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
    1 of 37
    OPEN HOUSE: Sunday 3/15 11:00 AM - 1:00 PM
    $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 321 Artillery Road Middlebury, CT MLS# 24155964
      1 of 1
      OPEN HOUSE: Sunday 3/15 11:00 AM - 1:00 PM
      $729,990
      4

      Beds

      2.1

      Baths

      3,300

      Sq.Ft.

      321 Artillery 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 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 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
      $629,900
      3

      Beds

      2.1

      Baths

      1,722

      Sq.Ft.

      3 Hunting Ridge Road

      Middlebury, CT

      View 16 Winding Trail 16 Middlebury, CT MLS# 24157092
      • Recently Listed with Virtual Tour
      1 of 41
      $625,000
      3

      Beds

      2.1

      Baths

      2,646

      Sq.Ft.

      16 Winding Trail 16

      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

      47

      Estimated median home price

      $569,500
      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 - 400K0
      $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 Family17
      Townhouse0
      Condo23
      Commercial0
      Rental5
      Lots and Land6
      Condo/Town/CoOp0
      CoOp0
      Multi Family1
      Mobile Home0
      Farms0

      (Data as of 3/5/2026)

      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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