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 223 Carriage Drive Middlebury, CT MLS# 24160037
$674,900
4

Beds

3.1

Baths

2,484

Sq.Ft.

223 Carriage Drive

Middlebury, CT

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

The time to sell is now! THE TIME TO SELL IS NOW!
View 408 Breakneck Hill Road Middlebury, CT MLS# 24164434
$625,000
2

Beds

2.1

Baths

1,848

Sq.Ft.

408 Breakneck Hill 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 6 Brookside Drive Middlebury, CT MLS# 24164000
  • Virtual Tour
1 of 40
$599,995
4

Beds

3.1

Baths

3,745

Sq.Ft.

6 Brookside Drive

Middlebury, CT

View 6 Brookside Drive 6 Middlebury, CT MLS# 24159958
$599,995
4

Beds

3.1

Baths

3,745

Sq.Ft.

6 Brookside Drive 6

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 3 Brookside Drive 3 Middlebury, CT MLS# 24145711
    1 of 36
    OPEN HOUSE: Sunday 4/26 1:00 PM - 3:00 PM
    $599,900
    4

    Beds

    2.2

    Baths

    4,200

    Sq.Ft.

    3 Brookside Drive 3

    Middlebury, CT

    View 3 Brookside Drive 3 Middlebury, CT MLS# 24146182
      1 of 35
      OPEN HOUSE: Sunday 4/26 1:00 PM - 3:00 PM
      $599,900
      4

      Beds

      2.2

      Baths

      4,200

      Sq.Ft.

      3 Brookside Drive 3

      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

      View 2 Arrowwood Court 2 Middlebury, CT MLS# 24163914
      • Recently Listed
      1 of 32
      OPEN HOUSE: Sunday 4/26 12:00 PM - 2:00 PM
      $599,900
      3

      Beds

      2.1

      Baths

      2,256

      Sq.Ft.

      2 Arrowwood Court 2

      Middlebury, CT

      View 36 Highridge Road 36 Middlebury, CT MLS# 24163482
      $585,000
      3

      Beds

      2.1

      Baths

      1,997

      Sq.Ft.

      36 Highridge Road 36

      Middlebury, CT

      View 66 Artillery Road Middlebury, CT MLS# 24164662
      • Recently Listed
      1 of 25
      $585,000
      4

      Beds

      3.1

      Baths

      2,691

      Sq.Ft.

      66 Artillery Road

      Middlebury, CT

      View 292 Park Rd Extension Middlebury, CT MLS# 24141966
      $574,900
      5

      Beds

      2.0

      Baths

      1,924

      Sq.Ft.

      292 Park Rd Extension

      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 1 Arrowwood Court 1 Middlebury, CT MLS# 24155854
      $569,500
      3

      Beds

      2.1

      Baths

      2,295

      Sq.Ft.

      1 Arrowwood Court 1

      Middlebury, CT

      View North Benson Road # 59 Middlebury, CT MLS# 24116892
      $568,564
      3

      Beds

      2.1

      Baths

      2,206

      Sq.Ft.

      North Benson Road # 59

      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 North Benson Road # 52 Middlebury, CT MLS# 24100213
      $560,753
      3

      Beds

      2.1

      Baths

      2,206

      Sq.Ft.

      North Benson Road # 52

      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

      $579,950
      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 - 300K3
      $300K - 400K2
      $400K - 500K4
      $500K - 600K32
      $600K - 700K7
      $700K - 800K11
      $800K - 900K4
      $900K - 1M2
      $1M - Max1

      Homes for Sale by Type in Middlebury, CT

      Property TypeCount
      Single Family35
      Townhouse0
      Condo26
      Commercial1
      Rental5
      Lots and Land4
      Condo/Town/CoOp0
      CoOp0
      Multi Family2
      Mobile Home0
      Farms0

      (Data as of 4/22/2026)

      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.

      Information on this this page is provided by the Smart Multiple Listing Service, Inc. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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