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288 Middlesex Avenue, Chester, CT 06412

Single Family For Sale

$2,995,000
$608/sqft
288 Middlesex Avenue, Chester, CT
Active
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4
Bedrooms
6
Bathrooms
4,926
Sq Ft
0.37
Acres
1800
Year Built

About This Home

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 dock 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.

Listed by Nancy Mesham (860) 227-9071 with Coldwell Banker Realty (860) 434-8600

Listing Snapshot

Price $2,995,000 Days on Our Site 0 days
Property Tax $25,363/yr Style Colonial
Year Built 1800 Total Sq Ft 4,926
Lot Size 0.37 acres HOA Fees N/A
Bedrooms 4 Full Bathrooms 4
Total Rooms 9 Half Baths 2

Key Features

Interior
  • 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
Outdoor
  • Balcony
  • Underground Utilities
  • Awnings
  • Gutters
  • Stone Wall
  • French Doors
  • Underground Sprinkler
  • Patio
  • River
  • Beach
  • Dock or Mooring
  • View
Nearby
  • Library
  • Medical Facilities
  • Park
  • Public Rec Facilities
  • Shopping/Mall

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 6
Garage Type Attached Garage, Detached Garage
Below Grade 300 sq ft

Systems & Utilities

Heat Hot Air
Fuel Oil
Cooling Central Air
Hot Water Oil, 50 Gallon Tank
Water Private Well
Sewer Septic

Schools

Elem Chester
Middle Winthrop
High Valley

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $2,114/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Aug 25, 2026 Listed $2,995,000

Frequently Asked Questions

How much does 288 Middlesex Avenue in Chester, CT cost?
This property is listed at $2,995,000, which works out to $608 per square foot.
How many bedrooms does 288 Middlesex Avenue have?
This home has 4 bedrooms and 6 bathrooms.
What is the square footage of 288 Middlesex Avenue?
The home is 4,926 square feet, situated on 0.37 acres.
When was 288 Middlesex Avenue in Chester built?
This property was built in 1800.
Is 288 Middlesex Avenue, Chester, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 288 Middlesex Avenue, Chester in?
This home is served by the Chester public school system, with Chester as the elementary school and Valley as the high school.
How do I schedule a tour of 288 Middlesex Avenue, Chester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Nancy Mesham · (860) 227-9071

Coldwell Banker Realty · (860) 434-8600

MLS# 24201816 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Aug 26, 2026 11:19 AM UTC