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For sale
    • $3,150,000

    288 Middlesex Avenue, Chester, CT 06412

    4beds
    4,926sqft
    : 
    $22,539/mo
    Get pre-qualified
    Single Family Residence
    Built in 1800
    2.65 Acres Lot
    $-- Zestimate®
    $639/sqft
    $-- HOA

    What's special

    Stunning turnkey waterfront compoundProtected viewsManicured groundsResidence and terraceRooted in historic designModern livabilityTimeless new england architecture
    Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.
    107 days
    |
    839
    |
    31
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Nancy Mesham Team,

    Nancy Mesham (860)227-9071,

    Coldwell Banker Realty 860-434-8600

    Source: Smart MLS,MLS#: 24166793MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 6
      • Full bathrooms: 4
      • 1/2 bathrooms: 2
      Rooms
      • Room types: Gym, Steam/Sauna
      Primary bedroom
      • Features: Balcony/Deck, French Doors, Full Bath, Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 247 Square Feet
      • Dimensions: 13 x 19
      Bedroom
      • Features: Walk-In Closet(s), Hardwood Floor
      • Level: Upper
      • Area: 192 Square Feet
      • Dimensions: 12 x 16
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      • Area: 132 Square Feet
      • Dimensions: 11 x 12
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      • Area: 154 Square Feet
      • Dimensions: 11 x 14
      Dining room
      • Features: Hardwood Floor
      • Level: Main
      • Area: 289 Square Feet
      • Dimensions: 17 x 17
      Family room
      • Features: Wet Bar, Fireplace, French Doors, Hardwood Floor
      • Level: Main
      • Area: 306 Square Feet
      • Dimensions: 17 x 18
      Kitchen
      • Features: High Ceilings, Built-in Features, Granite Counters, French Doors, Kitchen Island, Hardwood Floor
      • Level: Main
      • Area: 432 Square Feet
      • Dimensions: 18 x 24
      Library
      • Features: Bookcases
      • Level: Main
      • Area: 99 Square Feet
      • Dimensions: 9 x 11
      Living room
      • Features: Gas Log Fireplace, French Doors, Hardwood Floor
      • Level: Main
      • Area: 465 Square Feet
      • Dimensions: 15 x 31
      Media room
      • Features: Palladian Window(s), High Ceilings, Partial Bath, Hardwood Floor
      • Level: Upper
      • Area: 704 Square Feet
      • Dimensions: 22 x 32
      Office
      • Features: Bookcases
      • Level: Main
      • Area: 132 Square Feet
      • Dimensions: 11 x 12
      Other
      • Features: Half Bath, Steam/Sauna
      • Level: Lower
      • Area: 255 Square Feet
      • Dimensions: 15 x 17
      Heating
      • Forced Air, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Cooler, Water Heater
      • Laundry: Lower Level, Mud Room
      Features
      • Sound System, Sauna, Entrance Foyer, Smart Thermostat, Wired for Sound
      • Doors: French Doors
      • Windows: Thermopane Windows
      • Basement: Full,Storage Space,Interior Entry,Partially Finished,Concrete
      • Attic: Access Via Hatch
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 4,926
      • Total interior livable area: 4,926 sqft
      • Finished area above ground: 4,626
      • Finished area below ground: 300
      Video & virtual tour

      Property

      Parking
      • Total spaces: 6
      • Parking features: Attached, Detached, Garage Door Opener
      • Attached garage spaces: 6
      Features
      • Patio & porch: Patio
      • Exterior features: Balcony, Awning(s), Rain Gutters, Stone Wall, Underground Sprinkler
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      • Waterfront features: Waterfront, River Front, Dock or Mooring
      Lot
      • Size: 2.65 Acres
      • Features: Landscaped
      Details
      • Parcel number: 941338
      • Zoning: R-2
      • Other equipment: Entertainment System

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Shake Siding, Cedar
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1800

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Underground Utilities, Cable Available
      Green energy
      • Energy efficient items: Windows

      Community & HOA

      Community
      • Features: Library, Medical Facilities, Park, Public Rec Facilities, Shopping/Mall
      • Security: Security System
      HOA
      • Has HOA: No
      Location
      • Region: Chester

      Financial & listing details

      • Price per square foot: $639/sqft
      • Tax assessed value: $913,010
      • Annual tax amount: $24,724
      • Date on market: 4/13/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        4/13/2026Listed for sale$3,150,000$639/sqft
        Source: Smart MLS #24166793 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$144 +10.8%$5,320
        2024$130 -13.3%$5,320 +5.1%
        2023$150 +0.7%$5,060
        2022$149 $5,060
        2021$149 +2.8%$5,060
        2020$145 -0.7%$5,060
        2019$146 +0.7%$5,060 -5.6%
        2018$145 +2.8%$5,360
        2017$141 +30.6%$5,360
        2016$108 $5,360
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 06412

        Getting around

        8 / 100
        Car-Dependent
        1 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Chester
        • Middle: Winthrop
        • High: Valley

        Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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