - Max1

Homes for Sale by Type in Middlebury, CT

Property TypeCount
Single Family36
Townhouse0
Condo27
Commercial1
Rental5
Lots and Land4
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms0

(Data as of 4/25/2026)

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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