288 Middlesex Ave Chester, CT 06412
Estimated payment $18,646/month
Highlights
- Steam Room
- Sub-Zero Refrigerator
- 2.65 Acre Lot
- Valley Regional High School Rated A-
- Waterfront
- Colonial Architecture
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.
Listing Agent
Coldwell Banker Realty Brokerage Phone: (860) 227-9071 License #RES.0760007 Listed on: 04/12/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $24,724
Year Built
- Built in 1800
Lot Details
- 2.65 Acre Lot
- Waterfront
- Stone Wall
- Sprinkler System
- Property is zoned R-2
Home Design
- Colonial Architecture
- Concrete Foundation
- Frame Construction
- Asphalt Shingled Roof
- Cedar Siding
- Shake Siding
Interior Spaces
- Entertainment System
- Built In Speakers
- Sound System
- 2 Fireplaces
- Thermal Windows
- Awning
- French Doors
- Mud Room
- Entrance Foyer
- Steam Room
- Sauna
- Home Gym
- Concrete Flooring
Kitchen
- Gas Range
- Range Hood
- Microwave
- Sub-Zero Refrigerator
- Dishwasher
- Wine Cooler
Bedrooms and Bathrooms
- 4 Bedrooms
Laundry
- Laundry on lower level
- Dryer
- Washer
Attic
- Unfinished Attic
- Attic or Crawl Hatchway Insulated
Partially Finished Basement
- Basement Fills Entire Space Under The House
- Interior Basement Entry
- Basement Storage
Home Security
- Home Security System
- Smart Thermostat
Parking
- 6 Car Garage
- Automatic Garage Door Opener
Outdoor Features
- Balcony
- Patio
- Rain Gutters
Location
- Property is near shops
Schools
- Chester Elementary School
- Winthrop Middle School
- Valley High School
Utilities
- Central Air
- Heating System Uses Oil
- Underground Utilities
- Private Company Owned Well
- Oil Water Heater
- Fuel Tank Located in Basement
- Cable TV Available
Listing and Financial Details
- Assessor Parcel Number 941338
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $24,724 | $913,010 | $410,760 | $502,250 |
| 2024 | $22,323 | $913,010 | $410,760 | $502,250 |
| 2023 | $21,400 | $720,530 | $392,510 | $328,020 |
| 2022 | $21,256 | $720,530 | $392,510 | $328,020 |
| 2021 | $21,256 | $720,530 | $392,510 | $328,020 |
| 2020 | $1 | $720,530 | $392,510 | $328,020 |
| 2019 | $20,744 | $720,530 | $392,510 | $328,020 |
| 2018 | $20,360 | $751,010 | $436,450 | $314,560 |
| 2017 | $19,797 | $751,010 | $436,450 | $314,560 |
| 2016 | $15,140 | $751,010 | $436,450 | $314,560 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 04/12/2026 04/12/26 | For Sale | $3,150,000 | -- | $639 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $925,000 | -- | |
| Warranty Deed | $925,000 | -- | |
| Executors Deed | $267,900 | -- | |
| Executors Deed | $267,900 | -- |
Source: SmartMLS
MLS Number: 24166793
APN: CHES-000004-000000-000015
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