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MLS 24201816 For Sale Open House Updated September 30, 2026
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288 Middlesex Avenue

Chester, Connecticut 06412

$2,995,000
On market 35 days
288 Middlesex Avenue
1 / 38

About This Property

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.

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,Beach,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

$2,995,000

On market 35 days

Beds
4
Baths
6
SqFt
4,926
Type
Single Family
County Middlesex
Garage 6
Rooms -
Lot Size 2.65 Acres
Property Tax $26,139
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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