The latest in luxury property, lifestyle & culture, curated just for you.

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont
  • France
  • Monaco

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont
  • France
  • Monaco

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont
  • France
  • Monaco

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont
  • France
  • Monaco
  • Site Map
  • Terms
  • Privacy
  • Cookie Preferences
  • Do Not Sell or Share My Personal Information
  • NYS Housing Discrimination Disclosure Notice & Form
  • NYS Standard Operating Procedure
  • NYS Tenants' Rights to Reasonable Accommodations for persons with disabilities
  • California Consumer Privacy Act Notice
  • Texas Consumer Protection Notice
  • Texas Real Estate Commission Information About Brokerage Services
  • Text of NYC Human Rights Law
  • New York City Commission on Human Rights
  • NYC Source of Income Discrimination Information
  • NYC Source of Income Discrimination Tenant FAQs

THE SOURCE OF THE DISPLAYED DATA IS EITHER THE PROPERTY OWNER OR PUBLIC RECORD PROVIDED BY NON-GOVERNMENTAL THIRD PARTIES. IT IS BELIEVED TO BE RELIABLE BUT NOT GUARANTEED. FOR COLORADO VIEWERS, INFORMATION ABOUT NON-COMMERCIAL PROPERTIES IS PROVIDED EXCLUSIVELY FOR YOUR PERSONAL, NON-COMMERCIAL USE.

575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2026 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY. LISTING DATA REFRESHED ON SEP 29 2026 AT 1:24 PM.

DOUGLAS ELLIMAN IS A LICENSED REAL ESTATE BROKER IN CALIFORNIA WITH LICENSE # 01947727, COLORADO WITH LICENSE # EC100053892, CONNECTICUT WITH LICENSE # REB.0314827, THE DISTRICT OF COLUMBIA WITH LICENSE # REO40000160, FLORIDA WITH LICENSE # CQ1020232, MARYLAND WITH LICENSE # 645270, MASSACHUSETTS WITH LICENSE # 422764, NEVADA WITH LICENSE # 1454643, NEW JERSEY WITH LICENSE # 0572105, NEW YORK WITH LICENSE # 10991211812, TEXAS WITH LICENSE # 9008706, AND VIRGINIA WITH LICENSE # 0226035659.

SCAMMERS ARE IMPERSONATING REAL ESTATE AGENTS AND USING ACTIVE LISTINGS TO REQUEST FAKE DEPOSITS. SHOULD YOU HAVE A QUESTION ABOUT THE LEGITIMACY OF A DOUGLAS ELLIMAN AGENT OR LISTING, PLEASE CONTACT THE AGENT DIRECTLY VIA THE “AGENTS” LINK IN THE TOP MENU. DOUGLAS ELLIMAN WILL NEVER ASK FOR ANY PAYMENT TO RESERVE, HOLD, OR VIEW A PROPERTY. THESE CHARGES ARE PROHIBITED UNDER NEW YORK LAW. IF YOU RECEIVE A SUSPICIOUS REQUEST FOR MONEY, DO NOT SEND FUNDS. REPORT IT TO THE NYS DEPARTMENT OF STATE AND NOTIFY DOUGLAS ELLIMAN. YOU CAN READ THE NEW YORK STATE DEPARTMENT OF STATE'S CONSUMER ALERT HERE.

This website has been translated using automated software for convenience. While reasonable efforts have been made to ensure accuracy, machine translation may contain errors and is not a substitute for human translation. Translations are provided “as is,” without any express or implied warranty regarding their accuracy, reliability, or completeness. Some content (including images or videos) may not be translated accurately. The official version of this website is the English version. Any discrepancies in translation are not binding and have no legal effect; the English version controls.

POWERED BY PURLIN.AI

288 Middlesex Ave

chester, CT 06412

$2,995,000

  • 4 BR
    4 BA, 2 HALF BA
    approx. 4,926 SF

Interested? Let's Connect

Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by manicured grounds and a broad terrace leading gently to the water. A six-pile, deep water dock with two slips and a 16-ton lift is designed for serious boaters, while paddling is enjoyed from the floating dock and a small beach. Rooted in historic design and masterfully renovated in 2010, the residence blends timeless New England architecture with modern livability. Equally suited to weekends on the water, extended family gatherings, or multi-generational living, the property offers flexible spaces designed to entertain and live comfortably. Find a total of six garage bays for auto collections, boats, or a workshop. Minutes away discover Chester Village restaurants and artisans. Just across the river, the Goodspeed Opera House adds celebrated cultural dimension, and the neighboring seasonal Connecticut Valley Railroad evokes the region's rich history. The quiet elegance of East View offers a rare opportunity to experience the Connecticut River at its most extraordinary-where boating, history, culture, village life, and natural beauty converge.

Details

4,926 Sq Ft

2.65 Private Acres Lot Size

other

Built in 1800

MLS/Listing ID 24201816

Amenities & Features

Parking - Detached Garage

Lower Level

Sauna

Awnings

Balcony

Patio

Construction - Frame

Style - Colonial

Convection Oven

Dishwasher

Dryer

Well

Septic System

River

Stone Wall

French Doors

Washer

Range Hood

Microwave

Gas Range

Estimate my mortgage

TOTAL MONTHLY COST

$0

  • PRINCIPAL & INTEREST

    $0

  • PROPERTY TAXES

    $0

  • Common Charges

    $0

HOME PRICE
DOWN PAYMENT
TERM
INTEREST

Interested In 288 Middlesex Ave?

SMART

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.

Copyright 2026 SmartMLS, Inc.