288 Middlesex Avenue Chester, CT $ 3,375,000
288 Middlesex Avenue
$ 3,375,000
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288 Middlesex Avenue

Chester, CT, 06412
$ 3,375,000
Bedrooms4 Baths4.2 Sq 4,926

Monthly Estimate*

$ 21,056

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Single Family Home for sale in Chester, CT

for $3,375,000 with 4 bedrooms and 4 full baths, 2 half baths. This 4,926 square foot home was built in 1800 on a lot size of 2.65.

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, perfect for the enthusiast. Set on 2.65 acres this property offers elegance, privacy and a front-row seat to the natural beauty of the Connecticut River just over one mile to Chester Village and a bit more than two hours from New York.

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Single Family Active

Price

$ 3,375,000

Bedrooms

4

Full Bath

4

Half Bath

2

Property Type

Single Family

Taxes

$ 24,724

Style

Lot Size

2.65

Year Built

1800

Town/City

Chester

MLS | Web ID

24124960

Features
General
Zoning R-2
Neighborhood N/A
County Middlesex
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.65
Directions Middlesex Avenue water side. Follow driveway to the end.
High School Valley
City Chester
Elementary School Chester
Sq Ft Total 4926
DOM 34
Year Built 1800
Style Colonial
Year Built Source Public Records
Energy Features Thermopane Windows
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Interior
Cooling System Central Air
Total Rooms 11
Basement Description Full Storage Interior Access Partially Finished Concrete Floor Full With Hatchway
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Exterior
Water Source Private Well
Lot Description Professionally Landscaped Water View
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* Excluded Features
List By
Nancy Mesham

Listing Agent

Coldwell Banker Realty

Broker

nancy.mesham@cbmoves.com

Email

Affordability Calculator

$23,116
Per Month
91%
9%
0%
Monthly Principal & Interest
$21,056
Monthly Property Taxes
$2,060
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3042126 Elementary School
4789714 Middle School
Valley High School High School
Pricing History
DatePricePrice ChangeDescription
10/15/2025$3,375,000 Listed Price

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288 Middlesex Avenue, Chester, CT, 06412 is a Single Family Home for sale at $3,375,000 with 4,926 sqft and a lot size of 2.65. 288 Middlesex Avenue has 4 bedrooms, 4.2 baths, and was built in 1800. The property's zip code is 06412 which is in Chester, CT