Local Listings | Available Today




Property Description
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.
Features
Heating System:
Hot Air
Cooling System:
Central Air
Basement:
Full, Full With Hatchway, Concrete Floor, Interior Access, Partially Finished, Storage
Appliances Included:
Dishwasher, Microwave, Range Hood, Subzero, Dryer, Washer, Gas Range, Wine Chiller, Convection Oven
Foundation Type:
Concrete
Heat Fuel Type:
Oil
Exterior Features:
Patio, Underground Utilities, Balcony, French Doors, Gutters, Stone Wall, Awnings, Underground Sprinkler
Exterior Siding:
Shake, Cedar
Interior Features:
Cable – Available, Auto Garage Door Opener, Security System, Audio System, Sauna
Fireplaces Total:
2
Parking Total Spaces:
0
Hot Water Description:
Oil, 50 Gallon Tank
Lot Description:
Professionally Landscaped, Water View
Water Source:
Private Well
Address Map
Street:
Middlesex
Street Number:
288
Floor Number:
0
Longitude:
W73° 32′ 45.3”
Latitude:
N41° 25′ 59.2”
MLS Addon
Office Name:
Coldwell Banker Realty
Agent Name:
Nancy Mesham
List Agent MLSID:
MESHAMNL
List Office MLSID:
CBRB54
Tax Year:
July 2025-June 2026
Directions:
Middlesex Avenue water side. Follow driveway to the end.
Elementary School:
Chester
High School:
Valley
HOA Fee Amount:
$0
Parcel Number:
941338
Property Tax:
$24,724
Virtual Tour:
Click Here
Zoning:
R-2

Single Family For Sale

288 Middlesex, Chester, 06412

4 Bedrooms
4 Bathrooms
4,926 Sqft
$3,150,000
Listing ID #24166793
Basic Details
Property Type :
Single Family For Sale
Listing Type :
For Sale
Listing ID :
24166793
Price :
$3,150,000
Bedrooms :
4
Baths Total :
6
Bathrooms :
4
Half Bathrooms :
2
Square Footage :
4,926 Sqft
Year Built :
1800
Lot Area :
2.65 Acre
City:
Chester
Zipcode:
06412
Style :
Colonial
Agent info
RE/MAX Right Choice
43 South Main Street, Newtown CT 06470
Mortgage Calculator
$
$ %
years
%
$ %per year
$ %per year

$
Contact Agent

A full-time agent with RE/MAX for 17 years. Marketing Business Degree WCSU. Volunteer Danbury Hospital. RE/MAX Executive Club. Read More…