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
OPEN HOUSE: Sunday 3/1 12:00 PM - 2:00 PM
$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
$729,990
4

Beds

2.1

Baths

3,300

Sq.Ft.

321 Artillery Road

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
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 2 Deer Run Road Middlebury, CT MLS# 24110714
$709,900
3

Beds

2.1

Baths

2,190

Sq.Ft.

2 Deer Run Road

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 14 Deer Run Road Middlebury, CT MLS# 24088127
$699,000
3

Beds

2.0

Baths

1,877

Sq.Ft.

14 Deer Run 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
  • Recently Listed with Virtual Tour
1 of 38
OPEN HOUSE: Sunday 3/1 12:00 PM - 2:00 PM
$629,900
3

Beds

2.1

Baths

1,722

Sq.Ft.

3 Hunting Ridge 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 10 Old Waterbury Road Middlebury, CT MLS# 24143678
    1 of 12
    OPEN HOUSE: Saturday 2/28 12:00 PM - 1:00 PM
    $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

    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 24 Ridgewood Drive 24 Middlebury, CT MLS# 24147226
    $574,000
    3

    Beds

    3.1

    Baths

    2,879

    Sq.Ft.

    24 Ridgewood Drive 24

    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 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

    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

    48

    Estimated median home price

    $571,074
    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 - 800K8
    $800K - 900K1
    $900K - 1M0
    $1M - Max2

    Homes for Sale by Type in Middlebury, CT

    Property TypeCount
    Single Family19
    Townhouse0
    Condo22
    Commercial0
    Rental4
    Lots and Land6
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms0

    (Data as of 2/27/2026)

    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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