View 24 Ridgewood Drive 24 Middlebury, CT MLS# 24147226
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Sunday 1/11 12:00 PM - 2:00 PM
$574,000
3

Beds

3.1

Baths

2,879

Sq.Ft.

24 Ridgewood Drive 24

Middlebury, CT

View 3 Brookside Drive 3 Middlebury, CT MLS# 24145711
  • Recently Listed
1 of 51
$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
  • Recently Listed
1 of 50
$659,900
4

Beds

2.2

Baths

4,200

Sq.Ft.

3 Brookside Drive 3

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 348 Kelly Road Middlebury, CT MLS# 24146072
$335,000
2

Beds

1.0

Baths

768

Sq.Ft.

348 Kelly Road

Middlebury, CT

View 152 Glenwood Avenue Middlebury, CT MLS# 24146106
  • Recently Listed
1 of 14
$299,900
2

Beds

1.0

Baths

1,085

Sq.Ft.

152 Glenwood Avenue

Middlebury, CT

View 637 Watertown Road Middlebury, CT MLS# 24145459
$524,900
3

Beds

3.1

Baths

1,918

Sq.Ft.

637 Watertown Road

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 292 Park Rd Extension Middlebury, CT MLS# 24141966
$599,900
5

Beds

2.0

Baths

1,924

Sq.Ft.

292 Park Rd Extension

Middlebury, CT

View 10 Old Waterbury Road Middlebury, CT MLS# 24143678
$699,900
5

Beds

4.0

Baths

2,345

Sq.Ft.

10 Old Waterbury Road

Middlebury, CT

View 51 Cross Road Middlebury, CT MLS# 24141874
$629,900
4

Beds

3.1

Baths

3,244

Sq.Ft.

51 Cross Road

Middlebury, CT

View 32 Yale Avenue Middlebury, CT MLS# 24138445
$389,000
3

Beds

2.0

Baths

1,861

Sq.Ft.

32 Yale Avenue

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 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

View 73 Yale Avenue Middlebury, CT MLS# 24132707
$334,900
2

Beds

2.0

Baths

1,099

Sq.Ft.

73 Yale Avenue

Middlebury, CT

View 11 Upper Whittemore Road Middlebury, CT MLS# 24136109
$459,000
3

Beds

1.0

Baths

1,120

Sq.Ft.

11 Upper Whittemore Road

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

Beds

3.0

Baths

2,878

Sq.Ft.

72 Carriage Drive

Middlebury, CT

View 281 Watertown Road Middlebury, CT MLS# 24130870
$499,900
5

Beds

2.0

Baths

2,428

Sq.Ft.

281 Watertown 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 541 Benson Road Middlebury, CT MLS# 24128030
$499,000
2

Beds

2.0

Baths

1,660

Sq.Ft.

541 Benson 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

57

Estimated median home price

$565,000
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 - 100K2
$100K - 200K1
$200K - 300K2
$300K - 400K4
$400K - 500K3
$500K - 600K22
$600K - 700K8
$700K - 800K8
$800K - 900K3
$900K - 1M1
$1M - Max3

Homes for Sale by Type in Middlebury, CT

Property TypeCount
Single Family30
Townhouse0
Condo21
Commercial0
Rental5
Lots and Land5
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 1/9/2026)

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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