288 Middlesex Avenue Chester, CT $ 2,995,000
288 Middlesex Avenue
$ 2,995,000
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288 Middlesex Avenue

Chester, CT, 06412
$ 2,995,000
Bedrooms4 Baths4.2 Sq 4,926

Monthly Estimate*

$ 18,911

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Single Family Home for sale in Chester, CT

for $2,995,000 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 0.37.

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. Chester taxes $25,363 and Haddam taxes $758 for a total of $26,139

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Single Family Active

Price

$ 2,995,000

Bedrooms

4

Full Bath

4

Half Bath

2

Property Type

Single Family

Taxes

$ 26,139

Style

Lot Size

0.37

Year Built

1800

Town/City

Chester

MLS | Web ID

24201816

Features
General
Zoning R-2
Neighborhood N/A
County Middlesex
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 0.37
Directions Middlesex Avenue east (river) side. Garage at the top of the drive belongs to this home as well as the attached 3-car heated garage. Follow driveway to the end.
High School Valley
City Chester
Elementary School Chester
Sq Ft Total 4926
DOM 2
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 9
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

$21,089
Per Month
90%
10%
0%
Monthly Principal & Interest
$18,911
Monthly Property Taxes
$2,178
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% 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
8/26/2026$2,995,000 Listed Price

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288 Middlesex Avenue, Chester, CT, 06412 is a Single Family Home for sale at $2,995,000 with 4,926 sqft and a lot size of 0.37. 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