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 0 White Birch Lane Middlebury, CT MLS# 24141986
  • Recently Listed
1 of 5
$1,600,000
Studio

Beds

0.0

Baths

0 White Birch Lane

Middlebury, CT

View 383 Leonard Road Middlebury, CT MLS# 24141215
  • Recently Listed with Virtual Tour
1 of 40
$889,900
4

Beds

3.1

Baths

3,220

Sq.Ft.

383 Leonard Road

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
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 105 Jericho Road Middlebury, CT MLS# 24133379
  • Virtual Tour
1 of 29
$465,000
3

Beds

2.1

Baths

2,364

Sq.Ft.

105 Jericho Road

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 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 225 Crest Road Middlebury, CT MLS# 24133783
$1,085,000
3

Beds

2.2

Baths

4,138

Sq.Ft.

225 Crest Road

Middlebury, CT

View 116 Yale Avenue Middlebury, CT MLS# 24131737
$489,900
3

Beds

2.1

Baths

2,311

Sq.Ft.

116 Yale Avenue

Middlebury, CT

View 7 Sandy Beach Road Middlebury, CT MLS# 24131596
$4,100,000
6

Beds

4.0

Baths

5,816

Sq.Ft.

7 Sandy Beach Road

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 182 Bayberry Terrace Middlebury, CT MLS# 24129568
$500,000
4

Beds

2.0

Baths

2,302

Sq.Ft.

182 Bayberry Terrace

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 80 Pine Hollow Drive Middlebury, CT MLS# 24127773
$750,000
4

Beds

3.1

Baths

2,806

Sq.Ft.

80 Pine Hollow Drive

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

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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