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    Middlebury, CT
    Map
    73 Properties Available

    73 Properties Available

    The average price in the selected areas has remained stable. Learn more
    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    42 White Avenue, Middlebury, CT 06762
    1/26
    Coming Soon

    $479,900

    3 Beds3 Baths2,112 SqFt

    42 White Avenue, Middlebury, CT 06762

    Listed by Justin Cabral of West View Properties, LLC

    8 Deer Run Road, Middlebury, CT 06762
    New

    $839,900

    3 Beds3 Baths2,450 SqFt

    8 Deer Run Road, Middlebury, CT 06762

    Listed by Jodi Dawley of Real Estate Two

    38 Avalon Drive, Middlebury, CT 06762
    1/20
    Coming Soon

    $779,000

    3 Beds3 Baths3,217 SqFt

    38 Avalon Drive, Middlebury, CT 06762

    Listed by Tracy Wilson of Lamacchia Realty

    168 North Farm Road, Middlebury, CT 06762
    1/40
    New

    $765,000

    4 Beds4 Baths3,302 SqFt

    168 North Farm Road, Middlebury, CT 06762

    Listed by Karen Stanco of Showcase Realty, Inc.

    111 North Street, Middlebury, CT 06762
    1/32
    New

    $3,400

    4 Beds2 Baths2,245 SqFt

    111 North Street, Middlebury, CT 06762

    Listed by Bonnie Wilson of Berkshire Hathaway NE Prop.

    72 Ridgewood Drive #72, Middlebury, CT 06762
    1/39
    New

    $569,900

    3 Beds3 Baths2,428 SqFt

    72 Ridgewood Drive #72, Middlebury, CT 06762

    Listed by Jay Irvine of Serhant Connecticut, LLC

    286 Mirey Dam Road, Middlebury, CT 06762
    1/38
    Active

    $975,000

    4 Beds3 Baths4,451 SqFt

    286 Mirey Dam Road, Middlebury, CT 06762

    Listed by Pam Famiglietti of William Raveis Real Estate

    443 Benson Road, Middlebury, CT 06762
    1/14
    Active

    $3,100

    4 Beds2 Baths1,766 SqFt

    443 Benson Road, Middlebury, CT 06762

    Listed by Levi Judqin of Brass Moon Realty

    178 Ridgewood Drive #178, Middlebury, CT 06762
    1/40
    Active

    $639,900

    3 Beds3 Baths2,414 SqFt

    178 Ridgewood Drive #178, Middlebury, CT 06762

    Listed by Patty Forbes of Berkshire Hathaway NE Prop.

    3 Winding Trail #3, Middlebury, CT 06762
    1/35
    Active

    $559,900

    3 Beds3 Baths3,179 SqFt

    3 Winding Trail #3, Middlebury, CT 06762

    Listed by Mayra Perez of Showcase Realty, Inc.

