View 8 Deer Run Road Middlebury, CT MLS# 24182002
$839,900
3

Beds

2.1

Baths

2,450

Sq.Ft.

8 Deer Run Road

Middlebury, CT

View 168 North Farm Road Middlebury, CT MLS# 24178550
  • Recently Listed
1 of 40
$765,000
4

Beds

3.1

Baths

3,302

Sq.Ft.

168 North Farm Road

Middlebury, CT

View 42 White Avenue Middlebury, CT MLS# 24181047
$479,900
3

Beds

2.1

Baths

2,112

Sq.Ft.

42 White Avenue

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 72 Ridgewood Drive 72 Middlebury, CT MLS# 24179784
  • Recently Listed
1 of 39
$569,900
3

Beds

2.1

Baths

2,428

Sq.Ft.

72 Ridgewood Drive 72

Middlebury, CT

View 286 Mirey Dam Road Middlebury, CT MLS# 24179200
  • Recently Listed
1 of 38
$975,000
4

Beds

3.0

Baths

4,451

Sq.Ft.

286 Mirey Dam Road

Middlebury, CT

View 178 Ridgewood Drive 178 Middlebury, CT MLS# 24177424
$639,900
3

Beds

2.1

Baths

2,414

Sq.Ft.

178 Ridgewood Drive 178

Middlebury, CT

View 3 Winding Trail 3 Middlebury, CT MLS# 24177196
  • Recently Listed
1 of 35
$559,900
3

Beds

2.1

Baths

3,179

Sq.Ft.

3 Winding Trail 3

Middlebury, CT

View 818 Middlebury Road Middlebury, CT MLS# 24177692
$385,000
2

Beds

1.0

Baths

1,489

Sq.Ft.

818 Middlebury Road

Middlebury, CT

View 1 Independence Circle 1 Middlebury, CT MLS# 24176712
$609,000
4

Beds

2.1

Baths

3,224

Sq.Ft.

1 Independence Circle 1

Middlebury, CT

View 1 Independence Circle 1 Middlebury, CT MLS# 24177570
$609,000
4

Beds

2.1

Baths

3,224

Sq.Ft.

1 Independence Circle 1

Middlebury, CT

View North Benson Road # 65 Middlebury, CT MLS# 24177098
$573,572
3

Beds

2.1

Baths

2,206

Sq.Ft.

North Benson Road # 65

Middlebury, CT

View 80 Anawan Avenue Middlebury, CT MLS# 24174618
$529,900
2

Beds

2.0

Baths

1,962

Sq.Ft.

80 Anawan Avenue

Middlebury, CT

View 10 Pelham Way 10 Middlebury, CT MLS# 24171754
$650,000
3

Beds

2.1

Baths

2,251

Sq.Ft.

10 Pelham Way 10

Middlebury, CT

View 397 White Deer Rock Road Middlebury, CT MLS# 24169624
$2,195,000
3

Beds

2.1

Baths

3,863

Sq.Ft.

397 White Deer Rock Road

Middlebury, CT

View 700 Watertown Road Middlebury, CT MLS# 24171374
$630,000
5

Beds

2.1

Baths

2,528

Sq.Ft.

700 Watertown Road

Middlebury, CT

View 15 Central Road Middlebury, CT MLS# 24160065
$694,900
3

Beds

2.1

Baths

2,870

Sq.Ft.

15 Central Road

Middlebury, CT

View 283 Whittemore Road Middlebury, CT MLS# 24169230
$519,000
3

Beds

2.1

Baths

2,500

Sq.Ft.

283 Whittemore Road

Middlebury, CT

View 301 Steinmann Avenue Middlebury, CT MLS# 24167075
$409,900
3

Beds

1.1

Baths

1,572

Sq.Ft.

301 Steinmann Avenue

Middlebury, CT

View 90 Fenn Road Middlebury, CT MLS# 24167501
$679,900
4

Beds

2.2

Baths

3,162

Sq.Ft.

90 Fenn Road

Middlebury, CT

View 24 Highridge Road 24 Middlebury, CT MLS# 24169215
$560,000
3

Beds

2.1

Baths

1,802

Sq.Ft.

24 Highridge Road 24

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

71

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 - 200K1
$200K - 300K2
$300K - 400K2
$400K - 500K3
$500K - 600K31
$600K - 700K14
$700K - 800K7
$800K - 900K5
$900K - 1M3
$1M - Max2

Homes for Sale by Type in Middlebury, CT

Property TypeCount
Single Family36
Townhouse0
Condo29
Commercial1
Rental4
Lots and Land4
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 6/7/2026)

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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