View 24 Ridgewood Drive 24 Middlebury, CT MLS# 24147226
$554,000
3

Beds

3.1

Baths

2,879

Sq.Ft.

24 Ridgewood Drive 24

Middlebury, CT

View North Benson Road # 55 Middlebury, CT MLS# 24086408
$548,828
3

Beds

2.1

Baths

2,462

Sq.Ft.

North Benson Road # 55

Middlebury, CT

View North Benson Road # 64 Middlebury, CT MLS# 24077175
$545,400
3

Beds

2.1

Baths

2,206

Sq.Ft.

North Benson Road # 64

Middlebury, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View North Benson Road # 62 Middlebury, CT MLS# 24152745
$545,400
3

Beds

2.1

Baths

2,206

Sq.Ft.

North Benson Road # 62

Middlebury, CT

View North Benson Road # 49 Middlebury, CT MLS# 24096137
$533,416
3

Beds

2.1

Baths

1,950

Sq.Ft.

North Benson Road # 49

Middlebury, CT

View 61 Sandy Hill Road Middlebury, CT MLS# 24148828
$529,900
3

Beds

1.1

Baths

1,811

Sq.Ft.

61 Sandy Hill Road

Middlebury, CT

View 283 Whittemore Road Middlebury, CT MLS# 24169230
    1 of 24
    OPEN HOUSE: Saturday 5/2 11:00 AM - 1:00 PM
    $529,000
    3

    Beds

    2.1

    Baths

    2,500

    Sq.Ft.

    283 Whittemore Road

    Middlebury, CT

    View North Benson Road # 45 Middlebury, CT MLS# 24089121
    $525,438
    3

    Beds

    2.1

    Baths

    1,950

    Sq.Ft.

    North Benson Road # 45

    Middlebury, CT

    View 541 Benson Road Middlebury, CT MLS# 24161553
    $525,000
    2

    Beds

    2.0

    Baths

    1,600

    Sq.Ft.

    541 Benson Road

    Middlebury, CT

    View 541 Benson Road Middlebury, CT MLS# 24161555
    $525,000
    3

    Beds

    3.0

    Baths

    1,600

    Sq.Ft.

    541 Benson Road

    Middlebury, CT

    View North Benson Road # 51 Middlebury, CT MLS# 24117506
    $523,920
    3

    Beds

    2.1

    Baths

    1,950

    Sq.Ft.

    North Benson Road # 51

    Middlebury, CT

    View North Benson Road # 66 Middlebury, CT MLS# 24093726
    $522,128
    3

    Beds

    2.1

    Baths

    1,950

    Sq.Ft.

    North Benson Road # 66

    Middlebury, CT

    View North Benson Road # 46 Middlebury, CT MLS# 24097231
    $522,128
    3

    Beds

    2.1

    Baths

    1,950

    Sq.Ft.

    North Benson Road # 46

    Middlebury, CT

    View North Benson Road # 53 Middlebury, CT MLS# 24086541
    $519,900
    3

    Beds

    2.1

    Baths

    1,950

    Sq.Ft.

    North Benson Road # 53

    Middlebury, CT

    View North Benson Road # 47 Middlebury, CT MLS# 24099635
    $509,900
    3

    Beds

    2.1

    Baths

    2,206

    Sq.Ft.

    North Benson Road # 47

    Middlebury, CT

    View North Benson Road # 50 Middlebury, CT MLS# 24118969
    $509,900
    3

    Beds

    2.1

    Baths

    1,950

    Sq.Ft.

    North Benson Road # 50

    Middlebury, CT

    View 38 East Ridge Drive Middlebury, CT MLS# 24158643
    $509,900
    3

    Beds

    2.0

    Baths

    1,780

    Sq.Ft.

    38 East Ridge Drive

    Middlebury, CT

    View 420 Charcoal Avenue Middlebury, CT MLS# 24167472
    • Recently Listed
    1 of 40
    $485,000
    3

    Beds

    2.0

    Baths

    1,575

    Sq.Ft.

    420 Charcoal Avenue

    Middlebury, CT

    View 18 Freedom Road Middlebury, CT MLS# 24163920
    $479,000
    3

    Beds

    1.1

    Baths

    1,492

    Sq.Ft.

    18 Freedom Road

    Middlebury, CT

    View 637 Watertown Road Middlebury, CT MLS# 24145459
    $450,000
    3

    Beds

    3.1

    Baths

    1,918

    Sq.Ft.

    637 Watertown 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

    $573,584
    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 - 500K5
    $500K - 600K34
    $600K - 700K8
    $700K - 800K9
    $800K - 900K5
    $900K - 1M2
    $1M - Max1

    Homes for Sale by Type in Middlebury, CT

    Property TypeCount
    Single Family37
    Townhouse0
    Condo27
    Commercial1
    Rental4
    Lots and Land4
    Condo/Town/CoOp0
    CoOp0
    Multi Family2
    Mobile Home0
    Farms0

    (Data as of 4/27/2026)

    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.

    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.

    © Copyright 2026 Smart Multiple Listing Service, Inc.