$3,150,000

288 Middlesex Avenue, Chester, CT 06412

  • 4 beds |
  • 6 baths |
  • 4,926 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1800
  • Property Lot Size Icon2.65acre lot
  • Property Parking Icon 6 car garage
  • Property Price Per Square Feet Icon $639/sqft
  • Property List Date Icon Listed 28 days ago

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.

Listing Status:
Active
Date Added:
April 13, 2026
Data Last Updated:
May 12, 2026 at 12:50PM
Listing Office:
Coldwell Banker Realty : (860) 434-8600
Listing Agent:
Nancy Mesham : (860) 227-9071
MLS ID:
24166793
  • General: Audio SystemAuto Garage Door OpenerCable - AvailableSaunaSecurity System
  • Rooms: FoyerGymMud RoomSteam/Sauna
  • Appliances: Gas RangeConvection OvenMicrowaveRange HoodSubzeroDishwasherWasherDryerWine Chiller
  • Laundry: Lower Level
  • Basement: FullStorageInterior AccessPartially FinishedConcrete FloorFull With Hatchway
  • A/C: Central Air
  • Heating: Hot AirOil
  • Fireplace: Fireplaces: 2
  • General: BalconyUnderground UtilitiesAwningsGuttersStone WallFrench DoorsUnderground SprinklerPatio
  • Style: Colonial
  • Roofing: Asphalt Shingle
  • County: Middlesex
  • Zoning: R-2941338
  • Restrictions: EasementsRight of Way
  • Water: Private Well
  • Sewer: Septic

This listing courtesy of Nancy Mesham , Coldwell Banker Realty

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

Ready to Start a VA Loan?

Get Started Veterans United Home LoansNMLS #1907  †
Get Prequalified »
Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

Location

Similar Listing

53-1 Selden Road Road, Lyme, CT 06371
Single-Family Home For Sale

$3,395,000

  • 5 bed |
  • 6 bath |
  • 4,734 sqft |
  • 9.05 acre lot
53-1 Selden Road Road Lyme, CT 06371

#24094694 - Coldwell Banker Realty