288 Middlesex Ave | Image 1
New
Virtual Tour
288 Middlesex Ave | Image 2
288 Middlesex Ave | Image 3
288 Middlesex Ave | Image 4
288 Middlesex Ave | Image 5
288 Middlesex Ave | Image 6
288 Middlesex Ave | Image 7

$3,150,000

For Sale

A day ago

288 Middlesex Ave, Chester, CT

House

MLS® 24166793

4 Bed

6 Bath

4626 sqft

6 Parking

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 4626 sqft
Garage Yes
Taxes $24,724
Days Active 0
Lot Size 
Approx. Age 1800
Avg. Price Per Sqft $680
MLS® Number 24166793

Property Address: 288 Middlesex Ave, Chester, CT, 06412-1226

Average square foot calculated using Size range provided by listing agent.

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.
MLS® Number24166793
Laundry LevelLower
Central VacNo
FireplaceNo
Acreage
Exterior
GarageYes
Approx. Age1800
BasementFull, Storage, Interior Access, Partially Finished, Concrete Floor, Full With Hatchway
DrivewayAttached Garage, Detached Garage
Garage Spaces
Heat
A/C
Heating Fuel

Extras

Rooms

Bedroom 2:Upper Level11 × 14 ft
Bedroom 3:Upper Level11 × 12 ft
Living Room:Main Floor15 × 31 ft
Bedroom 1:Upper Level12 × 16 ft
Kitchen:Main Floor18 × 24 ft
Library:Main Floor9 × 11 ft
Dining Room:Main Floor17 × 17 ft
Other:Upper Level13 × 19 ft
Other:Lower Level15 × 17 ft
Family Room:Main Floor17 × 18 ft
Office:Main Floor11 × 12 ft
Media Room:Upper Level22 × 32 ft

Price History

-End Date
Not Sold YetSold Price

For Sale

Apr 13, 2026List Date
$3,150,000List Price
  • Commute

Commute

Starting Address
Destination Address
288 Middlesex Ave, Chester, CT

Like what you see?

Complete the form and we'll be in touch. No login necessary.

Add a Comment
Loading...

Similar Listings

Comparable Properties