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 18 Freedom Road Middlebury, CT MLS# 24163920
  • Recently Listed
1 of 32
OPEN HOUSE: Sunday 4/12 11:00 AM - 1:00 PM
$479,000
3

Beds

1.1

Baths

1,492

Sq.Ft.

18 Freedom Road

Middlebury, CT

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

Beds

3.1

Baths

3,745

Sq.Ft.

6 Brookside Drive

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 6 Brookside Drive 6 Middlebury, CT MLS# 24159958
  • Recently Listed with Virtual Tour
1 of 40
$599,995
4

Beds

3.1

Baths

3,745

Sq.Ft.

6 Brookside Drive 6

Middlebury, CT

View 19 Deer Run Road Middlebury, CT MLS# 24162678
$900,000
4

Beds

2.1

Baths

3,100

Sq.Ft.

19 Deer Run Road

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 390 Middlebury Road 3 Middlebury, CT MLS# 24162922
  • Recently Listed
1 of 15
$119,900
850

Sq.Ft.

390 Middlebury Road 3

Middlebury, CT

View 36 Highridge Road 36 Middlebury, CT MLS# 24163482
  • Recently Listed
1 of 27
$585,000
3

Beds

2.1

Baths

1,997

Sq.Ft.

36 Highridge Road 36

Middlebury, CT

View 1140 Southford Road Middlebury, CT MLS# 24162191
  • Recently Listed
1 of 13
$399,000
Studio

Beds

0.0

Baths

1140 Southford 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

View 314 Porter Avenue Middlebury, CT MLS# 24161984
$349,900
3

Beds

2.0

Baths

1,440

Sq.Ft.

314 Porter Avenue

Middlebury, CT

View 541 Benson Road Middlebury, CT MLS# 24161553
  • Recently Listed
1 of 24
$525,000
2

Beds

2.0

Baths

1,600

Sq.Ft.

541 Benson Road

Middlebury, CT

View 541 Benson Road Middlebury, CT MLS# 24161555
  • Recently Listed
1 of 20
$525,000
3

Beds

3.0

Baths

1,600

Sq.Ft.

541 Benson Road

Middlebury, CT

View 38 East Ridge Drive Middlebury, CT MLS# 24158643
$509,900
3

Beds

2.0

Baths

1,780

Sq.Ft.

38 East Ridge Drive

Middlebury, CT

View 223 Carriage Drive Middlebury, CT MLS# 24160037
$699,900
4

Beds

3.1

Baths

2,484

Sq.Ft.

223 Carriage Drive

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

Beds

2.1

Baths

3,198

Sq.Ft.

366 Charcoal Avenue

Middlebury, CT

View Lot 41 Somerset Drive Middlebury, CT MLS# 24158747
  • New Construction
1 of 9
$939,000
3

Beds

2.1

Baths

2,878

Sq.Ft.

Lot 41 Somerset Drive

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 16 Winding Trail 16 Middlebury, CT MLS# 24157092
$625,000
3

Beds

2.1

Baths

2,646

Sq.Ft.

16 Winding Trail 16

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

63

Estimated median home price

$574,000
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 - 500K2
$500K - 600K28
$600K - 700K10
$700K - 800K10
$800K - 900K2
$900K - 1M1
$1M - Max2

Homes for Sale by Type in Middlebury, CT

Property TypeCount
Single Family28
Townhouse0
Condo26
Commercial1
Rental5
Lots and Land6
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms0

(Data as of 4/9/2026)

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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