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 38 Avalon Drive Middlebury, CT MLS# 24180471
$779,000
3

Beds

2.1

Baths

3,217

Sq.Ft.

38 Avalon Drive

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

The time to sell is now! THE TIME TO SELL IS NOW!
View 42 White Avenue Middlebury, CT MLS# 24181047
    1 of 26
    OPEN HOUSE: Sunday 6/14 1:00 PM - 3:00 PM
    $479,900
    3

    Beds

    2.1

    Baths

    2,112

    Sq.Ft.

    42 White Avenue

    Middlebury, CT

    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

    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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