+1(203) 461-3880 jcontessa@wpsir.com
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    Chester, CT
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    17 Properties Available

    17 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)
    288 Middlesex Avenue, Chester, CT 06412
    1/38
    Open Sat 11AM-2PM

    $3,150,000

    4 Beds6 Baths4,926 SqFt

    288 Middlesex Avenue, Chester, CT 06412

    Listed by Nancy Mesham of Coldwell Banker Realty

    226 Middlesex Avenue, Chester, CT 06412
    1/39
    Under Contract

    $695,000

    4 Beds3 Baths2,029 SqFt

    226 Middlesex Avenue, Chester, CT 06412

    Listed by Peg Mitchel of Coldwell Banker Realty

    59-61 Wig Hill Road, Chester, CT 06412
    1/38
    Active

    $724,000

    5 Beds3 Baths3,862 SqFt

    59-61 Wig Hill Road, Chester, CT 06412

    Listed by Joe Kelly of William Pitt Sotheby's Int'l

    6 Pelton Hill, Chester, CT 06412
    1/40
    Under Contract

    $738,500

    3 Beds2 Baths1,982 SqFt

    6 Pelton Hill, Chester, CT 06412

    Listed by John Zubretsky Jr. of Century 21 AllPoints Realty

    15 Hazen Street, Chester, CT 06412
    1/33
    Under Contract

    $199,900

    3 Beds1 Bath748 SqFt

    15 Hazen Street, Chester, CT 06412

    Listed by Anthony La Penna of Exceptional Real Estate LLC

    26 Ferry Road, Chester, CT 06412
    1/14
    Under Contract

    $850,000

    4 Beds2 Baths8,382 SqFt

    26 Ferry Road, Chester, CT 06412

    Listed by Anthony Velez of VC Property Group, LLC

    1 Ferry Road, Chester, CT 06412
    1/40
    Under Contract

    $650,000

    3 Beds3 Baths2,752 SqFt

    1 Ferry Road, Chester, CT 06412

    Listed by Jennifer D'Amato of Real Broker CT, LLC

    79 Middlesex Avenue, Chester, CT 06412
    1/32
    Under Contract

    $425,000

    2 Beds1 Bath1,470 SqFt

    79 Middlesex Avenue, Chester, CT 06412

    Listed by Gigi Giordano of Compass Connecticut, LLC

    15 Liberty Street, Chester, CT 06412
    1/39
    Active

    $7,500

    4 Beds5 Baths4,708 SqFt

    15 Liberty Street, Chester, CT 06412

    Listed by Lynn Lehrman of Re/Max Valley Shore

    Turkey Hill Road, Chester, CT 06412
    1/19
    Active

    $99,900

    1 Acres

    Turkey Hill Road, Chester, CT 06412

    Listed by Charles Kroopneck of Charles Kroopneck Real Estate

    10 Denlar Drive, Chester, CT 06412
    1/30
    Active

    $1,450,000

    28,525 SqFt

    10 Denlar Drive, Chester, CT 06412

    Listed by Susan Malan of William Pitt Sotheby's Int'l

    21 Main Street, Chester, CT 06412
    1/37
    Active

    $1,200,000

    3,000 SqFt

    21 Main Street, Chester, CT 06412

    Listed by Maureen Evans of William Raveis Real Estate

    189 Middlesex Avenue, Chester, CT 06412
    1/7
    Price Dropped by $495K

    $4,200,000

    21,905 SqFt

    189 Middlesex Avenue, Chester, CT 06412

    Listed by Stephen Press of Press/Cuozzo Realtors

    43 Bokum Road, Chester, CT 06412
    Active

    $200,000

    2.25 Acres

    43 Bokum Road, Chester, CT 06412

    Listed by Nicholas Tomanelli of Coldwell Banker Realty

    3 Inspiration Lane #1, Chester, CT 06412
    1/24
    Active

    $5,500

    4,000 SqFt

    3 Inspiration Lane #1, Chester, CT 06412

    Listed by Kevin Brignole of Spaulding Realty Group, LLC

    132 Main Street, Chester, CT 06412
    1/4
    Under Contract

    $975,000

    23,467 SqFt

    132 Main Street, Chester, CT 06412

    Listed by Janet Peckinpaugh of William Pitt Sotheby's Int'l

    11 Kings Highway, Chester, CT 06412
    1/11
    Active

    $238,500

    1.5 Acres

    11 Kings Highway, Chester, CT 06412

    Listed by Rachel Welch of William Raveis Real Estate

    • 1
    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