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MLS 24166793 For Sale Open House Updated April 22, 2026
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288 Middlesex Avenue

Chester, Connecticut 06412

$3,150,000
On market 9 days
288 Middlesex Avenue
1 / 38

About This Property

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.

Property Details

Interior

Heat
Hot Air — Oil
Cooling
Central Air
Fireplaces
2
Basement
Full,Storage,Interior Access,Partially Finished,Concrete Floor,Full With Hatchway
Interior Features
Audio System Auto Garage Door Opener Cable - Available Sauna Security System

Exterior & Lot

Roof
Asphalt Shingle
Construction
Construction
Waterfront
River,Dock or Mooring,View
Exterior Features
Balcony Underground Utilities Awnings Gutters Stone Wall French Doors Underground Sprinkler Patio
Lot Description
Professionally Landscaped Water View
Garage & Parking
Attached Garage Detached Garage

Utilities & Systems

Water Source
Private Well
Sewer
Septic
Energy Features
Thermopane Windows

Community & Schools

Elementary
Chester
Middle
Winthrop
High
Valley
Nearby Amenities
Library Medical Facilities Park Public Rec Facilities Shopping/Mall

Appliances

Included
Gas Range Convection Oven Microwave Range Hood Subzero Dishwasher Washer Dryer Wine Chiller

288 Middlesex Avenue

Chester , Connecticut 06412

$3,150,000

On market 9 days

Beds
4
Baths
6
SqFt
4,926
Type
Single Family
County Middlesex
Garage 6
Rooms -
Lot Size 2.65 Acres
Property Tax $24,724
Assessed Value $913,010
Year Built 1800
Style Colonial
Zoning R-2

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
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Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: CBRB54.

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