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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
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    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    420 Charcoal Avenue, Middlebury, CT 06762
    1/40
    Coming Soon

    $485,000

    3 Beds2 Baths1,575 SqFt

    420 Charcoal Avenue, Middlebury, CT 06762

    Listed by Bethany Lydem of Stone Crest Realty LLC

    2 Arrowwood Court #2, Middlebury, CT 06762
    1/32
    Open Sun 12PM-2PM

    $599,900

    3 Beds3 Baths2,256 SqFt

    2 Arrowwood Court #2, Middlebury, CT 06762

    Listed by Mary Ann Hebert of BHGRE Gaetano Marra Homes

    3 Brookside Drive #3, Middlebury, CT 06762
    1/36
    Open Sun 1PM-3PM

    $599,900

    4 Beds4 Baths4,200 SqFt

    3 Brookside Drive #3, Middlebury, CT 06762

    Listed by Shagufta Zahid of S Factor Realty Group LLC

    24 Highridge Road #24, Middlebury, CT 06762
    1/40
    New

    $560,000

    3 Beds3 Baths1,802 SqFt

    24 Highridge Road #24, Middlebury, CT 06762

    Listed by Jay Irvine of Serhant Connecticut, LLC

    271 Shadduck Road, Middlebury, CT 06762
    1/32
    New

    $432,000

    3 Beds2 Baths1,288 SqFt

    271 Shadduck Road, Middlebury, CT 06762

    Listed by Stephen Mele of Houlihan Lawrence

    122 Crest Road, Middlebury, CT 06762
    1/37
    New

    $825,000

    3 Beds3 Baths3,253 SqFt

    122 Crest Road, Middlebury, CT 06762

    Listed by Heather Dever of Showcase Realty, Inc.

    245 Upper Whittemore Road, Middlebury, CT 06762
    1/29
    Under Contract

    $815,000

    3 Beds3 Baths2,990 SqFt

    245 Upper Whittemore Road, Middlebury, CT 06762

    Listed by Donna Bannon of BHGRE Gaetano Marra Homes

    851 South Street, Middlebury, CT 06762
    1/40
    New

    $950,000

    5 Beds3 Baths3,301 SqFt

    851 South Street, Middlebury, CT 06762

    Listed by Jackie Desmarais of Showcase Realty, Inc.

    64 Watertown Road, Middlebury, CT 06762
    1/32
    Active
    3D

    $759,900

    3 Beds4 Baths4,094 SqFt

    64 Watertown Road, Middlebury, CT 06762

    Listed by Olivia Bueno of William Raveis Real Estate

    408 Breakneck Hill Road, Middlebury, CT 06762
    1/30
    Active

    $625,000

    2 Beds3 Baths1,848 SqFt

    408 Breakneck Hill Road, Middlebury, CT 06762

    Listed by John Donato Jr of Showcase Realty, Inc.

    66 Artillery Road, Middlebury, CT 06762
    1/25
    Active

    $585,000

    4 Beds4 Baths2,691 SqFt

    66 Artillery Road, Middlebury, CT 06762

    Listed by Maria Taylor of Klemm Real Estate Inc

    192 Breakneck Hill Road, Middlebury, CT 06762
    1/16
    Under Contract

    $427,000

    4 Beds2 Baths1,422 SqFt

    192 Breakneck Hill Road, Middlebury, CT 06762

    Listed by Maria Pinheiro of RE/MAX RISE

    193 Ridgewood Drive #193, Middlebury, CT 06762
    1/40
    Active

    $649,900

    3 Beds3 Baths2,658 SqFt

    193 Ridgewood Drive #193, Middlebury, CT 06762

    Listed by Timothy Drakeley of Drakeley Real Estate, Inc.

    18 Freedom Road, Middlebury, CT 06762
    1/30
    Under Contract

    $479,000

    3 Beds2 Baths1,492 SqFt

    18 Freedom Road, Middlebury, CT 06762

    Listed by Karen Stanco of Showcase Realty, Inc.

    6 Brookside Drive, Middlebury, CT 06762
    1/40
    Under Contract

    $599,995

    4 Beds4 Baths3,745 SqFt

    6 Brookside Drive, Middlebury, CT 06762

    Listed by Nikki Defrancesco of Coldwell Banker Realty

    6 Brookside Drive #6, Middlebury, CT 06762
    1/40
    Under Contract

    $599,995

    4 Beds4 Baths3,745 SqFt

    6 Brookside Drive #6, Middlebury, CT 06762

    Listed by Nikki Defrancesco of Coldwell Banker Realty

    19 Deer Run Road, Middlebury, CT 06762
    Under Contract

    $900,000

    4 Beds3 Baths3,100 SqFt

    19 Deer Run Road, Middlebury, CT 06762

    Listed by Jodi Dawley of Real Estate Two

    200 North Farm Road, Middlebury, CT 06762
    1/40
    Under Contract

    $750,000

    4 Beds4 Baths3,360 SqFt

    200 North Farm Road, Middlebury, CT 06762

    Listed by Jackie Desmarais of Showcase Realty, Inc.

    36 Highridge Road #36, Middlebury, CT 06762
    1/24
    Active

    $585,000

    3 Beds3 Baths1,997 SqFt

    36 Highridge Road #36, Middlebury, CT 06762

    Listed by John Pistorino of RE/MAX RISE

    390 Middlebury Road #3, Middlebury, CT 06762
    1/15
    Active

    $119,900

    1 Bath850 SqFt

    390 Middlebury Road #3, Middlebury, CT 06762

    Listed by Steve Colon of Oxford Realty

    80 Pine Hollow Drive, Middlebury, CT 06762
    1/31
    Under Contract

    $749,900

    4 Beds4 Baths2,806 SqFt

    80 Pine Hollow Drive, Middlebury, CT 06762

    Listed by Gina Farra of Keller Williams Realty

    314 Porter Avenue, Middlebury, CT 06762
    1/13
    Under Contract

    $349,900

    3 Beds2 Baths1,440 SqFt

    314 Porter Avenue, Middlebury, CT 06762

    Listed by Dawn Ciappetta of Coldwell Banker Realty

    771 Watertown Road, Middlebury, CT 06762
    1/21
    Active

    $3,850

    3 Beds2 Baths3,079 SqFt

    771 Watertown Road, Middlebury, CT 06762

    Listed by Amanda Engala of Tier 1 Real Estate

    541 Benson Road, Middlebury, CT 06762
    1/20
    Under Contract

    $525,000

    3 Beds3 Baths1,600 SqFt

    541 Benson Road, Middlebury, CT 06762

    Listed by Joseph Martino of Joseph Martino Real Estate

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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