288 Middlesex Avenue, Chester, Connecticut

$2,995,000

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4

Beds

6

Baths

4,926

Square feet

0.37

Acres

About 288 Middlesex Avenue

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.

Features of 288 Middlesex Avenue

MLS® # 24201816
Price $2,995,000
Bedrooms 4
Bathrooms 6.00
Full Baths 4
Half Baths 2
Square Footage 4,926
Acres 0.37
Type Single Family For Sale
Style Colonial
Status Active

Community Information

Address 288 Middlesex Avenue
Area N/A
City Chester
County Middlesex
State Connecticut
Zip Code 06412

Amenities

Features Thermopane Windows
Parking Attached Garage, Detached Garage
# of Garages 6
Is Waterfront Yes
Waterfront River, Beach, Dock or Mooring, View
Has Pool No

Interior

Interior Features Audio System, Auto Garage Door Opener, Cable - Available, Sauna, Security System
Appliances Gas Range, Convection Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Chiller
Heating Hot Air, Oil
Cooling Central Air
Fireplace Yes
# of Fireplaces 2
Has Basement Yes
Basement Full, Storage, Interior Access, Partially Finished, Concrete Floor, Full With Hatchway

Exterior

Exterior Shake, Cedar
Exterior Features Balcony, Underground Utilities, Awnings, Gutters, Stone Wall, French Doors, Underground Sprinkler, Patio
Lot Description Professionally Landscaped, Water View
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Chester
Middle Winthrop
High Valley

Additional Information

Date Listed August 26th, 2026
Days on Market 15
Zoning R-2
RE / Bank Owned No

Listing Details

OfficeColdwell Banker Realty

Listing Map

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Listing information last updated on September 10th, 2026 at 8:56am EDT.