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288 Middlesex Avenue, Chester, CT 06412

Single Family For Sale

$3,150,000
$639/sqft
288 Middlesex Avenue, Chester, CT
Active
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4
Bedrooms
6
Bathrooms
4,926
Sq Ft
2.65
Acres
1800
Year Built

About This Home

Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.

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

Listing Snapshot

Price $3,150,000 Days on Our Site 64 days
Property Tax $24,724/yr Style Colonial
Year Built 1800 Total Sq Ft 4,926
Lot Size 2.65 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
  • 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 $2,060/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Apr 12, 2026 Listed $3,150,000

Frequently Asked Questions

How much does 288 Middlesex Avenue in Chester, CT cost?
This property is listed at $3,150,000, which works out to $639 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 2.65 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# 24166793 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated May 6, 2026 10:40 PM UTC