288 Middlesex Avenue, Chester, Connecticut

$3,375,000

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4

Beds

6

Baths

4,926

Square feet

2.65

Acres

About 288 Middlesex Avenue

East View is a long-admired Connecticut Riverfront property, a rare offering that perfectly marries historic provenance with elevated modern living. The circa 1800 home was masterfully renovated and expanded in 2010 with an architect's eye and a reverence for its storied past. Meticulous attention to detail is found in the extensive millwork, custom built-ins and hand-hewn beams lending warmth and character throughout. Expansive windows frame water views from nearly every room - north to the Haddam bridge and south across Lord's Island. The kitchen is the heart of this home with a grand center island, top end appliances and custom cabinetry. The adjacent living and dining rooms allow for effortless entertaining. There is a handsome family room with wet bar, a library and office. Sunrise over the river greets you in the private primary bedroom, a sanctuary with a balcony. Three additional bedrooms are sited on the north end of the home with two full baths. You will find a home theatre/media room and a gym with sauna-spaces designed to restore mind and body. Outdoors, the grounds slope gently from the bluestone patio to 285' of water frontage where a six-pile, two-slip dock awaits. Completely re-engineered and rebuilt with a 16-ton lift and an additional floating dock, this is a captain's dream. At low tide, stone steps reveal a sandy beach, perfect for a dip or kayaking. For vehicles, find a heated, 3-bay garage attached and an additional 3 bay garage with storage,

Features of 288 Middlesex Avenue

MLS® # 24124960
Price $3,375,000
Bedrooms 4
Bathrooms 6.00
Full Baths 4
Half Baths 2
Square Footage 4,926
Acres 2.65
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, 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, Zoned, 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 September 9th, 2025
Days on Market 26
Zoning R-2
RE / Bank Owned No

Listing Details

OfficeColdwell Banker Realty

Listing Map

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Listing information last updated on October 20th, 2025 at 6:20am EDT.