View 366 Charcoal Avenue Middlebury, CT MLS# 24158517
$750,000
4

Beds

2.1

Baths

3,198

Sq.Ft.

366 Charcoal Avenue

Middlebury, CT

View 200 North Farm Road Middlebury, CT MLS# 24163117
$750,000
4

Beds

2.2

Baths

3,360

Sq.Ft.

200 North Farm Road

Middlebury, CT

View 80 Pine Hollow Drive Middlebury, CT MLS# 24161366
$749,900
4

Beds

3.1

Baths

2,806

Sq.Ft.

80 Pine Hollow Drive

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 28 Hunting Ridge Road Middlebury, CT MLS# 24079497
  • New Construction
1 of 41
$739,900
4

Beds

2.1

Baths

2,466

Sq.Ft.

28 Hunting Ridge Road

Middlebury, CT

View 20 Hunting Ridge Road Middlebury, CT MLS# 24160275
  • New Construction
1 of 29
$735,900
3

Beds

2.0

Baths

1,877

Sq.Ft.

20 Hunting Ridge Road

Middlebury, CT

View 321 Artillery Road Middlebury, CT MLS# 24155964
$729,990
4

Beds

2.1

Baths

3,300

Sq.Ft.

321 Artillery Road

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 70 Pine Hollow Drive Middlebury, CT MLS# 24158024
$700,000
3

Beds

2.1

Baths

2,734

Sq.Ft.

70 Pine Hollow Drive

Middlebury, CT

View Lots 12,13, 14 Mirey Dam Road Middlebury, CT MLS# 24152234
$699,900
Studio

Beds

0.0

Baths

Lots 12,13, 14 Mirey Dam Road

Middlebury, CT

View 84 Munson Road Middlebury, CT MLS# 24145916
$689,000
4

Beds

3.2

Baths

3,254

Sq.Ft.

84 Munson Road

Middlebury, CT

View 223 Carriage Drive Middlebury, CT MLS# 24160037
$674,900
4

Beds

3.1

Baths

2,484

Sq.Ft.

223 Carriage Drive

Middlebury, CT

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 193 Ridgewood Drive 193 Middlebury, CT MLS# 24163290
$649,900
3

Beds

2.1

Baths

2,658

Sq.Ft.

193 Ridgewood Drive 193

Middlebury, CT

View 408 Breakneck Hill Road Middlebury, CT MLS# 24164434
$625,000
2

Beds

2.1

Baths

1,848

Sq.Ft.

408 Breakneck Hill Road

Middlebury, CT

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

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

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

69

Estimated median home price

$585,000
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 - 200K2
$200K - 300K3
$300K - 400K2
$400K - 500K3
$500K - 600K32
$600K - 700K8
$700K - 800K11
$800K - 900K4
$900K - 1M2
$1M - Max1

Homes for Sale by Type in Middlebury, CT

Property TypeCount
Single Family35
Townhouse0
Condo26
Commercial1
Rental5
Lots and Land5
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms0

(Data as of 4/20/2026)

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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