    818 Middlebury Road, Middlebury, CT 06762
    1/35
    Under Contract

    $385,000

    2 Beds1 Bath1,489 SqFt

    818 Middlebury Road, Middlebury, CT 06762

    Listed by Brandy Hall of Higgins Group Real Estate

    1 Independence Circle #1, Middlebury, CT 06762
    1/34
    Under Contract

    $609,000

    4 Beds3 Baths3,224 SqFt

    1 Independence Circle #1, Middlebury, CT 06762

    Listed by Christine Aquila of Coldwell Banker Realty

    North Benson Road #65, Middlebury, CT 06762
    1/9
    Under Contract

    $573,572

    3 Beds3 Baths2,206 SqFt

    North Benson Road #65, Middlebury, CT 06762

    Listed by Renee Lovley of Century 21 AllPoints Realty

    10 Old Waterbury Road #3, Middlebury, CT 06762
    1/7
    Active

    $1,050

    1 Bed1 Bath450 SqFt

    10 Old Waterbury Road #3, Middlebury, CT 06762

    Listed by Jeff Corcoran of Corcoran Properties, LLC

    80 Anawan Avenue, Middlebury, CT 06762
    1/40
    Under Contract

    $529,900

    2 Beds2 Baths1,962 SqFt

    80 Anawan Avenue, Middlebury, CT 06762

    Listed by Drew Slack of ERA Insite Realty Services

    397 White Deer Rock Road, Middlebury, CT 06762
    1/34
    Active

    $2,195,000

    3 Beds3 Baths3,863 SqFt

    397 White Deer Rock Road, Middlebury, CT 06762

    Listed by Peter Klemm of Klemm Real Estate Inc

    10 Pelham Way #10, Middlebury, CT 06762
    1/2
    Under Contract

    $650,000

    3 Beds3 Baths2,251 SqFt

    10 Pelham Way #10, Middlebury, CT 06762

    Listed by Timothy Drakeley of Drakeley Real Estate, Inc.

    700 Watertown Road, Middlebury, CT 06762
    1/39
    Price Dropped by $19K

    $630,000

    5 Beds3 Baths2,528 SqFt

    700 Watertown Road, Middlebury, CT 06762

    Listed by Erin Giguiere of Regall Realty, LLC

    15 Central Road, Middlebury, CT 06762
    1/38
    Under Contract

    $694,900

    3 Beds3 Baths2,870 SqFt

    15 Central Road, Middlebury, CT 06762

    Listed by Mary Ann Hebert of BHGRE Gaetano Marra Homes

    283 Whittemore Road, Middlebury, CT 06762
    1/24
    Under Contract

    $519,000

    3 Beds3 Baths2,500 SqFt

    283 Whittemore Road, Middlebury, CT 06762

    Listed by Jennifer Sisco of RE/MAX Heritage

    301 Steinmann Avenue, Middlebury, CT 06762
    1/36
    Under Contract

    $409,900

    3 Beds2 Baths1,572 SqFt

    301 Steinmann Avenue, Middlebury, CT 06762

    Listed by Dawn Ciappetta of Coldwell Banker Realty

    90 Fenn Road, Middlebury, CT 06762
    1/35
    Price Dropped by $20K

    $679,900

    4 Beds4 Baths3,162 SqFt

    90 Fenn Road, Middlebury, CT 06762

    Listed by Mary Ann Hebert of BHGRE Gaetano Marra Homes

    24 Highridge Road #24, Middlebury, CT 06762
    1/40
    Under Contract

    $560,000

    3 Beds3 Baths1,802 SqFt

    24 Highridge Road #24, Middlebury, CT 06762

    Listed by Jay Irvine of Serhant Connecticut, LLC

    420 Charcoal Avenue, Middlebury, CT 06762
    1/40
    Under Contract

    $485,000

    3 Beds2 Baths1,575 SqFt

    420 Charcoal Avenue, Middlebury, CT 06762

    Listed by Bethany Lydem of Stone Crest Realty LLC

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    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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    image0 (1)Fusion

    William Pitt Sotheby's International Realty

    Jay Contessa Lic# RES.0816734

    +1(203) 461-3880 jcontessa@wpsir.com

    470 Main Street, Ridgefield, CT, 06877

    Get My App

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    SITE MAP

        Home
        My Listings
        1. Featured Listings
        2. Sold Listings
        Communities
        1. Ridgefield
        2. Redding
        3. Fairfield
        Sell My Home
        Services
        Resources
        1. iBuyer Guide
        2. Affordability Calculator
        3. Mortgage Calculator
        4. Market Snapshot
        About
        1. My Story
        2. My Resume
        3. Client Survey
        4. Testimonials
        5. Contact Me
    image0 (1)Fusion

    William Pitt Sotheby's International Realty

    Jay Contessa Lic# RES.0816734

    +1(203) 461-3880 jcontessa@wpsir.com

    470 Main Street, Ridgefield, CT, 06877

    Get My App

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility