View 72 Carriage Drive Middlebury, CT MLS# 24131536
$649,900
4

Beds

3.0

Baths

2,878

Sq.Ft.

72 Carriage Drive

Middlebury, CT

View 51 Cross Road Middlebury, CT MLS# 24141874
  • Recently Listed
1 of 40
OPEN HOUSE: Saturday 12/6 11:00 AM - 1:00 PM
$629,900
4

Beds

3.1

Baths

3,244

Sq.Ft.

51 Cross Road

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

The time to sell is now! THE TIME TO SELL IS NOW!
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 24 Ridgewood Drive 24 Middlebury, CT MLS# 24122594
  • Virtual Tour
1 of 39
OPEN HOUSE: Sunday 12/7 12:00 PM - 2:00 PM
$599,900
3

Beds

3.1

Baths

2,879

Sq.Ft.

24 Ridgewood Drive 24

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 126 Colonial Avenue Middlebury, CT MLS# 24122855
$599,000
3

Beds

1.1

Baths

2,531

Sq.Ft.

126 Colonial Avenue

Middlebury, CT

View 541 Benson Road Middlebury, CT MLS# 24128030
$579,900
2

Beds

2.0

Baths

1,660

Sq.Ft.

541 Benson Road

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 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 27 Winding Trail 27 Middlebury, CT MLS# 24133988
$565,000
3

Beds

2.1

Baths

2,680

Sq.Ft.

27 Winding Trail 27

Middlebury, CT

View 23 Caveson Court 23 Middlebury, CT MLS# 24135107
$565,000
3

Beds

2.1

Baths

2,547

Sq.Ft.

23 Caveson Court 23

Middlebury, CT

View 23 Caveson Court 23 Middlebury, CT MLS# 24135113
$565,000
3

Beds

2.1

Baths

2,547

Sq.Ft.

23 Caveson Court 23

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 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 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

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 North Benson Road # 49 Middlebury, CT MLS# 24096137
$533,416
3

Beds

2.1

Baths

1,950

Sq.Ft.

North Benson Road # 49

Middlebury, CT

View 2 Dogwood Court 2 Middlebury, CT MLS# 24111129
$530,000
3

Beds

3.1

Baths

3,103

Sq.Ft.

2 Dogwood Court 2

Middlebury, CT

View 13 Caveson Court 13 Middlebury, CT MLS# 24137483
$530,000
2

Beds

2.0

Baths

2,011

Sq.Ft.

13 Caveson Court 13

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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