View 775 South Street Middlebury, CT MLS# 24151632
  • Recently Listed
1 of 40
$2,850,000
8

Beds

6.2

Baths

9,619

Sq.Ft.

775 South Street

Middlebury, CT

View 0 White Birch Lane Middlebury, CT MLS# 24141986
$1,600,000
Studio

Beds

0.0

Baths

0 White Birch Lane

Middlebury, CT

View 6 Deer Run Road Middlebury, CT MLS# 24128666
$810,000
3

Beds

2.1

Baths

2,190

Sq.Ft.

6 Deer Run Road

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 18 Deer Run Road Middlebury, CT MLS# 24099002
$799,900
3

Beds

2.1

Baths

2,190

Sq.Ft.

18 Deer Run Road

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 117 Crest Road Middlebury, CT MLS# 24147892
$759,000
4

Beds

2.1

Baths

2,753

Sq.Ft.

117 Crest Road

Middlebury, CT

View 200 North Farm Road Middlebury, CT MLS# 24124893
$750,000
4

Beds

2.2

Baths

3,360

Sq.Ft.

200 North Farm 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 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 2 Deer Run Road Middlebury, CT MLS# 24110714
$709,900
3

Beds

2.1

Baths

2,190

Sq.Ft.

2 Deer Run Road

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

Beds

3.2

Baths

3,254

Sq.Ft.

84 Munson Road

Middlebury, CT

View 3 Brookside Drive 3 Middlebury, CT MLS# 24145711
$659,900
4

Beds

2.2

Baths

4,200

Sq.Ft.

3 Brookside Drive 3

Middlebury, CT

View 3 Brookside Drive 3 Middlebury, CT MLS# 24146182
$659,900
4

Beds

2.2

Baths

4,200

Sq.Ft.

3 Brookside Drive 3

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 3 Hunting Ridge Road Middlebury, CT MLS# 24155317
  • Recently Listed with Virtual Tour
1 of 38
$629,900
3

Beds

2.1

Baths

1,722

Sq.Ft.

3 Hunting Ridge 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 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 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

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

48

Estimated median home price

$564,918
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 - 300K4
$300K - 400K1
$400K - 500K1
$500K - 600K22
$600K - 700K8
$700K - 800K7
$800K - 900K1
$900K - 1M0
$1M - Max2

Homes for Sale by Type in Middlebury, CT

Property TypeCount
Single Family19
Townhouse0
Condo22
Commercial0
Rental6
Lots and Land6
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 2/23/2026)

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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